🎧 From EMT to BA to Sr Product Manager: This is Yolanda's Journey
Meet Yolanda - She's a SPRINT alum who leveraged the program to land her first official Product Manager title after nearly 10 years working in and around software teams. She's one of the kindest, most ambitious Product Managers I know and it was a joy to reconnect with her. 🫶
If you're trying to transition into Product Management or you're on the job search for your next Product role, this is a must listen episode.
We talk about:
How she transitioned into the tech industry (from being an EMT! 🚑)
How building automations at US Bank was a gateway to Product
Navigating a windy career path of Product-adjacent roles
Her job search by the numbers (160 applications -> 3 final rounds -> 1 offer)
The importance of networking and LinkedIn in her job search
Highlights of the job search, interview process, and offer negotiation
Her advice for job seekers in this market
The ups and downs of starting a new job
Setting goals, staying accountable and building strong trust in a new role
Could you use some support on your product job search?
Whether you’re new to Product Management or looking for your next role, the job search can be tough. If know you need guidance, strategy, and end-to-end support, learn more about my SPRINT coaching program that helps Product Managers land their first (or next!) role.
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Jess Sherlock (00:00)
This is what's so interesting about product management. And I think that your experience is so representative of product that in my opinion is just as valuable and just as important as any other product management, but it's often not what we think of when we think of product management, right? We think of the social networking app that we use on our phone, or we think of the app that we use to buy.
lots of products and get them delivered to our house. But what we forget is that most companies, if they don't already have technology to support their business operations, they're going to need it. So what you were working on, while it wasn't what customers were buying, without
Yolanda M. (00:30)
Mm-hmm.
Jess Sherlock (00:36)
an efficient and effective intake system, the business would not be able to operate nearly as effectively,
Jess Sherlock (00:42)
Welcome to another episode of AFTER THE CERT the career podcast for product managers who've collected all the certifications and taken all the courses and still feel stuck in their product career. I'm your host, Jess Sherlock, product management career coach. I know firsthand what it feels like to be overwhelmed, lonely, and stuck in your product career. And I'm on a mission to help you feel confident and empowered to take the lead your product career and achieve your unique career goals.
on me for practical and actionable advice, plus relatable stories from PMs navigating the messy middle of their career.
And remember, if you're feeling stuck with your product management job search, worried about making a great impression during your first 90 days in a new product job, or you want to position yourself for a promotion at work, I'm here to help. You can check out my coaching programs at jesssherlock.com slash apply.
and book time on my calendar so we can chat.
Let's get into it.
Jess Sherlock (01:38)
So Yolanda, thank you so much for joining. I was just thinking back about when we met and feeling a little nostalgia. I think we did our intro call back in April of 2024. And it's like crazy for me to think about.
how much growth you've had in such a short period of time, and that actually, I think you have now done all three programs inside of my coaching community, plus some time as a community member. And as someone who ⁓ was quite skeptical of me at first, which we'll get into that later, ⁓ but yeah, I know you very well. We've been working together for long time. I am just so proud of you and how you've really taken the reins on your career.
Yolanda M. (02:08)
You
Jess Sherlock (02:28)
And so I wanted to bring you on so that folks who are wanting to get into product or who have had roles that are near product, like you have lots of roles where you're kind of in, near, around product, but never really had the title and wanted to finally, officially get into that role. I think your story's a really interesting one and I want folks to hear the nitty gritty details that they won't.
usually hear about someone's career and what it really took to make this shift. So thanks for being here.
Yolanda M. (03:00)
Yeah, thanks
for having me and I'm you're not tired of me yet.
Jess Sherlock (03:04)
Not at all. Not at all. ⁓ So tell us a little bit about yourself first and then we'll talk a bit about your career journey and where you're at now.
Yolanda M. (03:14)
Yeah, I've been in product for about 10 years. I started off my career as an EMT and then took a trip and fall right into product. I know it doesn't sound any what, you know, in any way related, but we'll get there. ⁓ Other than that, I live in Phoenix with my husband. ⁓ I like to bake and go to cool breweries and check out different cities and travel.
⁓ It's what I'm doing when I'm not working.
Jess Sherlock (03:47)
Yes, I
know. And I often wish that you were closer because you'd fit right in here. Like, Phoenix and Denver are not too dissimilar, but I would have loved for you to be able to come to some of the in-person Denver events. But someday, someday I'll have a retreat and I'll bring everybody around. So you were an EMT. I forgot that about you. ⁓ I recently, I have this thing for...
medical drama shows. So I rewatched all of Grey's Anatomy a couple years ago and now I've been like watching all, I'm trying to get my hands on everyone I can find on Netflix. So I'm currently watching The Resident. So anyways, I feel like I know everything there is to know. I feel like I could be a doctor or a nurse. Like I've start, and probably what they do is they just repeat things on the show. And so then you feel smarter, but I'm like, they have a cardiac tamponade. We need to release the pressure. So anyway.
Yolanda M. (04:30)
Hahaha.
You
Jess Sherlock (04:44)
Some might be wondering, how did, those are two very different career paths. How did that happen? So tell me, like how did product even get on your radar as something you might want to do? Like, and why the shift from EMT to software?
Yolanda M. (04:59)
Yeah, I was going to be an EMT. I wanted to work in emergency medicine. I did work as an EMT for two years, and I worked with children with developmental disabilities ⁓ for about a year after my initial EMT certification. At the time, I was living in Phoenix, and I had decided to move to Tucson, ⁓ not knowing that what I had been doing in Phoenix as an EMT was completely different than what Tucson did.
⁓ Different cities, different states, different cities, different towns, all have different requirements for how they hire EMTs. And so what I wasn't aware of is that by moving to Tucson, I wouldn't actually be able to work as an EMT. And if you don't work as an EMT for six months, you have to recertify. So at that time, I had to think about whether or not I wanted to recertify, how difficult it was going to be to continue to go down that path. Was it even what I wanted to keep doing?
And so I had an opportunity to just think about it. At the end of the day, the decision was made for me, because I decided to move back to Phoenix. And I was like, I'm not putting up with any of that. So I took a temp job with US Bank. And during my time with US Bank, I was there for four years. And I had five different jobs. ⁓ Yeah, think primarily what I was trying to do at the bank was figure out
Jess Sherlock (06:09)
Yeah.
Wow.
Yolanda M. (06:26)
what I wanted my career to be. And in doing that, I tried to automate a lot of what I was doing. And with each thing that I made easier for myself and made easier for others, led me to more opportunities. So I went from that entry-level position to a project analyst role. And with the project analyst role, I started to shadow business analysts. And
provide them with details and requirements that they needed, and started to learn that that was an actual career path where I could work more closely with technical people. I could provide them with the details and requirements they needed to build technology solutions. And so I found out that that was something I really enjoyed doing. And it didn't hurt that my husband is a software developer. At the time, he was just my boyfriend.
You know, he kind of gave me the confidence to know that I could communicate with engineers at that level and I could, ⁓ he let me know that there were more roles outside of business analysts that I could be good at and could be interested in. And kind of just gave me that little nudge to go and figure out what those roles were.
Jess Sherlock (07:20)
you
That's awesome and so handy when you have someone. It's a common thing actually that I've heard from people is they hear about product because a friend or a coworker or someone says, have you ever thought about being a product manager? And they're like, well, what's that? ⁓ So that's not entirely uncommon. But that's a really cool like start into the role through US banks. So you mentioned you were automating some things.
it's clearly a project analyst or even a business analyst, they're usually giving some sort of requirements to developers. So tell us a little bit about that, like what types of things you were automating and also what sort of product you were responsible for.
Yolanda M. (08:22)
Yeah, think like a lot of people working in technology, I was lazy. I didn't want to have duplicate data entry. I wanted things to be a little bit more seamless. I didn't want to have to manually gather reporting and information like that. And so I utilized Excel and Microsoft Access to build
sort of little applications that I could input data in one place and have it populate throughout different areas. for example, I had a Excel workbook and we had all of these different documents that needed to be completed to get a loan origination file started for a mortgage. And so instead of me going and like typing first name, last name into 30 documents, I...
put them all into Excel so that way I would have like a front sheet that I would enter everything in and it would automatically populate in all 30 documents. And then a big old button I could just push to print it all out on legal size paper.
Jess Sherlock (09:28)
⁓
Yeah, mean, that's a product in a way, right? I mean, guess that could be something you could sell, but like you identified this problem, it was for yourself, certainly, but then you produced a solution, that's awesome. And a lot of the best product managers are tinkerers. We realize it in hindsight, right? Or we're lazy, it's like, there's gotta be a faster, easier way. yeah, that's such a clear signal to me that your product was the right fit.
Yolanda M. (09:56)
Yes. Yeah, I had to write some VBA, like macro code to make it all work seamlessly. And what was really cool about that was it did start off with something that I just wanted to do for myself to make my day to day easier. And my boss's wife was actually working in the, guess they called it a communications team, but it was basically a business team that was responsible for making sure
Jess Sherlock (09:56)
It was only a matter of time.
Yeah.
Yolanda M. (10:24)
All of the loan officers had what they needed. And so my wife ran that team. And she saw what I had done and actually took it and made it a tool for all of the sales folks within our region. So they all actually used that workbook to accelerate their own ability to create those files. Yeah.
Jess Sherlock (10:43)
No way. And so you
didn't, it's not like you set out being like, I'm gonna show them I can be a PM. You just started doing and it was useful enough that they started using it. That's amazing. It is amazing. All the more reason to just, be as helpful as you can be and only good things will come of that, right? Like be the one who tries to solve problems and maybe even comes up with a solution.
that's what's gonna get people's attention. So did that lead to more opportunities at US Bank? This is slowly coming back to me, because I remember you told me all these things over a year ago, but this is reminding me of why when we had our intro call, I was like, I'm sorry, why have you not had this product manager title? This is very producty. what ended up happening at US Bank? Did you get promotions, and then what was next for you?
Yolanda M. (11:11)
Mm-hmm.
Mm-hmm.
Yes, ⁓ with that I ended up getting a promotion as a project analyst and kind of doing a lot of the same stuff, like just sort of automating, creating tools and tool kits for the sales team to be able to make their jobs a little bit faster, a little bit easier. And then I started using Access to make a database for them so that way they would have more robust reporting.
on some of the pilots and things that they were doing. ⁓ And with that, I started writing more code. And there was a particular challenge that I was facing, and I wasn't sure how to make it work within the tool itself. And I had asked my husband, was like, hey, I found online that you could add code with a button to do this action. And I started to.
describe to him what I needed to do. And he's like, yeah, we can figure this out. And so he pops on and starts to code, actually figure out how to add the JSON code that was needed to power this. And I was communicating what I needed and he was building it. And he's like, yeah, yeah, you could do this job. You know, like we were saying, right? People sometimes are like, hey, have you ever heard or thought about?
being a product owner or being a product manager. And that was kind of the moment where he started putting that sort of title on there and telling me like, hey, people get paid to do this.
Jess Sherlock (12:59)
Yes, they
do. They do. And this experience that you had unbeknownst to you at the time, but I can see it very clearly. This was, you were building internal tools. You were building internal products, which is a really great starting point for PMs who are trying to get experience and actually building things, working with developers, because companies are more likely to hire someone.
who's a little bit more junior early in their career to work on an internal tool because it's less risky, it's a little less visible, right? Versus like you were working on all of these internal tools to enable team members, which is very helpful, very important, but you didn't have to worry about go to market or how do we market this new feature or price this new app or whatever it is. It's not like you were building the mobile app that 10 million business banker
Yolanda M. (13:43)
Mm-hmm.
Jess Sherlock (13:53)
customers were using, right? Much higher risk. But you still very much so got those transferable skills. So let's talk about where did you go next? So you had all this experience at US Bank. You were starting to hear from your now husband, hey, here's this role I think you should have. So tell us about the next few jobs that you had, because you had bounced around a lot. I remember seeing on your LinkedIn, it was like...
you kept shooting for product and you kept landing like right there, right next to it or at a company doing product but not with that title. yeah, give us kind of the quick version of those series of roles leading up to that, your second most recent role.
Yolanda M. (14:35)
Yeah, with building those tools and learning that there was this really awesome great role that I would be good at, I started to look first at US Bank. What is the role that would allow me to get closest to software development? Because they do have a mobile app. They do have consumer-facing products. So what could I do to get closer to that? ⁓
Jess Sherlock (14:51)
so smart.
And that's
often the best place to start, right? So like, if you had had that opportunity, 100 % recommend. Because people know you, you have a reputation, very smart, very smart. What'd you find out?
Yolanda M. (15:10)
They did have business
analyst roles, but they didn't have product, necessarily product roles. And so I had an opportunity to work more closely with the business analysts on some of their changes that they were making to internal tools. And so I started working with them, and I was like, OK, I could totally do this job. And so when there was an opening, I did apply for it. I didn't get it.
but I was not discouraged. I was like, there's a job out there for me somewhere. And if it's not here, I'm gonna go find it. And so I started to look around and try to find other similar roles. And so I left US Bank as a project analyst and I went into a technical business analyst role after that. And it wasn't quite, we said I'm product adjacent, right? It wasn't quite.
the end goal that I was looking for, that I was seeing in all of the podcasts, and that I was reading about or hearing about from my husband or other software development friends, but it was closer. And then from there, I took another business analyst job. Eventually, I did get into a product owner role, because I had started to meet people. I had started to get closer to developers. My husband,
he started getting higher up in organizations, meeting more people, introducing me. And so I did eventually land into a product owner role at a software development startup. So that was great. It was the first one that I was into.
was multifamily software. It was like a CRM for multifamily technology. And when I took that role, I was the only product owner. It was a brand new role for me. It was actually a brand new role for the team. The team had, while they were running Scrum, they didn't have all of the right titles and roles.
Jess Sherlock (16:42)
That's right.
Yolanda M. (17:03)
So I was very adamant that I wanted it to be a product owner role. Before that, they had business analysts. And I was like, come on, you're doing Scrum. And so I kind of got that title that I was looking for there and was able to truly figuring out how to work within a software development team. But there wasn't anybody to learn from.
Jess Sherlock (17:09)
You're like, not again!
Yeah, and in
that role, if I remember correctly, you were running all the sprint ceremonies, you were prioritizing the backlog. How much opportunity did you get in that role to be more strategic and like own the roadmap or was it more execution?
Yolanda M. (17:42)
It was more execution. It was a founder-led product. And so a lot of the strategy was set by the founder and what they wanted their company to be and how they wanted their product to run. ⁓ So while I had some input and I did work directly with the founder's CEO, ⁓ so I did have an opportunity to bring ideas to him and to help foster the ideas that he was having and ask good questions. Ultimately, he was the one driving.
the priorities and what we were building. But I did get a lot of freedom to help design those solutions. So working right along with the lead engineers and with the designer to actually come up with the solution itself and then break that work down and execute that work. They didn't really mind or care what the solution was as long as they got to call it whatever it was that they were calling it or it had the function that they were expecting.
Jess Sherlock (18:40)
that organization in your mind mature in terms of product? Were you getting the opportunity to do customer discovery or measure the effectiveness of the things that you were building or might you categorize it as more of what we might call a feature factory?
Yolanda M. (18:59)
a little bit more feature factory. I think towards the end there, I was starting to find opportunities. We built a BI tool. And so with that, we were starting to find opportunities within the user journey that we would be able to help build other features and functionality based on. But for the most part, it was the leader of the company, the founder hearing.
what others were doing, what his competitors were doing and wanting to beat them to it or to match what they were doing or do better. And so there was a lot of shifts in priority sort of based on that.
Jess Sherlock (19:35)
Mm-hmm, yeah. And it was B2B, so I imagine it was also largely sales-led. It didn't necessarily matter if we had the data to prove that something was being used. It was very much like, we'll sell this deal if we get this thing done, or we're more likely to get this deal if that thing is already done. Is that all right? Yeah. Yeah, yeah. Classic, classic. OK, so about how much time had passed then from becoming aware of product to when you finally got that product owner title.
Yolanda M. (19:39)
Exactly.
Yeah, yeah.
geez.
Jess Sherlock (20:05)
I'm thinking it was a few years. Like this wasn't like a six month. I know you're probably pulling it. You can pull up your legs.
Yolanda M. (20:10)
I I'm pulling it up right now. I'm like, hmm, how long was
it?
Yeah, I think it was three years. Three years.
Jess Sherlock (20:18)
Yeah, so it took some time.
It took some networking. took patience. Okay, from there then, this is where things get interesting. Cause I remember you telling me about your career journey and all of a sudden I was like, wait a minute, you became an engineer, but you didn't, but your titles. So tell us about the next few titles you had, cause they're kind of all over the place.
Yolanda M. (20:41)
Yes, so I did learn a lot in this product owner role with the multi-lending family company before I moved on. some of that was I was working so closely with the engineers. I was a bit of a team lead. There wasn't a lot of us. It was a very small team. But I was leading discussions. And I really enjoyed it, really liked it. When I moved on to a new
product owner role, there was a couple things I was looking for with that. One, I wanted to learn more. So I wanted to work with a bigger team of product managers so that way I could learn more. But I didn't want to give up being so close to the team. And so what I learned through that was there was a bit of a hybrid sort of role where you're leading a team and working a little bit closer with what the technical solution is.
while still executing the product vision. So still not quite getting into strategy, but that execution sort of aspect of it involved some technical design work. And so I found a job that sort of ticked those boxes. was very compelling to me. It was still a product owner title at the beginning. But three months or so in, I actually ended up taking a
engineering manager role.
Jess Sherlock (22:08)
That's
right. What? Yeah, tell me about that.
Yolanda M. (22:14)
Yeah, I think it was...
Jess Sherlock (22:18)
I think that person is the people manager, maybe for the engineers on that team. think partner to a product manager. I think very good coder. So what? Tell me more.
Yolanda M. (22:30)
Yeah,
and I definitely did ⁓ support the engineers on that team. I did one-on-ones. I talked to them about their career path and all of that. But the biggest aspect of that role was actually the technical solutioning and helping come up and design the technical solution to meet the product need. Why was that way?
Who knows?
Jess Sherlock (22:58)
And this was HealthTech at this point, right? So it wasn't the
first, what was it, a massive like replatforming? This was your like quintessential career experience that we ended up talking about on your resume, I think, if I remember correctly.
Yolanda M. (23:04)
Yes.
Yes. Yep,
I helped redesign and relaunch their flagship product.
Jess Sherlock (23:15)
That's right. That's right. Okay.
you're at this health tech company, which was also B2B. ⁓
Yolanda M. (23:21)
It was B to B to C.
Jess Sherlock (23:23)
Okay, okay. And what did they do at a high level?
Yolanda M. (23:26)
⁓ health plans and payers would work with us to match their members to digital health products so they would pay for those products given that they saw improvements on their conditions. So we would track how well they were doing on those, ⁓
Jess Sherlock (23:26)
You
Yolanda M. (23:44)
platforms and then we would submit the claims on behalf of that I didn't know at the time, but it's called a two-sided marketplace. And so that's what we were. We sat right in the middle of that two-sided marketplace where we brought members to products that could help solve their problems and then sent the data back and forth.
Jess Sherlock (24:03)
Got
it, yes, I remember when you learned that phrase. It was an aha moment for you. Okay, so this job, you were there a couple years, this was your first foray into health, which I don't think was on purpose, but it just so happened that your next few roles were in and around health, including where you're at now. So.
Tell us about that period of time in health, especially your time at mind where you were for almost three years.
Yolanda M. (24:31)
Yeah, I went from that engineering management role into a scrum master role and
Jess Sherlock (24:40)
What about that one?
There's another random title. There we go.
Yolanda M. (24:43)
Yep, yep, Scrum Master. And then when I joined Mind, my title there was, Solutions Manager, Technical Solutions Manager. ⁓ Which again, you know, is a title that doesn't make a lot of sense. Definitely in this industry of health tech or just within product management at all. And so...
Over the last, I would say, six years or so, I discovered that there's really not a very big product management community within Arizona. And so a lot of the jobs and roles, the titles don't make a lot of sense, but what I've done in every single role has been the same.
working with stakeholders, defining what the product is, working on product strategy and what it's going to take to bring that strategy to life by communicating and working with engineers. I've literally have done that in every single role since US Bank, but not necessarily with that title.
Jess Sherlock (25:44)
And let's talk about this time at Mind. So I guess first let's give folks a little context. So Mind 24-7, what's the business and what part were you responsible for?
Yolanda M. (25:54)
They are a mental health organization. So they have clinics within the state of Arizona to help folks who are in a mental health crisis. ⁓ They also have programs to help bridge individuals who come out of a mental health crisis and need to find long-term support, whether it's therapy or psychiatry. It's a very needed service within our community, and I was very proud to have been a part of it. My role there
had a lot of different aspects to technology as a whole. It wasn't just product management, but I actually really helped to build and drive their technology stack all around the business. So from business applications all the way through to the medical record system that they're using within the clinic.
And within the last year that I was there, I also helped to build and develop a intake product. And that one I actually did the design work and some of the engineering work to develop a low code solution to their intake problem, which was really wanting to make sure that they were collecting the right information timely and getting people to see a provider as soon as they could.
based on acuity and when that person arrived at the clinic.
Jess Sherlock (27:16)
And This is what's so interesting about product management. And I think that your experience is so representative of product that in my opinion is just as valuable and just as important as any other product management, but it's often not the focus or necessarily what we think of when we think of product management, right? We think of the social networking app that we use on our phone, or we think of the app that we use to buy.
lots of products and get them delivered to our house. But what we forget is that most companies, if they don't already have technology to support their business and their business operations, they're going to need it. So what you were working on, while it wasn't what customers were buying, right? It wasn't the product that the company was selling, you know, mental health support. That was the product. But without
Yolanda M. (27:55)
Mm-hmm.
Jess Sherlock (28:09)
for example, an efficient and effective intake system, the business would not be able to operate nearly as effectively, right? I think I remember you telling me, was it like, I can
Yolanda M. (28:17)
Mm-hmm.
Jess Sherlock (28:19)
vaguely remember it was like a stack of 10 sheets or something and it used to take people, what was the issue? Why did you build this intake process? Because there was a very significant problem here that's no different than any other, right? Like identifying a product problem and then using technology to solve it.
Yolanda M. (28:26)
Hahaha
Yeah.
Jess Sherlock (28:37)
What was that problem that triggered the whole intake system revamp?
Yolanda M. (28:42)
Well, they're using an Excel spreadsheet to track when patients had arrived and a series of sticky notes to track where they were. And ⁓ the biggest challenge with that was in order for them to have any idea how long it was truly taking from the time somebody arrived to the time somebody left.
Jess Sherlock (28:45)
Okay.
Yolanda M. (29:06)
⁓ They had to have a person who was able to see in all the chaos that was the clinic who was where. What time did they come in? What time did they actually speak to provider and enter that into their EMR system, which we could then pull out from a data perspective and show in reporting. But it really depended on somebody entering that information into the system, which is not always going to be accurate.
Jess Sherlock (29:31)
my goodness.
Yolanda M. (29:33)
And there are other issues where we had handwritten intake forms. And so being able to read somebody's handwriting and be able to input that into a system, we would just end up at the end of the day where these individuals who were checking patients in and out all day just had a stack of papers to input at the end of the day. And so you don't have that real time tracking of
where the patients are, how long it's taking for them to get in, what happens if something changes within their acuity during their assessment, how do you get that person then reprioritized based on that level of acuity. it just was a problem that, maybe it wasn't the most important problem at the organization, but it was one that I could solve by helping build a product. I could help solve.
Jess Sherlock (30:23)
It sounds pretty important to me. I mean,
the idea in 2025, the idea of a human having to enter a stack of paper. Like if I go to a doctor's office and I have to fill out a handwritten form, get, I don't know, maybe it's the product manager in me, but I'm like.
Yolanda M. (30:36)
You
Jess Sherlock (30:45)
worried you're not gonna be read my handwriting. I'm like, can you just give me the damn keyboard and I'll type it in myself? Like, why are we playing this game of telephone? to ⁓ bring it back to the point though, the point remains, which is product management at the core is identifying a problem, a customer problem and or business problem that can be solved scalably through technology. And that is literally what you were doing here.
Yolanda M. (31:14)
Yes.
Jess Sherlock (31:14)
And it
was in support of, right, it was an enablement to what the business was offering as its primary offering. But certainly the P &L looked better because of the work you were doing, right? I presume we saved money on headcount, I hope, right? Or if we didn't save money on like those hourly employees, I hope at the very least they were able to dedicate their time to more valuable efforts than data entry. I would hope that we also saw better ⁓ patient outcomes.
Yolanda M. (31:26)
Mm-hmm.
Mm-hmm.
Jess Sherlock (31:44)
because we were able to better monitor their care. And then I can't imagine that there were certainly probably errors in the data entry. So hopefully there was also better patient outcomes because of better entry. So all to say, ⁓ were you working on the product that was being sold? No, but it was absolutely an enablement, technology enablement to the product being as effective as possible.
So what's the problem Yolanda? mean, at this point we hadn't even met. you, for all intents and purposes, it sounds like you were doing product, right? So what led you to consider coaching?
Yolanda M. (32:26)
Yeah, well that was three years in. At that point my title was Director of Technology. And yes, Director of Technology Solutions. And the product part was the solutions, I guess. But there was a lot of other work that I was doing beyond the product piece. I was also helping to manage the help desk. I was...
Jess Sherlock (32:34)
Yes, let's our technology solutions or something, right? Something like that.
you
Yolanda M. (32:55)
helping to manage changes to our EMR system, which was the actual evaluations that the providers were taking. I was helping with just so much more outside of product management. And my job started to really change and take a focus on technical project management, which was not something that I, yeah, IT, I started feeling like IT. I started feeling like,
Jess Sherlock (33:15)
More like IT. It was like pretty to feel like IT
Yolanda M. (33:22)
A lot of my job was trying to figure out where to cut, right? Where to cut technology expenses and things like that. And it just wasn't something that I ever saw myself really doing. And so I wanted to get back into a more traditional product management role. Even though we just had this conversation about how I did not have a traditional product management path at all. But I...
Jess Sherlock (33:47)
you
But I remember when you came
to me, you had this sense of like, I want to work on a Scrum team again. Cause also you were doing everything, which was a great experience at mind. But you were, you were like, I'm tired of doing the design and the requirements and the customer research. And sometimes even building it, you were, was it power apps? You were building also, you were like shipping out power apps, mini apps, like they were hotcakes.
Yolanda M. (33:57)
I was doing everything. Yeah.
Mm-hmm.
Yeah, I wanted to work closely with an engineering team again, like a full engineering team instead of just like one guy. He was a great guy, but I wanted to work with the team again. I wanted to work on a product where the product or what I was working on was actually the product being sold and the revenue generating application itself. I missed sort of
working on a team and shipping a product. And so I wanted to get back into that. And I just didn't really know how. It had been so long since I had really been looking, well, looking for a job, building a community or connecting with people. And sort of, I wasn't quite sure how to get back into that. So I wanted to find a coach who could help me figure out what my next steps were.
but I really wanted them to be focused in product because that's where I wanted to go. And I wanted somebody that could understand my uniqueness and the uniqueness of the role I was trying to get into to help me figure out all of those skills that I have that are transferable and how to really make them shine.
Jess Sherlock (35:26)
Yeah, yeah. let's talk about like, did you choose me? Because I remember you were pretty skeptical of me. I think I told you this story about how you were one of the first people who was like, I'm gonna need to talk to a previous client. You were like,
Yolanda M. (35:35)
you
Jess Sherlock (35:48)
Why should I trust you? Which I so appreciate. I actually love that about you, what led you to decide that we would be a good fit?
Yolanda M. (35:58)
Yeah, think I looked back at my message history to prepare for the podcast a little bit to remind myself of all of those good things. I was, yeah, it was definitely hard on you, but I was hard on others too. I was fair and equal. ⁓ Three years prior to that, I was assessing vendors for a lean startup. And so I definitely... ⁓
Jess Sherlock (36:13)
Okay.
Yolanda M. (36:25)
was utilizing some of that. I wanted to know sort of what you brought to the table, what was your differentiator. But I was also, like I said, really focused on wanting to make sure that I found somebody who knew this role, knew product management, and that it wouldn't just be like a cookie cutter course, it wouldn't just be another certification.
It wouldn't be me just watching videos and all that kind of stuff. I wanted it to be a little bit more personal. And I felt like even if there was a workbook or some videos to watch, that would be in combination with meeting with somebody versus it only being a course. And so I felt like your program had a little bit of all of that. And I also felt like there were options of being able to
Jess Sherlock (37:10)
Yeah.
Yolanda M. (37:19)
sort of figure out what was gonna work best for me and what I needed versus just kind of getting what everybody else was gonna get off the shelf.
Jess Sherlock (37:26)
Yeah, yeah. I have your notes pulled up here from our intro call, which is, I call now the alignment call. And I giggle, because now, mean, you told me, your answer to the question of like, tell me about your career today, was like six paragraphs. And your challenges, very much what you've described. But yeah, you said in terms of what you were looking to accomplish.
Yolanda M. (37:31)
geez.
Jess Sherlock (37:52)
I want help assessing my career options, determining a path for achieving a fulfilling career and writing my resume to better align with these goals. And ⁓ girl didn't even have a LinkedIn. One of her goals was to set up a LinkedIn. That still makes me so good, so good. I was like, well, we can have an impact here.
Yolanda M. (38:02)
⁓ no.
Jess Sherlock (38:19)
Step one, we're gonna get you a LinkedIn. Step two, we're gonna figure out what to put on it. ⁓ So let's talk about the job search, because what's really interesting here is that you came to me essentially for SPRINT You wanted help with the job search. You wanted to hyper-focus on that, but you did have a day job, which is not uncommon for folks who want to join SPRINT. A lot of times, the day job's gonna help you make it through the job search time period.
So tell us a little bit about the, like you started coaching and the job search was a part of your goal, but we were also kind of supporting your day job. So let's talk about the job search part specifically and what it was like to work through creating LinkedIn, but also deciding on a job search strategy given your really varied background, you know, and then updating your resume. Like, what was that like for you?
Yolanda M. (39:17)
Yeah, I wanted to, I needed help, right? I needed help understanding and identifying what it was I was even looking for in my next role. I knew that I wanted to get back into product management. I wasn't sure if I wanted to be at a director level or if I wanted to be an individual contributor. I felt like, mm-hmm.
Jess Sherlock (39:37)
Because you had been managing people, I forgot. You were
managing people at Mind. ⁓ So we did, yeah, there was a lot of conversations around, should we look at that? Should we not look at that? Yeah.
Yolanda M. (39:47)
Yeah, and I really enjoyed being a people manager. enjoyed, I guess really what I enjoyed out of that was mentoring. I enjoyed helping other people find out what's great about them and bring that out and help them look at their challenges differently and overcome those challenges on their own. So I really enjoyed the mentoring and coaching aspect of a management role.
But I did not enjoy more of the administrative tasks that is involved in being a people manager or department lead, right? ⁓ The budgets and things like that weren't something that I enjoyed doing. I don't know who does, but it wasn't me. ⁓ And so, yeah, so I wanted help in figuring out what it is that I liked, what I didn't like, where I wanted to go with that. ⁓ And then...
Jess Sherlock (40:28)
Some people do! Some people do!
Yolanda M. (40:40)
knowing that I had a bit of a task in getting, I wanted product management in that title. So being able to figure out how to redo my resume in a way that really made what I have done in those roles that were truly product shine so that there was no question that I had the skills and the experience to lead or be part of a product team. ⁓ And then I also ⁓
needed LinkedIn, I needed to build a community. It had been a while since I had been part of any sort of product related community or even technology related communities, being that, you know, obviously, during the time that it was with mind was right after COVID had happened. So there weren't a lot of in person, you know.
Jess Sherlock (41:28)
That's right. And
your last couple jobs, sorry to interrupt you. I just remembered your last few jobs had actually come through friends or previous coworkers. I tease you about not having had a LinkedIn, but truly you didn't need it. You had a good circle. It was just limited. So I think by the time we worked together, one of your goals was to get connected outside of that small, like you had really tapped all the potential you could in the group of folks you already knew.
Yolanda M. (41:47)
Yes.
Yeah, yeah, my Rolodex was running thin.
Jess Sherlock (42:01)
Yeah, yeah, so
we got you a LinkedIn. I'll never forget when you're like a recruiter messaged me. Is that a good thing?
Yolanda M. (42:09)
I was like, is this a scam?
Jess Sherlock (42:12)
good side it means it's working ⁓
Yolanda M. (42:15)
But yeah, I needed
that, you know, I needed that ⁓ digital resume, right? And I needed to figure out how to find a community and how to reach out to other people and network because I knew that that would be a big part of my job search. I wasn't naive enough to think that I could continue to just get jobs from friends ⁓ or that I could just keep like cold applying to companies and expect to get
my resume on top of the giant stack of resumes that they were already looking at. So I knew I needed to build that community and I didn't want to build that networking and I didn't want to wait until I absolutely needed it. You kind of have to do that ahead of time.
Jess Sherlock (43:00)
Yeah. Well, and I mean, that brings up a good point. So here we are chugging along. We got your resume adjusted. We took some liberties with some of the titles. And I remember our conversation about your most recent role in particular, where I was like, we got to get rid of this director of technology solutions nonsense. And we're just going to call you a director product, which for anyone listening is a really common technique that I use because it's okay to make an adjustment to a title if it's still accurate in terms of level.
Yolanda M. (43:17)
you
Jess Sherlock (43:29)
Right? So if you were, for example, a product owner and essentially it was just a product manager role, it's okay to shift it from PO to PM. What would not be okay would be to shift like a PO role to a principal PM title, obviously, right? Cause then you're just fibbing about the level. But I remember we really worked through like, how do we talk about your superpower? How do we position your ability to wear a lot of hats as a strength?
Yolanda M. (43:44)
Mm-hmm.
Jess Sherlock (43:59)
how do we ⁓ really highlight your technical skills and all this work you've been doing with low code, no code systems and integrations, as well as like a sprinkle of people leadership, right? And using more producty language with a lot of what you were doing, right? Instead of saying you were taking in requirements from stakeholders, it's like we highlighted the fact that you did in-person discovery to watch processes and figure out where the gap in the customer journey was.
It's not that like what we did was just refine and adjust the language we were using to talk about your experience. So it sounded more producty. And then we had our work cut out for us to get you to also speak about it more producty, which wasn't hard, but it's, is a shift a bit to highlight. You know, we were working towards these particular goals. They happen to be geared towards the goals of an internal product, but still goals nonetheless. Here's what you did. Here's the outcome it generated. And, and that.
Yolanda M. (44:57)
Mm-hmm.
Jess Sherlock (44:59)
I landed pretty well. have your numbers here from your job search. So tell us a bit, tell us the data on your like job search funnel ⁓ that led to this new job.
Yolanda M. (45:08)
Yeah.
Sorry, I closed it earlier for some reason. Yeah, so I, over the course of, I think it was six months, yeah, over the course of six months, I had applied for 160 jobs. Yeah.
Jess Sherlock (45:14)
That's alright.
That was that. And were you editing
your resume for each one?
Yolanda M. (45:34)
I had a couple of points that I ⁓ put in and out depending on swap. That's the word I was looking for, excuse me. I had a couple points that I would swap in and out depending on the type of role because I did apply for director roles. I applied for more technical product facing roles versus ⁓ more strategic product facing roles.
Jess Sherlock (45:38)
Mm-hmm. Yeah.
Yeah, yeah. Hats off.
Yolanda M. (46:03)
So I did take the liberty of moving in and out a few pieces here and there. And then I also wrote cover letters and I tried to make those as customizable as possible, but I did have a couple of ⁓ boilerplate ⁓ templates that I could use for different types of cover letters.
Jess Sherlock (46:21)
Yeah.
Yeah. And it surprises people when I say my philosophy is like, ideally you have one resume. ⁓ But in your case, it is different enough, you know, a director level role versus a technical PM role. And you actually, because you had a day job, you were willing to take a little bit longer in the job search if need be. And honestly, we wanted to run it as a little bit of an A-B test because we weren't quite sure where you'd get some bites. ⁓
Yolanda M. (46:27)
Mm-hmm.
Mm-hmm.
Jess Sherlock (46:50)
So you apply to 160, how many screener calls? Okay, I did the math on this before. 12 screener calls. So people are often surprised when I say in this market, I'm actually pleased if I see someone get over a 5 % conversion rate between applications to screener calls. So you're at about, I think almost 8%. Which, yeah, so when you say, oh, was 160 applications and I got it.
Yolanda M. (46:55)
12.
All right.
Jess Sherlock (47:18)
12 callbacks, a lot of times people are like, wah, wah. But really, that's not terrible, but it is why I really say focus on applying. And it's not a spray and pray. You were not applying to jobs you were not qualified for. It's like we had identified the types of jobs you would have a strong, you would be really capable of doing and really competitive for.
Yolanda M. (47:42)
Mm-hmm.
Jess Sherlock (47:45)
And the goal was apply to a high volume of those so that we can get bites Cause the thing to remember is out of those 160, whether we like to admit it or not, some percentage of them are ghost jobs. Some percentage of them have already been filled or are already like their hiring process is underway and you're just too late. Right. And some percentage of them, ⁓ you just weren't the most competitive, right? You weren't selected for a screener call. So you think about it that way. It's like,
Yolanda M. (48:03)
Mm-hmm.
Jess Sherlock (48:12)
it's not really 160, there's some unknown percentage that just, it was bad timing to begin with. So it is a little bit of a numbers game. Okay, so 160 applications, we had about an 8 % conversion rate to screener calls, 12 screener calls, where did it go from there?
Yolanda M. (48:29)
So I had there were two that I like chose not to move forward with ⁓ After the screener call. Yeah, had that I had that luxury early on especially, know that I was being picky I was wanting to really find something that not only met my you know basic requirements of like title and pay but also met my my requirements more on
Jess Sherlock (48:34)
Good for you.
Yolanda M. (48:54)
What type of organization was it? What type of work would I be doing? What was the mission? So I had that opportunity and there were a couple that just didn't align with that. So I was able to go ahead and just move forward. It wasn't right for me.
Jess Sherlock (49:09)
All right, good for you.
Yolanda M. (49:11)
⁓ I had, like you said, some just closed. There were two that actually closed during the interview process where they didn't hire anyone at all. They just closed the role for whatever reasons.
Jess Sherlock (49:22)
That happens
a lot of times like budgets get frozen, something changes at the company. Yeah, that happens quite commonly.
Yolanda M. (49:29)
Yeah, five straight up rejections, just five where I didn't, you know, they didn't ask me back. ⁓ I did get into the final rounds of three roles and ⁓ one of those is the one that I received an offer for and ended up taking. So I did get into the final ⁓ round for three of those roles, which I was proud of.
Jess Sherlock (49:35)
That happens.
Cool. Yeah.
Awesome. And yeah,
congratulations. That's amazing. And these were all P. Do you remember where they all senior PM?
Yolanda M. (49:59)
No, it was a mix. I had actually let me look it up. So I had One was a man an engineering manager role. That was one of the ones where I did get into the See two seen three senior product roles One group product manager and then the rest were director
Jess Sherlock (50:04)
I know I'm training her.
Okay, good for you, good for you. So it's not like we were undercutting your ability. It's not like we were going haywire with the roles you were applying to. These were all very much kind of like in the ⁓ bullseye area-ish of what we wanted for you to target. ⁓ Do you remember too, I didn't tell you to prepare these answers, but off the top of your head, were they all in health tech or did you go outside of health? I think you decided to go broad, right? And not necessarily stay in health.
Yolanda M. (50:51)
So the majority of them were in health tech. ⁓ I applied for things outside of health tech. But the ones, let's see here. Actually, no, it's pretty spread out. ⁓ I applied for a restaurant, fast casual chain. I applied for a car dealership. ⁓ I applied for, yeah, it was actually pretty, pretty.
Jess Sherlock (51:08)
cool.
Yolanda M. (51:19)
Pretty diverse, but the ones where I got the furthest along in the interviewing process ⁓ were health tech, mental health or digital health solution type products.
Jess Sherlock (51:31)
Yeah, it doesn't surprise me. doesn't surprise me. A lot of companies, especially in this market in the last year or so, there's been a preference towards domain expertise. It's believed to be less risky. You'll ramp up faster. We'll talk about your new job. see if any of that is true. So you ended up taking one of them. With the three where you got to final round, do you remember, did you do a take-home assignment for all of them?
Yolanda M. (51:54)
No, I did a take-home assignment for ⁓ two of them. Actually, no, one of them, only one.
Jess Sherlock (51:57)
Two of them, okay.
Yeah,
it's interesting. was gonna say, couldn't remember, but there are definitely some folks who are getting lucky. Most of the time there's a take-home assignment, but I have had a handful of folks who just, it doesn't happen and it's kind of cool. Like it's a little less work. Can you tell us about the take-home assignment? Just like roughly what the structure was and how that went.
Yolanda M. (52:15)
you
Yes, so the take-home assignment for this one ⁓ was a scenario. It felt like an actual true scenario to the organization. And it's actually the place where I ended up accepting the role. So I can say that it's actually pretty true to ⁓ what they were trying to do. But it was essentially ⁓ taking a manual process and figuring out how to make that process digital as part of their digital solution.
Jess Sherlock (52:50)
That sounds right up your...
That sounds like what you'd been doing. Was that very comfortable for you?
Yolanda M. (52:58)
It was, it was actually a pretty comfortable one for me. where I struggled was wanting to make sure, because they wanted you to go through sort of your thought process as well as what you would pitch as the solution, right? And so I talk a lot. I write a lot. So being able to figure out how to shorten it up and get to the point ⁓ was definitely, I think, the hardest part of it.
It was trying to figure out, making sure to clearly articulate what my mental process is when assessing a problem and figuring out a solution. And so being able to write that down in a way that would resonate with, I can apply this to any situation.
Jess Sherlock (53:39)
Yeah.
Exactly.
Yeah, and that's something I tell folks a lot in the SPRINT program is the take-home assignment in the case is really to see how you think. So it's a lot about showing your math. It's not so much about the answer that you get to. And so the better you can do at showing that you have a repeatable way, you know, maybe that's a framework or a process that you like to use, like the double diamond process, for example, of like spending a lot of time in discovery and the problem space before you move on to solution.
Yolanda M. (53:55)
Mm-hmm.
Jess Sherlock (54:16)
But it's also about making sure that you're not like rigid, too rigid about your processes, right? So the more senior of a role you're applying for, the more you wanna show that you can flex and be adaptable to context and, you know, unique trade-off decisions that might surface. yeah, like, do you remember in the process of ⁓ getting, moving forward in these interviews as you and I, like,
Yolanda M. (54:20)
Mm-hmm.
Jess Sherlock (54:43)
I was supporting you, remember, DMs and voice memos and ⁓ what was that like to have a partner in that, knowing that when you got a curve ball, you could be like, Jess, what do I say?
Yolanda M. (54:56)
Oh yeah, it was 100 % needed. know, MVP trophy goes to Jess. Like there were moments where it wasn't just that I needed guidance on, you know, I hadn't interviewed in a long time. I hadn't been through these types of interviews in a long time where I knew nobody right at the company. So it wasn't only that I needed support in like, hey,
what should I do for a take-home assignment, which I had never done before in any job ever. So like what was expected, but also just getting through sort of some of the jitters, right, before an interview. Like, hey, this is a different role for me. This is really on the marketing side. I've never done anything like this before. How do I make sure that they know that I can do this job? So being able to talk that out with a partner and with somebody who
⁓ knew me and knew what my resume said and what I was trying to go for and could really help me connect those dots. Like that's something that I couldn't just call up my bestie and ask. Like she's a teacher. She's great and she'll tell me I'm great, but she wouldn't know how to connect those dots for me.
Jess Sherlock (56:10)
Yeah, absolutely, absolutely. So you got an offer. Tell us about that. Was it good? What was it?
Yolanda M. (56:14)
Mm-hmm
Well, it was good. I ended up in an individual contributor role. I did, yeah. And I think part of my concern with going from a director role to an individual contributor role was, am I going to need to take a pay cut for that to happen? I didn't. I did not need to take a pay cut for that to happen. And I think part of, you know,
the beauty in again being connected to you and your community was to know how I was ⁓ pricing myself, like what I was pricing my value at and how did that compare to peers and other people in the role and being able to understand and know if I was asking for too little at the beginning. And so that was also an area where having you there was super helpful.
So yeah, so I got the offer. The offer was at the dollar amount that we had discussed during the interview process, but I felt like the PTO was a little bit low and I kind of wanted a little bit more in that offer. I didn't really feel like I needed to ask for more money, but I wanted to make sure that I was able to take the time off that I needed. I was especially concerned with going back into a software startup.
would if I would be able to ⁓ take the breaks that I know I would need to be able to stay fully engaged with the development efforts. So that was something that you helped me with in figuring out like.
Jess Sherlock (57:56)
forgot about that. We got you another week or two weeks. That's right. Okay. Which is important to you because wasn't it, you take like a international trip every year, right? Which is one of the things that was going to suck up almost all the vacation they were initially going to give you.
Yolanda M. (57:59)
another week. ⁓
Yeah, I
try to go to like Maui every year and then every other year I try to go on an international trip. So I know right, poor me. ⁓
Jess Sherlock (58:20)
I'm so
jealous. One of my other clients right now is in Portugal, that punk. She was messaging me. was like, ⁓ that's next on my list. on my list. Yeah. I'll never forget when I got the message from you. I got the offer, which then it triggers that milestone call to talk offer and to talk negotiation. the tendency can be...
Yolanda M. (58:27)
Yeah.
I went to Portugal last year in October. It was amazing.
Jess Sherlock (58:44)
you know, I've been looking for so long or I've gotten this far, like I don't want to lose it now. Sometimes folks are scared to negotiate. I think you were even a little bit like, I don't know, it seems like a, like a throw away, like, do I really, maybe, I don't know, I don't want to lose it over a week of vacation. But generally speaking, companies expect that you're going to counter with something and vacation is a relatively easy thing to get unless the company has some sort of policy of like,
Yolanda M. (59:05)
Yeah.
Jess Sherlock (59:13)
everybody gets treated the same, but if the company's willing to be flexible, PTO is a really cheap way for them to come up, because it does have a cash value, but it's pretty insignificant compared to asking for a bonus or a salary increase. So congratulations. And ⁓ one thing we didn't mention, but I think is sort of funny in hindsight is you actually got laid off suddenly and unexpected. I don't remember the details with the business, but
Yolanda M. (59:21)
Mm-hmm.
Yeah.
Jess Sherlock (59:40)
while you're doing your day job, things are going well, you're looking for this new job, kind of out of the blue, a layoff had happened, but it turned out to be perfect timing, I think.
Yolanda M. (59:51)
I mean it was as perfect as timing as a layoff could possibly be. ⁓ You know, had already been engaged with you. had already been, we had gone over the hard parts, right, of really getting myself out there and positioned. I think I had already been interviewing with ⁓ possible companies, feeling like I was getting pretty close to some finals on a couple of those.
And yeah, I was laid off. ⁓ I like to pat myself on the back and say I made it through round four of layoffs. It was just a really hard year for the organization. And ⁓ they were having to have a reduction in force in order to keep doing the good things that they were trying to do. And I was just, it was my time. Yeah.
Jess Sherlock (1:00:38)
Yeah, yeah. What a blessing. A blessing, I
think, in the long run. And it was shortly thereafter. It was within 60 days, like well within your severance, I believe.
Yolanda M. (1:00:48)
Oh no, was,
yeah, it was very quick. I had already had the first couple of interviews with the company that I ended up going with and I was pretty far along and pretty confident that I was finding the right place. So yeah, so I think that I ended up getting an offer and starting all within, I wanna say a month of the actual layoff. Yeah, I think it was a little over a month.
Jess Sherlock (1:01:13)
Wow, I knew it was fast, but wow. Well, congratulations.
So you start this new job. Tell us what this company does first, because it is HealthTech, ⁓ but it's an actual senior product manager role. You're working on the revenue generating product. So what's this company do?
Yolanda M. (1:01:25)
Mm-hmm.
Yes, this company
is ⁓ called Home Thrive. And what we do is we have a product and dedicated social workers who help people who are family caregivers. So these ⁓ companies will offer this as a benefit for their employees. And they can download our app, and they can work with our social workers.
to basically help them help the people in their lives. So it's really cool. ⁓ I enjoy being part of it. It's a younger company. It's a smaller ⁓ engineering team, a smaller product team, but we're small but mighty.
Jess Sherlock (1:02:15)
Yeah. And would we call this a two-sided marketplace?
Yolanda M. (1:02:20)
close, I have happened
to have been working on some of our partnerships. ⁓ But we are very clear that the partners that we're working with are an extension of the services that we provide. So not a marketplace. But it's B2B2C. And from a technology perspective, I am ⁓ helping make sure that we have all the information needed to match people to services that can actually help solve some of the tasks.
Jess Sherlock (1:02:32)
Got it. Got it. So we're B2B2C.
Yolanda M. (1:02:50)
and problems that they have within the caregiving space. So maybe finding additional resources for them or giving them expert advice and being able to match them to those partners and programs.
Jess Sherlock (1:03:02)
Yeah,
yeah. someone who's, golly, I have friends and even my parents, lots of close acquaintances who have been caregivers of parents or family members. And so, yeah, I can appreciate. Those folks need all the help they can get. So it's very cool work. know Mission, ⁓ being sort of a mission-driven company that aligned with your values was really important. So it's not only exciting that you got to get a pay bump, you got to get closer to product, but you also got to work on something that...
Yolanda M. (1:03:18)
Mm-hmm.
Jess Sherlock (1:03:31)
is actually aligned with your personal values, which is great. So tell me about that feeling when you first got the offer.
Obviously you're excited. It's what you had hoped for. But now you also have to do the job. So like, how are you feeling? Like, what was your confidence like knowing that, okay, I got it, but now I have, you know, I impressed them during the interviews, but now I have to actually go do this job. How are you feeling?
Yolanda M. (1:03:47)
Mm-hmm.
Yeah, this is another spot where I came to you and I was like, I know I know how to do this job, but like, what if I don't? What if I somehow forgot how to actually prioritize a backlog or write a user story? ⁓ You know, some of those fundamentals because I just hadn't had a need to make, nobody was watching how it was doing it at mind and even.
a couple companies before that, because I had just gotten so far removed from the general product space that as long as I was meeting the needs, nobody cared how I was doing it. And so I was concerned. I wanted to make sure that I still had the fundamentals down ⁓ and that I could still communicate to other product people in a way that... ⁓
that made sense, right? And still, like we said earlier, how do I talk about all the things that I've done that are product in the right tone, in the right terms, so that I do ⁓ look like I know what I'm talking about?
Jess Sherlock (1:05:17)
Yeah, yeah,
yeah. And so you did decide to sign up for SCALE What made you decide that that was the right thing? What was the thing you were most excited about in signing up for SCALE right at the beginning of that brand new role?
Yolanda M. (1:05:37)
Yeah.
It seemed like a good opportunity, right, to ⁓ make sure that I was doing the things that I should be doing to ensure that I'm successful right away. ⁓ And giving me confidence, right, to know that, like, I do know how to handle these situations. And then also to hold me accountable to the goals that I was setting.
as part of that, because I didn't want to just sort of fall back into old patterns. I wanted to make sure that I was continuing to grow and develop within this role, that I was taking this as an opportunity to really leverage those fundamentals and shine in the role.
Jess Sherlock (1:06:27)
And can you remember moments, because I remember some of our early conversations about team dynamics and things and I know you're still at the job so you whatever you're comfortable with but can you remember a particular challenge that like having me as your like phone a friend during the first 90 days where that really was clutch like can you think of moments where it might have gone sideways?
if you didn't have that phone a friend available.
Yolanda M. (1:06:57)
Yeah.
Yeah, I haven't had to share a sandbox in a while. ⁓
Jess Sherlock (1:07:09)
There's other PMs. What do I do?
Yolanda M. (1:07:10)
You
There's other people with opinions. ⁓ But yeah, we laugh about it. But when you don't have to compromise very much in your role just because you're the only one and there's no one to challenge you, ⁓ you get used to that. So when you take a role that now there's other people, you're the newbie, you're the new kid on the block.
And there's an established product already, so there's history there. And there's team dynamics, right? There's people that are already used to working together. Not only did I have to remember how to play well with others, but I also had to help my team.
play well with others too because I did join a small team. So there were already team dynamics there that they had to let me into. They had to remember to tap me on the shoulder as well. so, ⁓ yeah, so having you in my corner and having my phone a friend really gave me an opportunity to assess that. Like, why was I so upset? And what was...
what was an approach or a solution that I could leverage to help us get back on track and not make it seem like I was upset when it came to actually talking and handling the conflicts. But how could I move past that in a way that ⁓ made me seem like the team player I was truly trying to be?
Jess Sherlock (1:08:55)
Exactly, exactly. There was a lot of managing up that we talked about too, because I think while you have product leadership, there's opportunities, I think, where you actually bring in some really smart practices around prioritization and roadmapping and planning ⁓ that this team clearly can benefit from. But getting that alignment and influencing people who are above you, that's also tricky. And I know you kind of came in.
I worry that you might've come in a little hot, right? Had we not had the opportunity to have some of those conversations first and sort of, okay, let's let the big feelings out, but now let's talk about the right way to actually navigate this.
Yolanda M. (1:09:36)
Yeah, I think there's
a balance, right, to coming into a job and showing your experience and strengths and skills from the beginning, knowing like, hey, I'm here, I know what I'm doing, I can take this job and run with it, ⁓ to also being like, I'm open to learning and open to experiencing or learning from your experiences as well and truly being a team player in that way. ⁓
So I think if I didn't have you, definitely, more from like fear, right? And concern of not wanting to look like I didn't know what I was doing could have come in a little bit too hot because I felt like I had something to prove. So having your support and being able to walk through those situations as they were arising within that first 60 days, 90 days, you know, really made a difference.
Jess Sherlock (1:10:35)
Yeah. Yeah. And you, I know some of our early conversations were a lot around really digging into how your product area was contributing to the larger business goals and also really understanding those business goals that hadn't really been socialized, I think in the early part of you being there, ⁓ which led to you got some FaceTime actually with your team. think I saw you post on LinkedIn. It was very exciting to see you show up in my newsfeed. ⁓
But yeah, you actually, I think it was in your first 90 days or not long after, not only did you kind of have to show up, the ground running, you actually, you were starting to influence some of the conversations about team structure, how we would split ownership between multiple teams. And then you even got the chance to go be onsite. So some of our work together was, it was really around those stakeholder management, stakeholder relationship skills.
⁓ navigating ambiguity, navigating trade-offs. And so how did that in-person time go? How did you feel going into that? It seems like it could be little nerve-wracking as a newbie.
Yolanda M. (1:11:42)
Yeah, definitely.
I think, ⁓ you know, something that you coached me through too is not being too prepared, like not trying to plan a whole presentation that might get skipped because we don't have time. And then I'd feel bad about all the time I spent on it. So I think some of some of like being a perfectionist and wanting to over prepare, ⁓ you know, having you help kind of talk me through that so that I wouldn't push for something that just wasn't right because I
spent time on it. ⁓ Yeah, so like that was helpful. And then I think I also, I had some strong opinions that I think ⁓ I wanted to make sure I started bringing people along that journey with me. ⁓ And I wanted to influence from within the team. I didn't want to come out and say like, well, this is the proper way to do this. And here are my cited resources.
Jess Sherlock (1:12:14)
Yeah, yeah, like, yeah.
I'm right, you're wrong.
Yolanda M. (1:12:42)
⁓
But I wanted it to be applicable and approachable and for people to help see why this is a good solution for them. And so you really helped me to come up with that kind of pitch on how to get people to see that and how to influence from a place, from, you know, without having authority, right?
Jess Sherlock (1:13:05)
And it was funny, think there was one thing where you just, you ended up creating a template or something. Because I was like, if you want to create it for yourself, and I'll tell you what, if other people like it, they're going to ask you for it. And didn't they? There was something where, yeah.
Yolanda M. (1:13:19)
We're still working on that, ⁓
but at least the, I think the biggest win for me was I had been saying that we want to track our outcomes. We want to be outcome driven. We want our roadmap to be outcome driven. So we want to think about what outcomes we're trying to achieve with everything that we're doing. And so I had been saying that quite a bit during the onsite and near the end, I started to hear other people saying that and we still are.
I'm still working on getting our actual outcome-driven roadmap together, but as you can imagine, when you're in flight, it's just a little bit tough sometimes to change how things are going. But even with that not being a full template change yet, I see it more in our PRDs. I'm hearing people talk about outcome-driven results more ⁓ and trying to think through why are we doing this? What are we hoping it achieves?
How are we going to experiment? ⁓ How do we know we won? So those sort of things are coming out more. And I really feel like ⁓ I contributed to that discussion and feel good about the direction we're going in when it comes to that.
Jess Sherlock (1:14:20)
That's amazing. Yeah.
100%. Congratulations. I'm so proud of you. Not only did you get the job, but you had always said to me that whatever job you landed at next, you wanted to make sure that you had that upward mobility, but that you had the opportunity to lead, whether that meant people leadership or not. And so I just love that the company is obviously encouraging you to step up, but they're also reacting really well when you do.
Yolanda M. (1:14:35)
Thank you.
Jess Sherlock (1:14:58)
Like you've clearly built the trust that's allowing you to have this influence. It just shows, right? That's not an accident when you start saying certain things and it catches on, but that's really telling. So congratulations. ⁓ So as we start to wrap up, I am curious. So the job market today, I know you, so you landed the job in December. So.
Yolanda M. (1:14:59)
Yeah.
Yes.
Thank you.
Jess Sherlock (1:15:26)
and now we're in May, but still very recent, what advice would you have for someone who is either about to embark on a job search or maybe they're in the thick of the job search? What advice do you have for them or maybe what advice would you have given yourself if you could go back?
Yolanda M. (1:15:46)
Yeah, I definitely think that having created my LinkedIn early on before I really needed that network of support before the layoff happened was super important and helpful. So building out that community and that network and having people ⁓ that I could ask questions of and that I could ask for support was super important.
⁓ So would definitely say that even if you are just early on in thinking about maybe starting to look for a new job, doing those activities early on is definitely a benefit. ⁓ And, you know, 160 applications is a lot of applications, but keeping with it and making sure to learn from those experiences, so having a moment to assess what went well and what didn't go well with
each ⁓ interview that you have so that we can continue to improve is definitely, I think, important when there are just, you're just applying for so many things. Because if you, at the end of the day, just keep applying for the same thing or don't make those changes to your resume or ⁓ don't adjust in any way, you're not necessarily going to get a different result.
Jess Sherlock (1:17:06)
Yeah, yeah, it was pretty amazing actually while you were sharing about your job search, you had all those numbers. I know you had to look them up, but I talked to a lot of folks who don't really track and I get it. It's annoying and it's like a list of your failures, you know, you could look at it that way. But I think it's also a really helpful source of data because we were able to identify, like you said, you were getting more traction with health tech. Given that.
Yolanda M. (1:17:30)
Mm-hmm.
Jess Sherlock (1:17:31)
you were able to be more strategic and look for those, right? Knowing that you tended to go further. So as annoying as it is to track that data, I would plus one that, that if you are job searching right now, consider tracking that data and just like a good smart PM does on their product, like learn from the data that you have, even if it's limited.
Yolanda M. (1:17:51)
Exactly, yeah. ⁓ And I think the...
⁓ finding a community and support too. Like don't want to undersell your contribution to my success. ⁓ I do really truly think that having a partner, having a coach, somebody who understands what I'm trying to achieve was so helpful because I think that going to just any career coach wouldn't have yielded the same results because they wouldn't have been able to help me get out of my own way when it comes to
really defining what I was looking for in a product role and how to really make that shine. So I think that as much credit as I get, you get equal credit because you truly were a partner in that journey.
Jess Sherlock (1:18:45)
Yeah, aww. It was fun. I love doing it, but I also feel like when you first came to me, were, I don't know, on the outside looking in for whatever, almost like you were like, well, I want to be in there with all the rest of the product managers. But yet when you would show up to group coaching, I was like, you fit right in. And eventually you really took to that. Or you're like, I do.
Yolanda M. (1:19:01)
you
Jess Sherlock (1:19:10)
It was amazing the times you were able to provide some coaching to other folks in the community during hot seat coaching. And I was like, see, she knows her shit. She is so, yeah, I love, I just love the growth that I've seen in you. And, and in fairness, I didn't know a whole lot about the Phoenix and Arizona market. So through you, got to learn as well. I reached out to, I think a dozen people that I knew who had ended up down there and, and was able to determine that it wasn't just you, that the product scene was pretty.
Yolanda M. (1:19:38)
Yeah.
Jess Sherlock (1:19:40)
early on and titles were weird and yeah, there weren't a lot of places to network. I think sometimes you have to seek that out because it's just not going to be naturally there. Here in Denver, we have a lot of resources, ⁓ but yeah, that's not something you had access to. So very important. ⁓
Yolanda M. (1:19:57)
Yeah.
And I will
say one last thing, too, just as advice. Being able to really redo my resume in the way that we did it, ⁓ the job I ended up getting was from applying to a company that I had no connection to. So I did apply. It was a cold apply. I did apply to a lot of jobs where I did have a connection to. ⁓ And I would say out of those 12 phone screenings, actually,
Jess Sherlock (1:20:18)
That's right, it was a cold apply.
Yolanda M. (1:20:29)
Only two of those were somebody that I had been referred to. Only two of the 12. So I just want to call out that being prepared and having a really good resume that does set you apart can make a big difference too. So definitely follow the pattern there for Jess's resume template.
Jess Sherlock (1:20:34)
There you go.
Yeah, yeah. Well, and it's interesting because folks will get really attached to those referrals and referrals can be really helpful. Don't get me wrong, but. They don't always pan out, and so I think it's a it's just like anything. Diversification is important, but I always tell folks get referrals when you can, but also a cold apply. But you know it's it's a different part of your strategy, but as you're showing can absolutely be just as effective. ⁓ It is a numbers game.
Yolanda M. (1:21:12)
Mm-hmm.
Jess Sherlock (1:21:22)
So what about, last thing here, what about advice for folks who are maybe about to start or have just started a new job and just came out of a long, grueling job search? What advice would you have for them or what would you go back and tell yourself if you could go back to day one?
Yolanda M. (1:21:39)
Yeah, setting goals, I think, is really helpful. And then having a way to to hold yourself accountable to those goals so that you are sort of leading yourself in that role versus waiting for your manager to tell you who to go reach out to and how to get started. Being able to say, when you meet with your manager, to say, oh, I would like to speak to my top
stakeholders, who are they? And being able to lead yourself is going to show that you're an independent worker, a self-starter, but also give you confidence in your role, right, during that critical time where you are trying to prove yourself and you are trying to learn about a new company, sometimes new ⁓ responsibilities within your role. So if you can set
goals that you can achieve and look back on, you're just going to feel that much better about actually starting that role.
Jess Sherlock (1:22:40)
Yeah. And if you're lucky enough to have a manager who gives you a 30, 60, 90 day plan, great. It's very uncommon in my experience. You didn't get that, did you? No. It sounds like magic. I mean, it sounds great, but the reality is like product managers, there are very high expectations on product managers, especially senior and above. And so being able to show that initiative, like you said, is huge. And first impressions matter.
Yolanda M. (1:22:46)
you
No.
Jess Sherlock (1:23:09)
So getting to that first win or that first thing that you're shipping, whatever it looks like in your product, that has to be the goal. ⁓ And so in the SCALE program, if it sounds appealing, if it sounds like, okay, gosh, I wouldn't even know where to start with my 30, 60, 90 day plan. I mean, the SCALE program literally sets one out for you and we would meet regularly twice a month to go through the plan. There's a workbook, there's, you we're gonna start by understanding the company.
mission, vision, values, we're going to talk about how your product fits into that. We're going talk about the goals of your product. We're going to talk about how to identify your stakeholders, how to talk to them. Of course, we're going to get out, learn our customers, learn our product, and so on and so forth. if you feel like you'd want a weekly plan, right, because you truly don't know how to start, ⁓ that can be tremendously helpful because you're already so overwhelmed, right? It's like New Kid, the
Computers new every system is new like everything is new. So if you need something to kind of help ground you and focus you that's literally what SCALE is built for so ⁓ Well Yolanda What is next for you? What goal are you working towards? I miss you, but I Know you'll come back, but we took the training wheels off for a bit. So what are you working on? And yeah, what's coming up next?
Yolanda M. (1:24:25)
Yeah.
Yeah, well, right now I've been primarily focused on some of these really great partnerships that we're working on to help make sure that we are providing services for our members who need us. So that's been really, really great. I think what I am most hopeful for is continuing to just have an impact on this product and on this team. I think I'm really set up.
for success in that way. ⁓ I think I've built a good relationship now with my manager and my peers to where there is mutual trust. ⁓ And I think my voice is being heard. So my goal now is just to continue on that momentum, continue to lead when it comes to the way we do things, taking my experiences and all of the good advice that I get from
from you and other people that I follow and watch and listen to, taking all of that advice and being able to actually ⁓ have an impact on how the team works overall, I think is pretty much where I'm trying to lead at the moment.
Jess Sherlock (1:25:45)
Wonderful,
wonderful. I think for you, it's like getting in some good solid reps, right? You no longer have to be distracted by all this stuff like in your previous role where you got to do product a percentage of the time, but you had all these distractions constantly pulling you away. So I'm excited to see you just like stack up a whole bunch of reps, a bunch of accomplishments, right? Like make sure you're tracking these projects, you're tracking the outcomes you're driving.
Yolanda M. (1:25:51)
Mm-hmm.
Jess Sherlock (1:26:12)
This feels like you're in the thick of just building that muscle. And at some point, you're going to be ready for more. But right now, I think you're just in the thick of just let's get some good solid reps in and see the fruit of your labor.
Yolanda M. (1:26:25)
Yeah, feels exactly. It feels good
to achieve. I know it sounds silly when I say it that way because I am an overachiever and so I'm always achieving. But in the sense of like achieving towards what I really valued and what I really wanted to see ⁓ come to fruition, which is be a good product manager, build a good product, right?
So being able to achieve in that simple way has felt really good. And I'm really enjoying just being a product manager, as silly as that sounds. But it feels good.
Jess Sherlock (1:27:06)
I'm excited for you. Well, thank you so much for joining and you know how to reach me. We will talk to you soon.
Yolanda M. (1:27:12)
Yeah, thanks for having me.
