🎧 From Theater School to Solopreneur to Product Analyst: This is Amanda's Story

Episode 14
Written By Jess Sherlock

Meet Amanda - She's a SHINE alum who felt lost in her Product career but found the courage to test out a stint as an entrepreneur, then take an unexpected (but perfect!) role once she got clear on her unique career vision.

She's an absolute star and it was so fun to catch up and hear how her new job has been going. 

We talk about: 

  • How she transitioned into a Mental HealthTech start up (after being a teacher and then selling cowboy boots in rural Colorado 👢🤠)

  • How working in Sales, Retail and e-Commerce was actually a perfect gateway to an Associate Product Manager role

  • What it was really like to navigate a squiggly career path and imposter syndrome

  • The real value of getting clear on her personal career vision

  • Launching her business - real talk

  • The ups and downs of her year as an entrepreneur and how it set her up for success in Product

  • The move back to a stable, salary job in HealthTech

  • How she picked between two very different job opportunities - P and Product Analyst

  • Why prioritizing community was the unlock she didn't know she needed

Ready to SHINE in your Product Management career? ✨

Learn more about my SHINE 1:1 coaching program for Product Managers seeking promotion and greater leadership impact. It's designed to help you grow your confidence, stand out as a strategic thinker, and take the next big step in your career.

READY TO SHINE?



  • Amanda Gaffney (she/her) (00:00)
    something that you said to me that will forever stick with me really early on was what, you don't think you can do that thing because you've never done it before?

    you kind of showed me that circular logic of imposter syndrome

    course you're an imposter. Everybody's an imposter.

    Jess Sherlock (00:13)
    and we all have to go through it a first time.

    Jess Sherlock (00:16)
    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/apply.

    and     book time on my calendar so we can chat.

    Let's get into it.

    Jess Sherlock (01:12)
    All right, hey everybody. We're here today with one of my favorite clients. And I always have to say one of my favorite because I think everyone else might get upset, but secretly, secretly, not so secretly. We've been chit chatting. Before we even got on the podcast, we were chit chatting for a half hour catching up and I had to be like, all right, time out. We need to actually record this podcast. we have, oh no.

    Amanda Gaffney (she/her) (01:23)
    But do you? But...

    Started podcasting before the podcasting began.

    Jess Sherlock (01:41)
    I know. And even before the podcast

    existed, I think some of our coaching sessions could have been podcast episodes, we the opportunity. ⁓ So, as always, and I shared this with you, but a reminder for anybody who's listening is, you know, product careers...

    Amanda Gaffney (she/her) (01:47)
    think that's right.

    you

    Jess Sherlock (01:59)
    are always unique is what I've found. Is like there are no two product managers who have the same exact degree, the same exact career experience, or even the same goals. And that's my favorite part about working with product managers is that pretty much the only thing we share is what? Like our temptation to overachieve and be perfectionism ⁓ and maybe like a dab of willingness to tackle the most gnarly problem.

    Amanda Gaffney (she/her) (02:16)
    Our perfectionism.

    Jess Sherlock (02:27)
    even if it might burn us out or overwhelm us, we're just like up for any challenge. So, yeah, very relevant. So we're gonna talk about your career and what I always think is really interesting is peeling back the layers and really like looking behind the curtain at, you know, more than just what might show up on your LinkedIn. Cause I think if someone goes to your LinkedIn, they take a peek at your titles, they look at what you're doing now, they might be like, okay, makes sense.

    Amanda Gaffney (she/her) (02:30)
    yes, let's go. ⁓ Relevant to the discussion today, I feel.

    Jess Sherlock (02:56)
    That's fine, but I'm excited because I know the background and I know what came before your current role. I know what led you here and I know the why around your career vision and why you made some of these decisions. So I'm really excited for folks to hear your story and I would encourage you, like I have, tell us all the ins and outs because that's what people want to hear.

    Amanda Gaffney (she/her) (03:21)
    I'll be judicious in what I share.

    Jess Sherlock (03:26)
    All

    right, so let's start with an introduction. So I know you very well, but tell us a little bit about yourself and then how you even heard about product or how product even got onto your radar.

    Amanda Gaffney (she/her) (03:37)
    Yeah, right on. I'm Amanda Gaffney. I'm currently a product data analyst at Connect for Health Colorado, which I'm so excited to talk about because it's a fairly new position almost four months ago. So excited. But a little bit about me as a person, I am a mom to

    a seven year old who is the most precocious, smart, funny, delightful human being on the planet. also just a huge nerd. So I play a lot of D &D and other tabletop games, board games, love a puzzle. I'm an outdoorsy person, started learning to snowboard this past year. So got some.

    sick muscles out of doing such a challenging sport. ⁓ And I love, love hiking, ⁓ creative stuff.

    I'm from New York. Remember, we're both from New York. Yeah. But I'm from the downstate zone. But I moved to Colorado in 2012, up in Northwest Colorado just beyond.

    Jess Sherlock (04:24)
    That's right! That's right, I can hear it now.

    Okay.

    Yeah, so let's talk career. And here's my first question for you. So most people when they're kids do not...

    say they want to be a product manager. This is not like, want to be a nurse. I want to be an astronaut. I want to be a product manager. Maybe someday. But yeah, I'm always curious. Can you remember not only when product first even got on your radar, but when was the point

    Amanda Gaffney (she/her) (04:46)
    Right.

    Mm.

    Jess Sherlock (04:58)
    that you knew product was your calling or it was the thing that was most natural to you.

    Amanda Gaffney (she/her) (05:01)
    Yeah.

    Yeah, So I didn't know this job existed until like 2.73 days before I took a job as a product manager, which

    Jess Sherlock (05:15)
    Okay.

    Amanda Gaffney (she/her) (05:16)
    Yeah, it was really interesting because I was leaving another company where I was the ⁓ customer service manager. And so I was looking for other positions in that same vein. I found Sondermind, which is a Colorado based company. It's now nationwide, which is really exciting to have been part of that journey. Super awesome. But they had just gotten series a, they were hiring for a bunch of positions and they had a customer operations manager position. And I had used Sondermind.

    But back before they were Sondermind to find my first therapist, like they were fairly new. And it was literally like, we got an email from someone and they lean over to one of their like handful of therapists, like, do you want to take this client? But even then, even in their, essentially their MVP, was like the easiest experience I ever had finding a therapist. And so was like, I want to work for the, I'm so passionate about mental health. I really was looking for a mission that makes the world a better place. And

    they were hiring for a role that I was qualified for. I went up against who is now one of my dearest friends, but she had a ton of scaling call center experience. She was a hundred percent the right person to hire for that position. But they were like, stick around because like stuff's changing real fast right now and we're hiring for a lot of stuff. We think we could find something for you. And so for the next like few weeks, I was kind of ⁓ passed around to different execs like

    talking about what was their goal for their organization, timeline for certain things. And there was a lot of like, we think you could be good at this. Are you interested in that? It might be about three months before we're talking about it. We don't know if we need it. Like the way series A tends to be like, let's do it. We're doing stuff. And ⁓ I happened to, yeah, I got a call from the VP of product. And he was like, you know, we'd really want to talk to you about being our first.

    Jess Sherlock (07:02)
    Yeah, totally.

    Amanda Gaffney (she/her) (07:12)
    product manager, like, and it would be an associate product manager role. And I was, I was like, yeah, I'm in like, sign me up. I'll sign the contract today, whatever. Also, what is that job? I don't know. I don't know what that is. If you think I'm qualified, sign me up. I had no idea. And so, ⁓ yeah, totally. Yes. All, all of that. I mean, I was saying that during my.

    Jess Sherlock (07:31)
    Yeah, we were just so excited about the company and the mission and probably the people from the sounds of it that.

    Amanda Gaffney (she/her) (07:42)
    interview, felt like really challenged. I felt like I grew from the interview and I'm like, yes, we are growing. We are learning, which I love. And so was talking to you before we started here around how like product management is a very hard thing to describe to people who are not technology startupy type people.

    Jess Sherlock (07:47)
    And you should.

    Amanda Gaffney (she/her) (08:01)
    And so as the VP of product at the time was trying to explain to me what my role was going to be, and why my skills were going to transfer to it and all of that. I, like, I just, I knew nothing. I learned everything every 30 seconds was a new learning experience from that first time. So yeah, super, super awesome. And

    Jess Sherlock (08:20)
    That's amazing. That's amazing.

    Amanda Gaffney (she/her) (08:23)
    I had a really nice turning point where when you're a front lines person and you're doing more of the like, interfacing with see a lot of the problems that are happening, right? What's pissing customers off. What's not functioning well, like where planning or execution is falling apart. Like you see all of that from the backseat.

    And then you end up like shouting into the void, like, why won't anyone listen to me and fix this part of the product? And so to your question about when did I realize it was my calling? was pretty quick where I was like, ⁓ I get to do, I get to do it. I have to make it. Like I take in all of these problems from customers and I actually get to be like time to go fix the software, which is awesome. And also,

    Jess Sherlock (08:49)
    Yeah.

    Amanda Gaffney (she/her) (09:10)
    funny to sit in that other seat where you're the one who's pissing people off because you're not solving all the problems, which was was a fun perspective shift to have. So yeah, I was super excited to solve problems. And then I just got to be like a real nerd for the craft of product, which kind of stuck with me. I just think it's I think it's real fun. And it's never boring. And it's always challenging. There's always learning. And so yeah.

    Jess Sherlock (09:14)
    Yeah.

    Amanda Gaffney (she/her) (09:39)
    Sticking with it, I think.

    Jess Sherlock (09:39)
    Yeah.

    Yeah. Amazing. So we're going to walk through the details because my favorite part of walking through someone's career is we know the point at which you started doing product. But what I want to do now is look at the career overall.

    So zoom out before we zoom back in and talk about when our paths crossed. give us the overview of your career at large. But tell us a bit about the details of those roles and the transitions that might not be immediately obvious if we were to just look at your LinkedIn.

    Amanda Gaffney (she/her) (10:13)
    My insane resume, so I guess it's probably worth going back to college, or maybe to my fourth grade yearbook actually where this was originally captured. when I was a kid, I wanted to be an actress which is so funny because like over time I realized I have massive stage fright.

    which is so funny because I'm like, hopelessly attention seeking, like, please give me all of your attention, but also don't look at me. So I, I went to college and originally started with a psych major, but really quickly switched over to theater arts. And I thought I was going to do more of the acting kind of stuff.

    But I found one stage fright and two, I had more of a knack for set design type stuff and crew technical backstage stuff. And I also got really passionate about educational outreach theater. working with kids and doing programs with them to write and perform plays. And so I found myself like a very much more like backstage-y operational kind of person. Yeah, and so after college, I

    to a lot of theaters, all of that. And then I kind of my wild card, just, shot my shot at Teach for America.

    I had done so much educational theater and engaging kids and all of that, but like, that's the story I told. And I was so fortunate that I got in and I got to go to Louisiana for two years and teach in this remarkable, awesome community, like so great. I miss it all the time, but I found I really loved teaching. And a theme with me is that I was terrible at it at first and then over time, like built the skills.

    another theme of me is being dropped into a job that I have zero minutes of experience with. So yeah, taught first grade, moved to New Jersey, taught second grade for a minute. And then I taught middle school English and social studies. And that's when I moved to Colorado. So it's so funny. People get scared in executive meetings, including me sometimes, but I'm like, I have just spoken to sixth graders. I am not afraid of these people. I've seen worse.

    Jess Sherlock (11:56)
    Wow.

    That's so funny.

    Yeah, they have like fallen asleep, zoned out, ignored you, probably bullied you from the seat. Like, I can't imagine. Who knew? Who knew? Sixth grade English could prepare you for, you know, an exec meeting. That's amazing. So you moved to Colorado, then what?

    Amanda Gaffney (she/her) (12:11)
    you

    Yeah.

    I'm like, I've been through this, kids. I don't need this. Yeah. ⁓

    Yeah, exactly. Yeah.

    Yep.

    Yeah. And so I taught there and then, you know, like so many people, unfortunately, I got super burnt out as a teacher and I had no idea what I was going to do next. But I knew that for my mental health, I needed to take a significant shift. Could have been a break, could have been whatever, but something needed to change. ⁓ I also knew that my husband at the time and I were moving to Denver five months after I stopped teaching. I'm like,

    What do you do for income in five months, especially in rural Colorado? It was up in the, the Northwest corner. so I ended up, ⁓ this, this is probably the weirdest job I've held or the most ⁓ inconsistent with the rest of my story. But I sold cowboy boots at a Western wear store in steamboat Springs. So I wanted the yellow signs. Yes. I know non-Colorado people might not know it, but it's like.

    Jess Sherlock (13:05)
    Yeah.

    Wait, hold on, the one with the yellow signs?

    Amanda Gaffney (she/her) (13:28)
    If you drive from Denver up into Steamboat Springs, up into the mountains, you pass dozens of these bright yellow signs, because this is like, yes.

    Jess Sherlock (13:34)
    does it everywhere. the funny thing is I

    can see the sign. I've done that drive more times than I can count. What is the name of that store?

    Amanda Gaffney (she/her) (13:43)
    FM light and sons Yeah. Yeah. Right. Yeah. Yeah. I will endorse you. I'm just slinging cowboy boots. And again, zero minutes of experience in retail or anything resembling cowboy, cowgirl, horse, nothing.

    Jess Sherlock (13:45)
    That's it. This episode not officially sponsored, but not not officially sponsored. If someone at FM Lite and Sons would like to reach out, you can find my email at jesssherlock.com. So you're selling cowboy boots. I'm not.

    How am I just now hearing about this?

    That might be the most Colorado answer I've ever gotten from someone.

    Amanda Gaffney (she/her) (14:13)
    I don't...

    what I

    really liked and then I just went and sold western wear. Yeah, it felt like such a left turn. And I also felt really lucky because that's like such a special thing to get to do. And yeah, right. Yeah. I really, really loved retail. I don't know if people say that, if that's words people say, but like, I got to make people happy.

    Jess Sherlock (14:27)
    Yeah, a cult following there, that place.

    Amanda Gaffney (she/her) (14:40)
    all day and that felt really nice to me and it's not that there weren't like I mean retail is not all rainbows but like yeah.

    Jess Sherlock (14:41)
    Yeah!

    That's so interesting.

    Yeah, well looking back, can you pinpoint skills that were definitely transferable during that time to what you're doing now?

    Amanda Gaffney (she/her) (14:57)
    from to

    what I'm doing now. ⁓ Yeah, it's funny going back to the VP of product trying to explain to me what this job was. The thing I was bringing to the table was deep knowledge of my users and customers, because if you're going to sell to somebody, you need to get to know them, you need to get to know their problems and their circumstances and the context of what brought them into that store in the first place. And then,

    Jess Sherlock (15:21)
    Absolutely. ⁓

    Amanda Gaffney (she/her) (15:21)
    proposed solutions to them and test the waters

    to see what's feeling good to them before I just launch into a speech about some $600 cowboy boots. Like you have to really understand. Yeah, that was not even the most, there's some fancy stuff up in there, okay? Yeah. You could.

    Jess Sherlock (15:32)
    $600? I guess I've never bought...

    Well, now I just learned something new today. ⁓

    I'm also hearing tailoring your message, because I'm sure you also probably had to communicate why a boot or two boots cost that much to someone who may not understand what it is that they're purchasing. I would certainly be asking why they cost so much. ⁓ Interesting.

    Amanda Gaffney (she/her) (15:46)
    Yeah.

    Totally. Yes. Yes.

    Totally. Yep. Yep.

    Jess Sherlock (16:02)
    So you're swinging cowboy boots. You're trying to figure out.

    Amanda Gaffney (she/her) (16:04)
    Hahaha

    Jess Sherlock (16:06)
    what's next, you're in a new state. So tell us what happens then.

    Amanda Gaffney (she/her) (16:11)
    moved to Denver and this question comes up again, right? Cause this was only supposed to be this like short stint. And then I was going to figure out what big girl job I was going to get when I got to the big city. And, ⁓ I was just like, honestly, like, I think I want to continue with retail and see where this leads. it is tough to go from

    teaching where I have high degree of stability and such a salary or whatever. So making a choice to go to retail, which a bit less stable and the pay is not as high was like, I was really choosing something because it made me happy or I enjoyed it versus these other things that are also important, but just kind of fell by the wayside for me. And so I ended up working at it's funny, like I consider this like my first startup. It was a little.

    baby boutique Honey Bee Baby Boutique in Aurora, Colorado. But it was great. I got to help this couple open this store.

    And I was also there on the day that it closed. Like they really tried, they did something really, really special on that time. It was amazing to be part of it. then ultimately it just wasn't, it wasn't the journey. was not to continue. that was, it was such a cool experience. Like I was like, I'm going to do operations and projections so that I can, you know, talk about inventory. I'm going to research brands. I'm going to also, I'm going to do merchandising. Like I just got, I'm going to.

    Jess Sherlock (17:28)
    one.

    Amanda Gaffney (she/her) (17:32)
    design our Shopify site and put all the content on there. Like it was just, this is the beauty of an early, early, early startup. If that's the word for it, it's like you just get to do all the stuff and yeah. Yeah. Yeah.

    Jess Sherlock (17:41)
    Yeah, 100%. I would absolutely consider that a startup, right? And ⁓

    so that was a couple years.

    Amanda Gaffney (she/her) (17:49)
    Yes, before I started in tech world. ⁓ So I joined one of our vendors in the store. They knew that I was really passionate about their products, we'll say. they knew that I was over here slinging these baby carriers. It was a baby carrier company called Lillababy. And so when they heard that I had lost my other job and also I had found out two days before the store closed that I was pregnant.

    Jess Sherlock (18:02)
    Mm-hmm.

    Amanda Gaffney (she/her) (18:13)
    So it was like, I'm pregnant. I'm out of a job. It was just a moment in my life. know, I had had such a good relationship with this vendor. kind of honestly knew that that was a step I was trying to take in life. And so the store closed and it was like, Amanda loves this product. She's real newly pregnant. let's get her in here and find a spot for her. And so I got to join their customer service team. And again,

    lots of different opportunities here. I got to optimize our Zendesk instance and our help content. I got to organize and attend work events, like different trade shows and

    so I got to wear a lot of hats there too, which was really fun. did that for two years, worked for 13 straight months with a baby on my hip the whole time. Like childcare is really expensive. So I was typing with one hand and, you know, feeding a kid with the other. Again, choices that I make in life are very interesting, but yeah, I got to do that.

    Jess Sherlock (19:09)
    Wow.

    think that says

    a lot about the culture of the company.

    Amanda Gaffney (she/her) (19:20)
    Yes.

    Yes.

    Jess Sherlock (19:22)
    And if I remember correctly, when we started talking about your career experience, this was a period of time that you, kind of overlooked or maybe minimized a bit in your memory as it pertained to the direct applicability to what you were doing in product. And I can't remember the specific projects, but something around, I mean,

    Amanda Gaffney (she/her) (19:32)
    Hmm.

    Yeah.

    Jess Sherlock (19:43)
    not only were you working on their Zendesk integration e-commerce related details, was there an ERP initiative as well? Like, so there was.

    Amanda Gaffney (she/her) (19:50)
    Yes, my god, yes, how could I

    forget the most probably relevant thing that I did there to actual product? Yes, yeah, we... ⁓

    Jess Sherlock (19:55)
    Yeah, like there were, yeah, for being retail, you

    were involved in like, even as you're talking about it now, I'm like, there was a lot more that you were responsible for in this role beyond just, hey, buy this baby a carrier.

    Amanda Gaffney (she/her) (20:05)
    Yeah. Yeah.

    Nope. That was it. No, you're totally right. I think that was, it's so funny. Cause now I look back at the people I worked with and I'm like, they were, that's who I was going to be someday. Like the people gathering the requirements and helping figure out the solution and all of that. So yeah, we migrated, from QuickBooks to NetSuite and we were like automating all this stuff. We had just set up with a new warehouse.

    I was also our logistics shipping human for, for direct to consumer. Yeah. And so it was I was in all of these different like customer experience, the operations kind of stuff. And it was like, we were converting over to NetSuite in this new warehouse. And so I acted as like the functional SME for.

    Jess Sherlock (20:35)
    No.

    Amanda Gaffney (she/her) (20:54)
    the flow of orders. And so I wasn't collecting the requirements, but I was very much in the room, participating in providing requirements, seeing how they're collected, that was something that was a really cool experience and kind of early product for me.

    Jess Sherlock (21:08)
    Yeah, yeah.

    And what I find really interesting is like, you're not the first person whose early exposure happened even before you were aware of product. So this is the job you had before you officially had your product role. And what I constantly see with folks who are either trying to, officially get into product or folks who have been essentially doing product and have never had the title is when you really dig into the past experiences.

    Amanda Gaffney (she/her) (21:17)
    Yeah.

    Jess Sherlock (21:35)
    I mean, I do this often enough that they jump out and they feel really loud to me, right? But even just the work you've talked about so far, I can rattle off 25 skills that are transferable to product, right? There's stakeholder management, there's customer discovery, there's probably some amount of usability testing where when you're at that conference and you're fitting someone, if you realize, ooh, this is a use case we hadn't considered, right? And all of a sudden you're providing that feedback back to the product team.

    Amanda Gaffney (she/her) (21:46)
    Totally.

    Yes.

    Totally, yes.

    Jess Sherlock (22:04)
    You know,

    and the list, I think just goes on and on. And this is double edged sword, I think for product where there's this desire, I think for people to want to be a PM and you want to like check the box of I am a PM when, as we'll talk about product roles, take the shape of the people on the team and the stage of the company and the goals that they have at any given time. And so.

    Amanda Gaffney (she/her) (22:19)
    Totally.

    Yes!

    Jess Sherlock (22:30)
    the finish line kind of like is always moving. Like there is no point where you like, ta-da, you're now a product manager once and for all. It's like even the product manager was really successful last year. Right now, there's vibe coding during interviews and there's new expectations around understanding AI agents and other things. And so that's an exciting thing, but I think it can also create this lack of clarity.

    Amanda Gaffney (she/her) (22:42)
    Yeah.

    Totally.

    Mm.

    Jess Sherlock (22:55)
    around like, does it actually mean to be a PM? What skills are actually important? And so one of the things I love to help people with is be like, hey, you realize you were doing bits and pieces of this two, three, four jobs ago, right? And now you can actually like, that's a helpful story. That's a skill you can bring to bear. So there's a lot of that that you really had, I think. And you were just, in your mind, you're just the manager or customer success, but really, you know, you're like

    Amanda Gaffney (she/her) (23:06)
    Right.

    Mm-hmm. Yes. Totally.

    Right.

    Jess Sherlock (23:23)
    a chipmunk packing your cheeks with all these skills that you're gonna need later.

    Amanda Gaffney (she/her) (23:26)
    That's it.

    I'll just bury in my acorns, I'll find them later.

    Jess Sherlock (23:33)
    Yeah,

    So at this point, this is the transition you gave us a little glimpse of where you had been doing this customer success role, but then you get asked to do this associate product manager role. And I'm curious now as someone who has experience in the field, has met other PMs, is it clearer to you now what that VP saw in you?

    Amanda Gaffney (she/her) (23:33)
    you

    Mm-hmm.

    Mm-hmm.

    Yeah. Yes. the ability, this goes back to like the ability to deeply understand and suss out customer needs and then figure out how to meet those needs, is spot on. And that was the part that he emphasized over and over again. And I'm like, so what, you just need to like know your customers. Is that it? I'm a PM. I did it. We did it.

    And like that is the core of it, right? So I understand why that seemed, why that struck him as transferable now. And then to your point, I had a smattering of these like other things that I had done that proved out that I could apply those, skills in a very specific way. So yes, I get it now,

    Jess Sherlock (24:35)
    at this point, you've now officially made the jump into tech. This VC-backed, mental health tech startup, and I know you went through a couple different official roles, and then at some point, we got connected. So

    Amanda Gaffney (she/her) (24:40)
    Mm-hmm.

    Mm-hmm.

    Jess Sherlock (24:52)
    led you to seek out coaching?

    Amanda Gaffney (she/her) (24:54)
    So I, I don't know if I said this earlier, but not only was this a product manager role, it was the first product manager role at Sondermind. So we had a VP and then we had this new person coming in and, that was such a wild and cool experience because if you are the one person, you have to learn everything. You have to learn all the stakeholders, all the different

    user groups, internal, external, all of that. I had to learn a lot of the tech. Like I was, I was really lucky that I had a really good understanding of what was under the hood of what we were doing. I think I've told you before, like someone needed to sit down and explain to me what a database was. like I had a vague sense, it's just so funny to think of what I didn't know.

    Jess Sherlock (25:35)
    you

    Amanda Gaffney (she/her) (25:39)
    and what I had to learn so quickly.

    So at that time, the very problems I was focused on were focused on our intake funnel. like, how do we bring in clients, take in their information, which is so funny because I think Yolanda on one of your last episodes was saying she did the same thing, which I love.

    Jess Sherlock (25:55)
    Yep. ⁓

    Amanda Gaffney (she/her) (25:57)
    but it was like,

    how do we collect the information? How do we match it up to what we know about our clinicians? How do we get them into a first session as quickly as possible with the right person? which was a very, very intense position to be in for like a baby PM. Like when I look back at what was under my purview with seven months of experience under my belt, I just want to hug that girl like that.

    Jess Sherlock (26:14)
    Yeah.

    Yeah.

    Amanda Gaffney (she/her) (26:24)
    was really tough. ⁓

    Jess Sherlock (26:24)
    Yeah, yeah. it's something

    that, something I've said, it's a bit controversial, but I'll say it again. even the most junior product role, if you were to compare that to other roles in an organization, it's relatively more senior, right? Than the most junior analyst or the most junior customer success person or customer service person, like product holding so much of the decisions around

    Amanda Gaffney (she/her) (26:40)
    Sure.

    Jess Sherlock (26:51)
    prioritization or resourcing or other things that have a direct cost to the business if it works or doesn't. Yeah. And so I couldn't agree with you more. And this is why I think it's, a controversial statement, but I'm like, I don't believe that product management is a entry level role period. However, right. Associate product is an entry level role for product. It's a really tricky place. Like if, if you,

    Amanda Gaffney (she/her) (26:56)
    Direct cost, right? Yes, yes.

    Mmm. I had not thought of that.

    Mm-hmm. Mm-hmm. Right.

    Jess Sherlock (27:20)
    can imagine if you can think back to like going from strictly being a teacher and you didn't have that period of time where you had gotten experience with retail and then the experience at the role where you were doing retail and some operations and some migrations, those were the building blocks that gave you this sense of what does it take to execute on technology solutions? So that when you showed up here, that part you kind of already had under your belt.

    Amanda Gaffney (she/her) (27:25)
    Mm-hmm.

    Totally.

    Totally.

    Jess Sherlock (27:47)
    So then you could say, okay, someone needs to actually look at this process and propose a solution. That's a different level of thinking. Yeah, your other roles they weren't PM roles by definition, but they were absolutely the building blocks that set you up for success in this first PM role. Would you agree?

    Amanda Gaffney (she/her) (27:47)
    Mm-hmm.

    You're right.

    Totally.

    Totally,

    100%, yeah,

    Jess Sherlock (28:09)
    So during this time at Sondermind, what did that four and a half years look like from I don't know what an associate PM is to the company is obviously growing, getting more investment.

    Amanda Gaffney (she/her) (28:13)
    Mm-hmm.

    Yeah.

    Jess Sherlock (28:22)
    So how was your role in your day to day, maybe even your title, how was all of that affected as the company was growing?

    Amanda Gaffney (she/her) (28:29)
    Yeah. So I look back as an associate PM and I really was more of a product owner now that I understand the distinction between those things. So was very execution based, which I actually loved. think sometimes people can talk about those two things in like a value sort of way. I think they're both really important roles and suited to different kinds of mindsets. And so I actually think being a product owner was a great start for me, because I got to do some more of these sort of like the nitty gritty of it.

    Jess Sherlock (28:44)
    No.

    Amanda Gaffney (she/her) (28:56)
    so yeah, did that. And then like I said, kind of got slotted into this intake role. And that was the first time that I felt like I had to come to the table with a strategy. I needed to be able to articulate competition. I needed to be able to like hop into our Looker instance and pull out some data and ask some questions about that data.

    I was responsible for the scoping of things. Like before that, I really felt like I was like receiving the strategy and receiving the scope even. And then I'd go and write the tickets and huck them over to the engineers. So yeah, that, the onus on me during that time was, was way, way, way more intense. but it was great. I, I really, I loved working with my engineers.

    Jess Sherlock (29:30)
    Yeah, yeah, yeah.

    Amanda Gaffney (she/her) (29:44)
    I loved the problem set, even though it was a hard one to deal with. So my time in that role came to an end. we were looking for someone to be honest, more experienced in conversion funnels, someone more experienced than me in that way. And at the same time, we were standing up our platform and architecture team for the first time, breaking our monolithic architecture into microservices.

    so let's, again, let's retrace the steps a year and a half before that. like, what's a database? And then it is my job to help segment an architectural breakout roadmap and talk to our highly technical engineers and try to argue with them. I love them. Arguing, arguing is not a dirty word. Debate what the right scope is for each phase of this project.

    Jess Sherlock (30:20)
    debate. ⁓

    Wah.

    Amanda Gaffney (she/her) (30:27)
    ⁓ Another example of where I'm just fully out of my depth and just doing it. Had I ever heard the word microservice Nope, we were just doing

    Jess Sherlock (30:31)
    Mwah.

    Yeah.

    what was it like as the face of the product team to an extent? Because I imagine you also had to explain or bring along these non-technical stakeholders in the company who can't understand why you're just not building new features, right? Why are we doing this thing that's somewhat invisible? Was that a part of the job at that point too?

    Amanda Gaffney (she/her) (30:56)
    Yeah, and it was really it was slow going. this was like, I have so many moments where I look back on things I did and I wanna rewrite it. I could have made that case so stronger. I could have held the line better.

    You know, but the storytelling was, was really difficult, especially when you're looking at a business that's really gung-ho on a metric that is not related to the speed with which developers can deploy. They don't care. don't care. They're like, does it work? Is it coming soon? I hope there are no bugs. so yeah, I think a lot of times I did, I lost ground on prioritizing some of those, tech initiatives.

    Jess Sherlock (31:26)
    Yeah, I don't care.

    Yes.

    Amanda Gaffney (she/her) (31:39)
    And we would allocate some of our people toward these other projects. And so it was really slow, very messy, would have made a lot of different decisions. I now I understand so much more when I move into different, these different roles of like, ⁓ they're going through a microservices transition. I know how messed up that.

    can make things I get why that's challenging or why that took longer than, it's supposed to. And so, yeah, it was a really cool exposure to what engineers think about.

    Jess Sherlock (32:06)
    Yeah. I often get asked or you'll see on LinkedIn like debates and discussions around how many years of experience should someone have if they're an associate versus a PM versus a senior PM. And, and what I always seem to come back to is that that's not the right question to be asking. The question should be around what sorts of reps

    Amanda Gaffney (she/her) (32:23)
    I

    Jess Sherlock (32:27)
    has this person had. It's sort of like, you know, someone who is strength training, right? If you're going once a week versus three times a week, there's an immediate difference there. Even if you've both been going to the gym for a year, right? The number of times per week affects it. The other exercises you're doing affects it. The different styles of exercising you've been doing affects it. And so in product, when I think about quality of reps, I'm thinking about things like,

    Amanda Gaffney (she/her) (32:39)
    Yeah.

    Jess Sherlock (32:56)
    Is your work focused in on the needs of the business and good solid customer data? Did you measure the success of the things you built? Right. But then I'm also thinking about what parts of the process did you get exposure to? Because if all of your reps are on a product that's in maintenance mode, those are very different reps than a zero to one launch or, you know, that first go to market push of something brand new or even.

    Amanda Gaffney (she/her) (33:15)
    Totally.

    Totally.

    Jess Sherlock (33:23)
    iterations leading towards product market fit that continues to elude you. Or sunsetting a product, right? Like these are just, they're all different. And so it's interesting to hear you basically like you've been through a certain situation. Now you have the ability to identify that pattern. First of all, you now have this experience in your back pocket that you can pull from where, you know, baby PM Amanda would not have been able to anticipate what was to come because that was her first time through it.

    Amanda Gaffney (she/her) (33:38)
    Totally.

    Jess Sherlock (33:51)
    Even just the second time through a similar thing, you would have made better and different decisions because you knew more about what was coming. So this is the thing that I think is maybe the takeaway for this, for anyone who's listening and thinking about what your next job should be or could be is what are the reps you have had so far? And do you need more of the same or do you need diversity?

    Amanda Gaffney (she/her) (33:57)
    totally.

    Mm-hmm.

    Jess Sherlock (34:21)
    And you can't make that decision unless you know what's to come for you. Right? Because if you want to specialize or if you'd only wanted to be in mental health tech, then one could argue that staying in that world and getting more more reps and maybe going to another mental health tech company, like that would make a lot of sense for you. But this is a good segue, I think, during this period of growth and the company's growing. I know that was a big period of time for mental health tech in general.

    Amanda Gaffney (she/her) (34:26)
    Yeah, totally.

    Mm-hmm.

    Jess Sherlock (34:48)
    It's like the post-COVID timeframe. So there's lots of What led you to say, I think I need a coach, because this is when our paths cross. Tell us about that.

    Amanda Gaffney (she/her) (34:59)
    Yeah, yeah, yeah.

    So I had, there was sort of one more step in that journey before I came to you. And this is where I moved into this more product operations role. ⁓ Yes, my official title was Program Manager with a subtitle that was like ⁓ Product Process Manager. And it was under the umbrella of Product Operations. I now know it was straight up Product Operations is what I was trying to do.

    Jess Sherlock (35:09)
    That's right!

    Amanda Gaffney (she/her) (35:24)
    at that point I'd been there for about three years. And so I had kind of watched how like business and product had grown up together and grown away from each other and the different dynamics and that.

    Jess Sherlock (35:34)
    and

    Amanda Gaffney (she/her) (35:36)
    As we're talking about, how do we solve that? I'm, I'm looking at it with this like three years long back to series a, I was, I was here on day one of the product team kind And I was like, I think I see why this isn't working. I think I see how we can start fixing this problem. And so I just wrote up a job description for myself and was like,

    to anyone who will listen, I do this job? And this is where I got the title of program manager. That's what we were going to hire for. There was no additional conversation needed, right? It was like, she can do this job. She'll be on the product team. There are programs that need managing for sure. And she can kind of have this wider scope of responsibility as well. So yeah, that was, that was my journey there.

    Jess Sherlock (35:59)
    Alright.

    Yeah.

    at this point, our paths cross. something, yeah, something led you to think I should get a tell us a little bit about like what led you to think you need a coach or how did it happen that you stumbled upon me?

    Amanda Gaffney (she/her) (36:25)
    Yes, yes, yes. Now we are there.

    Jess Sherlock (36:38)
    And what was going on in your world that led you to think that?

    Amanda Gaffney (she/her) (36:41)
    Yeah. So I think,

    my role ended up shifting over time into something that was not as fulfilling for me. I wasn't doing as much of that like big strategy, big operations stuff that I enjoy. It wasn't as much enablement work. It kind of ended up being more like, you know, Scrum Mastery project based kind of stuff, which I'm not terribly good at. So I was feeling kind of unfulfilled and I saw that maybe like my time.

    at Sondermind might be done, which was a really hard thing to work through after having been there through so much.

    Jess Sherlock (37:09)
    Yeah.

    Amanda Gaffney (she/her) (37:12)
    and so I had this, this thought and, and you're talking about, ⁓ Ryan, who he was actually my coworker at Sondermind at the time and the one who took over intake from me when I migrated away from it. So yeah. ⁓ which he's just, he's such a delightful human and just.

    Jess Sherlock (37:19)
    That's right.

    Amanda Gaffney (she/her) (37:29)
    very talented and wonderful PM. And so I went to him being like, hello, important person in my product career, who I, it was opinion I trust. Like, I think I don't suck at products, but I don't know what to do now. What do I do? Um, and he was like, if you're really thinking about getting back into it. Well, and he knew that I had all these like confidence issues and I believed myself to have all of these skill gaps. And so he's like, if you really believe that, and you're really interested in going back into product.

    Why don't you talk to a coach? And by the way, my former coworker is a coach and I really like her and maybe you could go talk to her and see what she's doing. ⁓ and I think it took me a bit to invest in myself that way. Cause I was so low confidence at the time. It was like, what am going to do? Go pay for a coach to like tell me, no, you're not cut out for product,

    Jess Sherlock (38:04)
    Yeah.

    All right, so it's August, 2023. I get the intake form from you. You schedule an intro call with me, which is great. So I'd love to share what's in here, may I?

    Amanda Gaffney (she/her) (38:28)
    No. No, next question. Thanks. Yeah, actually, I would love to hear from that lady. I don't know what she was saying back then.

    Jess Sherlock (38:29)
    you

    Bye.

    Yeah, so you had two major things in mind, at least that you put in the form for us to talk about in that initial call. So you said, first of all, you wanted to dig into your strengths and your gaps, which aligns with exactly what you're saying. You had hit this point where you knew you were doing some things well, maybe not other things. And when you're in a startup environment like that, where there's no career ladder, I'm imagining that you weren't having career development conversations.

    Amanda Gaffney (she/her) (39:08)
    haha

    Jess Sherlock (39:09)
    Trying to make the best of the runway we've got.

    Amanda Gaffney (she/her) (39:12)
    I'm just finding like literally I'm like where's my next landing zone? Where's the next thing I can parachute into and just figure out while I'm there?

    Jess Sherlock (39:16)
    Yeah, yeah, it was very much

    like startup survival mode, right? So yeah, I imagine at that point you're going, I could use ⁓ just a bit of a read on where I'm at, which makes sense. And you mentioned, it seems like this was top of mind, because you mentioned your next career move and you just said you'd like to think through what it would look like, what might be a good fit, what might be fulfilling, and how you'd go about finding something like that. But then here's what's interesting is you literally said,

    Amanda Gaffney (she/her) (39:22)
    Yeah.

    Yeah.

    Jess Sherlock (39:45)
    I'm even trying to figure out whether return to product work is really what I want, which is quintessentially probably like what I hear so often from people is there's the signal, the common signal is either burnout where it's just like, I don't know, it's just drudgery or it's, am I any good at this? Do I even want to do this? I hear it so often, you called out specifically that your resume felt

    difficult because your career story had been winding and you knew you had the confidence issues and a little bit of imposter syndrome But at the time too, correct me if I'm wrong, your network was really limited. as far as, I guess I'm curious before we talk about what the coaching experience was like, what else had you tried? Was there anything else that you had tried prior to seeking out coaching?

    Amanda Gaffney (she/her) (40:38)
    Ooh, that's a really good question. Is crying into a bottle of wine an appropriate answer? So I, let's see, what did I try? I think.

    Honestly, I, you're totally right. I didn't have a huge network at the time outside of Sondermind. I do this sometimes when I'm in a job, I get like real tunnel vision about that community. And then people who I've worked closely with will move on to another company. And it's like, they might as well have winked out of existence until I think of them. I'm like, I love that lady. I should call her. I think so, yeah.

    Jess Sherlock (41:06)
    Yeah, that's not just you. I think that happens to a lot of people. like,

    yeah, so I don't think that's uncommon at all because why would you create a network when you're so busy? Your challenges are right in front of you. It doesn't feel like the time to go outside of that.

    Amanda Gaffney (she/her) (41:19)
    Right, right, exactly. Yeah.

    Yes, which is kind of the tough part, right? Because like I would go around to people I considered mentors inside of Sondermind, but these people had like years of watching my journey and years of investment in me as a person, like coworker relationship, friendship kind of stuff. They also knew the inner workings of Sondermind. so there is a benefit to that because they could help me sort of calibrate my position within the company.

    But what I didn't have and where I think it was helpful to go to a coach was I needed someone who did not have all of that context on me, did not have all of the context on the company. And so I, that's where I was like, where do I go? Do I take a course?

    Jess Sherlock (42:14)
    Yeah.

    Amanda Gaffney (she/her) (42:15)
    Do I just go and apply for a bunch of jobs and see who bites? But yeah, so I needed, I needed that third party and Ryan is someone whose opinion I trusted.

    particularly on the subject of talented people who I would like to meet. And so it was, you know, a bit of a, a bit of a no brainer to start with you. If I was going to go outside, start with something of a known quantity and you did not disappoint.

    Jess Sherlock (42:31)
    No.

    Yeah.

    Well, so let's talk about what that is because you and I have worked together for long enough, that we've seen how things have changed, how you have changed. And we were talking a little bit before the podcast about the role that you're in now and how in hindsight everything makes sense. But when you were in it and you're going, I've had these various roles, I know I can do things, but is this telling a cohesive story?

    Amanda Gaffney (she/her) (42:59)
    Yeah.

    Jess Sherlock (43:09)
    How do I do this? Where do I want to go? There were more questions than answers. So guess when you think back on our time together, are the specific things that either changed in your life or in your relationship to work that you would contribute directly to the coaching work that we did?

    Amanda Gaffney (she/her) (43:09)
    Right.

    my gosh. Yeah. So many things.

    You know, we haven't talked about what I did right after Sondermind, but I think something that you said to me that will forever stick with me really early on was what, you don't think you can do that thing because you've never done it before? do you remember saying this to me? It was like, yeah, you were like, hold on. Are you saying, what was it? You're like everyone who's ever.

    Jess Sherlock (43:46)
    That sounds like something I would say.

    Amanda Gaffney (she/her) (43:54)
    you know, founded a company can only be good at it if they founded a company before, or they can only do it if they've founded a company before. And that you kind of showed me that circular logic of imposter syndrome almost of like,

    Of course you're an imposter. Everybody's an imposter. We're all just like showing up to life. We're doing our best.

    Jess Sherlock (44:08)
    We all know.

    and we all have to go through it a first time.

    Yeah.

    Amanda Gaffney (she/her) (44:15)
    Totally, yeah.

    And to look, you helped me to look back over the past like you're doing now of think of all the things you didn't know back then and that you wouldn't have known if you hadn't just like stepped into a thing you've never done before. And that why not do it just because you haven't done it before has really stayed with me since you've talked about it. Because then it's like, it encourages confidence and bravery that I feel like I didn't have before.

    And I could show up with you and like, try some shit out and no, I was going to be bad and know, more open to feedback than I might've been in the past because of like pride issues or embarrassment, which I guess is like two sides of the same coin. So yeah, you helped with confidence, humility and bravery, just in like kind of that single, that single idea of trying stuff you don't know how to do.

    Jess Sherlock (44:54)
    I'm sorry.

    Yeah, leaving us all hanging, like a next step here.

    start working together. The very first thing we do and I do with every client in the SHINE program is we start talking about career vision because only you know what you want out of your career. What success really looks like out of your career. And we had some discoveries as we were doing that. And I have this vivid memory of getting a message from you that that it

    Amanda Gaffney (she/her) (45:34)
    you

    Jess Sherlock (45:35)
    It made sense, but it definitely happened very quickly. So tell us a little bit about what happened for you in that first month of working together.

    Amanda Gaffney (she/her) (45:44)
    Yeah.

    Yeah. I think that we had been working together for a month and then you sent me to Denver startup week with some homework. And I came out on the other side with something, something very unexpected. So I,

    woke up one day and the degree of sort of like dissatisfaction or the difficulty I was having like dragging myself to my laptop for that day, like officially was overwhelming. I had been kind of job searching, nothing was really sticking out to me. I had been noodling over the idea of entrepreneurship. And then this morning hit and I was like,

    It's time, I'm putting in my 60 days notice today and I'm going to start my own product strategy and operations consulting business. I don't know how to do that. but I've never known what I'm doing in this life. So I'm sure I'll figure it out. Yeah.

    Jess Sherlock (46:41)
    I think I was

    the first person you told. And I remember I got the message and you were like, by the way, I quit my job. We should probably talk about that today. And I was like, all right.

    Amanda Gaffney (she/her) (46:44)
    I think that's it.

    I think we literally

    had a session in like an hour and a half and I'm like, whatever you had planned, irrelevant now, because here's the new thing that we're talking I think you said something like, then we're going to do something a little different today. Yep.

    Jess Sherlock (47:01)
    Yeah. Yeah. But today's session, we should probably talk about that. So

    that's exciting. And as someone who considers herself quite entrepreneurial, me, I don't want it to be misconstrued. I hope, right? Like, guess, share with folks do you feel that that was something I had put in your head? like, guess, where did, this seems sudden, right? So like, how would you explain like kind of where this came from and how this came to be to someone who might think,

    Amanda Gaffney (she/her) (47:11)
    Mm-hmm, you are.

    good question. Right.

    Yeah.

    Jess Sherlock (47:31)
    you know, this was somehow prescribed upon you.

    Amanda Gaffney (she/her) (47:34)
    Yeah, I had a few mentors at Sondermind who

    I suppose things in me that I had a lot of trouble seeing in myself. So this was even as at my last PM role. I was actually a data science PM again. am I doing? You know, of why I joined that team was because it was an acquired team and that was our first acquisition and it was sort of like How do we integrate culture and tech and all of this? So I help

    integrate them further and launch our first instance of machine learning into the core product that we had, which was really exciting. So in that role, that was some of the best like mentorship and support that I had from like everyone around me. Like I was around such senior leaders and product people. And I was just getting constant feedback and learning. So in that time, some of those folks were asking me like,

    what do you want to do in life? Like those were probably the first times that folks were asking me about the career. And I had this itch in the back of my head that at some point I would like to do a thing like capital D, capital A, capital T, like do something. And I wanted to be the person like responsible for setting a vision. I wanted to be the person responsible for like

    Jess Sherlock (48:42)
    huh.

    Amanda Gaffney (she/her) (48:52)
    hiring people and growing a team and supporting those people and their growth and like I wanted to build something that You know, I could truly be responsible for So I had this this in the back of my head for a while, know I started my own babysitting business when I was in second grade like no big deal ⁓ but I so it's like always there, you know what I mean,

    And when you and I started having these envisioning conversations, think that was one of the first things I said or in my letter to self was that exact thing. And then you made the mistake of telling me that I could just do anything and that's not your exact words.

    Jess Sherlock (49:31)
    Exactly. But I did say you're,

    you are the only person who can stop you from doing a thing you want to do.

    Amanda Gaffney (she/her) (49:42)
    Yep. Yes.

    And so you're like, you if you want to test these waters, or if you want to go figure something out, go to Denver startup week and talk to a presenter after every session that you go to. And I also got the wild idea to just go to like the founders happy hour. just like walked my ass in there. Like, what am I, am I lost? Like what is happening? But

    I just got so inspired by some of the things that I saw there around people's journeys and how they just stepped into entrepreneurship. And so many of the folks I talked to after their sessions were like, just do it. They're like, it.

    Jess Sherlock (50:20)
    Yeah. Yeah. There's no,

    I mean, if you have an idea, you have something you want to do. only thing stopping you is you. In the SHINE program, I tell folks a lot of the time that when we sit and idolize a potential situation or a potential employer or a potential life change, right. Or imagine if you're like, Oh, wouldn't it be amazing to move to Alaska? Like you can spend a lot of time in your imagination. Right. But

    Amanda Gaffney (she/her) (50:42)
    Totally.

    Jess Sherlock (50:44)
    And that's fun, don't get me wrong, but until you actually go spend time in Alaska, I'm weirdly obsessed with Alaskan reality television shows, fun fact about me. Apparently they have a lot of mosquitoes in the summer, right? So it would take me five minutes in the summer months of being in Alaska to go, yeah, I don't want to be here. So yeah, that like action is what creates clarity. And I remember being so proud of you, but also like, it was so clear to me that you were taking steps.

    Amanda Gaffney (she/her) (50:53)
    Let's go.

    Yes.

    All good.

    Yeah.

    Jess Sherlock (51:13)
    that we're you an opportunity to try it on, right? So like, here are other people's stories about starting something to reveal that no one goes into it fully confident. And you've been using the word bravery, which I think is really important. So I think what people want to feel is confident, but confidence comes after doing something. What has to come first is the bravery to do the thing. The confidence comes from the fact that you did it. And so,

    Amanda Gaffney (she/her) (51:17)
    Yeah.

    Love that.

    Totally.

    Jess Sherlock (51:43)
    there was bravery in having those early conversations to kind of see through the lens of someone else's experience what it might look like so that pretty quickly started to realize, no one really knows what they're doing, right? Yeah. So tell us a little bit. At this point, you do have a full-time job. So we're going to talk about that in a minute.

    Amanda Gaffney (she/her) (51:52)
    Yeah.

    Exactly. Yeah.

    Jess Sherlock (52:07)
    ⁓ this entrepreneurial journey was not permanent, but this was a big moment. So tell us a bit about what you launched and if you're open to it, tell us a little bit about what your goals were. I know one of them was around. Could you replace your salary for example? And so yeah, tell us about some of those achievements and what it is that you actually launched.

    Amanda Gaffney (she/her) (52:17)
    Mm-hmm.

    Yeah, gosh.

    the first thing I did was launch a hot mess, right? Because I took my gumbo pot of random generalist skills that I had and was like, surely someone wants this giant pot of things. And so I don't, I honestly don't think I knew what exactly, I didn't know that I should hone in on the niche that I'm really good at.

    Jess Sherlock (52:42)
    Yeah.

    Amanda Gaffney (she/her) (52:58)
    what I did know about what I wanted to do is I had so enjoyed that work. Remember the like old coat, like that moment of I'm like helping things run better. I can see this. I knew that I wanted that feeling and I.

    found at least the idea really fulfilling that I might help other small and scaling startups kind of integrate that stuff that we had sort of retroactively built back in at Sondermind. I wanted to see like, can I hit other startups earlier, put this way of thinking and way of working into their DNA so that they can carry it forward through whatever their

    growth paths is or whatever pivots are going through or whatever. so that's what I knew. I knew that I wanted to help other people in that way. And then that's not at all what I did. I was like all over the map. You know, I did some, product analytics work for a global education company. I, helped a couple of founders together a product. I.

    you know, had a year long engagement with a learning and company and my roles varied as the, ⁓ product team I was supporting needed me to do. it was just really, it was a huge spread, which I think that ended up being the best. One of the best parts of it was the exposure to different industries, different sizes, different needs.

    it was just such a cool experience. So whatever I went in there with later became very irrelevant as I was just doing stuff.

    Jess Sherlock (54:31)
    I tell folks that a lot. if you're starting a services company, and we talked about this, that you have to start to draw a box around what you think you want to offer. But part of the initial goal is just get a client because so much of services is going to be shaped by what those clients need. You also have to start getting some income coming in. And then, of course, the ideal is that you

    Amanda Gaffney (she/her) (54:44)
    and a client.

    Jess Sherlock (54:52)
    can deliver some projects, get some word of mouth going, because inevitably you get referrals, which I know you benefited from. But as time goes on, and the same was true for the coaching business, like as time goes on, you start to figure out where the work feels really natural, almost doesn't feel like work. And it's interesting. I feel like I saw you get to that moment where you're like, they're going to pay me to do this thing. That's really cool.

    Amanda Gaffney (she/her) (54:56)
    Yes.

    Totally.

    Totally, yeah.

    Yeah, Yeah, totally.

    Jess Sherlock (55:19)
    And yeah,

    it is, I'm curious. So tell us about the skills. So one might think, ⁓ you you started consulting or freelancing, doing like kind of product work. But I know at the time our conversations were around how do you get business? How do you scope this work? And then of course, how do you actually do it? So I'm curious, like looking back, what product skills did you leverage or what new product skills would you say you built?

    during that year or so of entrepreneurship.

    Amanda Gaffney (she/her) (55:50)
    Yeah. I think the biggest one, I don't think I realized until I was a consultant, how much I relied on like the depth of relationships that I was able to form in in-house context and how integral that was to how I got work done at Sondermind.

    is non-existent when you're a consultant. Like you have no credibility beyond they clearly have recognized you as an expert, which is why you're in the room in the first place. But like, they don't know who you are. They don't know how you work. I had gotten by for a while

    established relationships. And so I think one thing that I learned was, it was a little bit twofold. Like one, how could I show up as the expert that was needed without any of that credibility? Like if I brought a thing to the table that I wanted them to implement or change or that I thought was going to help them, like I had that moment, that discussion, that hour they were paying me for whatever to like,

    simultaneously convince them of my idea, but convince them that like I was credible enough that they should walk away with the thing I was bringing to the table. And so my storytelling and my ability to speak a position and justify it with, with facts or data or whatever, whatever it was. I really, really needed to develop that early on. And I think because I didn't already have a relationship with those folks, the second thing I needed to learn was how.

    Jess Sherlock (56:54)
    Mm-hmm.

    Amanda Gaffney (she/her) (57:16)
    I thought I was really good at building consensus and bringing people in, but it's a different, it was a different level in consulting of an outsider by nature. So how do you them feel like it's their idea how do you validate their ideas and bring them in?

    ⁓ How do you create this very specific kind of relationship or the specific kind of culture so that there's good vibes in addition to expertise? I found that so challenging compared to in-house work, but it was such a great learning experience and something that I really use today as well. That was one of a million things.

    Jess Sherlock (57:42)
    Mm-hmm.

    Yeah, yeah. ⁓

    Yeah,

    But at a certain point you decided that this wasn't for you anymore. And

    You again wanted to embark on a job search, which led you now to your current role. So tell us a little bit about decision to leave entrepreneurship behind and do something else and tell us a bit about where you're at now.

    Amanda Gaffney (she/her) (58:17)
    Yeah. So, ⁓ back to getting to try on a lot of different companies and problems and hats and all of that. It became like really clear to me throughout this work that I don't just like product strategy. and I don't just like operations. I like those things in conjunction with each other.

    I think also, and there's some vulnerability in me talking about this, but I'm not the only one who's ever been through it. I struggled to find product market fit. was someone who wanted to work with small startups to help them, you know, transition their mindset from whether it's founder mode or whatever it is, to really start thinking about how do we get product done here now and how will we continue to get done?

    and I continuously found this imbalance of like the people who saw how I could help them often didn't have the money or the people who did have the money wanted someone with a different kind of experience or a different thing. And it was just becoming, unless I had four clients or unless I had one client who, you know, had the serendipity of they did have the money and I was doing the thing.

    without those those things. And these could fluctuate so much, right? Like the volatility of entrepreneurship, particularly in early days, it was very, very tough. the emotional roller coaster is real, the self doubt is real. all of those things just had me thinking like,

    I am really craving stability something that I really enjoy doing. And you know me, I'm a mega extrovert. And so the other thing around entrepreneurship is like, was lonely as hell. you, you can have a coach, you can have mentors, you can have friends, you can have old coworkers, but there's something so inherently lonely about doing your own thing, particularly if you're a solopreneur that like,

    did not fit with who I am as a person. And

    I knew that I wanted to work with a good team. I knew that I wanted to go back to mission-driven work. I knew that I wanted stability and I didn't know exactly what that meant, but I knew that whatever it was, it was the opposite of entrepreneurship. And I knew I needed to make some degree of salary so that I didn't lose my home and my daughter could eat dinner.

    Which, yeah, it is worth celebrating that like my daughter did not go hungry while I was doing this year and a half of work. Like that's probably the thing I'm proudest of is like food was on the table. The home was not lost. Yeah, so.

    Jess Sherlock (1:00:24)
    important things, very important things.

    Hahaha! ⁓

    Bye!

    That's amazing.

    Side note is you talk about it like there was no money, but I believe you replaced your salary. Am I right?

    Amanda Gaffney (she/her) (1:00:49)
    Yeah, I did. ⁓ By the end of the year, not quite, but the trajectory I was on in the first few months was, outpacing my monthly salary from my job before that, which was really exciting. So yeah.

    Jess Sherlock (1:01:03)
    Yeah,

    yeah. Volatility is real. So for anybody who's listening, who has done entrepreneurial work, that is a very real thing. And it's a real shift. I remember in our conversations of the level of ownership, the level of commitment, the level of thinking that is involved in just shifting from being a salary employee to doing your own thing and having to cover from, selling and marketing what you're doing all the way out to the doing of the thing.

    I'd be curious, like...

    Was that wasted time in your mind or as you look back now, how do you view that time, that season as you might call it?

    Amanda Gaffney (she/her) (1:01:34)
    No.

    Yes, season. I have zero regrets, is not to say it wasn't hard, which is not to say I didn't regret it in the moment, which is not to say that I do things very wrong in certain I don't regret it at all because it was the most significant amount of personal and professional growth I have done. You were talking earlier about the number of reps.

    and how like it's not the length of time, it's the number of this year and a half was like a pressure cooker on me of developing personal and professional skills. my imposter syndrome, she's gone somehow because you can't, because you can't be an imposter. There's a level of delusion I have found that you need to have as a founder slash entrepreneur.

    And like, yeah, one must. Hi, I'm Amanda and I have delusions. But it was really, I'm to your point of like, you're responsible for everything. if I sat there in self doubt, and I did sometimes, that was like a few hours or a few days that I was not working. And it was a self fulfilling prophecy.

    Jess Sherlock (1:02:28)
    I have a bit of delusion.

    you

    Amanda Gaffney (she/her) (1:02:49)
    If I believed I wasn't good enough, if I believed I didn't have something to bring to the table, if I believed all of that, what happened. That's what would happen is I wouldn't get a client or I wouldn't whatever. And so there was this element of ain't nobody got time for imposter syndrome. you can't have it. that's one of so many examples of where

    Jess Sherlock (1:02:58)
    Yeah.

    Amanda Gaffney (she/her) (1:03:07)
    I feel like it was very much like a metamorphosis into whatever it is I am today, a moth apparently.

    Jess Sherlock (1:03:13)
    Yeah, yeah. So tell us about the role you're in now and you see it fitting into that broader career vision for you personally. Because it's different. You're now a product analyst. This isn't necessarily what you set out to be, but tell us what was appealing about this role and what are you up to?

    Amanda Gaffney (she/her) (1:03:18)
    Mm-hmm.

    Yeah.

    Mm-hmm.

    Yeah, it's funny. back to the career vision thing. I have it now. Like I know elements at least of what I want to be doing for the next five years or so.

    I know that I would like to be leadership position around product operations. And I don't care what that title is. I just know that that's the work I love doing. And so when I returned to the job search,

    I tried to come at it with less of a, role do I want next? I'm starting to again, what gaps do I the way to that dream? like, Let's ignore the position for a second. What gaps do I have in my current professional life that could be solved in some way through the next thing that I do? And so,

    I job searched everything from like senior, whatever consultant to like straight up PM again to, manager, but what does that really mean when you get into the job description and kind of went back to that world of, of possibilities. And then I, so we had talked before about my lack of network and the tunnel vision you get when you're in a job. Another cool thing in the last year and a half was

    I have this wonderful, wonderful journey of like community building, reaching out to old coworkers who I haven't talked to in two years and meeting new people at networking

    so speaking of networking, I had met this...

    one person, and he and I were both at one of your AMAs And we just like immediately vibed, like we were clearly on the same page about what we thought exciting about product and we were taking a lot of the same things away from what you were saying. And it was like lighting us both up. So we just stayed in contact for a while, like every month or two we would meet up and you know, he'd talk about his work at Connect for Health Colorado, which is where I eventually landed.

    I'd talk about my entrepreneurial journey. We talk about our kids cause we, we both had young kids. And so it was like, we were just had one of our scheduled monthly check-ins and I was like, Hey, I think I'm thinking of transitioning out and I'm looking for product operations work. And here's what that actually means to me. And Eric was like, well, we have a job posted that isn't that, but maybe you would be interested in looking at it.

    and I look at it and it's like, title's wrong. Salary's wrong. Some of the technical skills wrong. but there was so much right about it I just gave myself chills. it was a really special, the really special moment. cause I'd been on LinkedIn, gone through all the things and like never, ever, ever did I put in product data analyst.

    Jess Sherlock (1:05:58)
    Yeah.

    Amanda Gaffney (she/her) (1:06:07)
    Like it just, it's, so, if you look at my resume now and you don't know what I'm doing, it seems weird. It's just a weird divide, but there was stuff in there around enabling data-driven decision-making and finding best practices in how data can fit into the product life cycle and using data to deliver strategic insights.

    Jess Sherlock (1:06:12)
    Yeah.

    Mm-hmm.

    Amanda Gaffney (she/her) (1:06:34)
    And coaching the team on these things. And there was something in there that think it was like consulting background preferred PM background preferred. The vibe of the job description was right. I had, you know, I thought Eric, I just thought the world of him. And I'm like, we're just going to apply. doesn't, it doesn't matter. We're just going to apply. and like, I just, cannot say enough about how wonderful the team was and how.

    Even just from these interviews, I felt like they were invested in my career path, like genuinely invested, not like where do you want to be in five years, but like, where do you want to be in five years and how will this role help you get there? And how can we, like, it was such an incredible, genuine, transparent, amazing experience I had another opportunity at the same time. And it was for a straight up PM role, another first PM in the business kind of role. And I'm like, I get to do it again. I'll do it over.

    Jess Sherlock (1:07:09)
    Yeah.

    Yeah.

    Amanda Gaffney (she/her) (1:07:31)
    But I, there was just something about this. I think you saw me turning on it where I'm like, I don't know what this title is. I don't know what's going on, this will not leave my mind And when I did the math from there to my career journey, it's like one gap that I have is as even as a product person where data is actually really important. It's a really important function for a product operations manager.

    I was like, got, I have gaps there. And so not only is this business telling me support your career journey and we can see a future where you're doing the thing you're describing, but also this job will enable me to get there.

    Jess Sherlock (1:08:09)
    I want to applaud your honesty and your vulnerability in the journey with me to really be open about was energizing for you, what was draining for you, what was important to you, what wasn't important to you. I continue to be so excited and so proud of you for giving yourself the opportunity to say, you know what, let me look.

    Amanda Gaffney (she/her) (1:08:09)
    We will.

    Jess Sherlock (1:08:31)
    pass the title and the salary and really see what this role is about. And to get the opportunity have the conversations with the team who I know as well. I've got some friends on that team, great team. And to hear about, know, this is the title now, this is the job now, but this is a growing team where I also believe that you will grow here in the ways that you're looking for. And so that vision that you worked so hard to establish and you

    Amanda Gaffney (she/her) (1:08:41)
    That's right.

    Jess Sherlock (1:08:59)
    iterated on in all those sessions with me, it's like that now, in a way, looking back, it's like the other job didn't make sense. It paid for, sure, and it was maybe the quote unquote correct title, but for you and the things that are really important to you in your career in terms of what you wanted to learn, but also you were looking for flexibility or culture.

    Amanda Gaffney (she/her) (1:09:09)
    I know. Right.

    Jess Sherlock (1:09:26)
    I don't think you would have gotten those things at that role if we really put these two roles side by side. so I just, for what it's worth, I see why you made the choice and I'm so glad to see that you've only been there a few months, but it's clearly been the right choice for what you were hoping to achieve.

    Amanda Gaffney (she/her) (1:09:29)
    Yeah.

    Absolutely.

    Yep. From a whole person perspective, from a professional perspective, they are mindful of giving me the opportunity to do things that really light me up, which is not always Excel spreadsheets but that is part of my job and I'm getting better at it and all the things. But there is a comfortable fuzziness to my role, but they always check in with me. They're like, we know this is not.

    what you've been hired for, it's not in the JD, we don't want it to be taking advantage of you. And if you're interested in doing this one thing, we could probably talk about it from a data perspective. so I just feel, I feel seen and treated like a person. And again, I just feel very like it was, yeah, I couldn't be happier. I'm, I'm just, I'm in it and I'm really happy.

    Jess Sherlock (1:10:12)
    Yeah.

    Yes!

    Last question for you. I ask this of everyone who joins.

    What's next or what do think might be next?

    Amanda Gaffney (she/her) (1:10:31)
    Yeah.

    I want to keep moving in the Prod Ops direction. And so I am not like trying to talk with, the folks at C4 about what like a timeline might look like for whatever that next step is. No one knows where the state-based insurance exchange, a lot's happening right now. There's a lot of moving pieces. ⁓

    Jess Sherlock (1:10:58)
    Yeah. Yes.

    Amanda Gaffney (she/her) (1:11:00)
    ⁓

    But just continuing to have those conversations, which they often open up with me and just kind of figuring out what that path is. And in the meantime, shoring up my data skills, I want to be really solid methods of analysis, the tool set around it. I'm going to be learning Python in the next little bit. I don't know if I need that on the day to day, but why the hell not? So there's things like that that I just stick it in my toolkit, look for more opportunities to assist with.

    Jess Sherlock (1:11:19)
    Yeah, do it.

    Amanda Gaffney (she/her) (1:11:25)
    product operation stuff just to keep those skills warm as well. continuing to network where I can and keep learning from people. So it's a lot of like, yes, yes, right. So it's a lot of like, I know what I want to be doing in one to two years.

    Jess Sherlock (1:11:32)
    Absolutely. Keep your head out of the sand.

    Amanda Gaffney (she/her) (1:11:41)
    And I know that in the meantime, I want to keep those skills warm and just continue learning and growing up to that spot so that I'm ready, right? When it's time to step in, I want to be really ready for it.

 

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Jess Sherlock
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