🎧 How I (Accidentally) Landed in Product Management
Think your journey into product management is unique?
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Most of us (myself included) have had a unique path into Product.
Hear about my journey and learn 3 MAJOR takeaways that will help you advance successfully on your own path in product management.
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Jess Sherlock (00:00)
It's a pretty recent trend that folks are being formally educated in product management in college and have a goal to get into product management. And I think that's pretty neat, but that certainly was not my case. And I think for many of us that was not at all the plan.
Jess Sherlock (00:18)
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 (01:15)
Hey everybody, welcome to the pod. Today we're going to talk about how I accidentally landed in product management. And I hear it all the time. Everyone says, ⁓ I landed in product in a unique way. I have this like really unusual background and it makes me laugh every time because I am fairly certain that I have seen it all. And I think all of us have had a unique path into product management. So I've seen engineers shifting to product designers.
researchers, mean data analysts, business analysts, program managers, ops. I've seen consultants from marketing agencies, consultants from strategy agencies, entrepreneurs turn product managers, veterans. I've even seen medical device reps go into product management. And a favorite previous student of mine actually came from athletic clothing product management to get into software product management.
It's a pretty recent trend that folks are being formally educated in product management in college and have a goal to get into product management. And I think that's pretty neat, but that certainly was not my case. And I think for many of us that was not at all the plan. We
weren't little kids saying we wanted to be product managers. But today I want to talk about how I got into product so that you know a little bit more about me.
but I also hope that you see yourself in the stories that I tell today and maybe through my own storytelling, you can see how your story, how the dots might connect later on in your career. And I also hope to help you see that your generalist experience and your unique background is actually a huge flex and can be so helpful as you're building great products for your customers.
I have worked with product managers for over a decade and I have taught product managers at General Assembly. I have built out curriculum for product managers at product school. I have coached dozens of product managers through finding new jobs, nailing their first 90 days and even getting promotions.
And what I love about product managers is that we're all cut from the same cloth.
We all tend to be these creative, multi-passionate overachievers. I don't know, maybe a little bit of perfectionism sprinkled in there too. We're usually the kid that raise their hand to lead the group project. We are the person who jumps at that new challenge that needs to be figured out or that new tool that needs to be tested. I feel like I can spot a product manager in the crowd and there's definitely a vibe to us.
I'm not surprised when folks tell me about their unique journey. And when I look back at my own career journey, it makes perfect sense in hindsight that I ended up in product. So I want to tell you about my career and tell you what feels really clear to me now so that hopefully you can get a little bit of fresh inspiration for your career and maybe anticipate how some of your own career dots are going to connect over time.
So I graduated high school at 17, talk about an overachiever. I was valedictorian of my class. And because I had taken a bunch of advanced placement classes, I had about a full year of credits ready to go as I joined college for my freshman year. I was also, fun fact, a DJ at a local radio station. So setting up my podcast equipment is very familiar. I was a real DJ. This was not a...
college radio station. was an actual highly rated, I think the second rated country music station in the upstate New York market. And that's where I'm from, by the way, is rural upstate New York up near Saratoga and Lake George. If you've ever been up in that direction. And so yeah, my name is Cricket. So hi, I'm Cricket and thanks for listening to Froggy 107.1. Yeah, it was a country station. A lot of folks give me crap for that, but it was a great time. so anyways,
Believe it or not, I didn't even know if I wanted to go to college, right? I grew up in this rural town. A lot of my family was in the trades or worked as corrections officers. And no one had really gone to And I was having fun working at the radio station. So thanks to my guidance counselor though, and a road trip to visit the school, it was literally beautiful. So I went to Ithaca College.
The campus is just incredible. It sits up on this hill. It looks out over Lake Cayuga. And the town is known for all of these gorges that are around, like in a very short driving distance and some short hikes, you could go see these like beautiful waterfalls and everyone would wear t-shirts that say Ithaca is gorgeous. It's a good pun. Anyways, as a poor kid, good grades, it was hard to say no to the nearly full ride scholarship. So...
I said yes and I thought, well, maybe I'll be a radio DJ. And I guess I had convinced myself that college would help with that. I don't know. So anyways, technically I went to film school. So at Ithaca, they had a television and radio program inside of their film school. And ⁓ no, if you're thinking Ithaca College, is that the college where that movie road trip was filmed? No, but they did use our name.
Anyways, I went to college, did a double concentration in photography and audio production. I learned how to develop black and white and color film, and I even developed my own black and white and color photography prints. I also spent hours in TV studios learning how to run cameras, set up lighting, and a show live on air.
And in my audio production courses, I learned how to mic a drum kit and how to mix and master audio recordings. And you might be thinking like, it's super helpful for product management. But actually, in hindsight, there were a few things that I learned that really set me up for my career journey. So number one, I learned crystal clear that I do not like to be a specialist. there were folks in my photography programs who were total tech nerds and
wanted to know the latest, greatest things about their camera lenses or whatever other technical aspect of their equipment. And I just, I don't know, I was bored by that. I didn't really want to keep up with all of the latest, greatest technology what I was really drawn towards was organizing groups of people towards producing a show or producing a thing. And so, mean, hello leadership, hello cross-functional teams.
Hello, stakeholder management, all very important skills management. I also learned that I really enjoyed the high stress environment and the high expectations, So if you're producing a live TV show, there's not a lot of room for error. And so you have to think on your feet. You have really show accountability and ownership and get things done. And then finally, I learned that I really did love to be creative.
But I wanted that creativity to have a purpose. I wasn't just like this creative to be for creativity sake type of person. I wanted to be able to see that whatever thing I was building or creating had some sort of outcome associated with it. So mean, if those things don't sound like product, I'm not sure what does. So after three years in college, because again, overachiever, I didn't need that fourth year, so I saved some cash.
on rent and whatnot and went out on my own after college.
And for those first few years out of school living in Cincinnati, Ohio, there was actually a pretty big video production ⁓ community, but it was a lot of like business video
So I bounced around a little bit as a freelancer. I was also doing some full-time work as a producer and editor for a local business marketing agency. So at that company, I was actually producing videos that were used for big companies to get various regulatory approvals. So for example, I got the opportunity to produce a video for Johnson & Johnson.
that was releasing a medical device and they needed to have testing videos of that device in use. So I got to go into an operating room and watch a gallbladder get removed. I'm convinced I can do that procedure by the way, very straightforward. Anyways, I would get back into the editing suite with my editor and produce a video that they could then submit to the FDA for approvals. So lots of, production that wasn't necessarily something you're gonna see on TV.
but very important for those businesses be able to do what they need to do to get their products out to market. So I'd spent a couple years doing this sort of dry business video production. And it wasn't until few years out of college that somebody I had met at that marketing agency had mentioned to me that there was another local marketing agency that I might be a good fit at. He knew they were hiring. I think he had worked there before as a copywriter.
Shout out to Rob if he ever listens to this. So yeah, he had worked at the company, thought I would be a great fit, made a recommendation to one of his friends and old coworkers. And I ended up landing at that company. And this was the job that ultimately started me on the journey to product in 2008. And I was there for six years. my first title at that company was actually an interactive analyst.
It means nothing probably to you, but I started basically as the hip 20 something with a nose ring and thick rimmed glasses that would be responsible for researching the haps with apps like Twitter and Facebook to basically give our business clients insights and feedback on whether they should be using these platforms and if so, how.
And that was really fun, actually. I got the opportunity to learn a little bit about marketing strategy and really got a glimpse into those products from the early days. So now it's a given that you're going to be on those platforms. But at the time it was this like scary new place for businesses to be. So after being in that role for a little while, I shifted into a digital project management role.
where I was leading projects for these big Fortune 500 companies. these projects were things like large-scale, multilingual website consolidation projects. So maybe a company had done some mergers and acquisitions, had a bunch of websites floating around and wanted to get them all onto one content management system. I was working on getting projects completed, which involved...
a lot of just execution and communication and stakeholder management. And I was taking those projects from basically the pitch where we would pitch the project to those companies or respond to an RFP all the way through to delivery. at the time, you know, remember this was the early 2000s, there really weren't mobile apps quite yet. So responsive websites were really important.
microsites and landing pages to support marketing was really important and email marketing campaigns was really important. So I got to work on these projects along with designers, typically graphic designers and developers. And I even started to conduct what I realize now was user research and usability testing. I didn't know that at the time, but I was, you know, working on
wireframes or sketches of what these things could look like to get my graphic designers to basically skin them, which if you know anything about UX design, that's essentially an interaction designer role or a UX designer role. So without realizing it, I was building these skills in designing effective software experiences to accomplish what these businesses wanted to encourage their customers to do. sounds a lot like product management, right?
So as you can imagine, demand for this type of work was growing tremendously at the time because if you didn't have any sort of digital marketing, you weren't existing. as this type of work was becoming more in demand at my agency, I was a part of pitching a project that was going to be led by our Denver office. So at the time I was working in Cincinnati, Ohio.
and got the opportunity to pitch this big project. We won it. It was a multi-million dollar project. And at the time, our Denver office just didn't have anyone with my skill set. And so they offered to move me to Colorado. I was able to lead that project, hire a team of folks, some additional digital project managers and ⁓ additional UX designers to help with the project. That's where I developed a lot of my leadership skills.
A lot of my team management skills learned how to hire. you know, looking back, I'm like, golly, that was, tons and tons of skills related to product management that I would later tap into.
And one of the biggest ones that I always tell folks who get the opportunity to learn product through an agency role or folks who are coming from an agency role and then are moving in-house is you really, typically see really strong stakeholder management and communication skills because you have to walk this very fine line of relationship building with your clients because they often do not understand
what you're working on. They don't understand why scope has to increase. They don't understand why something's taking that long. So really getting good at managing their expectations, managing up, because typically they're more senior in their organization than you might be, and really translating technical concepts to a non-technical stakeholder. Those are all skills that I developed without realizing it in those roles. So...
I was at that organization about six years, managed to get myself out to Colorado, which is awesome. If you're ever in this area, ping me on LinkedIn, I'd love to meet
So around this time, user experience as a concept and as a role was starting to become more popular, and it started to get on my radar at least. And so I knew I wanted to sort of shift gears and get the opportunity to actually work on software that wasn't for marketing purposes, but that was built to help customers do something or solve a problem. And somehow this company called
Effective UI got on my radar. It's a company based in Denver that I believe was sold to Ogilvy in recent years. at the time they were a very well-known UX agency.
I ended up getting hired there in a role called Lead Experience Architect. And I realized after, and I'll tell you why, I was essentially a product manager for hire in this I was working with giant Fortune 500 companies that were wanting to embark on what they were calling at the time, digital transformation. companies like Wells Fargo, Motorola, they would come to us saying,
hey, our competitors just launched a mobile app to manage your bank account. Should we have that? And what should it do? What should it look like? you know, looking back, I was essentially building one right after the other, these zero to one products for giant companies. And I was working with teams that look a lot like an agile team.
They would typically include some sort of researcher, some UX design resource, usually a visual designer, and engineering resources like backend architects and front-end developers. And yeah, it sounds a lot like an agile team. I was planning and facilitating the user research, market research, competitive research. And of course it was all based on like the scope of the project and the budget that our client had to spend.
But I was essentially going out and answering this question of, we have a mobile app? And if so, what should it include? What should it look like? I was pitching the MVP for a lot of these companies, very early products and along the way managing those client relationships and those stakeholders from pitch, where we were pitching the project to the delivery and launch of that thing. Now, one of the things that really frustrated me about that role was that
because I didn't actually work in-house at the company, I wasn't always able to see those products through to launch, or I wasn't able to see the specific data and results of the things that I had built. Or worse, sometimes those products were a little bit Frankensteined, meaning they might take our initial front and back-end development work, and as they were implementing it inside of their existing systems,
they might make adjustments and not exactly have it look how we wanted it to look. that was frustrating as time went on. And so ⁓ I was open to what else might be out there. ⁓ And so while I was busy doing this work that I now realize is product management, a good friend of mine, a previous colleague, he was actually someone who I met when I moved to the Colorado office of that previous company.
shout out to Brennan if you ever listen to this episode. He had moved on from that marketing agency to this little startup. I knew it was small. I think I'd heard it was in a garage. I honestly didn't think much of it. I figured it was his little side project. But he would send me often, would email me and say, hey, I'm working on this screen for our mobile app. Can you give me some input? Because he knew that I had been.
I'm essentially a UX expert. had been running a lot of usability tests. So was kind of like good free advice for him. And honestly, it was fun for me to help him out because that's what I like to do. And unbeknownst to me, he was often speaking very highly of me to his founders and just saying like, hey, this girl's good. Like when we have the budget, we should bring her on. Well, guess what? The company was about to close their series A and one of the co-founders who was running product decided it was time.
to start looking for that first product manager hire that would be outside the founding team. Guess who recommended me? Brennan. Nice of him. And I remember he reached out and he's like, hey, I want you to chat with this guy. He's our co-founder. I just would really love for you to meet him and maybe join the team, but see what's there. And honestly, it's funny looking back. was like, And I was interested and open to the idea because I was starting to grow frustrated with...
always being like a layer removed from what I was building But at the same time, I was like, well, this is like a nice gig and I like my coworkers. So I don't know if I'm ready for something new, but anyways, I was like, all right, I'll come do this meet and greet. We'll see. I love to meet people. So what's the worst that could happen? So I show up and he's like, Hey, we're looking to hire our first product manager. And I was like, I don't really know what that is, but okay.
He's like, well, me tell me a little bit about what you've been working on. Brennan's told me a little bit. It sounds like you have the same skill sets. Tell me a little bit more about it. So I remember I'd brought my computer with me, and I had been working on this really massive brand new account management system, I think it was, for one of our giant clients. And so.
I remember I literally just turned my laptop towards him and showed him the most recent presentation that I had shown to the stakeholders where I had walked through market and customer research to pitch the idea and then had prototyped out some ideas for how this app could actually look and work. And I'll never forget, he was super impressed and he was eating it up. And to me, was like, this is, do this every day. I've been doing this for years. Like, why is this such a big deal?
And that role was the major turning point in my career. Major. And it was all because I said yes to this meeting about a role that I didn't understand. you know, when I started, I was running the backlog for the entire bullpen of engineers. We were in person in this really hip, old brick building in downtown Denver. We had a bullpen of engineers that all like...
We were in a big circle with our backs facing each other, probably about a dozen engineers. We were doing about a million in ARR at the time and had about 20 people at the whole company. And yeah, over the almost four years I was there, we grew to 15 million in ARR. We grew to about 300 people, I think, and we had raised like tens of millions in additional VC funding. It was just insane hyper growth.
of the product, of the customer base. We had to move from SMB to enterprise customers, which was a whole can of worms. I'll probably unpack on a future episode of what those unique needs really are for selling into the enterprise. We expanded internationally, so we were getting into localization, globalization, translation. And we even added two more products to the portfolio
including a machine learning and image recognition product way back before. Yeah, it was cool. And that was just in four years. I went from being this solo PM, and then I was a director of product, leading four product managers, four product designers, and I think like eight agile teams. It was an absolutely insane ride. I wouldn't trade it for the world. And I learned so much. I often say that that was my...
accidental MBA, like my on the job MBA, because I had just such an awesome opportunity to see what growth inside of a SaaS company really looks like. I got to see that, what got us here breaks tomorrow. And when you're on a path of hyper growth, it's, it's a really fun ride. But I had some big takeaways. And this is really where where I want to offer some insights.
for you in thinking about your career journey and the decisions that you're making day in and day out. And so I have three takeaways for you. The first one is do good work. Just do good work. Your reputation at the end of the day is everything. Regardless of title, regardless of seniority in a company. People who had worked with me trusted me. They knew I got shit done.
They enjoyed working with me and that likeability and accountability just went a long way. And so yeah, do good work. Number two, over the course of your career, you're meet a lot of people. So build those bridges and maintain them. My relationship with Brennan and my openness to helping him when he had those design questions was key.
to that opportunity. Had I not responded or maybe sent him to somebody else, who knows if he would have thought to recommend me? And the thing about that is people often ask me, Jess, how did you get such a big network? How do you know so many people? And the fact of the matter is you have to build and maintain those relationships when you don't need anything. I work with people in my Sprint program, helping them with their product management job search and
I look at their LinkedIn, they've got like 120 connections and they haven't kept in touch with previous colleagues. And it's like, yeah, you know, it's kind of like it's kind of like brushing your teeth. It's easier to do, you know, a little bit every day, brush your teeth every day rather than trying to do a catch up once a year. And your network is the same. So so build those bridges, but maintain those bridges over the course of your career when you don't need things so that when you do.
you can reach out and get what you need, get some support from that network you've invested in. And the final takeaway I have is say yes, even when it scares you. Because I'll be honest, I had no idea what a product manager was when I was offered that job. I had to Google it, I'm not kidding. I remember Googling, like, when is a product manager? And seriously, I had major, major imposter syndrome. Like, all these people saw something in me.
And I was so afraid to let them down and it felt like the stakes were so high. But I'm so glad I said yes. Like I figured it out. I learned a ton. And yeah, I messed up. had mistakes just like the rest of them. I'll cover those in future podcast episodes. But I wouldn't trade it for the world. And you have to remember in those moments when you are making a big decision that most decisions are not final.
Most decisions are reversible, this one included. I didn't need to, but I could have quit if I didn't like it, or if I didn't end up feeling like I was good at it, or it didn't work out for some reason. But if I didn't say yes, I never would have had the opportunity to see if I could.
Now, unfortunately, at the end of that insane hyper growth startup experience, I did end up burning myself out. I burnt myself out completely and totally. Like, I needed a year to recover. I'm not exaggerating. We'll cover that in a future episode as well.
We were going 100 miles an hour every day. Every deal was a big deal. Every feature launch was a big deal. And I was sprinting.
when I needed to treat it like a marathon and I burnt out. And that's how I discovered my new career path as a product management career coach because I wanted to stay in and around product management. I loved being around product managers. And so again, this story, it makes perfect sense it like led me to where I am now. And so if you're at the early stage of your career, I would encourage you to
you know, trust the process and remember that we can't know what's going to come tomorrow, but trust that it will all make sense in hindsight. So in a future episode, I'll talk about my burnout journey, how I recovered, how you can avoid the same. It's certainly the inspiration for my Shine program where I help folks level up sustainably in product. But as we come to a close of today's episode,
Remember, talk is great, but I am big on action. And all of my coaching clients know this. I end every session with the same questions. Number one, what are your takeaways from our conversation today? And number two, what do you want to commit to doing and when? So with that, I'll ask you, what's one takeaway you want to put into action from this episode?
And if you're not sure, we'll give you some ideas. So here's idea number one. Careers are a long game. I told you to trust the process. So what could you do this week to just focus on doing great work?
Here's idea number two. Maybe there's an opportunity that you've been offered that scares you. Even if it's small, maybe you could say yes.
Or maybe in the spirit of building bridges when you don't need something, you could reconnect with someone who's maybe at a company that you admire or in a role that you admire. Reconnect with them now. Have a chat now when you don't need anything so that when you do, that connection is warm.
So with all that, I hope you enjoyed hearing my story and my accidental path into product management. thanks for listening. Remember to subscribe to be notified of new episodes just as soon as they drop. And if you have a career question in product management, connect with me on LinkedIn, send me a DM, comment on this episode.
or reach out to me by booking a call on my website at jesssherlock.com. That's three S's, J-E-S-S-S-H-E-R-L-O-C-K.com. And if there's another product manager out there that you want to share this with because you think they might find my journey interesting or see themselves in my journey, then please go ahead and share this with someone in your network. Maybe it's a good conversation starter for reconnecting with someone that you want to build a bridge with. And I'll see you next time on...
AFTER THE CERT.
