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Making the Move into Product

When I took my first tech job at Hired, I was a recruiter by trade. My business partner (we owned an Agency) and I worked on some product ideas (job board for Portfolio Managers at hedgefunds and a boolean generator for searching Linkedin via Google. We also applied to YC S7 for a Twitter news product) and I even shipped a physical product, the HoboHookah, which we designed, produced in China and eventually sold 10k units. But I was still new to tech. We were on the periphery in NYC's nascent tech seen (dominated at the time by FourSquare and Tumbler) and I was very much a novice.

So, a year in, when we were hiring our first PM I was like: Wait, what does this person do? It seemed simple. At the time, I felt our product (guided by the CTO and Senior Engineer) was making good progress: What did we need a PM for?

Fast forward a couple years, and I was the toast on the business side. Making good strides career wise, but by then it was clear our product strategy was fragmented. Too many ideas that weren't well thought through. A lot of features, but not a lot of strategy. Our CEO at the time, a cofounder, sensed it as well. We had stagnated product-wise even while our business was booming.

In retrospect, I should have fought harder for the right role. I knew deep down I was most interested in the product. Being on the business side, I knew that my success was ultimately contingent on having a great product. This frustrated me and while I tried half-assed to feel out the potential for me moving over to product, I instead followed the money and climbed the ladder.

Eventually it bit me in the ass. I was over my skies once we moved over to SaaS and was eventually layered. In a last ditch effort I tried to woo the new Head of Product to try and get him to take me as PM project, but years of under investing in the product side meant that he already had enough projects. My superlative understanding of the market couldn't make up for the brass tacks product work the Head of Product needed someone to take on asap.

I left Hired and did a bunch of consulting. The most fun I had was working on Dribbble's marketplace product. I founded another company, and eventually the lack of cash flow caught up to me. I had to go in house again. I focused first on Product roles, had some promising opportunities at ZipRecruiter and Lattice, but I couldn't land the product role I wanted. I went back to where my skills were most developed: Ops and Revenue at Triplebyte.

Triplebyte was an awesome experience. I feel like I really grew as a leader there and they had a strong PM org which I got to work closely with. Those experiences reified my desire to make my next move into a Product role.

Now, I'm at Impact as Head of Product and it is such a perfect role for me. I couldn't have come in at a better time, with the right folks around me to leverage my strengths in leadership, vision and marketplace expertise.

So, how did I make the move eventually?

First, it will always be easier to move into Product from another side of the business once you are already in house. There are a lot of dimensions to product and being in house and getting to work closely with the product sets you up best for an eventual lateral move.

That wasn't possible at Triplebyte, but I did take my time there to learn about Product Management and get as close to product as someone on the Revenue side can be. That prepared me well for making a move during an actual job search.

When you are trying to make the move to product, make sure to highlight in your resume the product things that you worked on. Specially, knowing the tools and lexicon and having built out product specs (even with support from a PM) is crucial for getting through product interviews.

You also need to seek out product opportunities that value your past work experience. For ZipRecruiter, they were looking for an internal facing PM for their GTM teams. I had high empathy for business teams and excellent understanding of the business team tool stack.  Those things helped, but the location (LA) didn't work for my family.

Finally, it really helps to be data oriented. Knowing how data is structured and how to query that data is very important in product. Every hiring manager is going to look for a PM that can discern success and failure, usually using data.

For Impact, it was all about how to approach understanding the user and finding product market fit. My early experience in Marketplaces was critical for the role, and I hammered that home during the interviews.

I also, prepared my face off. I was probing the interviewers for information on what they wanted and then thought deeply about the problems they were facing. I approached every interview as a PM would: Understanding the problem space and then being consultative in the solution space.

It worked, I was able to convince the leadership (and board!) that despite zero FTE experience as a PM that I was the best Head of Product they could hire.

Being in Product is really just the way you think about things. It's either really exciting or it's just a job. If it's the former, you can make the move, it just wont be easy, but preparation and passion will get you where you need to be.

I have lamented my lack of foresight while at Hired that I was not more dogged about making the move to Product until it was too late. Now, in retrospect, Im not sure if I would be as good of a Head of Product had I not had the experiences over the last 4 years. Regardless, it feels great being in the right function, doing work that I love. Staying focused on where I wanted to be, eventually got me there.

Trent Krupp

Currently Head of Product at Impact, a market network serving the entertainment industry. Previously, Head of Revenue at Triplebyte and Hired. Founded an agency in my 20's, sold it to Hired and became employee 5. Recruited for Atomic (VC), Credit Sesame and MakerSights. Helped the founders of recruitment tech startups Shift.org, Terminal and Beacon in the early days.

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