June 10, 2024

Nitty-gritty operational work: A Q&A with Assembled’s CSM turned Product Manager

Whitney Rose

Assembled just hit a significant milestone: 100 employees. In honor of the company’s journey from three Stripe alums in 2018 to triple digits in headcount six years later, we’re spotlighting early hires and the unique paths they’ve created for themselves at Assembled. You can find all their stories here.

David Patou is a Product Manager who originally joined the company as a Customer Success Manager. He isn’t as tenured as other employees featured in this series, but his story is a testament to the opportunities anyone can create for themselves at Assembled — even as the company continues to mature. In this interview, David shares why he was initially hesitant to join Assembled, what got him to change his mind, and how he forged an unconventional path into product management. His answers have been edited for clarity and concision.

Q. David, what were you doing before you joined Assembled?

A. I was working at Bain & Company, a management consulting firm, and was based in New York.

Q. How did you end up at Assembled?

A. I was a generalist looking to get operational experience. At the time, Assembled needed scrappy, low-ego generalists who were happy to get in and help move things along. I got connected to Jen (Ong Vaughan, former COO), who had been at Bain earlier in her career. After chatting with Jen and BZ (Brian Sze, co-founder), I decided to apply.

Q. How many people were working at Assembled at that time?

A. When I first spoke to Jen, there were about 35 people. By the time I joined, it was around 55.  I had a long recruiting process because, for a long time, I was not interested.

Q. Why is that?

A. I thought workforce management sounded boring and wasn’t convinced it was an interesting company to work for. But my view changed once I realized it’s a really hard problem with a lot of complicating factors, and it’s a crucial business issue for any company with a support team. There was no good solution on the market, so what seemed boring at first turned out to require a lot of smart people to solve.

After chatting with a few of the team members, I was also just really impressed by the talent. So, in addition to the mission being more interesting than I’d initially thought, I realized this was going to be a team of people I could learn a lot from.

Q. How did they change your mind about joining?

A. I think it was two things: the mission and the company itself. On the mission side, they explained why this operational problem is so difficult and what the symptoms are. After I got the offer, Ryan (Wang, co-founder and CEO) walked me through the Series B pitch deck, explaining what they told investors about why they started the company and the problem space they were targeting. Hearing the founders' vision for why this problem was so challenging and important made it a lot more attractive to me. I bought into that vision.

Then, from Jen, I heard a lot about how, especially early in my career, joining a startup like Assembled would be a great opportunity to get exposure to everything it takes to build a business. The company was still small and would be for the foreseeable future, which meant I could better understand what each function does. Coming from consulting, I didn't really know what each function actually did, and I had some guesses about what would be exciting and leverage my existing skills, but I wanted to keep doors open for exploring different roles and departments. I wanted a place that would offer that kind of exposure and flexibility in moving around if it ever came to it.

Q. What was your first role at Assembled?

A. I joined as a Customer Success Manager. It was just me and two other CSMs at that point, and they had been hired less than a year before me, so the team was still very new.

Jen, who had made the same transition from consulting to startup, had told me that there's a big bias against consultants moving into startups. The perception is that consultants can only make strategy presentations and don’t know how to actually do the nitty-gritty work. She emphasized that it was important to fight that bias head-on by going immediately into a deeply operational role. The options were customer success or product. I didn't have a technical background, and customer success felt like an easier transition because it involved managing relationships and projects, which had a lot of parallels with consulting.

Jen said that spending time in customer success would help me gain expertise in understanding our customers: what they’re looking for, the problems they’re trying to solve, and where they’re getting value from Assembled. This experience would give me credibility and open up doors elsewhere in the company. This advice proved to be true. I’ve found that being deeply involved in the details makes you more effective and trusted. If I had moved into any other role directly from consulting, there would likely have been skepticism about my recommendations since they wouldn’t have been grounded in the realities of the business.

Q. Now you’re a Product Manager. How did that transition happen?

A. I was a CSM for a few months and then got promoted to the manager role. Customer success was completely different back then. It was just three of us, and it was chaos trying to manage around 150 customers. I introduced segmentation to classify our customers into SMB, mid-market, and enterprise. This helped prioritize how much time and effort we allocated to different accounts. We then created different teams: a strategic team for larger customers and an SMB/mid-market team for smaller ones. I managed the strategic team for about a year, developing expertise in what our enterprise customers were like and the challenges they faced. I also helped scale the team by instituting a more repeatable process for enterprise customer success.

In parallel, Assembled didn’t have much product management at the time. Our engineers believed they needed to be close to the customer without a layer in between, which worked for a while but became hard to scale. On the success side, my team and I were hearing about customer problems all the time, but it was challenging to get the product team to build the right things. I ended up playing a de facto product manager role, meeting with customers and engineers, translating problems into potential solutions. I found I enjoyed this a lot.

Customer success is vital, but the nature of the job is to manage the current state of reality. I wanted to take what I’d learned from my work as a CSM and contribute to building a long-term solution. I initially joined customer success because it made sense, but my plan was always to eventually look around the business to see where I could move. Product management felt like a natural fit at that point.

I talked to Ryan and Sam (Peters, Head of Customer Success) about it, and we developed a transition plan. I had to go through the application process, but I officially transitioned to product management last November.

Q. What’s been the most challenging aspect of product management for you?

A. I thought the biggest challenge would be technical literacy since I don't come from a computer science background. But that hasn't been as difficult as I expected. Our engineering team is very patient and explains concepts to me, so I don't spend most of my time figuring out technical approaches — they handle that.

The harder thing is prioritization. We have so many problems and opportunities, and no shortage of good ideas. The challenge is deciding which good ideas to work on first and how to measure which idea is better than another. This job would be much easier if we had a bunch of bad ideas to discard. But most ideas we hear from customer teams, other teams, and even within the product team are good ideas that we would pursue if we had unlimited resources.

However, we are a resource-constrained startup. We don't have infinite engineers or time, and things are always harder than you think. The stakes are high when deciding which project to work on because there’s a significant opportunity cost of not doing something else. You have to be really sure that what you’re working on is worth it. That's been the most challenging part for me.

Q. You moved to San Francisco for this role. Was that a difficult decision?

A. Personally, it lined up with a good time in my life. I had been in New York for five years, and a lot of my friends were moving to different places. I was ready to make a transition, so I was way more open to it than I would have been earlier. When I first joined Assembled, I started as a fully remote employee and they asked if I would move to San Francisco, and I said, absolutely not. But later, I was more open to it.

I knew there would be career development value in being at the headquarters, sitting around where the leadership is, being with our engineering leaders, and being close to Ryan. I knew that would be better for my career.

I'm also super bullish on San Francisco. I think it’s a fantastic city that gets a hilariously bad reputation internationally. Everyone loves to hate on San Francisco, but I think that’s unfair. Sure, there are unideal things, but net-net, I think it's truly one of the best cities in the world.

Q. How do you fight imposter syndrome when stepping into new roles?

A. That's such a good question. I think this should be the universal message for startups: you have to be arrogant and confident to start a company in the first place. Who is anyone to say there's a problem in the world and that they can solve it better than others? That’s arrogance, but it’s well-founded arrogance because the problem still exists. Other people might have tried and been good at it, but you’re no better or worse off than anyone else.

Once you're in the startup environment, you're the best they've got. When I started as a PM, I had zero technical experience and zero familiarity with code. I was under no illusions — there are better product managers out there. But I happened to be the best they had at that moment. So, whatever my best is, it’s the best they have until they find someone better.

When I joined customer success, I was new to workforce management and customer success. Consulting at big companies is very structured, with clear roles and responsibilities, but none of that existed here. You have to fake it until you make it. It turns out nothing is that hard if you bring confidence and arrogance to it. You'll be effective if you try hard and don't let imposter syndrome get in the way.

Imposter syndrome is a given — of course, someone else might be better for the role. But in a small company, you really are the only option, so it’s not helpful to linger on that. My very first project was working with the infra team to develop a point of view on stability. Ryan chose this because it was the least customer-facing problem, requiring deep technical knowledge I didn't have. I had to make sense of it and come up with a recommendation.

Everyone, including me, Ryan, and the engineers, knew I didn’t have the technical know-how. My role was to ask good questions and develop a point of view through those questions. The engineers were very patient and helpful. Would it have been better to have an infrastructure PM with 10 years of experience? Absolutely, but they didn’t have one — they had me. What I came up with was net helpful. The bar I set for myself wasn’t about who could do it better, but whether I was better than the alternative, which was nothing. When moving into a new role, that's the bar to set.

Q. How have you felt supported at Assembled?

A. I think it's the mentality that we can only go up. Startups start from nothing, and while Assembled is more developed now, we still have way more to gain than to lose. We're in operational mode, so the mindset is: what's the worst that can happen? You might as well try something because, at worst, we're no worse off, and at best, it could unlock significant growth. This mentality is instilled from the top down.

One of Assembled's strong suits is that we don’t focus too much on rigid roles and responsibilities. It’s more about the job that needs to be done and who can do it. It’s very much an all-hands-on-deck approach. We collectively move the process forward by leveraging our strengths and helping each other with our weaknesses. This collaborative and outcome-driven environment ensures we focus on getting things done rather than sticking to strict job descriptions.

Among my peers, especially the engineers, it feels very collaborative. We know our strengths and take on tasks accordingly, and we help each other out where needed. For example, on projects, we determine which tasks someone can handle solo and which ones we need to work on together. This approach allows us to combine our skills effectively, making the work more productive and supportive.

Q. With the company’s growth, how has collaboration changed?

A. In some ways, it's a little harder. We now have more established departments and specialized roles. Customer success, for example, went from a team of three covering all customers to having implementation, SMB, mid-market, and strategic teams. This has led to more divisions of work, and there are always questions about who owns tasks that straddle these divisions. However, we still maintain an "all hands on deck" mentality.

Those divisions are helpful in areas where processes are more straightforward and repeatable. Conversely, for projects that stretch our capabilities, we operate in a very collaborative manner. It's a hodgepodge of people working together, not concerned about strict job roles because we're doing it for the first time. This approach allows us to focus on getting things done effectively.

Even with growth, we still operate towards the mission of solving problems efficiently. Leadership models this well; for instance, Ryan isn’t above jumping into meetings with SMB customers or traveling to visit them. This attitude permeates the company, where everyone strives towards long-term growth. We prioritize getting the job done over sticking to strict job descriptions.

Q. What advice would you offer to anyone interested in joining Assembled?

A. Make it clear what skills you bring to the table, but also show your eagerness to be part of an all-hands-on-deck environment. Be ready to roll up your sleeves and help wherever you can to contribute to the company’s growth.

While having the right skills is important, eagerness is perhaps even more crucial because skills can be developed over time, but eagerness is a personality trait. At Assembled, and likely at all startups, we need eager people, even if they don't have the perfect skill set. There's always more than enough work to go around, so being eager and ready to contribute is the most important thing.

Assembled is still growing! Check out our open roles.

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