6 Learnings from transitioning from a corporation to a small design agency as Product Manager

A couple of months ago, I decided to switch things up and changed jobs.
I joined Smooth Sailing, a small (<10 people) research-driven design agency, as a Product Manager, after 3 years of being a Program Manager at Stripe, a 6000-people fintech scale-up.
In short, I moved

• from a company to an agency
• a corporation to a small startup

This transition has been incredibly insightful for myself and I wanted to compare both experiences and share the learnings while they are fresh. Hopefully, they can inspire others that don’t feel like they belong in one structure or another.

More challenge and variety

Limitations of job titles

I believe that job titles and descriptions kill the dreams, aspirations, enthusiasm and productivity of many people. They put people in boxes and the box you’re in is the box you become.

As a company grows, role descriptions and responsibilities become more restricted. When I started at Stripe, there was no organizational chart in 2018, slowly but surely one was needed to understand all the different business units, and roles and to understand what each one was working on. Where made-up job titles made sense at one point, this needed to be standardized and followed by industry norms. The consequence of stricter job descriptions is that the work one is doing becomes limited in scope, more repetitive and dare I say - more boring. Where I took on organizing the ATH of the Dublin office, starting a baker’s community… at the beginning of my career at Stripe, I was hardly doing anything like that at the end of it.

In a start-up environment, this is very different. What’s in the job description of the handful of people, doesn’t cover all jobs that need to be done to keep the business afloat. At Smooth Sailing I also take on marketing plans, optimizing sales processes and helping form a long-term business strategy.

Career trajectories in corporate environments leave little room for variety

The next step in a corporate career is often to promote and move up the ladder. Moving up happens true either by becoming a manager or reaching the next level of expertise in your subject area. You become a true niche expert. In the time I am working for a start-up agency, I have witnessed exactly the opposite. I’m pulled in different directions on an hourly basis. Client A wants to spar and get my thoughts/expertise, client B wants me to develop a roadmap, in between I am sitting in on a prospect call. Very few tasks have been the same and as I take on more clients, my job description will expand in scope rather than become more narrow.

One could argue that variety isn’t a good thing. The discussion on whether being a Jack of all trades is a good or a bad thing, I’ll leave for another time. As a Product Manager, I thoroughly benefitted from a broad skill set. It allows me to have enough tools in my toolbox to come into any organization at any point of the product development life cycle and have an idea of what the best approach might be for that particular situation.

More agency and freedom

At SmoothSailing people are hired based on quality of work and their detail-oriented and user-centric approaches. This means there’s little need for management and oversight. We manage ourselves and if we don’t deliver adequately on a project, ultimately it will hurt ourselves. This gives tremendous agency. I am able to drive my own projects and determine the approaches that will work for my clients and me regardless of how other people in the organization are doing it. I feel empowered and more energized because I get to decide how/when I am going to run projects. With this freedom and agency also come challenges; keeping the organization together and aligned around shared goals and a shared belief on how to build great products. We try to alleviate misalignment by having weekly plannings, retro and demo meetings where we go over the work/clients of others to understand what everyone is working on day to day. Additionally we have a lot of in person offsites and bonding moments.

Need for more/better boundaries

With great flexibility, comes great responsibility. When you work flexible and adapt to the calendars and ways of your client, it also requires hard boundaries to keep being energized. Continuously shifting focus isn’t productive, and being available 24/7 to several clients isn’t advisable either. So in the big ocean of being flexible, you need to find structure and ways that work for you. I do so by organizing my work in big time blocks (mornings/afternoon) and I try to avoid working for several clients a day. For years I have split off my personal and professional communication devices. People know they can call me if it’s urgent, but it hardly happens. In an agency it’s more challenging to keep that boundary, especially if you’re not working for every client, every day. The way I alleviate that is by leveraging email and by setting expectations with clients when they can and cannot expect an answer from me, although I haven’t found the best way to do that yet.

Rapid knowledge expansion, but is that of benefit to the organisation?

Every time I start doing Product Management for a new agency client, I need to immerse myself in their world. That means; reading up on their documentation, chatting with stakeholders, going through their product(s) and tools… In a very short period of time, I gather enormous amounts of knowledge. For people that seek out knowledge and challenge, this keeps the day-to-day job interesting, but for the agency itself, some of that knowledge is not transferable. Imagine I become an expert in space exploration because that’s the industry my client is in. What are the chances that I will be able to re-use that knowledge? Did I just spend weeks gathering knowledge I might never use again?

Let’s look at it from the corporate angle... Imagine you’re with 1 company for 4 years. All the knowledge you gain about that company, including legacy knowledge, will exponentially increase in value over time. All of a sudden you’re this person that knew why this decision that doesn’t make sense today, made sense in 2018.

(As I am too new in an agency set-up, I haven’t reached a conclusion yet on whether or not the broad scope of knowledge one gathers as an interim Product Manager will ultimately be of benefit to the company or not)

More ability to bring yourself to work

The bigger a company gets, the harder it is to bring your full self to work in my opinion. A corporate environment runs on fixed, repeatable processes so the organisation can easily scale as it grows. You need to operate within those boundaries of the processes. Same for the culture. The culture of a corporation has been crafted over the years. It’s set out and quite fixed. You need to walk within those cultural lines. Start-ups on the other hand are nimble and undefined. With every addition of a team member, the culture gets defined quite a bit more. Because of this, it’s easier to bring yourself to work. Within my first month, I joked more than I did over the past year in a corporate company.

You spend more time communicating

If you’re an employee in a corporation and want to know if you’re doing a good job, you’ll know. Your bi-annual performance review will state very clearly whether you met expectations or not. With clients, however, it’s not as easy to tell. No matter how many check-ins you did along the way, sometimes it’s only towards the end of the contract you get direct feedback on whether they want to (and can) extend it or not. Similarly, with the work you’re doing. As clients are further removed from the actual work you’re doing, it requires more communication to ensure they are aware of what you’re doing and why. I alleviate this by sending weekly summary updates of the work we did and the planning for the following weeks, by following up on important meetings with the meeting notes and by starting every meeting with the direct question “are you still following what we’re doing?” and setting the context of where we’re at in the process.

Joining an agency was for sure a move outside of my comfort zone. One that gave me autonomy, flexibility, diversity and agency. But it requires an active approach on protecting boundaries, communicating more often and taking in a lot of knowledge. So far, so good! More than good.