From Enterprise to Startup: A Product Heart's Journey
For those thinking about taking the leap!
The title of this may seem odd to some. There are lots who believe growth in their career may be accomplished via the traditional path ‘from smaller company to enterprise’. I’ve come across quite a few product people over the course of the last 5 years who said they love the startup and scale-up life. I now count myself lucky as one of them.
When I joined my last company, I looked at my employee number and realized for the first time in my career, I actually knew my employee number. I was taught to stay safe with the bigger, stable companies - the ones that provide for you as you grow in life - one that has a name and has been around a while. I didn’t know until I was leaving the large organization I was with before my first small adventure that you can outgrow a company, no matter how big it gets.
Before I go any further, I want readers to know that I don’t NOT like the bigger companies. They provide many learnings, opportunities, at times more stability, and open lots of doors. I wouldn’t be here without the ones I was a part of. My goal is to help those who are nervous to leave their comfort zone, and to help them see that taking risks in their careers may bring them bigger rewards than they thought were possible, sometimes at an accelerated pace via the smaller companies.
The ‘dive deep’ things when you consider the leap…
When I made the decision to go smaller, I was the sole earner in my home with two young kids. Leaving a large company where risk with respect to company stability is generally less due to its maturity was the biggest hurdle to overcome. When thinking this through, you must do is your due diligence on the company and work on understanding what great startups and scale-ups look like. Proper research on funding rounds and investors, cash runway, upcoming company milestones, and founder track record are critical for you to do during the interview process.
If you’re like me and value a culture where you are a human building alongside other humans, you will also do your Glassdoor research, make some inside connections, and reach out to employees at various levels on LinkedIn who have been at the company for a meaningful period of time. As you progress in your process, talk to as many people as you can get access to. Think about your values. Do they align with the company’s values? The ones you can see on their site? Do their employees exhibit these values when you speak with them? Another tip someone mentioned is ask the difficult questions about transparency, autonomy, decision making, and yes, DE&I, and what it takes to get promoted or get a shot at the big opportunities.
Taking with you what you know
You may likely question whether you will be able to build for a whole new set of customers in a different market. This is not just because you’re going to a smaller company - it’s just what we think about as product people. Most of the time when you switch companies as a product person, you’ll end up needing to learn a new set of personas, needs and pain, market dynamics, and gain general domain knowledge in that space. You may or may not be in SaaS. You may or may not be building external products. Your imposter syndrome may or may not be elevated as you question all of this…
What you will bring with you is the product mind and skillset. Those two things are transferrable and will help you quickly get over all the time you’ll spend becoming a domain expert once you start. Part of the thrill of something new is learning something new while bringing to it something you love and are good at. They’re hiring you for a reason and they know you don’t know all the answers yet. Building great products, standing up product operations (or operations for the product team in general), and helping your customers get to their goals are not specific to any one industry or persona.
The People Things…
Product people are at the center of any company. If you are a product person and don’t feel that, then question whether you’re at the right place. Great companies today embrace our function to drive business outcomes and achieve bigger goals that go beyond product usage and delivering software. They understand the user experience with the product will make or break relationships and deals.
That experience I’m talking about goes beyond features you put in the actual product. Customers can feel when there’s disconnect inside an organization. The better you are able to build relationships with your partners across the business, the more likely you’ll be able to deliver a more solid overall experience that customers want to come back to because you’ll be on the same page, working towards that experience together.
If you’re solely focused on new features, you’re looking at one slice of the pie. Partnering with your CS team will allow you to understand pain points that impact churn and NRR when you consider what your product currently delivers. Conversely, if you’re only focused on enhancing current capabilities, you may be missing out on opportunities to gain new market share. Partnering with your Sales and PMM teams will allow you to understand where you can experiment with new capabilities, and bring both new and old customers along for the journey.
But all of that is difficult to do unless you put yourself out there and build solid relationships with the people and teams generating and keeping revenue. The earlier you do this in a smaller company, the better it is for you and your customers. When you’re in this sort of environment, it’s less likely that you’ll have process and/or systems in place to access all the data you need to make better product decisions. In meeting lots of people who love the thrill of smaller companies, I learned the mentality is shared - roll up your sleeves, and win together.
The access to customers
One thing I love hearing from my customers is ‘Sorry I was late due to a customer call’. Same. Access to customers for smaller, earlier companies is almost limitless, as long as you have defined your space well. People want to talk and share how you can solve problems for them. Do not deny them (and you) the chance.
Perhaps this is because there’s less red tape and processes as compared to companies that are larger. Maybe it’s because Sales and CS want you to talk to every customer as the product expert. Your investors may have access to a whole network you can tap into as you build something incredible. Or maybe people just really like your product and want to help you win. Whatever the reason, bask in the glory and the feeling that you are able to gain so much qualitative insight from customers.
If you’re an introverted PM, this is a wonderful way for you to spread your wings and get closer to problems and solving them. If you’re an extrovert, make sure you’re setting boundaries in your schedule so you can take your learnings back to your team with time to ideate and build. Customer time is precious, but it means nothing if you’re not learing and driving action from it.
The pace - buckle up
It’s no secret that you’ll likely put in longer hours (at least from time to time) at startups and scale-ups. The pace is something you’ll need to get comfortable with early on, but the best way to manage this is to learn how to establish your boundaries to keep your mental health in check.
One positive thing about the pace is that you’re moving faster, so hopefully you’re failing faster and learning more frequently about what’s working and what is not. This helps your overall team get product out the door faster and experiment in a more repeatable manner. Beware: the right environment needs to exist to allow for that last piece - experimentation is only successful when there is a healthy environment and stakeholders to support it. The earlier you can help influence and build a culture of healthy feedback and experimentation, the better the experience for the team (and your customers).
The opportunities after the opportunity
The last thing I will mention is that in a smaller company environment, there are often opportunities to fill gaps, or make something better. Raise your hand, because you’re more likely to get a yes if you want to do something to affect change in a smaller company than one where process is necessary to add something to your list. This probably goes without saying, but this shows that you are willing to go above and beyond to help move something forward, which does not go unnoticed by others in the company. This, combined with cross-functional collaboration, lots of customer time, and continuous learning while embracing the pace will give you more experience than you likely signed up for. Enjoy the ride.
Helpful links if you’re thinking about the move:
HBR - 3 Things to Consider Before Working at a Startup
Forbes - Want To Join A Startup? Consider Asking These 10 Questions First
Lenny: How the most successful B2B startups came up with their original idea