Observations From My First Year as CTO of a $1B Startup

Chris Bee
6 min readJan 2, 2022


Photo by Avel Chuklanov on Unsplash

Just over a year ago, I made the leap from a leadership role at Zillow to CTO at Lessen. It’s been a wild ride ever since. In just one year, we’ve grown Lessen from an early stage, seed-funded company with a modest $19M valuation and 50 employees to a $1B valuation and over 300 employees. We’ve built an amazing tech team full of great people who are dedicated to the mission and passionate about their work. The customer opportunities in front of us seem endless. Here’s a few things I learned (and validated) making the leap from big tech to helping build a unicorn startup.

Startups provide ultimate ownership. The nice thing about an early stage company is you and your team get to fully own solving problems and mitigating risks. There’s no one else to blame if things don’t go well. Challenges are a lot more motivating when you have the creative freedom to attack them head-on without the weight of legacy decisions, tricky organizational boundaries or massive tech debt that you often find in bigger tech companies. One other refreshing things about being in a smaller company is the relative low number of other people/plans/departments that you need to align with. If something needs to be done or an area needs to be addressed, my team and I have the ability to think big, take ownership and deliver results with minimal roadblocks. As we continue to grow at Lessen, we will build a culture that keeps ownership and team empowerment high.

You will wear a lot of hats. We’ve all heard this about early stage companies. However, I found you will wear hats you never thought about. For example, a typical day for me might include everything from deciding on endpoint security measures for contractors to writing copy for our website to negotiating office lease terms to shaping our new hire equity process to helping create a slide deck for a sales call to evaluating a new SaaS partnership. This is in addition to my “day job” of leading the tech teams, building the teams and helping ship product. This is true for not just my role, but every role in the company. In the early stages of a company, you really need to be comfortable being a bit of a generalist and enjoy solving problems, including a lot that are outside of your background. Nothing is out of scope.

Fundraising takes a lot of effort. While it is true that there is a lot of VC capital looking for a place to go right now, it does not mean that it freely flows to anyone who needs it. Fundraising takes real effort. There have been volumes written on the fundraising process. It boils down to having sound business fundamentals, showing the ability to scale and demonstrating how you are uniquely positioned to solve a large unmet need that people or businesses are willing to pay for. You need to be able to tell that story really well in your pitch deck and in your supporting documentation/financial modeling. Beyond that, there’s a delicate game of timing to play by gearing up to pitch to a lot of investors in a short burst of time, similar to listing a hot property for sale and specifying an offer review date. While doing all of this, you need to have your team and process established well enough that you can step away from much of the day-to-day for a month or two while fundraising.

Decisions have more impact. In a larger company, a single bad decision will not likely tank the company. However, in early stage companies, even small bad decisions can have lasting repercussions. For example, not prioritizing the right features, making a tech platform choice that slows you down or not having a thoughtful org structure can all cause major problems. Each person’s impact is outsized compared to big tech companies with thousands of employees in similar roles and layers of management. One employee or manager not aligned with the mission or struggling in their role can steer you off course quickly. It is important to have a strong set of company values, clear goals, a defined strategy and empowered teams. It is also important as a leader to be transparent, set clear expectations and give people the support and guidance they need so they can make good decisions independently. Investing in people and people process at a startup is crucial as each person’s impact is outsized, both positive and negative.

Recruiting takes real focus. While this true for any tech company, when you don’t have a household brand name or public equity and outsized perks to offer, the mission, the people and the opportunity matter even more. More than ever, people care about what they work on, who they work with and what opportunities they will have to grow. You need to have a noble mission, a great team culture and boundless opportunity for growth to recruit top tech talent. It is as much about having an exciting vision that is compelling as it is about the actual business and product that people will work on. In addition to the potential equity upside, personal growth potential and opportunity for impact are key reasons people will choose to join a startup. You need to make it clear to candidates how you will deliver an amazing career experience for them.

The problem space matters. Not every startup has the potential to be a $1B+ company. If you are considering an early stage startup, I think asking yourself if you can see this company 10x’ing is a key question. If you can’t see it from your point of view, it may not be the right fit. I’ve been introduced to a lot of startups over the years where I didn’t personally see that level of potential, but when I learned about Lessen at the end of 2020, I immediately saw the opportunity. I saw a huge need for technology in the property services industry. I saw an opportunity to build something that will help millions of people find sustainable work and build their small businesses. I saw a business model that had massive revenue attached to it. From my personal experiences plus my time at Zillow, I also knew there was a huge opportunity in this space. Property services work feels like one of the final frontiers that tech hasn’t truly transformed yet. I’m also personally passionate about marketplace problem spaces and matching skilled people with the need for their services, which is exactly what Lessen does.

It’s worth it. Making the decision to join an early stage startup has been both the most challenging and most rewarding career step I’ve made so far. I’ve been thinking about making such a leap for a long time and have had countless discussions with founders and startup recruiters over the years. However, it was very difficult to leave the secure positions I had in big tech that I worked really hard to achieve and take a risky leap into the unknown. Like some of you reading this, I’m married with young children, a big mortgage, and bills to pay. However, after a lot of self reflection in 2020, I knew leading a startup from the earliest stages was the only way I would ultimately feel fulfilled. I had to take all I learned and apply it in a meaningful way to a vision where the original product, teams, strategy and culture were still being created. Everyone’s story is different, but I finally feel like I’m exactly where I’m supposed to be.

There’s so much opportunity at Lessen, and we are just getting started. We are hiring! If you’d like to learn more, check out our open roles here.



Chris Bee

CTO at Lessen. Former Zillow., Uber, Amazon, Microsoft. Self-starter musing about leadership, product development and motivation.