How Being a Startup Cofounder helped my Big Tech Transition
Leadership lessons learned on my journey from a startup to a large tech organization
May 1, 2023
I recently joined Microsoft leading engineering efforts for the Virtual Events space. Before that, I cofounded LegUp, a startup in the early childcare space which we sold early last year. And before that, I was part of Expedia, serving as the CTO of the CarRentals.com brand. This trajectory took me from corporate engineering executive to startup founder and back.
The shift between these two worlds is large. I previously wrote about my transition into a startup cofounder role. I’ve been back at Microsoft for six months and wanted to share how lessons from my startup years shaped my current role.
Culture Matters
One of the big draws for me in starting a company was the ability to set the culture. To set the tone for how we operated and grew the company, beyond the technology decisions. At a startup, this not only matters, it’s critical to the success of your company. You can’t compete for talent without a hook to convince people to take a risk at a lower base salary.
But it matters in a large company too. I’ve long believed that every team has a culture — leadership teams can craft it or it can grow organically. But make no mistake there will be a culture, and if you’re not careful, it may not be what you want. It’s not enough to put together a set of values; you need to lead by example and continuously show them. My team had been through several reorgs, leadership changes, and product priority shifts over the previous year. My first task was to come in, reset the team’s culture and lay down a vision for our engineering efforts. My startup experience told me that it was more important to establish how we would operate before anything else.
Sense of Ownership
One of the reasons I moved to a startup was the ability to have an outsized impact. As I put it in my previous article
I wanted the thrill of change and an environment where what I did mattered. I wanted to grow and guide a company beyond the technical vision.
In my three years with LegUp, I achieved that. I didn’t just build a technology stack from the ground up - I shaped the culture and norms of the company. I went into childcare facilities to see how they operated. I gained an understanding of the challenges of filling openings from the provider perspective. Above all, I listened more than I talked.
We delivered a solution that solved a critical customer pain point. The problem was, while I had deep end-to-end responsibility, I was only impacting about 400 childcare partners. In considering a move back to Microsoft, the ability to impact hundreds of millions of monthly active users was attractive.
One thing that I brought with me to my new role is that sense of ownership. Many at Microsoft, especially in engineering roles, think of ownership as system responsibility. Being on point for livesite support, design reviews, and code reviews. I’m going beyond that and have been getting my team involved in customer calls — not just escalations but discovery sessions. I want my team to understand the customer pain points and end-to-end needs that go beyond our product. This sense of understanding helps us build what the customer needs, not what we think might be “cool technology”. By setting the right tone in my team, I’m encouraging and empowering everyone to hear this customer voice. You don’t need to lead an engineering team to have a true sense of ownership within a company.
You don’t need to lead an engineering team to have a true sense of ownership within a company.
Being Scrappy
LegUp was not a large company. We never had more than 6 engineers within the team, and we all had to roll up our sleeves to do what was needed. We tested new product features, doubling down on winners by flushing them out. We supported our cloud infrastructure. And we performed “internal IT” needs for the company all at the same time.
You might think that a big company doesn’t have these problems and compared to a startup there’s some truth to that. Separate teams focus on different parts of end-to-end product delivery, DevOps, and IT needs. But companies are tightening their belts. The largest tech companies have all had layoffs, many reducing their workforce 10% or more. Even though team sizes may be reducing, those left behind are expected to keep up the workload if not do more. A mindset of how to achieve more with less helps.
At Microsoft, this has meant clearly laying out our responsibilities and priorities. It means re-assessing what done looks like to focus on top customer needs. I’ve shifted my team’s responsibilities to leverage common work items and individual strengths. It takes resolve to execute without defaulting to putting together a case for more headcount. In today’s environment though leaders with this scrappy mindset will go farther.
Strategic Thinking
A reality of early startup life is the need to constantly think about the survival of the company. This means thinking beyond your product. It means thinking about how you position yourself, how to make sales and bring in revenue, which partnerships to pursue, and how to think about external fundraising.
Most mature companies don’t have this level of existential concern. To achieve their scale, they optimize locally — hiring and placing people in roles that let them become masters in a smaller surface area. This makes it harder to think or act outside your area, and consequently many feel they don’t have exposure to strategy. That was my mindset earlier in my career, but no longer after setting company direction from all angles. I’ve found that my management supports and encourages me to go beyond my bounds and be more involved in other areas. You may run into over protective individuals who make it seem otherwise, but if you’re a talented individual or leader, companies want you to look beyond your area to grow your skills and provide unique perspectives. My startup time turned this into a natural mindset for me.
Companies want you to look beyond your area to grow your skills and provide unique perspectives
Conclusion
I’m lucky that I’ve had a variety of different experiences in my career. Large company vs startup is one dimension, but if you have the opportunity I recommend giving both a try. You’ll find a lot of differences. But a lot of skills transfer and will give you a unique perspective in your team. After all, diversity of thought is a bedrock of a well performing team.