The Biggest Software Company Culture Mistake (& Other Advice From A Tech CEO)

Abby Sorensen July 2017 Headshot

A conversation with Isa Watson, CEO & Founder, Envested

Making The Cell Culture Media Of The Future – Today

Before Isa Watson launched a software company, she earned a Master’s in Pharmacology from Cornell and an MBA from MIT’s Sloan School of Management. Then she spent time as a chemist and data scientist at Pfizer, followed by a job on Wall Street as the VP of Digital Product & Strategy for JPMorgan Chase. Her background alone is fascinating enough to make you read what she has to say about running a tech startup. Watson’s talk, “Making Workplaces Work For Humans,” will be a highlight of the Business of Software conference on October 1-3 in Boston. She sat down with Software Executive magazine and SoftwareBusinessGrowth.com before the conference to share a preview of her talk.


Q: How did you end up in the software world?

A: I spent some time on Wall Street after business school working on strategy as a right-hand person to senior leaders. The one thing I found in the corporate world was that there is a strong correlation between grassroots employee engagement and the performance of those companies or divisions. I thought technology could solve a big part of this. I’m not a software person, but I am a product person. So to build the first version of Envested, I recruited an engineer from LinkedIn. My whole life and career have been built around trying to solve problems, and software is one way to do that.

Q: Let’s talk about culture. Why do so many tech companies want to talk about culture? And what aren’t they talking about and thinking about when it comes to culture?

Isa WatsonA: People expect a woman to give a talk about culture, right? What they probably don’t expect me to say is that culture has a huge impact on product and product development. People separate culture as a “nice to have,” but the reality is you aren’t going to have as strong of a product if you don’t have a strong culture. I can’t tell you the number of times people, including our investors, have been shocked to learn that our team is so small and has been able to produce so much. We were five people up until seven months ago, and even then we had customers like Wal-Mart. They didn’t even know we were that small.

The reality is a combination of different perspectives end up making the best solutions. For example, I believe in empowering engineers so they’re not just working in a bubble. Our team is a little shy of fifteen people, about half of whom are engineers. These engineers all attend our weekly product deep dive. It’s about a two-hour meeting headed by our product lead to help them get the full concept rather than just focusing on their particular code for XYZ. From time to time, we’ll also send an engineer with our product adoption specialist to see, on-site, how a new user gets set up. This way they understand first-hand what our users are like. It’s not like our engineers are on the road all the time, but they do get exposed to the real world, which pays dividends when it comes to the architecture. We have engineers who came from Google, Yelp, Zenefits. They are so incredibly curious about things they don’t know about.

Q: Aside from your talk, what other advice are you eager to share with other software entrepreneurs?

A: Being a founder and a CEO of a tech company, or even just any growing company, is really stressful. A lot of times we only think of what we need to do on the tech side or the budget side – all of the non-sexy things that go with being a CEO. But we also need to think about what will make an organization productive. When I talk about the evolving nature of the workplace, I’m not just talking about employee engagement. There’s a shift from focusing on work-life balance to understanding work-life integration.

Q: What is your biggest challenge as a CEO?

A: For me, it’s around prioritization and focus.

Q: What are some of the biggest mistakes you see companies make within their workplace?

A: Some of the biggest mistakes come from creating tenants of culture in a vacuum of just senior people who are usually middle-aged white men. Those senior executives will say, “These are the tenants of our culture,” and they miss the mark on how that resonates with the rest of the company. So then they’ll rewrite those tenants and spend tons of money on a consultant to help them. But that top-down presentation of culture is really hard to come back from. The best perspectives on culture come from the bottom up.

A lot of companies don’t empower employees to be honest and authentic. CEOs don’t realize that their perspective or view is actually not representative of the norm. Companies need to cultivate a culture of openness and create bottom-up opportunities to share feedback. What some companies are doing now to empower this bottom-up structure is to create a “culture committee” of peers who are junior and mid-level people. They’ll do things like create quarterly events and report back to the leadership team on employee feedback.

Q: Your talk at BoS is going to include advice on bringing your “best self” to work every day. What does that even mean?

A: If you think about when you are at your best in life, it’s almost always when you feel comfortable and can be yourself. I struggled with this on Wall Street because I struggled to “fit in.” I was surrounded by people in their 60’s who felt like work and life had to be totally separate, and I tried to do the same. But in my first review I got feedback that people didn’t trust me because they could sense I wasn’t being authentic. They didn’t understand that I was a 5’8” black woman who was a classical pianist with parents who were engineers because, in some ways, I would try to hide that background. For example, I’d find other pianists to jam with, but wouldn’t share that with coworkers.

Now I’m much more myself – I’m a millennial, I’m not afraid to say “that’s so dope.” But being your best self is about more than just your vernacular. It’s about being vulnerable too. I’ve had days where I tell our team, “Today isn’t the day. I’m moody, I’m stressed, I’m feeling pressure from investors.” When everyone can say that, you cultivate a much more cohesive workplace where people trust each other. It’s especially uncommon for men who have grown up in the U.S. to do this. Male CEOs have a lot of distance from their emotions, and it can be harder for them to bring their best selves to work.


Business of Software Conference USA 2018 is taking place in Boston at the Seaport World Trade Center, October 1-3. Other speakers this year include David Cancel (CEO, Drift), Rich Mironov (Author, The Art Of Product Management), Claire Suellentrop (CMO/Founder, Userlist.io), Jared Spool (Founder, UIE), and Tania Katan (Author, Creative Trespassing).

Tickets are available at a reduced rate for Software Executive Magazine readers – just enter the promotional code ‘SoftwareExec' to get a 20% discount