TCT Exclusive: Stephanie Friedman, Angel Investor, Advisor & Board Member

We’re thrilled to announce this week's exclusive with Stephanie Schatz Friedman, an experienced operator, Angel Investor, Advisor & Board Member.

With 20+ years of operating experience, she’s helped build and scale GTM teams with an excellent track record of success (SUSE Linux acq. by Novell 2004, Xamarin acq. by Microsoft 2016). She’s also an active angel investor (Netlify, amongst others), Board Member (Apollo GraphQL) and special advisor to the CEO (Zeplin and Front). We discussed:

Stephanie Schatz Friedman: Angel Investor, Advisor & Board Member

TCT: Thanks for sitting down with us, Stephanie. Let’s jump in.

How did you start out with regards to your career? 

I fell in love with sales and negotiations at a very young age. My mother was a single mother, and in order to pay for college I worked as a translator on over 120 international trade shows, translating negotiations between buyers and sellers from all types of industries. So by the time I finished college I had seen and heard more negotiations than most people half-way through their career. I became really passionate about understanding the psychology and the science of sales and negotiations. 

You joined Xamarin in 2014 as the first non-engineering hire and went on to build the sales and customer success organization from zero to almost $50M in run rate sales in less than 4 years. What was your secret for success?

I had collected a lot of deep experience in the different areas of sales (Enterprise, bottoms-up high-velocity sales as well as channel and partner GTM) and taking this leadership role at Xamarin allowed me to bring all of it together and become very intentional about what to do when. 

I set an extremely high bar for my team.

I would interview dozens of people before making one hire, and I focused on hiring people that were not only extremely smart and ambitious, but also kind and fun. As a result I really, really loved working with my team, even when the team was over 100 people; but most importantly, the people on my team also really loved working with each other. Many life-long friendships have been forged as a result of us working together at Xamarin, and building that team might actually be the accomplishment I am the most proud of.

Lastly, we were super customer focused; determined to delight our customers not only with our product but also in every interaction with our customer facing team. “Create value at every interaction” is great advice, but I think you need even more than that. I would phrase it: “Delight your customer with every interaction”. 

Shortly after, you were acquired by Microsoft. What was this transition like? What are the pro’s and con’s of being acquired by a large company? 

Being acquired by a large company is always a big change for a startup, and this was the 3rd time I was part of a company that was acquired.

I have nothing but good things to say about Microsoft.

I have the highest respect for Satya and his executive team, and Microsoft treated myself and my whole team extremely well. They were very thoughtful during the integration phase, and learned a lot from previous acquisitions on how to not kill a startup through an acquisition. 

The reality though is that in the end, an acquisition needs to make sense for the users and customers of the acquiring company, and that often means eventually integrating the product, and the team, into the larger organization. With that, automatically comes a significant change with regards to processes and decision-making style.

You took a sabbatical in 2010 to travel in between startups. What were some of the big takeaways from this trip? What would you recommend to people thinking of taking a sabbatical in 2021?

Getting out of your own reality and seeing the world from other people’s perspective is a very healthy thing to do. It puts everything into perspective, and also helps you appreciate everything you have. We spent most of our time traveling with a backpack through remote areas of Asia, Africa and South America (check out SheTravels.org for more on this).

Wherever you travel, there you are.

If you want to do something or change something, you just need to do it. Waiting for changing circumstances is never the answer. If you want to work out every day, for example, you need to find a way to build that into your daily routine, not wait for a time when you for some reason have less work. 

At that time, both my husband and I were in between companies and had the option to choose where we would want to settle down after our travels (we were living in Europe at the time). I realized that I wanted to be in the Bay Area, and stay involved in the technology and startup world. It’s such a great place to learn about new topics every day, and constantly talk to smart and ambitious people that are working on the coolest project. And if I can play a small role in helping some founders and companies along the way, that makes me very happy. 

Are you working on any passion projects? If so, can you tell us more about them?

Yes, I have been involved in animal welfare for quite some time and actually started a dog rescue organization (Love Dogs Rescue and Foundation) in 2019.

Even though I only spend a few hours a month on this topic, it is one of the most rewarding things I do. Every year, tens of thousands of homeless dogs have to be euthanized in California’s county shelters as the shelters keep running out of space. Our focus is on saving hundreds of homeless dogs every month by organizing and paying for transport from the California central valley to LA and San Francisco. Once in a city, those dogs are being adopted into loving homes often in a matter of days. I call this canine arbitrage :-) 

We also acquired a specialized medical van that we placed in the Central Valley and offer free spay / neuter clinics for people who otherwise couldn't afford the procedure. This will ultimately be the best solution to significantly reduce the number of unwanted and homeless puppies (and kittens). 

Most importantly though, I don’t only think about helping those dogs find a home, but often give so much joy to a person or family by adding a canine to the mix. 

I would love to engage other startup founders and investors on this mission, as so many of us enjoy having dogs in our homes and offices.

I am also an avid salsa dancer, and was even part of a performance team, but with COVID-19, that will have to be on hold for quite a while.

You’re an active advisor to a few high profile CEO’s. What are some of the biggest challenges they face today?

Most of the CEOs I work with really care about their people. 

Since COVID-19 hit, a pressing topic for CEOs has been around remote first work environments. CEOs are struggling for answers to questions like these:

“How can we bring the highly productive atmosphere we were able to create in the office, into a remote first environment, which relies heavily on video conferencing?”

Another big topic I often work on with founders is how to efficiently scale a company and build out a high-performing GTM team while still keeping it a great place to work. Questions like “What should the profile of my first sale hire be? When should I hire a VP Sales or Marketing?”. I spend a lot of time interviewing potential executive hires and helping founders build out and manage a powerful executive team. 

How did you get into Angel investing? What was your latest investment?

I ran a tight ship at Xamarin with regards to building out our go-to-market, but we also built a great culture, so that people loved working there. Overtime, VCs asked to introduce me to some of their portfolio companies, and then those founders started to introduce me to other early stage founders which quickly led to opportunities for early stage investing. 

My latest investment was Tailscale, a great company that is building a modern and easy to set up version of a VPN. They were doing great before COVID-19, and are now even more relevant as they make remote work easier and safer. 

What’s your secret for getting on the cap table?

I usually invest in companies when I really like, and respect the founder(s) and find myself looking forward to spending time helping their company grow.

What’s your biggest cap table “mistake”?

Saying no to an Angel investment in a great company (I knew that it would be a great investment) because of the fact that they were somewhat competitive to a company I had invested in before. 

What do you do when you don’t work?

We have a three-year old daughter and I just really enjoy spending time with her and my husband. I find the simplest things to be most fun, we will sit on the floor and read books or play games, or go on family hikes or bike rides. I imported the European tradition of using a box bike, and taking kids around that way is so much fun for them and at the same time great exercise for the adults :-)

The year is 2030. What’s the state of Enterprise Software?

Many more verticalized, specialized Enterprise Software solutions.

Many companies are still at the very beginning of cloud adoption, and it will have very much become the standard by then.

We have adopted an open-source approach for a lot of areas, other than just software development. 

Thank you for your time and thoughts, Stephanie. We look forward to the continued success of you and the various organizations you’re involved with!

In December, I profiled Canva, the unlikely Australian unicorn by CEO Melanie Perkins, for our Under 30 issue.

Now the design software company is valued at $6 billion after raising another $60 million amid a coronavirus usage boost.

https://t.co/sS07Zx3ivZ

— Alex Konrad (@alexrkonrad) June 22, 2020

Sources: Crunchbase, Twitter, LinkedIn