“How did they do that? How did they get there?” Companies succeed because of the people who build them - operating leaders who grow businesses to new heights and make decisions every day that can impact entire industries. Each month, our Operator Spotlight gives you the inside track from one of our incredible Operator LPs (Limited Partners) who are changing the game – building and scaling some of the world’s most successful companies. Read on for lessons learned and mistakes made, perspectives from the top, practical advice, and ideas on what’s next. 

This month, we spoke with Cathy Polinsky, CTO of the data privacy control center (and OpCo PortCo!) DataGrail and Board Director of Aetion. Cathy has an incredible background leading engineering and technical teams at iconic, groundbreaking tech companies like Shopify, Stitch Fix, Salesforce, Yahoo!, Oracle, and Amazon. Operator Collective’s founder Mallun Yen was an early investor in DataGrail, and introduced Cathy, then CTO of Stitch Fix, to Co-Founder and CEO Daniel Barber in 2019, as part of OpCo’s diligence process. The pain points DataGrail was solving resonated so much with Cathy that when there was an opportunity to bring on a few high value angel investors, Cathy joined with her first ever angel investment. After staying in touch over the last few years, the time was finally right - DataGrail welcomed Cathy as CTO in July, just ahead of their $45M Series C announcement. 

Tell us a bit about your journey leading Engineering, Product, UX, Security, IT (did we miss any?!) across these incredible organizations. What have been some of the throughlines across your career? 

I love leading a variety of technology teams. In addition to that list, I have also had roles leading quality, support and product design. My path to CTO started first through software development. I studied computer science in college and at the peak of the dot com era, landed at Amazon in 1999. Amazon was in full hyper growth mode, transitioning from selling books and video to becoming the everything store. From when I signed the offer letter to my first day, we doubled in size and then doubled again in my first 9 months. It was a thrilling time to be in an environment full of technologists coming together, building at scale to disrupt an industry. 
After working as an engineer at several companies, I transitioned to engineering management at Yahoo!. I worked on their advertising systems which today makes a lot of people uncomfortable, but we were maniacal about respecting customer data. It’s where I developed one major throughline across my career - trust. Building a strong culture of trust within your organization sets the tone for your customers, and ultimately the brand. It’s also where I picked up another throughline - the value of strong leadership. I interviewed for an IC role and a people manager role, and chose the latter.

I loved the transition from building software to leading teams. At Salesforce, I sat on the leadership team for an emerging business unit, exposing me to how various functions worked together. The experience and the vantage point across the end-to-end business really set me up to take on the CTO role at Stitch Fix. At Stitch Fix, I was in charge of product, engineering, security, and IT and helped take them public. These were all new things, but the partnership and mentorship from founder and CEO Katrina Lake was a key confidence boost. 

Having a broader leadership remit across the whole technical side of the company, and focusing on trust, ultimately led me to DataGrail. I’m passionate about data-driven technology as well as data privacy, and I love that I am working on a product where we help companies manage their privacy program so they can continue to grow their business.

What’s something people often get wrong about technical teams, and how do you manage against it? 

One thing that I hear managers say is that they want to shield their engineers from the rest of the business. I actually think that you should do the opposite. Great engineers that I know are really motivated by understanding how the products that they are building are being used and sold. They can make better product and design decisions when they hear of issues in the field or customer requests. And they get fired up when we close a big deal. But it is also important that they have clear prioritization and flow time to focus on their work. If you arm them with the right information about priorities and company strategy, then your engineers can make the right decision on how to stay focused, or even say no without you needing to shield them from other departments.

You’ve made the jump from larger enterprise companies to smaller, high growth companies - what have been some of the most impactful lessons from those moves? 

I am loving the stage that DataGrail is in right now! But one thing that I have learned through my career is that there are so many different lessons you can learn at different stages. In fact, the biggest benefits lie in taking insights and expertise from one stage and bringing it to another. 
The speed and flexibility of early stage company building is so exciting - you can put everyone in a room and make a fast decision or pivot. Everyone understands the business and the tradeoffs, and is in it together. Change is hard to do in a bigger company and can be much more significant. But you can see the impact at a much bigger scale. Stakes are high for later stage companies and you have more resources to invest. You’re also able to focus and specialize in a completely different way. 

I’ve learned a lot about myself through each move. I love to build, and am particularly enjoying applying lessons from my large-scale tech experience to this early stage energy when it comes to building teams and products.  That’s why the opportunity at DataGrail is so fulfilling - the moment we’re in is a very special one. 

Have you adapted any practices in response to the current macro environment? How are you thinking about your strategy for 2023, and any predictions for what’s to come? 

At DataGrail, we’re continuing to focus on building the best privacy platform in the industry. The current macro environment is not impacting our ability to grow and focus on our long-term mission.  In fact, we believe we’ve entered the privacy great awakening, which will only encourage more brands to put a bigger emphasis on building great privacy practices. We just raised our Series C, and we’re well positioned and funded. In truth, it’s a great time to be an early stage company that creates value. Privacy is mission-critical to every business, and we’re not slowing down. As we look ahead, more and more of the world’s population will be protected by privacy rights, only expanding the opportunity for DataGrail.  

What are the most important traits you hire for when building out your technical teams?

It’s important to understand what stage your business or team is in and make sure you are hiring the right team for the right stage. When you are just getting started and only have a few people on the technical team, they need to be able to do everything - from setting up the infrastructure, deployment pipelines, frontend, backend, quality and on-call. They also need to be able to talk to customers, interview and hire new engineers and architect systems. In that stage, you need people who have a broad range of skills and love wearing different hats. Over time and as you scale, you develop more specialization. You may have a team just focused on platform and infrastructure work and a team focused on developer tools and deployment pipelines. It doesn’t make sense for everyone to do everything and you’ll naturally attract more specialization. 
Regardless of stage, two things I look for most are drive and customer empathy. We work in an amazing industry that is constantly evolving, and I have found that the people who are most successful have a drive to solve problems and an obsession for customers. I love meeting people who love what they do and who are passionate about their craft, but who also have an inquisitiveness about others. Building new technologies and products is not always easy but through grit, persistence and customer focus, teams can accomplish amazing things.

How have you made a mark in your industry? What’s something you’ve done that’s perhaps counterintuitive in your field - broken any rules with interesting results? 

In some ways,  being a women CTO is being a rule breaker. It’s still one of the least gender diverse roles in the C-suite, more so even than the CEO role. Early on in my career, I didn’t want to break any rules or stand out as a woman; I just wanted to be valued for my work and my contributions.
The younger version of myself tried to emulate the aggressive tactics that I saw other male leaders use in times of conflict. But honestly, it didn’t work. It wasn’t effective and didn’t make me feel good. After I switched jobs, I told myself that I would never fall back on those same patterns and instead really invested in relationships with my peers and understanding different parts of the business. When conflicts or disagreements inevitably came up, it was those relationships that helped us stay focused on the problem and our customers instead of our egos. Only when I stopped trying to be someone that I wasn’t and instead felt comfortable with my own authentic leadership that I really grew as a technology leader and executive.

What’s a piece of advice you would offer to others who are just starting out in tech?

I often recommend people starting off in the industry, when they see problems that bother them, be a part of the solution. I went to Amazon in 1999 after graduating from college and everything was growing and changing so fast, which was particularly challenging as a recent grad. There weren’t any tech onboarding or training programs - so I helped organize one for new college grads. It wasn’t part of my day job, but I learned so much while gaining additional leadership skills. You can build credibility and experience when you help solve problems that you see.