What best prepared you, coming from a large legal org, to be a sole lawyer at a small company? What helped you in making the transition to running the legal team from scratch? I first joined Checkr as their GC when it was 60+ employees with a small legal team of 2 lawyers. When I joined Hopin as their first lawyer and CLO, it was about 250+ employees. At both organizations, I hired and grew teams with 20+ professionals as they both scaled rapidly. I was able to successfully transition to running and building a legal team from the ground up mainly because of my earlier experience at a small legal team at a startup. Given the small size of the legal team, I worked on every subject matter ranging from commercial, corporate to IP and even represented the company in a mediation. Doing so allowed me to become a great generalist who could issue spot any topic at hand and hone my prioritization skills given limited resourcing.

What issues did you tackle first? GCs should generally focus on whatever makes the deepest financial impact to the business and drives the business forward.

With that focus in mind, the first thing I tackled at Hopin was building out the commercial team to support sales. In any non-regulated company, you need to prioritize revenue and work on whatever deals have the highest monetary impact. I then tackled M&A and financings given the importance of these deals to the business. For example, in my first year at Hopin, we closed 6 M&A transactions and 2 financings, which is an incredible volume of deal activity for a 2-year-old startup.

At Checkr, which was a highly regulated business, my first priority was compliance because a compliant product drove revenue for that business. So it was important to focus first on building a compliant product to drive the business forward.

What substantive area did you hire for first? How did you make that decision and what did you look for in that person? This also depends on the industry. In a highly regulated industry like Checkr, I needed to hire compliance attorneys to ensure the product was compliant. I also needed to hire a commercial counsel in parallel to help sell the product.

In a non-regulated company like Hopin, I prioritized hiring and building out the commercial team since they support our revenue stream. I then hired a corporate counsel because we were incredibly active with corporate transactions at Hopin. Our level of M&A and financing activity was incredibly high, which is why I hired a corporate counsel earlier than most companies. But most companies hold off on a corporate hire until they are closer to IPO.

When hiring at a startup, I always look for someone who is flexible and agile since they will need to adapt their risk appetite in a startup environment. I also look for someone who loves to learn since they have to keep pace with the constantly changing nature of a startup business. In addition, I look for approachability, high EQ, and strong communication skills since they will need to build relationships with the business. The first group of lawyers will help set the tone and culture of the legal department to business and will help determine whether the business feels comfortable reaching out to the legal team so it’s incredibly important to find attorneys who are approachable and easy to understand.

What is the most rewarding part about building a legal team from scratch? I love the ability to shape the team culture and structure from the beginning by hiring the best talent and developing and promoting talent from within. It has been incredibly rewarding to groom leaders who can succeed after me and lead the organization in its next phase of growth.

I’m also passionate about building a tight and collaborative team who are approachable to the business. So it’s incredibly rewarding whenever I hear from our business partners that our legal team is the best team they’ve worked with and I take pride that I helped shape our legal team’s culture of partnership with the business to garner the respect of the business.

Building from scratch has its challenges, what made you want to take this on? While challenging, I have taken on building teams from scratch because I love shaping teams structure and culture from the start. It’s easier to shape culture, values, habits, and risk appetite from the beginning versus coming in as a new GC and trying to change legacy team structures, habits, and risk levels while trying to build trust with your new team in parallel.

What would you advise someone who's taking on a similar role/challenge? The great thing about being the first lawyer is that you have a blank canvas so it’s an opportunity for you to build a team that you’ve always wanted to be a part of. So think about all your learnings from what’s worked and not worked in your past roles and the times that you thought you’d do things differently than your former GCs and leaders. You have a blank canvas so use your past experiences and learnings to build the team of your dream!