“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.

Alyssa Harvey Dawson is Chief Legal Officer at CRM powerhouse HubSpot where she is responsible for the company’s legal and compliance teams. She has more than two decades of broad-based legal experience overseeing corporate governance, corporate, M&A and commercial transactions, enterprise risk management, compliance, data privacy, intellectual property, regulatory and governmental/public affairs. Prior to HubSpot, Alyssa was Chief Legal Officer at Gusto and has held senior legal positions with Sidewalk Labs, Harman International, Netflix, and Autodesk. Alyssa is also a Board member of AppLovin (NASD: APP) and Make-A-Wish Connecticut. She serves on the Advisory Board of Quello Center, the Advisory Board of Georgetown Law’s Initiative on Gender Justice and Opportunity and was a member of the Alumni Board of the Michigan State University Honors College and Aspen Institute’s Tech Executive Leadership Institute.

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Tell us a bit about your remarkable career journey. What have been some of your motivations across organizations and lessons learned?

After graduating with a Journalism Degree and from the Honors College at Michigan State, I wanted to work for a bit before getting an advanced degree. I had decided that Law School, with its critical thinking discipline and versatility, was the right way to go. I loved the idea of practicing in the heart of where laws were made, so Georgetown University Law Center appealed to me. When I was thinking about law firms, I wanted to go to firms that had a strong, broad-based corporate practice, had a reputation for giving associates substantive work right away and represented clients in industries that I cared about. Both Latham & Watkins and Cooley fit the bill. At both of those international law firms, I was responsible for transactions and advising sophisticated clients on how to move forward with key aspects of their business - whether through a merger or business partnership, collaboration, or by raising or providing venture capital financing, by licensing (in or out) technologies, getting key government approvals, public company work, etc.

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When I moved to companies, I kept pushing myself to be a part of teams or efforts where I was exposed to and had to master a lot of new things. For instance, at Autodesk, I went in thinking I would do more public company securities work and more M&A, and I ended up taking on new tasks and a series of roles with increasing responsibility, including managing sales legal matters and advising businesses. As a business unit attorney, which is sort of like a mini-GC, I needed to understand how to help the company structure terms for new business models, and really dig in and learn about intellectual property, antitrust, privacy and other really technical areas of the law.

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At Netflix, I developed a comprehensive intellectual property strategy in addition to working closely with business development and product teams to essentially put together a technology and products strategy that related to their then-emerging streaming video business model. This was an incredible time, full of growth opportunities and firsts. I had always prided myself on helping companies navigate risks, and this really expanded my thinking and approach. That work led me to Harman, the audio and infotainment company that was facing increased competition from non-traditional players and needed to shore up its tech transactions and global IP strategy, amongst other key initiatives, and I got the opportunity to put together and lead a strong and dynamic global team while fostering deeper ties with technology leaders. While there, I ended up doing a business development function and implemented a technology and brand licensing business, which was a fun adventure.

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It was after Harman was acquired that I realized that I had amassed this knowledge and understanding across an array of legal and business areas, mostly in tech, and I was interested in the next step and in both building and helping companies reach new scales. Sidewalk Labs, at the time an Alphabet company, gave me a tremendous opportunity to do that and then Gusto, which was further along on its journey and pushed me even further.

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And now at HubSpot, I love working with a strong, global team that is passionate about what we are trying to do for our customers and will not hesitate to explore new opportunities, like AI. If there is a common thread, at these companies, I was around people who believed deeply in what they were trying to achieve, cared about delivering to their audience and customers and wanted to be the best at doing it.

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HubSpot is well-known for its company culture. How do you achieve that reputation as a global, hybrid company?

We obsess over culture at HubSpot, just like we do our product. Our main focus is to build a company culture where people can do their best work. This means offering three flexible options for employees to choose from: @home, @office, or @flex. All HubSpot employees are empowered to choose what works best for them and build work around their lives, instead of the other way around. Embracing this global hybrid model has helped us create a more diverse workforce along with inclusive programming that ensures all employees are able to experience and enjoy HubSpot’s culture.

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What’s in store for the legal profession as new innovations like AI take hold? How do you stay ahead of the curve? How do you evaluate potential risks?

I love to embrace innovation and change. That’s why I have enjoyed being in tech all of these years because the pace of change is enthralling. When I think about AI, it has the ability to automate the routine and enable focus on higher level work. There are many tasks that we do everyday that it can have an impact on. At a higher level, the ability of AI to process and analyze massive amounts of information has the potential to be so impactful in the legal profession - right now you need a human to review, digest and assess when you do document review or diligence or are looking at the connections between a range of contracts or pieces of information, laws, legislation. Imagine an engine that can do that first cut of distilling, analyzing, summarizing and could do it with a high degree of accuracy. Or the first drafts of a brief, motion or argument. Those could be real game changers.

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The legal profession, like any other, should be aiming to stay not only current but also be looking ahead. That means leaning in, understanding and embracing new technologies. Here is my combination for staying ahead because it’s not any one thing: 1) stay connected with colleagues and businesses that you admire and useful news, industry and other information resources; 2) work with organizations like the Future of Privacy Forum and the BSA/Software Alliance; 3) find strategic, business-oriented pragmatic outside counsel, and 4) have an in-house team that is aligned with the business strategy, understands the value of taking smart risks and loves being innovative, creative problem-solvers.

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And, to evaluate risks, you have to make sure you are grounded in what will serve your most important constituency - your customers. You also need to have some foundational principles, like maintaining trust, being transparent, ease of use, ease of understanding, and doing what’s right. Those will help guide you. As you get further along in your company journey, having a good understanding of your company's risk tolerance, risk appetite and positioning is also key.

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Describe one pivotal moment in your career that was truly defining for you in one way or another - an opportunity that changed your life or a moment where you recognized defeat and changed course.

I have a few but one that stands out is from my first GC role. There was a moment where I realized that I needed to step up and take responsibility in ways that I had not had to before. I was thinking about ways that the organization needed to evolve and instead of looking for others to do it, I realized that I was accountable, had to have the hard conversations, had to make the decisions and it was my responsibility - I could not simply look to others. Knowing that you need to exercise your responsibility properly is an important realization. That was a key learning and lesson.

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What’s a piece of advice you would give to yourself 10 years ago, if you had the opportunity?

I have a bit! Relax; it will work itself out. Don’t fret about what you cannot control - focus on doing the best at what you can, take the feedback, there is a lesson to be learned in all of it, the good and the bad, and surround yourself with good people because no one walks this journey alone.

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What’s one thing you’ve done successfully, personally or professionally, to empower the next generation of underrepresented leaders? What’s one thing you want to take on next?

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Support promotions/advancements/access to growth areas for team members. I’ve had team members eventually become my successors in leadership roles or go on to lead or take on new areas that led to growth and development. If you are able to be in the room where things happen, people get discussed, speaking up is important.

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What I would like to take on next: I’m doing what I want to do next. We have a great opportunity at HubSpot and a core focus for me is creating the environment where folx can thrive and be their best. I also am on the Board of AppLovin, an advisor to and supporting of my universities - Georgetown Law and Michigan State University, where I get opportunities to give back. I’m also on the Board of Make-A-Wish Connecticut, plus this opportunity at Operator Collective. Each of these opportunities allow me to stay connected and in touch.

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What’s your secret super power?

Being flexible. I have a lot of opinions and perspectives but they are not always strongly held. I’m open and happy to follow a strong lead. If you have a good argument, solid rationale, reliable data or honestly a much more strongly and reasonably articulated conviction, I’m willing to give it a try. That’s why I like to surround myself with folks who are smarter and have different skills than me - there’s no one way and having a diverse set of folks around opens you up to so many more possibilities than you would otherwise come to on your own.