What is your favorite quote?

I’m going to repeat it verbatim because I just saw it and it’s from Miss Serena Williams and what she recently said in her Harper’s Bazaar article was, “It’s not about quitting when someone presents challenge. It’s about getting up when you are down, dusting yourself off, and asking, ‘Is that the best you got?'”

JENNIFER: What are your current responsibilities?

ALYSSA: I am general counsel and head of legal, privacy and data governance. That means that I’m responsible for all legal, compliance and enterprise risk management matters for the company. This includes areas such as transactions, privacy, data governance, intellectual property, commercial deals, licensing, government compliance, corporate governance, overseeing legal operations, litigation, you name it.

JENNIFER: What are you currently working on?

ALYSSA: Issues that relate to any of the above for Sidewalk.  We’re a relatively young company and I’ve spent the last couple of years building out a legal model and framework that is designed to align with and enable our company’s vision and mission – which is that we seek to combine forward thinking-urban design and cutting-edge technology to radically improve urban life for individuals who live, work, and visit cities. We’re currently working on a proposal in Toronto related to the development of a section of the waterfront, called Quayside.  My team and I have been spending a lot of time helping to develop portions of that proposal, and providing legal advice and guidance on the policies, plans, regulations, laws, and business arrangements that are necessary to implement it.

JENNIFER: What was the path you traveled to reach your current position?

ALYSSA: Well, it certainly was not straight.  I came to Sidewalk after spending about 20 years learning from and working with extraordinary people at different innovative law firms and companies.

My main goal after graduating from law school was to try to have a career working in situations that would align with my interests, and this resulted in me working with dynamic and compelling law firms and companies.  I knew or thought—I should say I thought—that I wanted to work on the business side of the law profession.  When I started out, I tended to do transactional and commercial-oriented work for companies, both at the law firms and then when I went in-house.  It was doing those types of activities that led to me to different positions, areas of responsibility, growth and development during my career that eventually allowed me to accumulate a set of skills and experiences that led me to my current position.

JENNIFER: What were the points in your career when you experienced the greatest growth?

ALYSSA: Whenever I pushed myself and took on responsibility that was outside of what would have seemed my wheelhouse at the time. And that started from the law firm days when I was at Latham & Watkins and then at Cooley. 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 venture capital financing, or by providing venture capital financing, by licensing (in or out) technologies, getting key government approvals, public company work, etc. And while in my previous life as a journalist (before law school), I reported on business matters, I had no specific experience actually making business happen for companies  until I reached the law firms and got an education in how businesses operate and function.

From the law firms, 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, more M&A.  However, I ended up taking on new tasks and a series of roles with increasing responsibility, including managing sales legal matters, advising businesses, etc., all as a business unit attorney – which is sort of like a mini-GC.  For example, I needed to understand how to help the company structure terms for new business models, and dig in and learn about intellectual property, anti-trust and other really technical areas of the law.

Then, when I was at Netflix, I developed for the first time in my career a comprehensive intellectual property strategy.  I worked closely with corporate development and product teams to essentially put together a technology and products strategy that related to their then-emerging streaming video business model. 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. While there, I ended up doing a business development function when I conceived andimplemented a technology and brand licensing business.

Now, at Sidewalk, we are breaking new ground on how city building and planning can be donein a more effective, innovative and impactful ways to improve the quality of life for individuals who live, work and visit cities. That has led to me diving more fulsomely into areas that I previously touched on more tangentially in M&A deals, like real estate, and has pushed me to develop a new model for how companies can use data and information more responsibly, pursuant to a clearer set of guidelines and ground rules that are tailored to benefit people.  I’ve found that whenever I push myself, that’s where I see the most growth.

What’s your superpower?

Not giving up.

JENNIFER: What are your tips for working with the C-Suite?

ALYSSA: I’m on the leadership team at Sidewalk and I work directly for our CEO. And my tips include-don’t be afraid of the unknown. Being a partner and a collaborator is key. Understand that you’re working to find solutions and not identifying problems. Figuring out a way forward is not a solo effort, and you have to get rid of the ego and focus on how you work effectively as a team, across teams, up, down, across, sideways. And realizing that everyone has their strengths and weaknesses, and we’re never going to get all that we need as a company with a limited, less diverse group of people involved. As a leader in the company, you have to enable and work to get the best out of people with the ultimate goal of moving the company forward and in the right direction.

JENNIFER: What are your top recommendations for risk management?

ALYSSA: It starts with integrity and having at your core, as a company, that you reward honesty and believe in doing things the right way. One of our values is “no short cuts” – and we try to promote that in all parts of the organization – but I do think it starts at the top and the behaviors that people see being recognized.

For a lawyer in a company, to do risk management properly, you have to make sure you understand and have exposure to as much of the big picture as you can, thus enabling you to put the risks into the proper perspective.  To be successful, you can’t be afraid of taking chances as a company. Companies don’t move forward being afraid and everyone needs to understand that, including as it relates to enterprise risk management. Risk management, to me, is about enabling smart, well-informed, positive activities to flourish while getting rid of careless, low integrity decisions and behaviors.

JENNIFER: What advice would you give to a first-time GC in your industry?

ALYSSA: Be value-additive. Listen. Find solutions, not just problems. Know your business. Figure out a way to get to a thought-out “yes”.

JENNIFER: How do you build and leverage your network?

ALYSSA: As you get busier, it becomes harder. Also, I know that, for me, having a family – a son and husband – made me evaluate priorities and focus on those activities that are going to have the most impact.

That meant really thinking about where I could grow and learn and engaging in activities with people, at events, that would aid in my development, round me out as an individual and a professional or provide me with the opportunity to be a mentor or collaborator.

What is your most memorable travel experience?

I have two. First, when my son and husband joined me in Barcelona after a business trip there. We spent a week exploring a new place and it was good to have that personal experience and to contrast it with the business one. The second is spending time at the shore with my immediate and extended family. We get a beach house, rent bikes, play in the water, relax, laugh, and enjoy.

JENNIFER: What are the most important qualities you look for when hiring outside counsel?

ALYSSA: Pragmatism, business-orientation, problem-solving, honesty. Tell me what I need to hear, not what you think I want to hear. I’m the client, I came to you for a reason, and for your expertise.  Provide that to me (and do not overcharge me).  Also, think about the team – part of our mission is to build inclusive communities; the counsel that represents us should reflect a diversity of experiences, skills and backgrounds.

JENNIFER: Before hiring someone, how do you decide whether they are cultural fit for your company?

ALYSSA: Our company is young but we have spent time thinking about our values and what is core to us. A key thing about cultural fit is seeing how people align with our values and if they resonatewith them.

I firmly believe, and this is something I learned at Netflix, that it’s okay if a company isn’t for you. Finding people that fit with what you believe in doing as a company, how you work, how you interact, and how you grow is critically important. I think sometimes even more than what skills, hard skills, people bring to the table. Because you’re always, probably, learning new things at a company in any event. But if you can learn and grow and fit in with where the company wants to grow, that’s going to be critically important for what you do and how you do it, regardless of what it is.

JENNIFER: What is the best part of your job?

ALYSSA: Finding a way forward and collaborating with others—working as a team. I was having a really good series of conversations the other day, just yesterday, with colleagues in different areas—our development team, our software engineering team, members of my legal team. And what made it great, what made the conversations great were how we were aligning on our vision and figuring out how we were going to move forward and achieve our company’s mission together. And that just gets incredibly exciting, when you feel like you’re going in a similar direction with really smart, talented people, who are good at their core.

If you could meet any person from the past or present, who would you choose and why?

My grandparents. They all passed when I was relatively young and I would like to talk to them about their lives.

JENNIFER: List 3 adjectives that describe the way you work and lead.

ALYSSA: Collaborative. Fair. Enabling. Give people the freedom to do their jobs and create an environment where people understand the sum is greater than its parts. If you take the time to hire good people, give them the opportunity to do their job to the best of their ability and be responsible for the outcomes of their work. I also like to push people beyond where they think their limits are. It goes back to what I said earlier about where I thought I grew the most. That’s when I pushed myself or somebody pushed me.  I aspire to create the conditions to let people thrive as part of a cohesive team.

JENNIFER:  Tell us about a problem you solved or an obstacle you overcame while practicing law.

ALYSSA: I’ll tell you about a most recent one. It hasn’t been solved yet. It’s a work in progress. It has to do with developing a responsible data-use framework at Sidewalk Labs.

One of the reasons why I cited it as one of the challenges is because we’re in a world where how you use and acquire the rights to use people’s information is part of a very real and dynamic conversation these days. One where you have many people with different perspectives- with very valid perspectives and concerns. As a company, we are trying to figure out the ways to provide a trusted process that would enable the responsible use of data and information to achieve a beneficial purpose.

We have put forth a responsible data use framework that we hope can work as a complement to existing laws and promote good practices about data collection and use. Practices which focus on having a beneficial purpose for collecting and using data, encouraging data minimization – only collecting the data that you really need – promoting good data handling practices, minimizing how much personal information you need to achieve that purpose, and facilitating the use of properly collected and de-identified data across many and not just a fewto enable many more benefits to be achieved.

JENNIFER: What challenges do you think in-house attorneys will face in the next four years?

ALYSSA: I mean, that certainly will depend on the industry that you’re in, but I think some of the biggest challenges would be working to enable business to take place in a more complex, technology-driven world. The practice of law is set up to have you think ahead, consider the consequences and develop solutions to manage those things. As new technologies become available, we need to evolve our thinking and our approach to problem-solving, figuring out how we can put forward frameworks and advance principles that will help our companies operate in an appropriate, fair, ethical and responsible way.

JENNIFER: How have you seen the legal industry evolve during the time you have been practicing law?

ALYSSA: I think in-house lawyers are being seen as more partners to business rather than as blockers. If engaged from the beginning and comprehensively, we are in a better position to be solution-oriented and move the ball forward. Businesses who get that tend to apply that partnership approach across the board and end up making more sound decisions.

Tell us about a cause or issue that you care passionately about.

I care passionately about figuring out a way to be united as a country. We have many more things in common as people that should unite us rather than divide us. And I feel passionately that we need to change the discourse and start making it more positive so that we can become the inclusive community that we are meant to be. It’s one of the reasons I was attracted to Sidewalk.

JENNIFER:  How/what would you like to see change in the legal industry?

ALYSSA: I’d like to see outside law firms figure out how to take more of a partnership approach with the companies they represent. I think the billable hour concept continues to make it challenging for law firms to fully function in that role. The better information that you have about what a business is doing and trying to do and how they are thinking about things, the more you’re going to be able to provide solutions and suggestions on how to do things. Whether that’s from a transaction, from a compliance-oriented perspective, or regulatory perspective. You’re challenged to do that when you’re talking to someone who bills you $1000 an hour.

I think that if the legal industry can figure out a way—they’ve tried it with alternative billing and they’re still working at it—to make engagements more cost effective, that could go a long way.

JENNIFER:  What’s an idea or technology that changed the way you work, and where did you come across it?

ALYSSA: That’s a good question. I think I saw dramatic improvements when we adopted a new IP management solution at my prior company. I thought that it changed the way my team was able to work with the business, because it enabled them to more effectively manage the portfolio to fit the needs of the business.

JENNIFER:  How do you employ technology to carry out your responsibilities?

ALYSSA: I look for tools that you can tailor to how your business actually operates instead of forcing the business to adapt to a generic tool.

JENNIFER:  What product/service would you like to see that will help you work more efficiently and effectively?

ALYSSA: I’d like to see refined billing models for law firms and streamlined contract management systems that are more intuitive about work flows and business needs.

JENNIFER:  What would you like service providers – i.e. –law firms and vendors to know about how they can be of greatest value to you?

ALYSSA: Think about how you serve up your work product. Don’t make it more work to consume. The client came to you to help solve a problem, don’t make it more cumbersome than you need to. Be efficient, effective and business minded.

Alyssa Harvey Dawson

Alyssa Harvey Dawson, Esq.

General Counsel and Head of Legal, Privacy, and Data Governance | Sidewalk Labs

Jennifer Silverman

Jennifer D. Silverman, Esq.

Head of Data Privacy and Cybersecurity Practice | Ellenoff Grossman & Schole LLP