Olga Mack: General Counsel, ClearSlide

#BakersDozen is a series of interviews with leading professionals in the fields of law, consulting, finance, tech, and more.

Tell us a bit about yourself?

First and foremost, I am results-oriented, pragmatic, and passionate about helping startups thrive and grow. I think of myself as a startup business professional who has knack for assessing and balancing risk and opportunities. I love to work cross-functionally and do the “impossible.” Usually what we think of as “impossible” is merely “improbable,” and achieving it is just a question of strategy.

Day to day, I’m active in corporate governance, human resources, recruiting, business development, cybersecurity, privacy, IP, and numerous other business and legal initiatives. I manage both legal and business teams and counsel executive level staff on a wide range of issues.

What do you do for a living right now?

I am currently General Counsel at ClearSlide, a mid-stage startup that is a leading SaaS sales and marketing engagement platform. I am also an advisory board member at TimeJoy and ChannelMeter, both early stage startups.

Why do you love startups?

Startups are an opportunity to learn, have fun, and gain a business perspective. Or, as my eloquent startup lawyer colleagues say, startups “require you to be the Swiss Army knife of lawyering” and they are “hair-raising fun!” Recently I wrote a more comprehensive article for the Association of Corporate Counsel (ACC) Docket that details why lawyers should consider joining startups.

Why did you decide to become a startup lawyer?

I decided to join a startup primarily for three reasons. One, I wanted to have a wider and more dimensional legal practice that challenges me daily, if not hourly, if not at every moment. These days I touch many legal issues on a daily basis. Two, I wanted to be more integrated with the business, learn business skills, and become a true business professional who happens to also be a very good lawyer. Startups are a very good opportunity to contribute to and lead in human resources, recruiting, finance, business development, product development, operations, strategy, cybersecurity, and numerous other parts of the business. Three, I aimed to improve my skills in identifying, mitigating, and, most importantly, evaluating risks and opportunities and become a true business leader in the process. And given the speed of most innovative startups I can’t think of a better place to gain these skills than a fast-paced, innovative, high-growth startup.

What skills do you need to become a startup lawyer?

Tolerance for uncertainty, comfort with ambiguity, a stomach for calculated risk-taking, enjoyment of speed, an open mind, and a love for learning are required skills for any professional, business or legal, who is thinking of joining a startup. These are table stakes skills. Of course, substantive knowledge and industry experience are always an asset for any job, including startups.

Who – or what – inspires you – and why?

My father has been my greatest inspiration, supporter, and coach throughout my life. He convinced me very early that our limitations, insecurities, and doubt are entirely in our heads. He also helped me learn that we each have a voice, and it is the most powerful tool we have, because the stories we tell about ourselves define us. These stories shape our identities, our dreams, and our destinies.

What advice would you give to the younger generation contemplating law as a career?

Gone are the days when lawyers just needed to know laws and maybe some finance. The sophisticated and effective twenty-first century counsel most definitely know laws and finance. She also knows statistics (yes, math!), uses technology, appreciates risk calculation, possesses emotional IQ and soft skills, understands the regulatory landscapes and political climate, integrates well in a business, and much, much more. Counsel are increasingly an integrated part of their business. They are increasingly more sophisticated, and often lead, as opposed to merely support, business initiatives.

What do you consider the greatest challenge facing the industry?

Technology such as artificial intelligence, IOT, space and virtual reality will transform the way we practice law and share legal advice in the next five to ten years. I am not convinced that collectively, as legal professionals, we are prepared to thrive as these changes unfold. So, the already intense legal profession may become even more intense as these changes transform the industry. Individually, each of us should expect this and decide how we will deal with it.

What do you see as the greatest opportunity for the sector looking forward?

Understanding and embracing twenty-first century technology will be key for the legal profession. Should we do it well, we will find our careers more fulfilling, our professional lives more integrated with the businesses we advise, and freedom to focus on fun, strategic, initiatives more effectively. So there is most definitely a light at the end of this legal tunnel.

If you had to do it all over again, would you?

Absolutely! I very much enjoy being a startup business professional and all the responsibilities and opportunities that come with it.

What would you do differently?

While I am generally satisfied with my life choices, I believe that one can never learn too much — either through more and different books, experiences, or people. I am a life learner and enjoy finding and addressing personal growth opportunities. So I will always wish I had done more learning.

What makes you get up in the morning and want to practice law and be a startup business professional?

It is the chance to do something new, be uncomfortable, catch myself in the moment of discomfort, pause to research and reflect, and intentionally make the best decision I can under the circumstances. These are the daily, priceless, growth moments of a startup business professional.

Wildcard Questions

If you weren’t doing this, what would you be doing?

What would a bird do, other than flying? It would likely be hard for a bird to imagine this alternative reality. After all, flying is what she does! That’s how I feel about being a startup business professional. Imagining an alternative reality is not as interesting as living in the current one. I practice law at a startup for the same reason birds fly — I love it, it is most enjoyable, and I am good at it.

What’s your favorite city?

I am comfortable in any city and exploring urban places is my passion. In fact, through all my travel, I’ve perfected urban exploration to an art form. Having international roots (I was born in Ukraine and grew up in Russia) and been in many countries on most continents, there is no place on Earth that I would not enjoy exploring. Just like joining a startup, enjoying a foreign city requires you to be curious and comfortable with being uncomfortable. And I have an abundance of these qualities!

What’s your favorite food?

My mother’s cooking, of course! It feels like home. Because at the end of the day, it is always good to return home and hug your loved ones.

Olga Mack thrives at navigating the intersection between business, law, and technology. She has managed both legal and business teams and counseled executive level staff on a wide range of issues. Olga has over ten years of cross-functional experience in corporate governance, intellectual property, security, privacy, litigation, and employment law. She is also a certified information privacy professional and M&A and open source software specialist. Olga co-teaches a class on Financial Statement Analysis at UC Berkeley School of Law, and also serves on a Leadership Board of the San Francisco Bay Area Association of Corporate Counsel (ACC).

The opinions expressed in this interview are those of the interviewee, and not of their affiliated organizations or of High Performance Counsel.