Employee Spotlight #11: Clara Ma, On Deck's Chief of Staff Fellowship Program Director

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Clara is an Operational Generalist who has worked in early-stage startups for the majority of her career. Starting out as a technical recruiter, Clara got her first taste of startup culture while pitching software engineers on the impact they could make at an early-stage company before deciding to join a startup herself. Since then, Clara has found her niche in helping executives turn their visions into reality and she thrives in operations and execution. In Clara's career journey, she's been a Director of Special Projects, Operations Manager, Chief of Staff, and Program Director - all roles that operate in the messy middle of "generalist"!

On Deck's Fellowship Program Director Clara Ma.

Frederick Daso: What was your journey to becoming a Program Director for the Chief of Staff (CoS) Fellowship at On Deck?

Clara Ma: My journey into this role makes a lot more sense on paper than when I was going through it. My first job out of school was in technical recruiting, where I was recruiting mostly software engineers for startup roles at places like Warby Parker, Dollar Shave Club, etc. I had grown up in the Bay Area, and my dad was part of what I call the "Original Silicon Valley" - chip design and the sort - so being in the tech startup space seemed inherently part of my blood, but I didn't put that together till much later in my career. After selling engineers on why working at startups was so great (unlimited PTO! Ping Pong table at work! Make a real impact!), I sold myself into the experience and went to work at a startup myself.?

Ever since then, I've always been an early-stage startup employee who came wearing all the proverbial hats that a startup comes with. My second role was at a company where we were only 4 FT employees. The hat rack included everything from product management/design, sales, marketing, and anything else that my three other co-workers didn't cover. It was here that I started to build my "Generalist Toolbox" and move into these operational catchall buckets that so many Chiefs of Staff find themselves in.?

After a year of being a Chief of Staff at a Series A -> B startup under the wing of incredible multi-time CEO and co-founder Clement Delangue, I had the opportunity to pass on my knowledge and build a community of Chiefs of Staff at On Deck - my most fulfilling role to date. This role has combined my love of people and community and the learnings and challenges I had as a Chief of Staff to create something that I hope helps all Chiefs of Staff through this twisty, windy role.

Daso: There's a lot of conventional career advice about being a successful CoS, but are there any unorthodox lessons that you've learned through experience or mentorship that more of your fellow CoSs should know?

Ma: I love this question because the entirety of the Chief of Staff role can sometimes seem unorthodox! Instead of specializing, a Chief of Staff is the ultimate generalist. Instead of building hard skills, like programming and SQL and Excel, you succeed most in this role when you build up your soft skills around people management. I wrote down some of the hardest things about being a Chief of Staff in?my post here, but ultimately, I think success in this role comes down to relationships:

• The relationship you have with your principal
• The relationships you have with the people in your organization can help you get things down (not always leadership, but the ICs on the ground matter just as much!)
• The relationships you have with people outside of your org who can help you through the problems you haven't encountered yet (shoutout to my Mastermind group within On Deck's Chief of Staff fellowship)
• our relationship with yourself to understand your capacity and capabilities

Daso: What's the toughest project (professionally or personally) that you worked on as a CoS or in general? What were the most important lessons you learned from that project?

Ma: The toughest moment of my Chief of Staff career was making the call on when my Chief of Staff tenure was "done." Many Chiefs of Staff expect that their "tour of duty" lasts between the 18-24 month mark, and a good principal will constantly surface what might come next for you. I had the incredible opportunity to see my company through a Series B raise and go through the hiring and product growth as a fast-growing startup. But even as I navigated the breadth of special projects that composed my Chief of Staff portfolio, I couldn't see myself growing within that company - simply because I felt that my interest and appreciation of the Chief of Staff role was the actual Chief of Staff role itself.

I mean that I was most interested in what the Chief of Staff role meant from a wider lens and diving deeper into how the role functioned at more companies. Throughout my time as a Chief of Staff, I talked to countless other Chiefs of Staff to pick their brains about how they were spending their time, what challenges they faced, and why they took the role - all leading me to a deeper curiosity around what makes the Chief of Staff role so appealing to others and what resources are available to those who are looking to level up in their Chief of Staff roles. When the opportunity came around to build out this community of Chiefs of Staff, it felt like the perfect fit.?

Daso: Who are some of the most inspirational people you've gotten to work with during your tech career??

Ma: Lexi Lewtan - founder and CEO of Leopard.FYI and my former manager at AngelList. Lexi was the first to show me that you could make a career out of being a generalist and that the path forward isn't as straight and narrow as everyone always makes it out to be. She was also an incredible manager to me - always asking about where I wanted to grow and pushing me to exceed and go past my own mental limitations of what I was capable of doing. If it weren't for her, I don't think I would have pursued being a Chief of Staff, much less come to build a community of them. We remain close friends, and I'm always excited to hear about what she's working on and how she's thinking through creative solutions to the challenges she's facing.

Daso: How would you define your company's culture, and how does it create an environment where you can do your best work?

Ma: One of the things that drew me to On Deck's culture was?its definitions of non-values. Most companies have a pretty standard values page, and it's your typical "We value honesty, ingenuity, etc." I felt like non-values were an interesting way of distinguishing the working culture of On Deck from other companies. Instead of asking what the limitations are, seek to read between the lines and try things that might be outside the norm of convention. With this operating principle, I've been able to push the limits of my own building capacity. At On Deck, I've always operated under the "do it until there's an explicit 'no'" policy, and that's allowed me to be creative in ways that I haven't had the freedom to do before.?

Daso: What's one interesting thing (non-work related) that more people should know about you?

Ma: After a successful year at On Deck, I'm writing this while on a three-week mini-sabbatical to figure out my next move (at On Deck or otherwise). Being at startups can be an easy equation for burnout, and I'm grateful to On Deck for providing me the space to take a step back, reflect on my accomplishments for the year (and my career as a whole), and figure out what comes next. During my time off, I've been exploring new cities (and trying out being semi-nomadic), easing my way back into dance classes (something I grew up doing and loving), and bullet journaling A LOT. I'm a big proponent of taking time for yourself and that it's never too early to take a sabbatical. Time for ourselves is rare and uncommon in a world where hustle culture seems to be the new norm. Even though talking about burnout and mental health is becoming less taboo, I don't think we are doing enough to surface solutions and showcase those solutions in public.?

Daso: What's something you want to accomplish in your career that you haven't yet? What motivates you to get there?

Ma: I'd love to be a part of a founding team. With every role, I've been able to be somewhere earlier and earlier, and I've always relished the opportunity of truly being at ground zero. I'm motivated by a desire to see the day the seeds are planted and be there to help cultivate and grow a company from ideation to actualization.

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