Since graduation, I have spent a lot of time in the entrepreneurial space! Currently, I am the CFO at, a $1.2Bn Series C FinTech startup backed by Sequoia Capital, Index Ventures, Stripe, and Bezos Expeditions. Pilot builds advanced automation technology to streamline accounting, tax, and analytics for startups and small businesses.

It is a very dynamic environment; I spent half of last year leading a new product launch (from customer discovery to creating marketing collateral) and the rest of the time on hiring, strategy, and fundraising. Things are moving fast, we have grown revenue by 6x and tripled our headcount to 150 over the past two years!

Prior to that, I helped Dropbox scale from a Series B startup to a post-IPO public company, going from 200 employees to 2,000 employees. I served as VP of Corporate Finance & Strategy and led the strategic finance, corporate development, and investor relations teams.

Here are four highlights from HBS that I found very valuable:

1. Partnering with High Potential Startups in HBS Rock Accelerator

As a Rock Venture Partner, it was a highlight to co-lead the program design and directly advise two startups, including the winner of the HBS New Venture Competition Toolbox - YC S20 - where I currently serve as an advisor.

I also met Zoba at the Harvard i-Lab and introduced them to their lead seed investor - CRV.

2. Huge Range of Entrepreneurship Clubs at HBS

HBS offers a huge range of clubs and activities that cover all facets of entrepreneurship! Here is an example of a venture capital event where the VCPE Club, Tech Club, and Women in Investing hosted together.

I was joined by Zeya Yang (MBA 2019 and now a Partner at Andreessen Horowitz) and Madeline Keulen (MBA 2019 and now a founding investor at Victress Capital) as co-hosts.

3. You’ll Learn More in the Classroom Than You Think!

A few concepts from my HBS courses that I spend a lot of time thinking about at our startup today include:


  • What is our inbound and outbound marketing funnel?
  • How do we drive more awareness → trial → purchase?

Disruptive Innovation:

  • Where are there new market opportunities?
  • How do we think about downmarket vs. upmarket expansion?


  • What are the most important business components to de-risk?
  • How do our priorities change as we grow?

Legal (HBS’s Law, Management & Entrepreneurship and HLS cross-registration):

  • What are the key legal risks?
  • What are the most important elements in this contract?


  • How do I create psychological safety for my teams so they can do their best work?
  • What’s the best way to influence outcomes?


  • What are the long-pole items on this project/initiative that we need to start immediately?
  • What’s the bottleneck?

Independent Studies:

  • I had the opportunity to work with Professor Jeff Bussgang diving into YCombinator - we work with hundreds of YC companies at Pilot!


  • At a successful startup, the cost of capital greatly decreases over time (and valuation greatly increases over time) - what are high ROI uses of capital today and what should be deferred
  • HBS Finance starts with a lesson on working capital, and this is really important at a startup too. For most SaaS startups, customer prepayments are very important.

PS: If you plan to be a founder, remember that initially you will be the marketing/sales/finance/operations person! And if you are a VC, these are some key elements to assess.

Paul with Professor Ted Berk

4. Density of HBS Founders

Over 50% of HBS alums become founders and it shows! I have definitely had a fair share of unplanned run-ins with HBS founders on campus. For example, this was a run-in with Leslie Means (MBA 2015), Founder & CEO of Anomalie and Nick Alexander, Founder & CEO of Yoshi (MBA 2015); we then ended up having dinner at Leslie’s favorite Harvard Square restaurant - Alden & Harlow!

And that’s true in San Francisco as well! They say it’s a small world, and it is definitely even smaller as an HBS alum! Hope to see you around!