Elizabeth Bikoff, founder of Boxy.io, joins Sunny Ray to discuss building an AI chief of staff for early-stage startup founders. Elizabeth traces her winding path from growing up in Nice, France dreaming of Hollywood, to studying aerospace engineering in Toulouse, to a decade at PwC building a Salesforce practice from zero to 200 million in revenue, and later scaling roles at Apttus and early-stage startups. She opens up about the gendered double standards she faced on the partner track, the grief of leaving PwC without a job lined up, and how ChatGPT's emergence in 2022 sparked the idea for Boxy after being asked the same operational questions by founders over and over. She also shares an unexpected personal detail: she has completed 155 skydives. The conversation closes on how investor conversations reshaped Boxy's product, revealing that VCs wanted the same metrics transparency founders craved, pushing the company toward a shared control center for fundraising operations.
A 155-jump skydiver and ex-PwC partner track exec on burnout, bias, and building an AI chief of staff for founders.
What was your first skydive like?
It was a static line jump, not a tandem. You're attached to the plane by a line that opens your chute automatically at about 1,000 feet. I froze when it came time to jump without the static line, so I converted my training to accelerated freefall and just kept going from certification to certification. 155 jumps is actually small in the skydiving world, some people have tens of thousands.
Tell us about Boxy.io, what are you building?
We're building the AI chief operating officer or chief of staff for early-stage startup founders, helping with all the operational crap founders don't want to do. Our wedge right now is fundraising operations, managing your raise, cap table management. It's been fun working with partners to help founders keep building.
You met the general counsel of Boeing twice over coffee and he told you not to come work there. What did he say?
After a couple of coffees he was very transparent and said Boeing was big, firm, very male-oriented at the time, and mostly hired business people from the engineering side, not outsiders. He told me to go do something else and if I still loved the industry, come back to it later. It was disappointing because working at Boeing had been my dream.
You were on the partnership track at PwC and you walked. What was that conversation with yourself the night before you resigned?
It was like, what the heck was I doing, because I thought PwC was going to be my linear career forever, very French of me. I was burned out and felt the goalpost kept moving. I quit with no job lined up, and it felt like a death, a loss I had to grieve. It took about two years to get the PwC identity out of my system.
You've said expectations on women felt heavier than on men at PwC. Where did you feel that most concretely?
Even though I checked all the boxes on selling, delivering, coaching and hiring, I'd get feedback like there is noise in the system, you're too direct, my French side coming out too much. Meanwhile male counterparts barely selling anything, or treating people poorly, still made partner without that same scrutiny.
Boxy started as an ops in a box idea. What was the first version and what did you think you were building at the time?
The idea came after ChatGPT launched at the end of 2022, when I got tired of founders asking me the same B2B sales process questions over and over. I thought there had to be a better way to give that knowledge to founders at scale. I spent 2023 talking to as many founders and early-stage operators as I could before building anything.
What did you hear in those 2023 conversations that shaped the direction?
A friend and investor joked I was building Startup for Dummies but dynamic. Three themes kept coming up as the biggest time sinks for founders: fundraising, revenue operations across the customer lifecycle, and hiring and onboarding talent. That's what we took into 2024 with design partners, eventually landing on fundraising operations as our starting wedge.
What was the moment you realized investors also wanted the transparency you'd built for founders?
We always envisioned a control center with key startup metrics for founders. When we showed it to investors last year while starting to fundraise, they loved the metrics view and asked if we could give them that same visibility into their deal flow and portfolio companies. I realized investors had the same fragmented tools problem, juggling things like Affinity CRM and Airtable for standard metrics.
Building something daring? Sunny talks to founders like this every day. Fifteen minutes to see if your story belongs on the stage.
Claim your pre-interview