Ajay Vashee has been a general partner at IVP for about three and a half years. IVP, headquartered in California with a new office in London, helps breakout companies grow into enduring market leaders. With a 40-year record and 130+ IPOs, they have partnered with over 400 companies including Amplitude, Brex, Coinbase, Crowdstrike, Datadog, Discord, Klarna, Slack, Snap, and Twitter. IVP helps founders and CEOs lead rapidly growing companies with a selective, proven, pragmatic, and genuine approach.
Ajay and I recently discussed his path to IVP, his former CFO role at Dropbox, leading a team through an IPO, why he transitioned from finance to venture capital, and how building Legos with his daughters is one of his favorite pastimes.
Ajay grew up on Mercer Island, near Seattle. He attended Columbia University in New York, graduating in 2005 with a bachelor’s in economics and political science, and began his career as an analyst at Morgan Stanley. After a few years at venture fund NEA as a senior associate, Ajay realized he was being led to a different path.
“While at NEA, we were doing some category work on file sync and share, the category that Dropbox operated in,” he explains. “I fell in love with the company and ended up joining, leaving the world of venture to step into an operating role for the first time.”
Initially, Ajay joined to help build and scale the finance organization at Dropbox. This experience allowed him to recruit talent across the organization and build the team from the ground up. Ajay was responsible for building the accounting, FP&A, strategic finance, treasury, and real estate functions. He also managed mergers and acquisitions strategy and investor relations as head of corporate development. These responsibilities prepared him for the CFO role.
“All of our acquisitions as a company prepared me to step into the CFO role, which I did about a year before we filed to go public and roughly a year and a half before our IPO,” he said. Ajay was the CFO through the company’s IPO and the first 10 quarters as a public company.
The IPO and subsequent period included monumental growth for Dropbox, scaling from $45M in revenue to $2B in ARR and from 50 million to over 600 million users. Ajay learned valuable lessons about team dynamics and the importance of communication during this time.
“There was a different team for the IPO and the transition from private to public markets,” he said. “The team we had as a smaller startup was different from the team for the transition.”
Communication was crucial during the IPO. Dropbox maintained a disclosive culture, which had to be adjusted as they became a public company. The team stayed focused on long-term goals and customer base despite the cultural adjustment.
Ajay found balancing the IPO’s demands with maintaining what made Dropbox successful to be a key challenge. “The gravity of the earning cycle, especially being a CFO of a newly public company, is powerful,” he said. They managed expectations and shadow metrics, maintaining optimism and clarity in their vision and strategy.
Ajay’s working relationship with Dropbox CEO Drew Houston strengthened through the IPO process, highlighting the importance of trust and respect. “Our relationship was strengthened through the IPO process, and the positive momentum made the company even stronger,” he says.
Ajay joined IVP in 2021, returning to venture capital after working at NEA. He saw the value in helping other companies through their next stage of experience growth like Dropbox with IVP’s support. During his time at Dropbox, IVP helped the company scale significantly.
Vashee is committed to developing the next generation of financial leaders.
IVP currently has about 95 portfolio companies, with the majority being private and 15 to 20 percent public investments. Ajay has helped the firm with several investments, taking board or board observer seats. He led IVPs investments in companies such as DeepL, Jasper, Pigment, and Superhuman.
Ajay sees potential in finance professionals taking risks in their career paths. “With the rise of strategic finance talent, we may see more CFOs transitioning into venture investing roles,” he states.
Managing work and personal life involves a team effort. Ajay’s wife is the chief marketing officer at Figma, and they have two daughters. Both sets of grandparents live nearby, providing crucial support.
Ajay enjoys running and staying fit, taking advantage of the Bay Area’s hilly surroundings. He also loves building Legos with his daughters and is always on the hunt for a new set.
Looking ahead, Ajay is optimistic about rising finance professionals. “I’m most excited about the next generation of analytical talent in finance,” he says. “We invite those running finance at exciting tech companies to join the IVP CFO Collective and be part of our community.”