As they told it, at the end of Scale partner Rory O’Driscoll’s first meeting with John Rettig over a decade ago, Rory questioned whether John was the right fit for chief financial officer of BILL; today Rory considers John as good as a CFO gets.
In 2013, we first invested in BILL, founded in 2006, and Rory sat on its board from investment, through its IPO in 2019, and then stepped down in 2023. Rory joked he and John could chat for hours about their BILL war stories and where John’s helped take it in the last couple years, but they confined themselves to just 45 minutes at Scale’s recent CFO Summit in San Francisco.
We used our panel, “The CFO at the Center: Driving Financial and Operational Excellence,” to explore some of John’s hard-fought lessons over the past 11 and a half years at the company, which has grown into a leading end-to-end payments platform for enterprises with a market cap of over $4.5 billion. In late 2023, John added “president” to his title, and since then, in addition to his role as CFO, he’s overseen all of BILL’s go to market (GTM), operations, customer support, risk management, business development, and corporate development. We consider him a worthy role model for our portfolio companies’ CFOs, and we’ve collected a few lessons from his conversation with Rory.
Integrate into the fabric of the entire business
John’s biggest recommendation for CFOs was to get grounded in the whole company — the business model, strategy, growth drivers, team priorities, culture — from day one. “At the end of the day, the CFO role is not back office and only number-centric, but needs to be integrated into everything, the whole fabric of the business,” he said.
Keep in mind that the honeymoon period lasts at most 90 days, but that the imperative to stay on top of everything doesn’t go away. The role of the CFO, he said, should include being an enabler for the rest of the executive team and a partner to the GTM team.
Always be on the same page as the CEO
As mentioned above, when Rory first interviewed John over a decade ago, he was looking to see if John would be a good fit for BILL’s founding CEO, René Lacerte. John by now also recognizes how special this partnership is.
“In a constructive way, it’s like a team within a team,” he said. The CFO should be the CEO’s number-two, and they should have a specific gameplan on how to divide and conquer. This relationship also comes into play with the board, where the CFO needs to allow the CEO to own that relationship, keeping disagreements between them private (in all but the most dire of leadership emergencies).
‘Correct the truth’
John told Rory he was surprised when he first joined BILL that a sales leader and a finance leader couldn’t agree over a set of numbers. It was a potential disaster that needed to be addressed immediately, but it was not as easy as it may sound, and John said he learned there’s more art to it than science.
“As a senior finance person, you own the truth,” he said, and sometimes that requires “correcting the truth.”
Put simply, there can’t be competing success metrics. That’s not to say that the CFO needs to originate every success metric in the company, but they do need to make super clear that they have the final say, and that they need to bring others across the company into agreement. Further, it’s on the CFO to create an environment where it’s OK to fail or miss targets, marked by transparency and open discussions — not arguments over what constitutes success in the first place.
Always take a multi-year view of the business
As you go to $10 million, and then $100 million, and then $500 million, etc., each new growth profile comes with a new growth horizon. But you shouldn’t wait until you’ve exhausted the current growth profile to figure out the right level of investment for future horizons to drive future growth.
“The biggest thing I learned is that turning that into multi-year investment plans instead of just an annual investment plan is really important,” John said. He explained that in retrospect, the BILL team got caught up in short-termism, but it wasn’t until they began taking that larger view that they were able to scale.
This shift is what allowed them to realize that they needed to have their SMB customers grow alongside them through new products. That is what led to, among other things, the acquisition of corporate card/expense software company Divvy for $2.5 billion in 2021 — a move that Rory said, laughing, was scarily risky but that proved to be critical for taking BILL to its next iteration.
Have the right goals when considering going public
John has helped guide BILL through its IPO and two other rounds of converts. He said that CFOs and their teams need to measure the pros and cons of both the light of public markets, which isn’t always desirable, and the greater access to capital.
For BILL, getting access to cheap capital is what allowed them to buy Divvy, for example, and ended up the right choice.
Regardless, if starting to consider an IPO, it’s valuable to start building relationships with the sell side, and to know their cap table inside and out.
As it stands now, BILL is in good hands with John as the second-in-command with a full purview of the business, and as Rory told the audience, we like to think of his trajectory as an ideal path for an effective CFO.