Test match to T20 — Ananth Avva on the leaking CFO chair

Six months into Ananth Avva's first non-CFO role at Wrike, three executives walked out in quick succession. He looked around a board meeting and counted: the directors outnumbered the management team. The CEO split the company down the middle — product and R&D on one side, go-to-market and G&A on the other — and Ananth took the second half. He had been hired as a CFO-plus. He left Wrike a COO, and he has not gone back to the chair since.

That arc is the most interesting thing in this conversation, and it isn’t really a career story. It’s a diagnostic. The CFO seat that Ananth keeps choosing not to sit in is leaking on both sides — fewer “gold standard” IPO shots to keep operators in the chair, and a stronger pull from the product / sales / ops side for the operators who do cross over. The chair isn’t broken. The seat shape is changing.

The vanishing gold standard#

Ananth’s frame for the CFO seat is unsentimental. “The gold standard for a CFO is someone who can take a company public.” Twenty years ago that meant ~$100M of revenue and a $1B market cap; today it’s $250–500M and $5–10B before the smell test passes. The shots themselves are rare, and the bench for them is narrow.

The gold standard for a CFO is someone who can take a company public.

His own reckoning is candid. “Maybe I had a shot at one. And that was also a very loose one.” The board feedback was honest: he had never been a public-company CFO, so he was never going to be the safe pick. That’s not a slight — it’s risk management, exactly the kind he’d recommend if he were on the other side of the table. The compounding problem is that the math gets harder every year, and the alternative paths get more attractive in parallel.

Test match to T20#

Why operators cross. Finance, in his telling, is a test match — you can read the pitch, plan to it, and substitute over the next few sessions. Go-to-market is a T20: respond to the market in real time, and the bench is rebuilding underneath you while you bat.

Finance, you have the luxury of planning… The second you start going into go-to-market, it's chaos.

What this means in practice, at Wrike: half his calendar was hiring. The fast-twitch muscle had to be built from scratch — different lens on customers, different decisioning cadence, a relationship with product that goes deeper than the IR-deck level. “Going in and saying, wait, why are we doing the user onboarding like this? This seems like a lot, why can’t we do it differently?” That’s the operator’s product instinct, and it’s the muscle the CFO chair doesn’t naturally build. Once you have it, it’s hard to give back.

Learn the business#

For the CFOs who stay — and most do — Ananth’s most useful prescription is also his most-mocked cliché: learn the business. The teeth are in what he means by it.

Learn the business. Like you should actually understand the business.

The gotcha list: most finance professionals can name the metrics, but ask them what the engineering attrition rate is, what the average cycle to fill a senior backfill is, what inflation premium they’re baking in for DevOps and SecOps roles in this cycle — and the room goes quiet. That’s not a budgeting failure. It’s a credibility failure with the operating team, who already know the answers. His prescription is mechanical: one hour, once a quarter, with product and pricing on the rev-rec implications of new monetization moves. “Most people are good corporate citizens — if they know that, then they will hustle to do it.” The cost is an afternoon; the saved fire drills run into months.

Day negative thirty#

The single most under-done discipline in his read of the chair: pre-join diligence. Most CFOs treat the first 100 days as a planning surface; Ananth treats day one as already late.

I'm shocked at how little diligence CFOs do before they get into the company. You have every right to go very deep.

The asymmetry is real — a CFO candidate has more legitimate access to a company’s internals than any other senior hire. Financials, board turnover history, the billing system, the sales-tax exposure, an actual invoice. “Not Vista or Thoma Bravo-type deep diligence, but pretty close.” Investor + operator, which is the PE posture, not the VC one. The pattern he likes best is the trial-run-as-advisor — short engagement, equity-only or even free, in exchange for a front-row seat to the books. By day one, the gap analysis is done and the first 100 days has a real shape.

What to listen for#

The full episode runs the longer cricket-and-CFO arc, the test match / T20 / IPL run-rate set, and the CEO–CFO–board triangle Ananth says he’s actually struggled with most. The closing line is his wife’s, and it has aged into a personal heuristic: “Your job is not that important. No one’s going to die.” For a chair that increasingly carries the cybersecurity, ESG, and Silicon Valley Bank dossiers, it lands harder than it should. Listen to the episode in full at /podcast/ep-006-anant-avva; for the other IPO-readiness essays in the catalogue, see Karan Bhople, Rakib Azad, and Arvind Agarwal, or /topics/ipo-readiness.