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When Sales is "Crushing It" But Finance Knows You're In Trouble

When Sales is "Crushing It" But Finance Knows You're In Trouble

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When the board sees “record quarters” and Finance sees paper-thin margins, you don’t have a growth engine — you have a slow-motion car crash.

In this episode of Revenue Remix, Summer Poletti (Founder & CRO of Rise of Us) sits down with William Lieberman, founder and managing director of The CEO’s Right Hand, to talk about what healthy growth actually looks like when sales, finance, and operations are rowing in the same direction.

William has sat in the room for the messy growth conversations most founders avoid: discounting that quietly destroys margin, bloated sales teams after a fundraise, and “crushing it” top line numbers that never translate to cash in the bank.

If you’re a CEO, CRO, or revenue leader trying to scale without breaking your economics, this one hits close to home.

In this episode, you’ll hear:
  • Why “we just need more pipeline” is usually the wrong diagnosis And how CEOs miss the real problem hiding in their back office, systems, and cost structure.
  • The metric William checks first to see if growth is real or fake How to look at gross margin by product, service line, and client to decide what to scale and what to kill.
  • A simple rule for firing unprofitable clients (and why it’s a finance job to say it out loud) Plus: how to align sales comp so reps stop dragging loss-leader deals in the door.
  • What sales should never be allowed to do alone The deal-approval process William recommends so Sales, Finance, and Customer Success all sign off on pricing and scope.
  • How to use new funding without ending up with a bloated sales org and fragile unit economics Including: what to model, who to hire first, and where nearshore + AI support actually makes sense.
  • Sales comp mistakes that quietly blow up your P&L Why paying full commission on signature is dangerous, and how William structures payout to keep reps invested in profitable, live customers.
  • The one recurring meeting where Sales and Finance actually help each other What should be on the agenda, who’s in the room, and how to make it about solving revenue problems instead of pointing fingers.
  • A practical way for CEOs to stop the “it’s their fault” food fight William’s favorite role-reversal exercise to get leaders out of blame mode and back into solving hard problems together.
About William Lieberman

William Lieberman is the founder and managing director of The CEO’s Right Hand, a firm that provides fractional CFO, CHRO, and COO services to growth-stage companies that need serious strategic finance and operations support—without building a giant back office.

He’s a long-term operator and fractional CFO who:

  • Has helped CEOs navigate fundraising, scaling, and restructuring
  • Knows exactly what happens when sales is “crushing it” and the numbers still don’t work
  • Brings a pragmatic, operator’s lens to aligning sales, finance, and operations around real, sustainable growth

If you’re a founder or CEO who suspects your P&L is hiding more than it reveals, William is the kind of partner you want in your corner.

Connect with William
  • 🌐 Website: The CEO’s Right Hand – tcrh.co
  • 📧 Email: william@tcrh.co

If this episode hits a nerve, share it with a CEO, CRO, or sales leader who keeps saying “sales is crushing it” — and quietly worrying what Finance really thinks.

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