Having Gone Through Sh*t Is an Asset: Yext CFO’s Playbook for the Tough Times
Run the Numbers
Navigating Growth: The Need for a Deal Desk
This chapter explores when and why companies should establish a deal desk, particularly as they grow and engage in larger enterprise contracts. It emphasizes the need for structured processes to balance flexibility with necessary controls in contract negotiations. The discussion also covers the strategic integration of legal resources and the importance of learning from others' experiences to streamline operations and avoid pitfalls.
With a decade of experience at Yext, a company now approaching half a billion in ARR, Darryl Bond has seen it through negative EBITDA margins, executive turnover, and company-wide resets. In this episode, he sits down with CJ to talk about his approach to the finance function, which involves prioritizing growth over compensation, tackling the messy problems head-on, making the hard P&L calls in the “grey zones,” knowing when to ask for help, and staying focused through the tough times. Darryl shares how he scaled from controller to CFO, and how, in the process, he made sense of the chaos, led with transparency, and built a high-impact finance function that doesn’t just report the numbers, but also drives the business. He explains the role of systems and processes in scaling operations, the mistakes he made early in his management journey, and why relationship-building has been the real unlock in his career. They dive into building deal desks, what operational excellence really means, and capital allocation decisions that actually start with listening to the customer.
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LINKS:
Darryl Bond on LinkedIn: https://www.linkedin.com/in/darryl-bond-788b962a/
Yext:
https://www.yext.com/
CJ on X (@cjgustafson222): https://x.com/cjgustafson222
Mostly metrics:
RELATED EPISODES:
“Run Toward a Tough Market” — Developing the Hard and Soft Skills To Be a Great Finance Leader —
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TIMESTAMPS:
(00:00) Preview and Intro
(02:49) Sponsor – RightRev | Navan | Rillet
(06:54) The Reasons for Darryl’s Career Loyalty
(08:58) Prioritizing Learning Over Comp
(11:09) What Yext and Its Finance Function Looked Like in 2015
(15:40) Sponsor – Pulley | Brex | Aleph
(20:03) Choosing Which Messy Problems To Take On
(22:00) The Right Time To Create a Deal Desk
(23:39) When To Bring General Counsel In-House
(24:36) Asking for Help and Building a CFO Network
(28:25) What Operational Excellence Looks Like in the Finance Team
(31:11) Staying Focused Through Tough Times
(35:39) Making the Hard P&L Calls In the “Gray Zone”
(37:05) The Importance of Talking to Customers
(38:30) A Guide to Communicating the Bad News
(40:25) The Role of Systems and Automation in Gaining Control of the P&L
(43:07) Capital Allocation Decisions: Yext’s Two Recent Purchases
(45:06) Build, Buy, or Partner
(47:57) The Pros and Cons of Being a Sub-$1B Public Tech Company
(49:38) How To Get (and Lose) Sell-Side Analyst Coverage
(51:04) What Excites Darryl Most About Yext’s Current Stage
(53:13) Long-Ass Lightning Round: A Career Mistake
(54:36) Advice to Younger Self
(56:17) Finance Software Stack
(57:42) Craziest Expense Story
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SPONSORS:
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#CFOLeadership #FinanceLeadership #FinanceStrategy #OperationalExcellence
#BusinessTurnaround #CapitalAllocation
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