If you work for a software company, odds are that people make up 80-90% of your business’s costs. Today’s guest argues that in order to effectively manage a company’s greatest asset, the CFO should be heavily involved in shaping the company culture. Bill Tole is the CFO of TrustRadius, a trusted platform where tech buyers find real reviews. He is skilled in creating structures around ambition and breaks down how TrustRadius creates and implements Objectives and Key Results (OKRs). He explains how they differ from KPIs, why they fail, and how to set aggressive but achievable goals. He discusses the Rule of 40 and why it’s essential for the rest of the company to understand it. Bill also shares how CFOs can influence culture from a finance perspective and why a lack of failure is a cause for concern.

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LINKS:

Bill Tole on LinkedIn: https://www.linkedin.com/in/bill-tole-0a99789/

TrustRadius:

https://www.trustradius.com/

15Five:

https://www.15five.com/

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics:

http://mostlymetrics.com

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Less but Better: Miro’s Justin Coulombe on the Power of Strategic Divestment in SaaS:

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TIMESTAMPS:

(00:00) Preview and Intro

(02:15) Sponsor – NetSuite | Planful | Tabs

(06:00) TrustRadius’s Business Model

(09:20) OKRs at TrustRadius and Finance’s Role in Them

(14:07) Finance’s Role in Asking the Stupid Questions

(15:58) Sponsor – Rippling Spend | Pulley | Navan

(20:10) How To Set Aggressive but Achievable Goals

(23:19) The Ideal Number of OKRs

(24:21) Leaving Room for Failing or Innovating

(25:57) OKR Derivatives at Department Level

(27:36) Why OKRs Fail

(28:55) Rewriting or Killing Off an OKR Mid-Way

(29:51) Where To Track Your OKRs

(32:03) Applying the Rule of 40

(34:39) Educating the Org on the Rule of 40

(37:34) EBITDA Versus Free Cash Flow for Calculating Rule of 40

(39:24) The CFO As the Culture Leader

(43:21) Using Money To Change the Culture in a Positive Way

(45:42) Mistakes CFO’s Make When It Comes to Culture

(47:06) Long-Ass Lightning Round: Why Failure Is Okay

(51:41) Advice to Younger Self

(53:44) Finance Software Stack

(55:12) The State of SaaS Fragmentation or SaaS Sprawl

(57:28) Craziest Expense Story

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SPONSORS:

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Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.

Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.

#failure #companyculture #OKR #KPI #Ruleof40

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