Navigating Career Turmoil in the Financial Industry

Todd Rakow, CFO of Gladly joins CJ for this deep dive into usage-based revenue models, strategic finance leadership, and the complexities of managing growth at scale. Todd shares tons of tactical insights, including building out the usage-based model, forecasting customer usage patterns, commissioning sales reps, and teaching your teams to distinguish between reoccurring and recurring revenue. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a one-of-a-kind flexible financing program until April 15th, 2024.

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Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

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TIMESTAMPS

(00:00) Preview

(01:11) Intro

(02:31) Sponsor: Maxio | Netsuite

(06:09) Usage Based Benchmarks: Here to Stay?

(08:01) Understand ARR and its Components

(10:30) Recurring or Reoccurring?

(12:33) Computing Gladly's ARR 

(18:13) Seasonality and Alternative Methods to Better Track Revenue

(22:25) Sponsor: Thoropass

(23:45) Commission Structures And Incentivizing Sales Reps

(27:28) Avoiding Foot Faults in Usage-Based Models

(28:57) Frameworks for the Day-to-Day

(31:36) Strategic Leadership, Customer Support and Success 

(32:50) Being a CFO: A Series of Long Uncomfortable Conversations

(36:12) Removing the Stigma Around CFOs

(37:45) Todd's Insights on the Difference Between a Good and a Great CFO

(40:07) Forging a Good Relationship with Your CEO

(43:29) Long Ass Lightning Round: What Did Todd Mess Up in His Career?

(45:37) What Would Todd Tell His Younger Self?

(50:35) Todd’s Software Stack - Sponsored by Tropic

(52:41) Craziest Expense Request

(53:30) Wrap