How Strategic CFOs Get It Wrong

On this week’s Run the Numbers, CJ sits down with Steve Isom of Bloomerang to break down what a “strategic CFO” really is. They cover the shift from reporting to operating, why customer orgs drive SaaS value, and how AI is reshaping the finance role. —SPONSORS:RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.comBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run—LINKS: Steve on LinkedIn: linkedin.com/in/steveisomjrCompany: https://bloomerang.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview1:25 Intro2:55 Welcome Steve Isom3:13 CFO to COO promotion5:02 Having a pulse on every function6:51 Defining "strategic CFO"7:19 Tying strategy to value creation9:27 Being embedded in the rhythm of the business10:55 Finance leaders as commentators vs. team captains12:25 Sponsors — RightRev | Rillet | EY15:33 Killing projects as a core skill18:14 Activity doesn't equal impact19:16 Project Steve killed20:39 Taking over the customer org at Bloomerang22:18 Why acquisition is a cash-losing exercise23:07 LTV lives post-sale24:39 Most vulnerable area: customer success25:24 Ruthless CSM segmentation26:30 Nonprofits don't think about your software29:21 Sponsors — Spendhound | Brex | Aleph32:43 CFO running ops35:52 Metrics vs. humans37:18 Skip levels and what they reveal39:01 Incentives drive the wrong outcomes40:22 Customer-introduced delays as a key sub-metric40:27 Unit economics become tangible when you're accountable42:17 Going deep on AI45:13 Motivating your team to experiment with AI46:02 AI for personal projects47:05 Resource allocation in a vibe-coding world48:42 Does AI efficiency just mean more work?50:32 What excites Steve about the future of finance leadership52:08 Finance leade