Encouraging Team AI Experimentation

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. 

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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/CJ

Rillet 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/cj

EY 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/techstartups

SpendHound 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.com

Brex 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/metrics

Aleph 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

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LINKS: 

Steve on LinkedIn: linkedin.com/in/steveisomjr

Company: https://bloomerang.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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TIMESTAMPS:

0:00 Preview

1:25 Intro

2:55 Welcome Steve Isom

3:13 CFO to COO promotion

5:02 Having a pulse on every function

6:51 Defining "strategic CFO"

7:19 Tying strategy to value creation

9:27 Being embedded in the rhythm of the business

10:55 Finance leaders as commentators vs. team captains

12:25 Sponsors — RightRev | Rillet | EY

15:33 Killing projects as a core skill

18:14 Activity doesn't equal impact

19:16 Project Steve killed

20:39 Taking over the customer org at Bloomerang

22:18 Why acquisition is a cash-losing exercise

23:07 LTV lives post-sale

24:39 Most vulnerable area: customer success

25:24 Ruthless CSM segmentation

26:30 Nonprofits don't think about your software

29:21 Sponsors — Spendhound | Brex | Aleph

32:43 CFO running ops

35:52 Metrics vs. humans

37:18 Skip levels and what they reveal

39:01 Incentives drive the wrong outcomes

40:22 Customer-introduced delays as a key sub-metric

40:27 Unit economics become tangible when you're accountable

42:17 Going deep on AI

45:13 Motivating your team to experiment with AI

46:02 AI for personal projects

47:05 Resource allocation in a vibe-coding world

48:42 Does AI efficiency just mean more work?

50:32 What excites Steve about the future of finance leadership

52:08 Finance leaders who don't use AI won't get hired

52:13 Credits

#RunTheNumbersPodcast #CFO #StrategicFinance #SaaSFinance #FinanceLeadership #CFOtoCOO