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/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
—
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
—
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
Run the Numbers