Going Deep on AI and Building with Claude

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:

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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