Is Your AI Paying Off? Your CFO Wants Proof ft. Rod Cherkas (HelloCCO)

Is AI still an experiment on your customer success team, or is it delivering results?

In this episode of Unchurned, Rod Cherkas, CEO of HelloCCO and author of The Chief Customer Officer Playbook for the AI Era, joins Josh Schachter to talk about what post-sale leaders need to do now. Rod shares findings from his research with nearly 200 post-sale leaders, explains why CFOs are asking for proof of AI's impact, and gives a practical path from scattered pilots to measurable results. The conversation covers governance, change management, and the leadership habits that make AI stick, along with a real example of AI automating a painful handoff process. If you're planning for 2027, this episode gives you a clear way to think about it.

What you'll learn

- How to connect AI initiatives to the metrics your CFO cares about

- Why leader adoption matters more than tool rollouts, and how to model AI use for your team

- How to pick 4–5 key metrics and align AI pilots around one or two of them

- A simple way to start with a company-grounded AI assistant, without overbuilding the knowledge base

- When to buy enterprise AI tools and when (and when not) to build on top of them

- How to assign an AI champion on your team and create a practical rollout structure

- What the future of customer success roles may look like, and which skills will matter most

Timestamps

0:00 - Preview

1:10 - Introduction & Meet Rod Cherkas

3:15 - Why CFOs want measurable AI results

5:20 - Rolling out AI with governance and expectations

6:28 - Why leaders are resisting change

10:20 - Lessons from his time at Marketo for the AI era

12:38 - Frontline innovators who are ahead of the curve

13:45 - Focusing on continous L & D

15:10 - Automating the sales handoff

17:30 - Starting simple with a company-grounded AI assistant

20:10 - Measuring AI impact with key metrics

22:28 - Why change management takes longer than expected

23:37 - Delegating AI vs. leading it yourself

27:35 - Role modeling and making AI part of daily work

30:15 - Build vs. buy: what to build and what to avoid

33:35 - The future of customer success

---

Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com

---

Where to Find the Guest

Rod Cherkas: https://www.linkedin.com/in/rodcherkas/

---

Where to Find the Hosts:

Josh's LinkedIn: https://www.linkedin.com/in/jschachter/

Unchurned Substack: https://unchurned.substack.com/