Episode 59: Customer Success Automation

In this episode of the RevOpsAF podcast, co-host Camela Thompson sits down with Joe Di Grande, former VP of Sales & Customer Success at Business Insider and now founder of Joe Does Tech Touch, a consultancy helping companies scale their post-sales operations. Together, they explore the often-overlooked world of Customer Success Automation—where small wins, clean data, and cross-functional alignment can make the difference between churn and long-term growth.

Why CS Automation Often Goes Wrong

Too many teams rush to implement automation without first addressing the basics. Joe warns that leaders frequently chase shiny new tools (especially AI-driven ones) instead of focusing on the problems they already have.

“You can’t really automate unless you have clean and accurate data. That’s always the first step people forget.” – Joe Di Grande

Rather than building 15-step renewal sequences out of the gate, operators should identify core KPIs and use automation to reinforce them—whether that’s shortening time-to-value, streamlining onboarding, or flagging at-risk accounts.

Start Small: Internal-Facing Automations

Joe recommends starting with internal-facing automations before exposing them to customers.

For example:

• Queueing up recommended emails or in-app messages for CSM review (instead of sending them automatically).
• Delivering playbooks when accounts show risk signals.
• Automating repetitive internal tasks like contract reminders or health check prompts.

This “internal-first” approach reduces risk while creating efficiency. As Joe puts it:

“Serve the information to the rep before serving it to the customer.”

Data Foundations for CS Ops

Data quality is the lifeblood of effective automation. While sales ops often have firmographic data in order, CS needs different inputs to succeed:

• Contract dates (start, midpoint, renewal)
• Contact roles (day-to-day, decision-maker, financial approver)
• Product usage at both the account and end-user level
• Engagement history (support tickets, last inbound activity, survey results)

RevOps can help by enforcing required fields in CRM systems like Salesforce or HubSpot, aligning onboarding requirements, and running audit reports to catch errors before they cascade into automation failures .

For more on building reliable data pipelines that fuel automation, check out our prior digital event on data quality excellence in RevOps.

Fixing the Sales-to-CS Handoff

One of the biggest friction points is the sales-to-customer-success transition. Without structured handoffs, CS teams are left in the dark about use cases, integration requirements, or even basic contract details.

Joe recommends requiring essential fields at opportunity close, passing them into account transfer docs, and validating them in kickoff calls. But he also stresses balance:

“Your CS team might ask for 48 fields. Sales will give you zero. Meet in the middle—figure out the six most critical pieces of information you can’t live without.” – Joe Di Grande

This pragmatic approach ensures alignment without overwhelming sales teams or stalling deals.

We’ve also written about why the sales-to-CS handoff is often the weakest link in the customer journey—and how RevOps leaders can fix it. Read the full article here.

Health Scores, Surveys, and Pitfalls to Avoid

Health scores remain a contentious topic in CS Ops. Joe predicts AI will eventually improve their accuracy but cautions that they’re still highly subjective and prone to manipulation.

He also highlights the risk of misusing surveys: too many companies ask customers only about their CSM, not about the actual product experience. As Camela points out, that creates misleading data. Instead, teams should layer usage data, survey results, and account-level insights to build a more holistic view.

If you’re rethinking customer health scoring, this podcast episode on delivering customer value and the evidence of impact will be helpful.

Best Practices for CS Automation

Joe closes with a set of battle-tested best practices:

• Audit before you automate – know where data lives, how it flows, and whether you can rely on it.
• Start with exclusions – define who should not be in your automation to prevent embarrassing mistakes.
• Roll out gradually – begin with a small segment (e.g., long-tail accounts) before scaling to the broader base.
• Create audit dashboards – reports that flag when expected automations fail to trigger or when “impossible” scenarios appear (e.g., prospects with active contracts).
• Set leadership expectations – automation carries risk; get buy-in before scaling programs.

“Automation can break at any point in time. Start small, experiment, and make sure leadership understands the risks as you scale.” – Joe Di Grande

For a broader playbook on automation across RevOps—not just in CS—see our digital event recording on GTM infrastructure for the AI era.

Final Thoughts

This episode is a masterclass in applying RevOps discipline to Customer Success. By grounding automation in data hygiene, focusing on internal efficiencies, and aligning sales and CS, Joe demonstrates how even small, low-risk automations can deliver outsized impact.

Looking for more strategies to level up your CS Ops? Check out our blog, join our community and subscribe to our YouTube Channel for more insights.