Scaling Success: Revenue Growth and AI in Sales with John Schoenstein

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Sep 18, 2025

In this engaging discussion, John Schoenstein, Chief Revenue Officer at Customer.io, shares his expertise in scaling sales teams from startups to enterprises. He emphasizes the importance of repeatable revenue systems and pipeline generation as essential skills for success. Schoenstein dives into leveraging data and AI to enhance sales productivity, offering practical tips for optimizing tools and ensuring pipeline hygiene. His insights into fostering a customer-centric culture and manager enablement provide valuable strategies for B2B leaders aiming for growth.

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INSIGHT

Talent And Managers Drive Scalable Growth

Talent quality and frontline managers matter at every stage of growth.
As you scale, managers must enable reps to be independently effective rather than owning every deal.

ADVICE

Hire Reps Who Will Own Outbound

Do recruit reps who want to evolve from inbound to outbound selling as you scale.
Train and incentivize territory ownership because inbound will dilute with headcount growth.

INSIGHT

Few Patriots Build A Winning Culture

A few passionate 'patriots' can create a winning culture and inspire peers.
Look for team-sport, leadership traits during hiring to surface those people.

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In this episode of the Revenue Builders Podcast, our hosts John Kaplan and John McMahon are joined by John Schoenstein, the CRO of Customer.io. The discussion dives into Schoenstein's extensive experience in scaling companies from startup stages to large enterprises, touching on key topics like repeatable revenue systems, the importance of talent, and sales rep productivity. The conversation also explores the integration and impact of AI on sales processes, how to create effective revenue systems at various growth stages, and the cultural and operational shifts necessary for scaling. Schoenstein emphasizes the significance of data, training, and customer-centric approaches in driving successful sales teams. The discussion offers valuable insights for B2B sales leaders looking to understand and implement strategies for scalable and efficient growth.

ADDITIONAL RESOURCES

Connect with John Schoenstein: https://www.linkedin.com/in/john-schoenstein/

Learn more about Customer.io: www.Customer.io

Email John about joining the Customer.io team: john.schoenstein@customer.io

How leaders are driving growth and scalability in 2026: https://hubs.li/Q03JN74V0

Watch Force Management’s C-Level Panel Discussion on Growth, Valuation and Execution: https://bit.ly/4p6kyGS

Enjoying the podcast? Sign up to receive new episodes straight to your inbox: https://hubs.li/Q02R10xN0

HERE ARE SOME KEY SECTIONS TO CHECK OUT

[00:02:36] Scaling Companies: Insights from John Schoen Stein
[00:03:41] The Importance of Talent in Sales
[00:11:16] Pipeline Generation and Sales Leadership
[00:16:50] Building a Winning Culture
[00:18:28] Implementing Repeatable Revenue Systems
[00:30:02] The Role of Data and Rev Ops in Scaling
[00:32:58] Pipeline Focus and Sales Rep Productivity
[00:34:09] Measuring Sales Rep Productivity
[00:35:27] Regional Productivity and Investment Decisions
[00:36:05] Analyzing Sales Data for Insights
[00:38:35] Sales Productivity in Startups
[00:40:00] Remote Work and Sales Productivity
[00:41:42] Encouraging Creativity and Adaptability in Sales
[00:45:52] AI in Sales and Revenue Leadership
[00:49:05] Implementing AI in Sales Processes
[01:02:06] Customer Engagement and AI at Customer.io

HIGHLIGHT QUOTES

[00:05:32] “Talent matters at all levels. You want people who are competitive, coachable, and curious.”
[00:08:33] “You can’t own your territory if you’re depending completely on inbound leads.”
[00:12:54] “Patriots go to battle with you when it’s hard. Mercenaries leave when things get tough.”
[00:16:57] “Pride is the precursor to winning, and winning is the precursor to pride.”
[00:39:57] “If you’re not looking at sales productivity, you’re missing a precursor to whether people will make it.”
[00:46:28] “AI should be a copilot—helping reps win, not just adding more inspection.”
[00:47:10] “Sellers that do not have AI acumen are going to be replaced by sellers that do.”

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