Revenue Builders Podcast Episode Summary

Episode Overview

Episode Title: Scaling Success: Revenue Growth and AI in Sales with John Schoenstein
Hosts: John Kaplan and John McMahon
Guest: John Schoenstein, CRO of Customer IO
Date: September 18, 2025

This episode dives deep into the realities, mindsets, and mechanics of scaling revenue organizations. With extensive experience at startups and enterprise giants, John Schoenstein shares actionable strategies for building repeatable revenue systems, managing talent, leveraging data, and embracing AI in modern sales processes.

Key Topics & Insights

1. The Foundations of Scaling: Talent & Repeatable Revenue Systems

Consistent Attributes for Success:

• Talent is a foundational pillar at all company sizes.
  • Prioritize competitive, coachable, curious salespeople with a sense of urgency.
  • Great frontline managers are vital, especially early on.
• Systems and processes must evolve with scale.
  • Small companies: Scrappy, hands-on management is critical ("You might be involved in all the deals").
  • Larger organizations: Empower managers and reps to operate more independently and efficiently as the business grows.

Quote:
"Talent for sure, it matters at every size of company. Right. No matter what."
– John Schoenstein [03:14]

2. Startup vs. Scale: Who Makes the Transition?

Nuances in Talent Across Stages:

• Not every great startup operator thrives at scale, and vice versa.
• Only a fraction of reps can (or want to) evolve from inbound-driven startup sales to outbound-driven, scalable sales organizations.
• Sales reps must aspire to be where the company is headed, not just where it is.

Quote:
"About 50%, maybe even less...can make the jump from startup mode to scalability mode. You really have to want that."
– John Schoenstein [07:34]

Mercenaries vs. Patriots:

• Cultural distinction between transactional "mercenary" reps and "patriot" reps invested in the mission.
• Small teams need a few patriots to set the tone and inspire others.

Quote:
"You only need a couple patriots...people who are going to go to battle when it's hard...that tends to inspire those who work for them."
– John Schoenstein [13:52]

3. Laying the Groundwork for Repeatability

Building Revenue Systems:

• Early stages: Focus on deal flow, manager involvement, and nailing your ICP (Ideal Customer Profile).
• Avoid chasing 'whale' deals at the expense of repeatable wins.
• Develop common language/playbooks for qualification, sales plays, and pipeline management.
• Invest in future-enabling systems while driving current quarter results (aim for a 70/30 split in focus).

Quote:
"Lay that train track while driving the train...focus on today's deals, but also on building systems that will take you to the next phase."
– John Schoenstein [19:40]

Tent Poles for Scaling:

• Identify and anchor crucial elements (ICP, value proposition, engagement model, success profiles) early, but stay flexible with data-driven adaptations.
• Losing these tent poles leads to organizational confusion and cultural erosion.

Quote:
"If you don't have the poles in the tent, you're not going to have a village that can scale."
– John Kaplan [26:51]

4. Leveraging Data and Revenue Operations for Growth

Data-Driven Decision Making:

• The RevOps function is essential: "It's all about data. It starts there."
• Focus on input metrics (pipeline, win rates, sales cycle by segment) instead of outputs alone.
• Move from anecdotal deal chasing to rigorous weekly pipeline inspection, surfacing risks early.
• Sales productivity per region, new/existing deal size, new logo acquisition, and retention are critical metrics to monitor.

Quote:
"Once you get to...25, 30 million, if you're not looking at the pipeline every week...you're going to get burned on the outcome later."
– John Schoenstein [30:56]

Quote:
"Sales productivity is number one...It tells you everything. It's your factory output."
– John McMahon [34:09]

Remote-First Challenges:

• In remote organizations, productivity tracking and transparent dashboards are even more important.
• Publicly reward creativity, adaptability, and constant learning to maintain culture and engagement.

Quote:
"We obsess about productivity...and making sure everybody can see the scorecard so that everybody understands."
– John Schoenstein [39:26]

5. AI in Sales: Practical Applications & Mindset

Cultural Adoption of AI:

• Success with AI isn't just technical, but cultural—embed it into every process, not just bolt it on.
• AI accelerates forecast accuracy, pipeline inspection, and time savings for reps.
• Trust but verify: Use AI to cross-check human judgment (e.g., leveraging Gong for conversation analysis).
• AI enables proactive customer success (churn risk scoring based on product telemetry).

Quote:
"It's more about adopting it culturally. How does it become a part of every single process?"
– John Schoenstein [46:27]

Stack & Integration Challenges:

• Main tools: Salesforce, Gong, SalesLoft, ZoomInfo, UserGems.
• Biggest frustration for reps: Tool overload and the need for seamless integration.
• Protect reps' time—integrate tools natively in workflows to minimize context-switching and distraction.

Quote:
"What's frustrating for reps is having to context shift between multiple different tools."
– John Schoenstein [54:19]

AI Promise vs. Reality:

• Market skepticism remains; sales leaders are wary of "tech sprawl" and tools that serve managers more than reps.
• The goal: AI as a 'copilot,' not a replacement—freeing up rep time so they can increase human selling moments.

Quote:
"If you can help me fly my mission faster, more accurate, safer, and help me fly more missions, save more people, make more money...that’s what sellers are looking for."
– John Kaplan [57:10]

Quote:
"Sellers that do not have AI acumen are going to be replaced by sellers that do. No question in my mind."
– John Kaplan [59:06]

6. Customer IO: The "AI-First" Customer Engagement Platform

What is Customer IO?

• A platform for tech-savvy organizations to create personalized, automated omnichannel messaging journeys.
• Uses first-party data and AI to maximize engagement, conversion, and retention via email, SMS, in-app, and more.

Quote:
"Our mission is really to transform the way companies communicate with their customers...building the most trusted customer engagement platform for product-led companies."
– John Schoenstein [62:24]

Recruiting & Contact:

• Customer IO is rapidly growing and hiring.
• Contact: john.schoenstein@customer.io

Timestamps for Key Segments

• 00:22-03:06: Introduction to John Schoenstein, career context
• 03:06-07:10: Core attributes for scalable sales teams and the challenge of talent evolution
• 09:49-13:52: Patriots vs. mercenaries, startup vs. scale sales rep mentalities
• 19:40-26:32: Establishing systems/processes—"tent poles" and the dangers of losing them
• 30:56-33:32: Importance of data, RevOps, pipeline inspection
• 34:09-43:36: Sales productivity, measuring inputs/outputs, remote team management
• 45:45-46:27: Cultural embrace of curiosity, learning, and AI's future role
• 46:27-55:08: AI use-cases, tools, and integration, practical examples
• 55:30-59:06: The reality of tech sprawl, importance of seller-centric AI, and the 'copilot' debate
• 62:24-64:52: Customer IO pitch, mission, and contact info

Notable Quotes

• On Talent:
  "I tend to like people who are competitive and operate with a sense of urgency... coachable, curious and want to learn more about the customer." (John Schoenstein [03:16])
• On Scaling:
  "As you scale...you want your frontline managers enabling reps to operate at scale and be more independent." (John Schoenstein [03:54])
• On Moving Upmarket:
  "To get to 500 million, you're definitely going to have to be moving upmarket a bit... you've got to hire that DNA into the company so everyone else can see what good looks like." (John Schoenstein [25:25])
• On AI:
  "We're a kind of an AI-first product... something that's really helped us is our CEO, Colin, has been all about AI in the culture, in everything we do." (John Schoenstein [46:27])
• On Productivity:
  "It's a balance between making sure there's enough activity of the right kind... so that productivity then is being carried through." (John Schoenstein [40:31])
• On seller value:
  "Pride, once you get to that point, like, you've got something special, it's a place people want to be, and a place people don't want to leave." (John Schoenstein [17:49])

Memorable Moments

• The hosts and guest openly discuss the challenge of remote team management and sharing best practices when "the energy of the office" is missing [39:26-43:36].
• Lighthearted debate about the term "copilot" when referring to AI as an assistant—not a leader—in sales [57:10-59:14].
• A passionate call-out on salespeople embracing AI or risk getting left behind in the industry [59:06].

Conclusion

This episode offers a masterclass in building, scaling, and future-proofing B2B revenue organizations, blending timeless leadership insights with pragmatic advice on data, culture, and AI. John Schoenstein's real-world experience makes this a must-listen for anyone invested in sales, revenue operations, or go-to-market strategy.

Contact John Schoenstein: john.schoenstein@customer.io
Learn more: Customer IO

For more Revenue Builders episodes and resources, visit Force Management.