Tyler Will (VP RevOps, Intercom) breaks down how Intercom overhauled its go-to-market engine after shifting to AI-first products.

What we cover:

- Why too many revenue leaders obsess over success metrics but ignore the inputs that actually drive them

- The specific comp plan changes Intercom made when moving from seats to usage-based pricing... including giving reps MRR credit for overages without forcing awkward contract conversations

- How post-sales motions fundamentally change when you're monetizing resolutions instead of seats

- Tyler's four principles for comp plans that actually work

Also discussed: When to do a real comp overhaul vs. minor tweaks, why RevOps teams are getting bigger before they get smaller, and using Claude Code to query Snowflake directly.

Chapters:

00:00 Introduction and Guest Background

01:59 Shifting Focus From Success Metrics to Input Metrics

06:06 AI Literacy Required for Modern Revenue Leaders

09:24 Selecting Metrics Without Micromanaging Behavior

17:01 Intercom's Internal and GTM AI Transformation

20:01 Shifting to Resolution-Based Pricing Models

25:46 Evolving the CSM Role for Consumption

28:53 Adapting Compensation Plans for Usage-Based Revenue

33:52 Core Principles for Variable Compensation Design

44:37 Aligning Compensation Strategy With Product Roadmaps

52:00 Restructuring RevOps and Hiring GTM Engineers

56:44 Automating RevOps Tasks With Cloud Code

01:05:58 Impact of AI on SDR and Success Teams

01:09:10 Specific Internal AI Use Cases at Intercom

01:15:20 Quick Fire: Good vs. Great CROs and Advice

Jason Lemkin (Founder & CEO @ SaaStr) returns to talk about replacing his sales team with 20+ AI agents.

What you'll learn in this episode:

- Why Jason stopped paying six-figure SDRs who ghost—and what he built instead

- The 70,000 AI-sent emails that drove 15% of SaaStr London revenue

- How to pick your first AI tool (hint: do a 2-vendor bakeoff, not 10)

- Why Salesforce is suddenly the hub every agent needs

- The "incognito test" every GTM leader should run on their own website

(And a whole lot more!)

Thanks for tuning in. Catch new episodes every Wednesday.

Subscribe to Topline Newsletter.

Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech.

Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast!

Chapters:

00:49 Introduction and Jason's Investment Philosophy

04:07 Evaluating Founders and the "Why Now" Question

09:32 The Step Function Change in GTM AI

14:15 Managing Conflict Between Multiple AI Agents

17:43 Replacing Human Sales Teams with AI Agents

21:50 The Importance of Forward Deployed Engineers

24:57 The Terminal Decline of Mid-Pack Sales Roles

30:09 Finding the Internal GTM Nerd to Lead AI

34:15 Executives Must Roll Up Sleeves and Implement

46:22 Fixing Inbound and Support with Instant Answers

53:15 Why You're Failing To Source The Right Tools

57:27 Evaluating Incumbents vs. AI-Native Startups

01:02:41 The Salesforce Renaissance and Agentforce

01:09:45 Triple, Triple, Double, Double in the AI Era

01:15:28 Choosing Between High Intensity and Lifestyle Roles

Hiring a VP or CRO has never been tougher (or more important). Asad Zaman, CEO of Sales Talent Agency - and one of the most trusted voices in GTM recruiting - joins host Kyle Norton to talk about how GTM leadership hiring is changing fast.

They dig into:

- Why AI broke the traditional interview process, and what they do now instead

- How to build a robust hiring scorecard that performs miles better than a fluffy job description

- The trade‑offs that actually kill VP hiring processes

- How top CROs should evaluate future leaders (and spot "pre‑peak" talent)

- The biggest blind spot CROs have when hiring VPs

I mean... who isn't curious about the tested frameworks from the guy behind 1,000+ GTM placements a year?

Thanks for tuning in. Catch new episodes every Wednesday.

Subscribe to Topline Newsletter.

Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech.

Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast!

Chapters:

00:34 Guest Introduction: Asad from STA (Sales Talent Agency)

02:30 Today's Topic: The Challenge of Leadership Hiring

04:14 How AI Has Changed Executive Hiring

07:53 The Rise of the AI-Native Leader

10:26 Market Polarization: Talent Demand and Layoffs

19:03 The New Definition of a Great Leader

24:22 Building an Effective Leadership Hiring Scorecard

29:15 Defining Problems, Jobs to Be Done, and Constraints

35:11 Compensation Psychology and Negotiation Pitfalls

40:34 Mapping the Market and Operationalizing the Scorecard

49:27 Modern Interview Design for Senior Roles

53:12 Teaching as a Core Leadership Skill

56:27 Live Whiteboarding: Replacing Case Studies

01:01:54 Evaluating Candidates for Peak Performance and Potential

02:03:31 CROs' Biggest Blind Spot in Hiring VPs of Sales

Allison Metcalfe's path to CRO was built on systems thinking, multiplier leadership, and a journalist's instinct for "why." In this episode, Kyle and Allison talk through what separates good revenue leaders from great ones, and how to actually lead peers and execs, not just manage them. And maybe we shouldn't tell you this, but… Allison even reveals her hardcore alter-ego that helps her better ride the highs and lows in the CRO role.

Thanks for tuning in! Catch new episodes every Wednesday.

Subscribe to Topline Newsletter.

Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech.

Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast!

Chapters:

01:47 Allison Metcalfe's Career Journey

03:41 Non-Traditional Path to CRO

05:16 Architecture Thinking and the AI Era

07:25 Systems Thinking and Curiosity in Revenue Leadership

09:01 Managing Executive Relationships

10:56 Discovering Multiplier Leadership

18:44 Decision-Making Without Consensus Paralysis

24:30 Building Healthy Executive Relationships

30:11 Authenticity and Connection in Remote Work

33:09 Using Enneagram for Team Understanding

38:00 Radical Empathy Across Departments

46:27 Collaborating Effectively with Finance

53:21 Navigating 2026 Planning Conflicts

58:26 Data-Driven Decision Making and Change Management

01:03:32 Quick Fire: Career Lessons, Alter Egos, and Book Recommendations

Peter Grant helped take Siebel from $39M to $2B in revenue and was employee #9 for Salesforce in Europe. He knows exactly what a platform shift looks like. Now, as the CRO of You.com, Peter argues that the AI wave is moving 30x faster than the internet era—and your current sales playbook is already obsolete.

In this episode, Peter strips away the hype to focus on the operational reality of running an AI-first GTM organization. He explains the skill stack today's sellers need, why your team needs to understand APIs, and the specific benchmarks you need to hit to survive the next two years. Plus a whole lot more!

Thanks for tuning in. Catch new episodes every Wednesday.

Subscribe to Topline Newsletter.

Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech.

Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast!

Chapters:

00:00 Peter Grant's Career and Revenue History

07:32 Choosing You.com and Pivoting to Enterprise

11:46 How AI Search Transforms Sales Discovery

16:12 The Speed and Scale of AI Sales

20:55 Embedding AI Agents into Existing Workflows

27:11 Benchmarking Enterprise AI Spend and Adoption

33:14 Solving the Employee AI Literacy Gap

38:59 The Evolution of the Sales Rep Profile

43:06 Implementing and Prioritizing AI Transformation

52:05 The Hard Reality for Sales Laggards

59:30 Investing Upfront Time to Master Prompting

01:03:10 Why Revenue Leaders Must Be Context Setters

01:10:12 How Tactics Dictate Strategy in Enterprise Deals

01:12:49 Rapid Fire: Leadership Advice and Lessons

Bolt.new blew past past $40M ARR in just one year with only 50 people. In this episode, Bryan Adams, VP Sales at Bolt.new sits down with host Kyle Norton to break down how go-to-market operates at a hyper-growth AI company.

Bryan shares some of their tech stack, and gets real about leadership—hiring "adults," firing fast, and focusing on what reps actually need to win.

If you're leading a modern GTM org, this one's worth your next commute.

Thanks for tuning in! Catch new episodes every Wednesday.

Subscribe to Topline Newsletter.

Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech.

Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast!

Chapters:

01:30 Meet Brian Adams, VP of Sales at Bolt.new

02:06 What Is Vibe Coding and How Bolt Works

03:54 Building Successfully with Bolt's "Plan" Feature

06:11 Layering Builds and Iterative Development

08:47 Real Use Cases Built with Bolt

10:24 The Build vs. Buy Decision Framework

12:57 Inside Bolt's Go-to-Market Tech Stack

13:59 Using Freckle to Unmask and Enrich Leads

15:08 AI-Powered Prospecting and Support Automation

17:41 Shifting GTM Strategy: From PMs to Engineers

19:54 Outbound Strategy, Target Accounts, and LinkedIn Engagement

25:13 How RevOps and SDR Growth Teams Collaborate

29:13 Bolt's Growth, Scale, and Competitive Landscape

33:03 Competing in a Knife Fight Market

36:56 Contract Structures, Compensation, and Profitability

40:38 Hypergrowth Lessons and Leveraging Automation

44:47 Leadership Philosophy: Empowerment and Accountability

48:08 Building Trust and Team Culture

51:17 Leadership, Firing Fast, and Team Integrity

52:59 Quick Fire: Great vs. Good Sales Leadership

54:32 Hard Lessons, Best Advice, and Book Recommendations

57:13 Closing Remarks and Outro

Clio's SVP of Global Sales, Jenny Dingus, joins Kyle Norton to talk about why the "people × quota" revenue planning model is terrible, and what they're using instead.

Jenny shares how Clio's $1B acquisition flipped their planning model, how they forecast in high-uncertainty markets, and what "drawing the owl" looks like in real life.

If you run revenue and you're tired of spreadsheet fantasy planning (or just want to know what two senior GTM leaders are thinking about these days), worth a listen!

Thanks for tuning in! Catch new episodes every Wednesday.

Subscribe to Topline Newsletter.

Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech.

Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast!

Chapters:

02:15 Jenny's Career Journey from RingCentral to Clio

04:00 Vertical SaaS and Expanding Market Opportunity

06:10 Disruption, AI, and Modernizing Legal Tech

08:00 Educating a Skeptical Market on AI Adoption

10:15 The Myth of the "People x Quota" Growth Model

12:05 Why Linear Capacity Planning Still Persists

14:45 The Integrated Planning Alternative

17:10 Planning Amid Product Launches and Acquisitions

20:15 Quotas, Motivation, and Momentum in Sales Teams

23:00 Multi-Factor Revenue Planning and Emerging Markets

27:05 Managing Speculative Growth Bets and Reforecasting

31:10 Balancing Capacity and Demand in High-Growth Environments

34:40 Strategic Congruence: Playing the Right Company Game

38:30 Communication, Change Management, and Leadership Alignment

43:45 Inside Clio's Acquisition and GTM Integration Process

48:40 Leadership Communication Principles and "Feeling" the Message

52:00 Frontline Enablement During Massive Change

56:45 Building Continuous Feedback Loops and AI-Enabled Training

01:00:30 Quickfire: Lessons in Leadership, Humility, and Focus

01:04:00 Favorite Reads and Closing Reflections

How do you stand out when your feature list looks like everyone else's? In this episode, Jonathan Leaf, CRO of BambooHR, joins host Kyle Norton (CRO at Owner.com) to break down how he's built competitive edge in undifferentiated markets—from Softchoice to AWS, RingCentral, and now BambooHR.

Jonathan shares how to:

- Win when products look the same

- Stay maniacally focused on a specific segment and ICP

- Use values and leader visibility to drive accountability and performance

- Build organizational rhythm that fuels execution

Thanks for tuning in! Catch new episodes every Wednesday.

Subscribe to Topline Newsletter.

Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech.

Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast!

Chapters:

00:00 Introducing Jonathan Leaf, CRO of BambooHR

01:06 Career Journey: From SoftChoice to AWS to BambooHR

03:14 Inside BambooHR: Scale, Customers, and Focus Areas

04:35 Defining SoftChoice and Competing Without IP

06:25 Competing in Crowded, Undifferentiated Markets

09:37 Building Differentiation Through Mission, Focus, and People

11:39 How Culture and Customer Experience Win Deals

17:02 Being Prescriptive: Focusing on the Right Market Segment

21:42 Hiring for Mission Alignment and Go-to-Market Evolution

26:38 Testing and Validating Sales Profiles with Data and AI

29:47 Inspecting Strategy and Operating Cadence for New Growth Bets

39:12 Why Execution and Focus Win in Competitive Markets

40:09 Positioning Products Beyond Features and Selling Peace of Mind

43:15 Point-of-View Positioning and Radical Transparency in Sales

47:19 When the Sales Experience Reflects Customer Experience

49:29 Culture as a Revenue Driver and Operationalizing Company Values

57:55 Maintaining Culture During Change and Leading with Visibility

03:52 Building Alignment and Empowerment Across the Executive Team

12:26 Lessons in Career Patience, Growth, and Self-Balance

13:42 Quickfire: Leadership, Learning, and Hard-Earned Lessons

Kyle Norton (CRO at Owner.com) sits down with JD Saint-Martin, President of Lightspeed Commerce, to unpack how he went from startup founder to public-company executive. They discuss scaling Lightspeed from $75M to $1.2B in recurring revenue, and the leadership lessons behind that growth. The conversation covers building high-performance sales cultures, promotion systems, enablement investment, RTO and culture philosophies, and more.

Thanks for tuning in! Catch new episodes every Wednesday.

Subscribe to Topline Newsletter.

Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech.

Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast!

Chapters

00:01:51 – Startup to Acquisition

00:03:34 – Global Upbringing & VC Start

00:04:03 – Scaling to $1.2B ARR

00:05:25 – Growth Through SaaS & Payments

00:05:44 – Founder to Exec Transition

00:07:21 – Empathy From Doing Every Role

00:09:11 – Leading 3,500 Employees

00:11:07 – "Roll in the Mud" Leadership

00:13:28 – Early Lessons & Advice

00:16:37 – Building High-Performance Culture

00:18:28 – Candid Hiring & Fit

00:21:42 – Transparency in Recruiting

00:22:06 – Obsession With Metrics

00:23:55 – Inputs vs Outputs

00:24:58 – Manager Pyramid Framework

00:27:57 – Promotions & Company Values

00:29:42 – Elite Points System

00:33:29 – Systemized PIPs

00:36:20 – Retaining Top ICs

00:40:31 – Investing in Enablement

00:42:05 – COVID & Lost Osmosis

00:45:06 – Return-to-Office View

00:49:18 – GTM Owns Enablement

00:51:05 – Balancing Autonomy & Consistency

00:53:32 – Payments & Compensation

00:55:35 – No Work-Life Balance

00:59:41 – Energized by the Work

01:18:34 – Favorite Book & Takeaways

01:20:13 – Closing & Outro

Tara DiCristo-Schmitt (CRO at Houzz) joins host Kyle Norton (CRO at Owner.com), to explore how elite sales leaders build culture, trust, and clarity.

Drawing lessons from her time at ADP and HubSpot, Tara explains why vision beats velocity, why recognition is an underrated tool, and why forecasting is more about trust than it is about simple numbers. A candid, tactical conversation about getting the best from your teams.

Thanks for tuning in! Catch new episodes every Wednesday.

Subscribe to Topline Newsletter.

Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech.

Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast!

Chapters

00:00 – Introduction

01:00 – Tara's Career Journey

03:15 – ADP Sales Culture

06:20 – Shift Away from Structure

09:00 – Rebuilding Outbound Motion

11:00 – Recognition and Team Motivation

15:00 – Trust as Cultural Foundation

17:30 – Vision Beats Velocity

21:00 – Setting and Communicating Vision

25:30 – Company-Wide Recognition Rituals

32:00 – Execution Model for Hard Times

39:00 – Building Trust and Credibility

47:00 – Hiring for Trust and Self-Awareness

52:00 – Forecasting Through Trust