E37: Jason Wolf on Uncovering Hidden Growth Opportunities in Go-To-Market
The Revenue Leadership Podcast with Kyle Norton
Release Date: 06/18/2025
E62: CRO Life: from a $20B Exit, to a Hyper-Growth AI Org (Michelle Donnelly, CRO @ Crescendo)
The Revenue Leadership Podcast with Kyle Norton
Crescendo went from zero to $100M ARR in under two years. And today’s guest, CRO Michelle Donnelly, is leading the revenue team. In a market where every AI competitor claims the exact same capabilities, Michelle argues that "trust me" sales tactics don’t work anymore, and what her team is doing instead. She explains why she banned traditional sales demos in favor of building functional prototypes using prospect data (sometimes within 24 hours). Michelle also breaks down the transition to outcome-based pricing and how she she’s working to compress new rep ramp time. All this, and a ton...
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E61: GTM Strategy: 5 Insights from 500 B2B SaaS Companies (Jeremey Donovan, EVP Sales + CS at Insight Partners)
The Revenue Leadership Podcast with Kyle Norton
As EVP of Sales and CS at Insight Partners, Jeremey advises over 500 B2B SaaS companies. In this episode, he reveals why the top 10% of performers are actually expanding their outbound teams, not cutting them. And we cover a ton, including: The Outbound Paradox: Why winning companies are doubling down on SDRs while everyone else pulls back. Build vs. Buy: Why purchasing point solutions right now is a "risky business" (and the case for building your own). The Great Consolidation: How AEs are absorbing the SDR function and what it means for your org chart. The CRO Differentiator: The one...
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E60: The Claude Code Era: Mastering Autonomous GTM Agents (Jordan Crawford, Founder @ Blueprint)
The Revenue Leadership Podcast with Kyle Norton
Jordan Crawford (Founder @ Blueprint GTM) returns with a reality check for GTM leaders: The ChatGPT era is over. We’re entering the season of Claude Code. That means you can move past static prompts and brittle workflows. We are now in a world where autonomous agents write code, execute complex goals, and learn recursively. Jordan breaks down how to set up local environments where context compounds over time, allowing you to deploy "infinite interns" against your most manual processes. A few of the topics we cover: The 3 Eras of GTM AI: Why we’ve graduated from ChatGPT (text) and...
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E59: Usage-Based Comp, AI, and the End of the SDR (Tyler Will, VP of RevOps @ Intercom)
The Revenue Leadership Podcast with Kyle Norton
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...
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E58: Replacing Your Sales Team with AI Agents (Jason Lemkin, Founder & CEO @ SaaStr)
The Revenue Leadership Podcast with Kyle Norton
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. to Topline...
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E57: The New Rules of Executive Recruiting in the AI Era (Asad Zaman, CEO @STA)
The Revenue Leadership Podcast with Kyle Norton
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)...
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E56: Becoming a CFO Whisperer & Revenue Architect (Allison Metcalfe, CRO @ Zenoti)
The Revenue Leadership Podcast with Kyle Norton
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. to Topline Newsletter. , the #1 podcast for founders, operators, and investors...
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E55: GTM AI Advice from a Salesforce & Siebel Veteran (Peter Grant, CRO @ You.com)
The Revenue Leadership Podcast with Kyle Norton
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....
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E54: $40M ARR with 50‑Person Team (in less than a year) - Bryan Adams, VP Sales at bolt.new
The Revenue Leadership Podcast with Kyle Norton
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. to Topline Newsletter. , the #1 podcast for founders,...
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E53: Sales Capacity Planning That Doesn’t Suck (Jenny Dingus, SVP Global Sales @ Clio)
The Revenue Leadership Podcast with Kyle Norton
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. to...
info_outlineJason Wolf, President of FullStory and former CRO at Ping Identity and SAP Ariba, joins Kyle Norton to share how companies unlock step-change growth by entering new markets, building new capabilities, and aligning cross-functional teams. Jason has led revenue growth from $200 million to $1.6 billion and brings hard-won lessons from scaling globally.
He explains how to time multi-product and multi-region moves, validate new growth bets, and build strategies driven by customer pull rather than competitor pressure. Jason also covers the role of go-to-market in product innovation, how to focus teams around renewals, and what it takes to scale with speed and precision.
Thanks for tuning in! New episodes of The Revenue Leadership Podcast drop every Wednesday.
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Key chapters:
(00:00) - Jason Wolf's Impressive Journey
(02:00) - Defining New Growth Horizons
(03:25) - Building Character Through Change
(04:10) - Mental Map for Growth Opportunities
(05:00) - What Growth Truly Means
(06:30) - Finding and Serving New Buyers
(07:53) - Stated vs. Observed Truths
(10:00) - Deciding Where to Grow Next
(14:38) - Lessons from Expanding Globally
(18:30) - Staging Product and Geographic Expansion
(25:23) - The Pioneer's Mindset in New Markets
(35:52) - Go-to-Market's Role in Product Innovation
(44:50) - The Rise of the Specialist
(57:57) - The New Revenue Algorithm
(1:12:00) - Driving World-Class Alignment