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!

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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.

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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.

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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.

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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

Head of GTM Engineering Everett Berry returns to join Kyle Norton (CRO at Owner.com) for a rapid-fire Q&A on how Clay structures its ops, automates everything from QBR decks to redlines, and experiments with the next wave of AI-native sales tools.

Thanks for tuning in! Catch new episodes every Wednesday.

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00:00 — AI Q&A Format: Everett Berry returns to talk AI and GTM

01:02 — Inside Clay's GTM Engineering Team: structure, size, and stack

06:08 — Reporting Lines: How GTM engineering fits under Clay's leadership

06:26 — Matrix Org Design: RevOps, Finance, and cross-functional ops

09:05 — Balancing Self-Serve vs. Sales-Led Growth

10:54 — When to Add a CRO-type role

13:12 — Clay's Favorite AI Tools: Dust, Crosby, Granola, and Gong

15:39 — How Legal Ops Got Automated with Crosby

18:44 — Top Internal Clay Use Cases: content creation and sequencing

19:41 — Clay's Sequencer and the Future of Sales Engagement

20:27 — The "Pane of Glass" Future for Reps

24:33 — Custom-Built Sales Stacks and Telephony Gaps

26:30 — The Rise of Text- and DM-Based Selling

28:49 — New Frontiers: WhatsApp, iMessage, and automation in DMs

32:02 — Does AI Replace Sales Reps? Not so fast.

33:47 — Creative, Expert-Level Selling in the AI Era

40:47 — Education, Creativity, and the Future of Work

42:51 — How to Convince Your CEO to Invest in AI

45:48 — When to Hire a GTM Engineer (and why the "Golden List" matters)

48:21 — Closing Thoughts: It's a great time to build in GTM

In this episode, Kyle Coleman (Global VP Marketing @ ClickUp) joins Kyle Norton (CRO @ Owner.com) to unpack the evolving marketing landscape.

The double Kyles dig into:

• The growing problem of "work sprawl."

• The rise of AI-powered marketing teams

• How to get better results with lower headcount

• Why the best leaders today focus less on empire-building and more on process-building

• And a whole lot more

Thanks for tuning in! Catch new episodes every Wednesday.

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Episode Chapters:

1:02 – The Changing Mandate for CMOs

6:00 – From Process Management to "AI-ification"

10:40 – The New Responsibility of Marketing Leaders

13:45 – Managing Campaigns in the AI Era

17:15 – Domain Expertise Before Prompting

19:15 – Positioning ClickUp as an AI-Native Company

24:40 – Aligning Marketing, Product, and AI

27:35 – Leadership Philosophy in the Age of AI

33:00 – Horizontal Leadership and Cross-Functional Alignment

35:25 – Blurring Lines Between Sales, Marketing, and Product

41:00 – Owning Metrics and Healthy Friction

44:35 – Building an Applied AI Center of Excellence

46:57 – Operating in AI-Native vs. Traditional SaaS Environments

48:13 – Helping Traditional Companies Modernize with AI

53:05 – Change Management and the Challenge of Adopting AI

55:32 – Where Marketing Teams Should Start with AI

58:45 – Standing Out Amid Market Noise

1:00:31 – Owning the Language and Evangelizing the Problem

In this episode, Kyle Norton, CRO of Owner.com, is interviewed by Sophie Buonassisi from the GTMnow Podcast. He shares the decisions and frameworks that helped take the company from $2M ARR to over $50M and a billion-dollar valuation. Kyle breaks down the bold early moves—like letting go of half the sales team in his first 45 days—alongside the pivotal role of setting a high talent bar, investing in RevOps early, and building scalable infrastructure. He also unpacks lessons on churn reduction, hiring for DNA over case study performance, and why strategic congruence across product, GTM, and fundraising is critical. Finally, Kyle offers his perspective on AI in go-to-market, balancing in-office vs remote work, and the leadership principles that drive long-term growth.

Episode Chapters:

(01:00) — Intro

(02:26) — Scaling to Unicorn

(03:21) — Bold Sales Reset

(05:33) — Early GTM Decisions

(13:22) — Fixing Churn

(16:31) — Hiring for DNA

(31:08) — Leadership Alignment

(33:23) — Data-First AI

(48:25) — Remote vs. In-Office

(55:26) — Leadership Principles

Cool links:

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In this episode, host Kyle Norton (CRO at Owner.com) sits down with his longtime colleague Steve Dinner, VP of RevOps at Owner.com. Together, they unpack how to build a revenue operations team that drives real business outcomes rather than just managing tools and processes. Steve shares lessons from his journey to becoming a world-class RevOps leader, and highlights why empathy, trust, and business alignment matter more than endless automation. The conversation touches on why ride-alongs are one of Steve's secret weapons, agile frameworks for RevOps, and what CROs should look for when hiring their first operations leader. Packed with insights from two seasoned operators, this episode is a must-listen for CROs, RevOps leaders, and anyone scaling high-growth revenue teams.

Thanks for tuning in! Catch new episodes every Wednesday.

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• (00:00) Introduction & Kyle sets the stage

• (01:25) Steve's background and path into RevOps

• (03:50) The importance of blending sales leadership with RevOps thinking

• (07:20) Empathy, rep experience, and solving business problems beyond tech

• (11:50) Winning big vs. losing small

• (19:15) Why trust and collaboration matter in cross-functional partnerships

• (23:55) Ride-alongs and staying connected to frontline reps

• (37:10) Transitioning RevOps to agile methodology

• (51:00) How CROs should think about hiring their first RevOps leader

• (1:05:10) Building the CRO–RevOps partnership and avoiding "yes/no" traps

• (1:13:20) Advice for new heads of RevOps

• (1:17:00) Hardest leadership lessons learned

Clay's Everett Berry breaks down how elite revenue teams are actually winning with AI today. We cover the GTM Engineer model Clay runs in-house, why prompt iteration and "taste" still matter, and the unsexy but vital work of segmentation, account scoring, and orchestration across the funnel. Plus, where AI SDR efforts go off the rails, and the concrete first steps a CRO should take to get real adoption and lift.

Thanks for tuning in! Catch new episodes every Wednesday.

Don't miss GTM2025 — the only B2B tech conference exclusively for GTM executives. Use code TOPLINE for 10% off your GA ticket.

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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!

Timestamps:

(01:16) — Guest intro: Everett Berry, Head of GTM Engineering at Clay

(02:09) — Origin story → growth roles → discovering Clay

(04:52) — What is a GTM Engineer? Clay's embedded (Palantir-style) model & why it works

(08:10) — Automating the busywork: pre-call research & more

(10:53) — Why many AI GTM pilots miss ROI, plus AI-SDR hype

(17:01) — Agent scope and lossiness, checks/evals, and prompt iteration best practices

(24:20) — Day-1 win: industry classification; when to use GPT vs. Anthropic for the job

(27:54) — CRO AI rollout sequence

(33:32) — Data foundations: pipelines, API realities, and org readiness

(41:25) — Org design: where GTM Engineering lives

(52:10) — Team & stage: roles to hire, GTME + RevOps + agency model; what to insource vs. outsource

(1:00:24) — Rapid fire questions

Dr. Michael Gervais, renowned high performance psychologist behind the Seattle Seahawks' Super Bowl win and mental coach to Olympic athletes and NASA jumpers, reveals the often-ignored psychological drivers behind elite sales and leadership performance. This episode challenges revenue leaders to rethink competition—not as a zero-sum game, but as a relentless pursuit to be their very best while elevating teammates.

Visit revenueleadership.findingmastery.com to get Dr. Mike's Morning Mindset Routine.

Thanks for tuning in! Catch new episodes every Wednesday.

Don't miss GTM2025 — the only B2B tech conference exclusively for GTM executives. Use code TOPLINE for 10% off your GA ticket.

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!

Key chapters:

(00:00) - Introduction to Dr. Michael Gervais and His High-Performance Psychology Impact (02:30) - Finding Mastery: Mental Training for Peak Performance (04:30) - Seahawks Legacy: Building Optimism and Mental Toughness in Teams (08:00) - The Power of Input Focus: Clarity and Culture Over Outcome Obsession (12:00) - Compete to Create: Redefining Healthy Competition in Sales and Sport (18:30) - The Teammate Mindset: Bill Russell's Blueprint for Winning Together (22:30) - Stress and Survival: Why Leaders Struggle to Foster Collaborative Environments (26:00) - Recovery Practices in Business: The Missing Link for Sustainable High Performance (29:30) - The 92-Second Morning Mindset Routine: Setting Your Signal Amidst the Noise (34:30) - Neuroplasticity in Leadership: Training Optimism and Confidence as Learnable Skills (37:00) - Felix Baumgartner's Mental Mastery: From Panic to Space Dive Success (42:00) - Shifting from Performance-Driven to Purpose-Driven Leadership Identity (47:00) - Purpose as the North Star: Aligning Thought, Word, and Action Under Pressure (49:30) - Journaling, Conversations, and Meditation: Practical Steps to Discover Your Why (52:00) - Introducing FOPO: Overcoming the Fear of People's Opinions (56:00) - The Evolutionary Roots and Neuroscience Behind FOPO (59:30) - Navigating the High-Stakes Sales Ecosystem: Combating Insecurity and FOPO (01:03:30) - Balancing Caring and Worry: Constructive Feedback vs. Destructive Noise (01:06:00) - The Framework to Overcoming FOPO: Unmask, Assess, and Redefine (01:09:30) - Leading Teams Through FOPO: Building Trust and Psychological Safety (01:12:30) - From Insight to Action: Applying Gervais' Mental Strategies in Your Sales Leadership