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1:12:06ENMax Freeman on Building Ramp’s Sales MachineGast: Max Freeman · Moderation: Harry StebbingsRamp’s sales leader explains how he hires, trains and equips sellers, from early outbound experiments to enterprise forecasting and AI-assisted research.
1:13:48ENPatrick Forquer on Selling Legal AI and Scaling Legora’s Revenue TeamGast: Patrick Forquer · Moderation: Harry StebbingsLegora’s chief revenue officer explains how his team runs pilots, trains salespeople and forecasts rapid growth, and shares company-reported performance figures.
1:14:23ENBecca Lindquist on Clay’s Sales Hiring, Compensation and AIGast: Becca Lindquist · Moderation: Harry StebbingsClay’s head of sales explains how she evaluates candidates, designs incentives and builds customer champions in a product-led business.
1:25:37ENCarles Reina on ElevenLabs Sales, Compensation and Global GrowthGast: Carles Reina · Moderation: Harry StebbingsThe ElevenLabs sales leader explains his approach to quotas, AI-assisted workflows, international markets and partner distribution.
1:05:06ENShaunt Voskanian on Figma’s Sales Motion, Quotas and CoachingGast: Shaunt Voskanian · Moderation: Harry StebbingsFigma’s chief revenue officer explains how self-service adoption connects to enterprise sales, and why quota targets are only one part of evaluating a representative.
54:12ENJulian Teixeira on Hiring Sales Teams and Building a Repeatable ProcessGast: Julian Teixeira · Moderation: Harry StebbingsThe 1Password CRO discusses early hires, team goals, outbound prospecting, compensation and inspecting deals as a company scales.
1:12:04ENCarlos Delatorre on Hiring Salespeople and Building a Repeatable PipelineGast: Carlos Delatorre · Moderation: Harry StebbingsThe Harness CRO explains why account executives should prospect, how he structures a weekly pipeline routine, and how sales leaders can train and evaluate their teams.
1:10:55ENMatt Plank on Building Rippling’s Sales Organization and Scaling OutboundGast: Matt Plank · Moderation: Harry StebbingsThe Rippling CRO explains how his team plans capacity, works with marketing, prices deals and adapts its sales model as the product portfolio grows.
1:13:42ENGuillaume Moubeche on Bootstrapping lemlist Through Sales and ContentGast: Guillaume Moubeche · Moderation: Harry StebbingsThe lempire founder describes the early sales work, product mistakes and content strategy behind a bootstrapped software business.
1:14:15ENZachary Bookman on OpenGov, Venture Capital and a $1.8 Billion SaleGast: Zachary Bookman · Moderation: Harry StebbingsThe OpenGov CEO discusses enterprise sales, founder–investor incentives, acquisitions and the long path to liquidity.
1:22:59ENDan Fougere on Building Datadog’s Sales Motion and Protecting PriceGast: Dan Fougere · Moderation: Harry StebbingsThe former Datadog CRO explains qualification, enterprise sales, discount discipline and the people behind a repeatable process.
1:08:51ENAJ Tennant on Enterprise Sales, Customer Success and HiringGast: AJ Tennant · Moderation: Harry StebbingsGlean’s sales leader explains how to move upmarket, make AI deployments successful and evaluate sales candidates.
1:00:46ENJeetu Mahtani on International Expansion, Sales and Customer SuccessGast: Jeetu Mahtani · Moderation: Harry StebbingsThe former HubSpot sales leader explains how to test a new market, build partner ecosystems and align sales incentives with customer outcomes.
1:11:51ENDavid Schneider on Scaling ServiceNow and Being a Useful InvestorGast: David Schneider · Moderation: Harry StebbingsThe former ServiceNow operator discusses enterprise sales, multi-product growth and board work, including the decisions he would make differently.
1:07:53ENChad Peets on Building Sales Teams, Hiring and Product CollaborationGast: Chad Peets · Moderation: Harry StebbingsThe sales recruiter and investor discusses early customer discovery, sales economics, onboarding and the trade-offs of scaling a team.
58:31ENBen Fiechtner on Deal Design, Forecasting and Building Sales TeamsGast: Ben Fiechtner · Moderation: Harry StebbingsClari’s chief revenue officer explains his quarterly sales cadence, how to find real buying constraints, and what he looks for when hiring.
45:11ENMark Roberge on Sales Hiring, Unit Economics and Moving UpmarketGast: Mark Roberge · Moderation: Harry StebbingsThe former HubSpot sales leader explains how founders can build a sales motion, align incentives and decide when enterprise customers are worth pursuing.
54:43ENAra Mahdessian on ServiceTitan’s Customer Focus and LeadershipGast: Ara Mahdessian · Moderation: Harry StebbingsThe ServiceTitan CEO discusses early financing, moving upmarket, pricing and how he tries to inspire a demanding team.
53:43ENAshley Kelly on Hiring, Onboarding and Scaling Sales DevelopmentGast: Ashley Kelly · Moderation: Harry StebbingsRippling’s sales-development leader discusses SDR roles, compensation, coaching and the practical challenges of growing a global team.
1:02:58ENLarry Shurtz on Hiring Sales Teams, Vertical Playbooks and ForecastingGast: Larry Shurtz · Moderation: Harry StebbingsThe Genesys sales leader explains how to prioritize, onboard and coach sellers, and why industry expertise must extend beyond the account executive.
1:15:57ENSam Blond on Hiring Sales Teams and Making Outbound WorkGast: Sam Blond · Moderation: Harry StebbingsThe former Brex sales leader explains how founders can hire early reps, diagnose demand bottlenecks and build more distinctive outreach.
48:02ENBrendon Cassidy on Early Sales Hiring, Discovery and OutboundGast: Brendon Cassidy · Moderation: Harry StebbingsThe sales leader explains how he evaluates first hires, builds a customer-centered playbook and reviews deals, while questioning conventional outbound tactics.







