From Chaos to Predictability: Pete Crosby’s Honest Lessons on the One to Ten Million Journey
Pete Crosby unpacks the biggest mistakes founders make on the $1M to $10M journey.
Reshaping GTM in the AI Era – Harrison Rose on repeatable GTM and scaling beyond Founder-Led Sales
Harrison Rose shares his insights on why founder-led sales must become repeatable, bootstrapping vs VC, and AI’s next GTM shift.
From Inception to Acquisition: Natasha Ratanshi-Stein on scaling Surfboard, stage-fit hiring and the importance of founder-led sales
Natasha Ratanshi-Stein shared her hard-won lessons on founder-led sales, real PMF signals, stage-fit hiring and scaling ACV.
Ego, Cash & GTM Discipline: Paul Fifield’s unfiltered lessons from building scalable businesses
Paul Fifield shares brutally honest lessons from scaling companies – why renewals can mask product risk and what CROs must master in 2026 as AI reshapes GTM.
Designing an AI-first Business – Bethany Ayers on hiring stage-fit leaders & the GTM playbooks that actually work in the AI era
Bethany Ayers shares how to scale from $2-10M ARR with stage-fit hiring, tighter ICP, better operating rhythms, and what “AI employees” look like in practice.
Matthew Stammers
From ICP clarity to cutting through AI noise, Matthew Stammers shares his hard-won lessons from scaling complex enterprise software businesses.
Tim Collin
From clarity of solution to the pitfalls of over-hiring, Tim Collin shares his three biggest lessons from 35+ years of scaling software businesses.
CRO Tenure: Why it fails (and how to fix it)
Hiring the right fractional GTM leader can be a game-changer for start-ups.
Bridging the Gap: The Graduation Crisis in Early-Stage Startups
Practical steps and actionable advice from founders, revenue leaders and VCs.
Harper Concierge Case Study
ScaleWise headhunted a Head of Sales to lead Harper’s transition from founder-led sales to scalable growth.