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.
Pearls of Wisdom with Matthew Stammers
From ICP clarity to cutting through AI noise, Matthew Stammers shares his hard-won lessons from scaling complex enterprise software businesses.
Pearls of Wisdom with 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.