Live Masterclass Series · August 2026

Lead like you've lived it.

Three live masterclass series — one for the CEO, one for the Founder, one for the CHRO. Not a consultant who studied it. Someone who built companies, raised capital, and sat in your exact seat.

3 sessions each 1:00 PM EST Live + recorded $599 per series
Who this is for

The receipts, not the theory.

Each series runs three live sessions across August — same day, same time, three weeks running. Come to the seat that's yours, or send the right person on your team. Every session is small, candid, and built on 25+ years of having actually done it.

Series 01
For the CEO
Growth, Boards, AI & Financial Planning
📅 Tuesdays · 1PM EST

Four things land on your desk at once — scaling the company, managing the board, answering for AI, and owning the numbers. Build the way you hold all four.

  • Navigating growth — leading the stage you're actually in
  • The board — from reporting to real partnership
  • AI strategy — the readiness work before the spend
  • Financial planning — the numbers that run the company
Session 1 · Aug 4
Session 2 · Aug 11
Session 3 · Aug 18
$599 / all 3 sessions
Enroll →
Series 02
For the Founder
GTM, Product & Investment
📅 Thursdays · 1PM EST

Three engines have to fire together — a go-to-market that lands, a product that evolves, and a raise that closes. Miss one and the other two stall.

  • Go-to-market — the motion that actually converts
  • Product — evolving AI-native, not AI bolted on
  • Investment — fundraising as a relationship game
  • Plus: the warm-intro outreach system + non-dilutive paths
Session 1 · Aug 6
Session 2 · Aug 13
Session 3 · Aug 20
$599 / all 3 sessions
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Series 03
For the CHRO
People Ops, Analytics, AI & the Roadmap
📅 Fridays · 1PM EST

Drive revenue, prove it with data, own the AI answer, and build a people roadmap that delivers org health and execution — all at once. I've sat in that seat.

  • People ops that drives revenue — not a cost center
  • People analytics — the numbers that move decisions
  • AI in HR — where it serves people and where it must never
  • The people roadmap — org health and execution on one page
Session 1 · Aug 7
Session 2 · Aug 14
Session 3 · Aug 21
$599 / all 3 sessions
Enroll →
How it works

Simple, live, built for a leader's calendar.

1

Pick your series

CEO on Tuesdays, Founder on Thursdays, or CHRO on Fridays.

2

Reserve your seat

Secure checkout — $599 for all three sessions in the series.

3

Show up live

Three weeks running, 1PM EST. Bring your real situation.

4

Keep the work

Recordings and worksheets to keep, plus live Q&A every session.

Reserve your seat

Three seats. Three honest series.

$599 per series — all three sessions included. Choose your series and reserve.

  • Three live sessions, same day & time across August
  • Live Q&A every session — bring your real situation
  • Session recordings to keep
  • Worksheets & signature frameworks for your seat
  • A People & Progress Report subscription — free, ungated, forever

Reserve your spot

Choose your series and secure your seat.

You're reserved! Check your email for confirmation and calendar invites.

Secure checkout via Stripe. You'll receive confirmation and calendar invites by email.

Questions, answered

Good to know.

What exactly am I signing up for?

One masterclass series — three live sessions on the same day and time across three weeks in August 2026. CEO series meets Tuesdays, Founder series Thursdays, CHRO series Fridays, all at 1PM EST.

What if I can't make a session live?

Every session is recorded and the recording is yours to keep, so you won't lose the material if life happens. That said, the live Q&A is where the real value is — come live when you can.

Can I take more than one series?

Absolutely — they're on different days, so many leaders wearing more than one hat take two or all three. Reach out and I'll sort a combined rate.

Who's teaching?

Kristy McCann Flynn — Founder & CEO of SkillCycle ($15M+ raised, Inc. 5000 ×3), Interim CHRO at Richemont, WeWork & MoneyLion, and advisor/investor across Work Tech. Lived every seat.