The problem with career coaching

Your coach has never sat in the chair that's interviewing you.

The coaching industry is built by recruiters and HR professionals. They're good at resumes and screening calls. Then you reach the conversation that actually decides it — a CRO asking how you'd hire against a $5M number — and the recruiter playbook goes quiet.

What coaching usually covers

Resume keywords and ATS optimization
What recruiters look for in a screen
Generic behavioral interview answers
Encouragement on a weekly call

What actually wins the room

The hiring math: how you'd build a team to hit their number, headcount by headcount
Anchor stories that prove you've seen it before — acquisitions, comp resets, lone wolves, terminations
A custom brief on their business walked in the door — hierarchy, gaps, your first 90 days
The questions that flip the interview, so they're selling you

What we build together

You don't leave with advice. You leave with assets.

Every engagement produces things you can put on the table — built with the same AI-native systems I use to run my own career, so you leave running your search like it's 2027, not 2019.

Your narrative, rebuilt

The walking deck and the story arc — from the Marine Corps line to the Microsoft number — so every answer lands as proof, not biography.

Anchor story bank

Eight to ten stories, drilled live, that cover every hard question: managing without the title, the acquisition, the boss you learned from, the mistake you'd never repeat.

The hiring math

Quota, ramp, headcount, comp. When they ask how you'd hit $5M, you build the model in front of them — and ask the questions that expose whether their plan works.

A custom brief per final round

For every serious interview: their org chart as best we can map it, where they're likely leaking, and your literal — not hypothetical — first 90 days. This is how offers get made in one meeting.

Your Executive User Guide

The one-page operating manual for working with you — communication, non-negotiables, cadence. The single fastest way to sound like a manager before you've had the title.

The package, negotiated

Offer structure, equity, severance, exit terms. I've negotiated these from both sides of the desk — and I don't let you anchor low. (Alongside your attorney where there's one involved.)

The transformation

From in transition to signed offer.

From a resume in the ATS pile→to a custom brief on the hiring manager's desk

From "I've never had the title"→to the candidate who builds the hiring plan in the room

From rehearsed answers→to anchor stories they repeat after you leave

From taking the first number→to a package negotiated like a deal

Start here, free

There Is No Tomorrow by Chris Dessi — book cover

There Is No Tomorrow. Read the first three chapters before you book anything.

I wrote this book at a kitchen table during the worst stretch of my career, on the morning the plan I'd bet everything on fell apart. It's the reason the Pressure Test exists. If you're in a transition right now, read these three chapters first. They're free, no form, no strings.

Read the first 3 chapters — free Get the book on Amazon

"Most reinvention after 45 doesn't look like a leap. It looks like a Tuesday where you say no to something you'd have said yes to at 35." Chris Dessi

Twice a week I send a short letter on using AI in your business and on life after 45. Same stories, same voice as the book.

Subscribe to the letter

How we work

Three ways in. Every one produces something you keep.

The Pressure Test

90 minutes, 1:1

$500

Bring the resume, the deck, and the role you want. I'll tell you where it's working, where it isn't, and exactly what I'd do next.

Straight read on your narrative and positioning
Your three anchor stories, identified
A written next-move plan within one business day
Credits in full toward the Sprint within 30 days

Book the Pressure Test

The flagship

The Transition Sprint

90 days, 1:1

$5,000

The full campaign — from first conversation to signed offer. Six working sessions, live interview drilling, and direct access to me between calls.

Everything above: narrative, story bank, hiring math, Executive User Guide
A custom brief built for every final-round interview
Live role-play before the conversations that count
Offer and package negotiation, end to end
Direct line to me between sessions — when the email lands, you don't wait a week

Start with the Pressure Test

The First 90

Your first 90 days in the new seat

$2,500

The offer is signed — now the real interview starts. On-call counsel while you build your operating rhythm and land your early wins.

Your 30/60/90, executed — not just presented
Team assessment and first hiring moves
Managing up: your first board or leadership readouts
For Sprint alumni only

Talk to me first

Fit

This works for a specific kind of executive.

This is for you if

You're an enterprise sales, revenue, or GTM leader with 15+ years in — at or leaving a Salesforce, a Microsoft, a scaled startup
You're making the jump to VP or above, and "you've never had the title" keeps coming up
You're negotiating an exit, a severance, or a package — and you want an operator in your corner, not just a lawyer
You're past 40 and want your search and your next role run AI-native, not AI-anxious

This is not for you if

You want a resume polisher — there are good ones at a tenth of the price
You want a cheerleader — I'll tell you exactly where you're falling short, kindly and precisely
You won't do the work between sessions — the assets get built by both of us

Proof

People I've coached run revenue organizations today.

For a decade the coaching happened for free, over calls like the one that convinced me to put this page up. Here's what the people on the other end say.

"A fifteen-minute meeting made me millions."

Gary Vaynerchuk — Chairman, VaynerX

"Constantly on the phone and sending e-mails to potential clients, it amazed me that Chris could keep up his almost superhuman pace day after day… A great salesman, mentor and friend, any company would be fortunate to have Chris working diligently for them."

Andrew Gothelf — Senior Director, Partner Marketing, Salesforce

"I had a front row seat to see Chris start companies, sell companies, publish multiple books, become a TV regular, keynote events, consult and give a Ted Talk. I also watched him take chances, work insanely hard, lead, be transparent and have a lot of fun."

John Zanzarella — Chief Revenue Officer, PerformLine

Seen on FOX 5 NY · CNBC · CNN · NBC · CBS · Keynotes in 17 countries · 2× Amazon #1 bestselling author

Book the Pressure Test.

Ninety minutes. $500. You leave with a straight read, your three anchor stories, and a written plan you could run without me.

Book the Pressure Test

Then what? Maybe nothing. If the plan is enough, run it — that's the point. If you want an operator in your corner for the whole campaign, the Sprint is there and your $500 comes off the top.