THE GUIDE JOURNEY: YEAR ONE
WHAT HAPPENS AFTER YOU SIGN
You’ve heard the pitch. This is the part after it: the week you sign, who calls you and how often, what you learn and in what order, and what the rest of the year looks like once you have clients. Self-paced, done with you, and honest about what we can’t promise.
YEAR ONE AT A GLANCE
6-12 WEEKS
of intensive onboarding, at your pace
1:1s
with your Guidologist, for as long as you want
3 SUMMITS
a year, generally February, May, October
3 DAYS
of Sales Mastery™ with Greg Cleary
GETTING READY FOR YOUR FIRST SESSION
At Pinnacle, onboarding means one thing: getting you ready to run your first session with a client. You’ve seen every tool and resource, you know where everything lives, and you could walk into a room with a leadership team and know what to do. Most Guides get there in six to twelve weeks.
FIRST
Your initial altitude check
Your first meeting is with Kaitlin Buckley, Pinnacle’s Chief Experience Officer, and Steve Cleary, your Guidologist. It covers the foundations, walks you through the Academy™, and shows you Trailhead™, the single login where everything lives.
Soon after, your welcome kit arrives. What’s in it? We won’t spoil the surprise.
EARLY ON
Branding, done for you
You fill in a bio and an intake form. Pinnacle builds the rest: your co-branded website, your personalized eight-page brochure, and your audition guide with your name on it. There’s a template if you’d rather do it yourself. Almost nobody does.
ALONGSIDE
Learning, at your pace
This is the time you really dive into the Academy™, and it’s built so you can’t get lost. And the courses follow the same order as a client engagement.
Steve is with you as often as you need. Weekly at first for most people, less once you’ve found your feet. He walks the onboarding playbook in whatever order you need: branding first if you’re ready, or “I have an Audition Thursday, what do I do?” if you’re not. He points you to the exact course.
USUALLY MONTHS 3–6
Sales Mastery™
Sales Mastery™ runs several times a year. You’ll enroll about two months ahead to do your pre-work, and for most new Guides it lands somewhere in months three to six.
The pre-work is the point. Before you arrive, you build a list of 25 people, research each one, and write the cards by hand. Pinnacle sends you the kit for three rounds of mailers:
25BOOKS75ENVELOPES75CARDS
A prep call with Greg Cleary, John Himmelstein, and Kaitlin Buckley sets the expectation plainly. Block the calendar, do the research, write the cards, because when you get there you’ll be on the phone.
After the three days, John runs a voluntary weekly accountability call with your cohort. Are the discovery calls turning into auditions? Are you doing another round of mailers? Most people stay until they don’t need it.
THE FIRST FEW MONTHS
Your first Summit
Summits happen three times a year, generally in February, May, and October, so your first one is never far off.
Before you go, Kaitlin runs a short cohort with the other new Guides who’ll be there, roughly ten of you, so you arrive knowing people and knowing how a Summit works. Some of those groups keep meeting for a year.
WHEN YOU’RE READY
The Audition
An Audition is your first working session with a prospective client’s leadership team. And it’s the last step in winning a client.
A warm call, then a discovery call with the CEO, which is usually where the decision gets made. Then the Audition, where the leadership team decides they want to work with you. You don’t present at them. You run a session.
WARM CALLDISCOVERY CALLAUDITION
You prepare three ways: the Academy™ Audition course, watching recordings of Greg running real discovery calls and auditions, and, if you want it, a mock Audition with Steve before your first real one. When it goes well, it goes fast, and most leadership teams decide that day or within days.
WHAT YOU'LL LEARN
The Academy™ covers the whole job, starting with the part new Guides ask about first: filling the practice. From there it follows a client engagement: the Audition, then Base Camp, then the quarterly sessions, then the annual. Several of the courses are full recordings of Greg running real sessions, so you watch a whole Base Camp before you run one. It is built to be used as you go, not finished before you start. We don’t expect anybody to spend four months watching videos.
01FILL YOUR PRACTICE3 Day Sales Mastery™02WIN THE CLIENTAuditions + Demos
03RUN BASE CAMPBase Camp 1, 2 & 3 + Demos
04KEEP THE RHYTHMQuarterly Sessions + Demos
05RUN THE BIG ONEAnnual Sessions + Demos
The Pinnacle Academy™ is one of eight things behind your Pinnacle Trailhead™ login — along with the Pinnacle Toolkit™, GOAT – The Pinnacle Guide Concierge™, the CRM, the assessments and more. See everything you get →
WHO'S IN YOUR CORNER
GREG CLEARY
FOUNDER & PINNACLE GUIDE
Runs Sales Mastery™. Recorded the discovery-call, Audition, Base Camp, and annual demos you’ll watch in the Academy™. New Guides can shadow his live client sessions, and if you have a real question the day before a session, he answers.
KAITLIN BUCKLEY
CHIEF EXPERIENCE OFFICER
Your first meeting, your pre-Summit cohort, and the standing answer to “who do I ask about this.” She leads the Guide Experience team, with Paige on your website and branding and Ashley on the paperwork, so the tech, the print, and the admin never sit on one person’s desk.
STEVE CLEARY
GUIDOLOGIST
Your go-to call. Weekly altitude checks through onboarding. He walks the playbook with you, runs your mock audition, and introduces you to the Guides you should know. As you need him less, the meetings move to every other week, then monthly, then quarterly. He’ll still check in a year from now.
JOHN HIMMELSTEIN
SALES MASTERY™ ACCOUNTABILITY COACH
A sales leader and a working Pinnacle Guide. He runs the weekly cohort call after Sales Mastery™, where “I learned it” turns into “I’m doing it.”
OTHER GUIDES
SHADOWING & SUPPORT
Shadowing is on your onboarding checklist: sit in on another Guide’s session in your first six months. Steve makes the introductions, often at your first Summit.
YOUR PRACTICE, YOUR PACE
Whether you put in a few hours a week or go all in from day one, it’s your call. There’s no required number of hours, they just determine how fast (and big) your practice grows.
WHAT WE WON’T PROMISE
We won’t promise you leads. Pinnacle trains you to build a book; it doesn’t hand you one. Sales Mastery™, the mailer kit, John’s cohort, and the audition course are the system, and you run it. We also won’t promise when you’ll land your first client. It depends on you, your network, and your hours, and we’d rather tell you that than guess.
WHAT FAST LOOKS LIKE
Five clients in three months takes full-time effort, Sales Mastery™, and a network you’ve already built. The Guides who’ve filled up that fast usually came in with an existing network, from prior work as a Vistage chair, a Culture Index advisor, or something like it. If you’ve never coached before, plan for a longer runway.
WHAT “DONE” LOOKS LIKE
A few paying clients. You’ve been through Base Camp with them and you’re into the quarterly rhythm. Greg calls the early self-doubt “head trash” and the first client doesn’t fix it. Somewhere around three to five, it goes quiet.
We won’t tell you what you’ll earn, because that depends on how many clients you win and how quickly. What we can tell you is the model: Guides charge an average of $4,000 per client per month, a full practice is around ten clients, and those relationships typically run five years or more.
MONTHS FOUR THROUGH TWELVE
Once you’re delivering, the year changes shape.
YOU BUILD THE PRACTICE
Another round of mailers, another set of discovery calls. John’s cohort keeps meeting. Steve moves to monthly, then quarterly.
YOU RUN BASE CAMPS
A multi-day working session with a client’s leadership team, then the quarterly rhythm, and eventually their first annual. And you’ll have watched Greg run before you do it.
YOU GET INTEGRATED
Every Summit you’ll get know more Guides. And when you’re ready, you join a summit circle: a small standing group for the questions that come after “how do I get clients.”
When you’re stuck at 9pmYou have a session tomorrow and a question tonight.A tool, a book, a resourceAsk GOAT™. It has read the whole Academy™.Your situationText Steve or Kaitlin. They answer.A difficult clientAsk Greg. Guides do, within a day of a session, and he answers.
NEW GUIDES' QUESTIONS ANSWERED
Six to twelve weeks for the intensive part, at your pace. Around three months, most Guides have a solid foundation.
No. Plenty of Guides keep working and give this a few hours a week until they have their first client or two.
Several times a year. You enroll about two months ahead to do the pre-work; for most new Guides it lands in months three to six.
Your first working session with a prospective client’s leadership team, the step where they decide to work with you. Not a test.
Access to the Pinnacle Trailhead™ which holds the Pinnacle Academy™, the CRM, the client meeting platform, the assessments, the valuation tool and GOAT™. You’re not assembling a stack of subscriptions in your first year. See everything behind the login →
No. Pinnacle trains you to build your own book and gives you the materials to do it. You run the system.
THE PLAN IS THE SAME FOR EVERYONE. THE PACE IS YOURS.
You’ve seen what the year looks like. The next step is us hearing what yours looks like.