The Next Mountain · Founding Cohort · Mid-to-Late June 2026
For leaders who understand the times — and want to know what to do.
AI will not replacewise leaders.But wise leaders will learn to lead with it.
Ten senior executives. Six one-hour Circles. One day at Whisper Ranch. Ninety days that change how you decide.
10
Seats in the founding cohort
6
One-hour Circles, biweekly
25+
Years of leadership coaching
90
Days · Mid-to-late June start
The program
A room you can’t find anywhere else.
Next Mountain Circles is the founding program of The Next Mountain — a community for senior leaders learning to climb wisely through the AI shift. Built by Jeff Caliguire and Jason Malec.
Most AI content is built for practitioners. This is built for the people they report to — executives carrying the calls that decide whether their organizations thrive or drift through one of the most consequential shifts in a generation.
Our working frame is Essence → Vision → Strategy → Tools. We don’t start with the tools. We start with who you are, what you’re called to build, and the discernment to know what only you can do — and what AI is genuinely good for.
Six one-hour Circles
Structured working sessions on Zoom, biweekly over 90 days, with between-session resources and reflection prompts.
Ten curated peers
Senior leaders — CEOs, CFOs, COOs — selected for their seriousness, not their industry. No passive observers.
One full-day intensive
An in-person day at Whisper Ranch in Boulder, Colorado — included in the founding seat for every cohort member.
“From the tribe of Issachar… men who understood the times and knew what Israel should do.
1 Chronicles 12:32
Next Mountain Circles is where that becomes possible.
Selection criteria
Ten seats. Deliberately limited.
We’re selective because the quality of the room is the product. Here’s who belongs.
- →You hold decision authority — CEO, CFO, COO, or equivalent — and you're accountable for how AI shapes your organization.
- →You want a trusted room of peers, not another webinar or vendor pitch.
- →You're past curiosity and ready for strategic engagement with real implementation pressure.
- →You believe wise leadership still matters — especially as the tools change.
Not designed for
- —Those seeking tool tutorials or hands-on technical training.
- —Passive learners — this is a working room, not a lecture series.
- —Leaders without authority to influence organizational AI decisions.
- —Anyone who can't commit to six one-hour Circles over 90 days.
Not sure where you stand?
Want to know where you stand before you decide?
The Next Mountain Readiness Assessment is a 5-minute self-diagnostic across eight dimensions of senior leadership in the AI shift. You’ll get a private report — your zone, your strongest dimension, your growth dimension, and three questions worth sitting with. No sales call. No pressure.
Take the Readiness AssessmentThe founders
Who you’ll be working with.
Leadership development
Jeff Caliguire
Twenty-five years coaching senior leaders through transitions. Built and sold a leadership development practice. Owner of Whisper Ranch. Jeff has sat with leaders in their hardest rooms — this one included. He brings the long view: what actually changes people who already know a lot.
Technology strategy & AI adoption
Jason Malec
Technology strategist and AI adoption advisor working with mission-driven organizations at the intersection of leadership and emerging technology. Jason keeps the conversation grounded in what’s actually happening — not what’s being marketed. He’s in the work, not just advising on it.
The full-day intensive
Whisper Ranch,
Colorado.
All founding members spend one full day together at Whisper Ranch — Jeff’s property in the Colorado mountains. Included in the founding seat. (You cover travel and lodging; we cover meals.)
Learn about the ranchThe investment
Founding member pricing.
25% below standard. Founding pricing locks for year two.
Founding Seat
$9,000
$12,000 standard
- ✓Six one-hour Circles on Zoom, biweekly over 90 days
- ✓One-day intensive at Whisper Ranch in Boulder, Colorado — included
- ✓Between-session resources and reflection prompts
- ✓Cohort peer access
- ✓Founding pricing locks for year two
Add private coaching
+$3,000
$6,000 standard
- ✓Three monthly 1:1 coaching sessions with Jeff Caliguire or Jason Malec
- ✓Continues for the 90 days of the cohort
- ✓Founding pricing locks for year two
Common questions
What people ask.
Applications open
Ten seats.
Applications close mid-June.
Or when the cohort is full.
A short application — about ten minutes. Jeff and Jason read every one personally. You’ll hear back within 48 hours.
Questions? hello@thenextmountain.ai