The Shift from Founding to Leading
The EdTech Roundtable is a confidential peer council where edtech founders and co-founders work through their hardest decisions with people living the same reality — and grow into the leaders their companies need.
Founder-CEO, co-founder COO, co-founder CFO — if you founded it and you're leading it, there's a seat for you.

A curated table. One seat is open.
Somewhere between founding and scaling, the job changes. The instincts that got you to product-market fit stop being enough. The company needs operating discipline, a real leadership team, and decisions made with judgment instead of adrenaline.
That change has a name. We call it the shift — from founding to leading. Every founder faces it. Most face it alone.
The reality
01
You can't be fully honest with your team, your board, or your investors. Every conversation has an audience. You're carrying decisions alone.
02
Everything routes through you. By the time the big call arrives, you've already made a hundred small ones that day.
03
Growth is happening in your head, not on paper. Every quarter is improvised.
04
Long sales cycles, district budget timing, evidence requirements, and procurement rules mean a wrong bet costs a year, not a quarter.
05
The company has outgrown your instincts. What got you here is not what gets you to the next stage — and you know it.
06
Funding is tighter, investors want efficiency, and the runway math is real.
07
You started this to help learners. Somewhere along the way, it became a company to keep alive. You want both back.
THE TABLE
It is a working council for leaders who want to be challenged and are willing to challenge others. A curated table of edtech founders and co-founders who understand your market because they operate in it — and who will tell you the hard thing in a room where it's safe to hear it.
Confidentiality is enforced, conflicts are managed, and candor stays constructive. We protect the space so members can be honest in it.
We model the candor we ask for, and we contribute what we've learned from building and advising in edtech — without becoming the loudest voices in the room.
A defined decision-making process means sessions produce decisions, not just discussion. Commitments are stated out loud, written down, and reviewed.
Introductions, referrals, check-ins, and peer support keep momentum alive when the table isn't in session.
Most peer groups can't tell you whether they worked. We build measurement in from the start — participation, follow-through, decision impact, and progress against your goals.
THE RETURN
Make the right call, not just a fast one — and stop learning everything the expensive way. Assumptions get tested before you act on them.
People who understand why a nine-month sales cycle is normal, why efficacy data matters, and what a district CTO actually cares about.
Grow into leading with confidence — stronger operating discipline, better delegation, more resilience — instead of just surviving it.
Build something that scales and still does right by students and educators.
Introductions, referrals, and relationships that would otherwise take years — from people who give before they get.
Generic groups don't understand district budget cycles, efficacy expectations, or nine-month sales cycles. We do — and so do the peers in the room.
A coach gives one perspective. A curated peer council gives several, from people living the same reality in real time.
Measurement is part of the model from day one. You'll know what your seat is producing.
THE NOW
The Roundtable is a true partnership — founded, curated, and facilitated together.
A trusted room, built on service, for leaders driving change in education.
We work alongside you, not from the audience.

Co-founder & Facilitator
has worked in EdTech for 40 years, leading sales teams, building multi-million dollar pipelines in twelve countries, and coaching sales professionals. Since 2009, his consulting practice has helped EdTech founders learn what he sees as the industry's toughest skill: understanding how districts make buying decisions. He wrote One More Question and created THE SHIFT: Insights from the Founder's Table, an interview series where EdTech founders say out loud what building a company really costs. After hundreds of these conversations, he reached one conclusion — and it led to this table.

Co-founder & Facilitator
has spent three decades as an operator, steering technology and digital publishing companies through transformation and aggressive growth. He has built and led teams from 10 to more than 100 people, carried revenue responsibility up to $143 million, and delivered award-winning operational results along the way. His career has been spent inside the question every founder eventually faces: how do you lead a company instead of just running it? That question — and the people asking it — is why he took a chair at this table.
Part of a bigger conversation. The Roundtable grew out of THE SHIFT: Insights from the Founder's Table — the interview series where edtech founders share what building really takes. The series is where founders tell their stories. The table is where they sit down and do the work.
TAKE A SEAT
Better decisions, made sooner, with people who understand the market and will hold you to them. Seats are limited and curated for fit — tell us a little about you, and we'll set up a conversation.