The team portal. Private.
For the Fractional 360 team. Please do not forward.
Every all-chairs working session: what was said, what got decided, and who owns what. Written from the recordings so nobody has to rely on memory or take notes in the room. Recordings are linked on each entry. If something reads wrong or unlike you, tell Chris and we will fix it.
Closing the session, Steve drew the line the whole thing had been missing. You can hire a great fractional CFO for forty grand a month and get real perspective for less than a full-time hire, and that is not what this is. Fractional 360 is Tom on the budget, Greg on the technology decision, and Henry on the breach, making one plus one plus one equal twelve. He also said plainly why he is here: he lost a dream job seven years ago, he is “pissed off for greatness,” and what he wants back is the chance to do hard, complex work with people he trusts. That close is now the vision on the portal.
“You're not getting a fractional anything. You're getting a badass global perspective into how to solve the most important things that will either set you up for explosive success and growth, or implosion and destruction. If you don't have us, you're going to hire one ninja with one sword. If you hire us, you get ten ninjas with their backs to each other, swords out, who can slay any giant.”
Steve Wymer, August 28, closing the sessionEvery chair took a run at describing their own offering. The more valuable half was hearing where each of us is not the right answer. Chris: brand-to-revenue leadership at a fractional level, making marketing defensible to the board and tying it to a number; startups get advisory, scale-ups fractional, carve-outs interim. Tom: on-demand senior financial leadership from FP&A and fundraising through audit readiness and board reporting, sweet spot growth-stage and IPO-aspiring, and he ruled himself out for seed and A rounds rather than overreach. Henry: security and privacy leadership that de-risks and lets the business accelerate, and he was candid that his model resists one line because he runs three (M&A work, fractional or interim backfill when a security leader quits, and breach response through legal under privilege); startups are out because they do not reach out. Sheren: startup through SMB, advisory and fractional, sweet spot roughly 100 to 2,000 employees. Michael: turning an existing customer base into a growth engine, with his own honest read that this lands as an attach to another chair rather than a standalone buy.
“I'm being a tough grader on myself. I want to make sure I'm a net plus, not a hand waver. I come into every room with credibility, and I would never put myself in a position where I'm not credible.”
Tom Fox, on declining the stages he is not right forOn the CHRO pitch specifically, but it generalizes to every chair: rather than leading with “I will set up your HR function,” lead with what they need now, what they will need next, and what they should not buy yet, plus the trigger points and the trade-offs. Sheren called it being the HR psychic. The conclusion the room reached is that we sell the sequence, not the service, and the most valuable thing we often say is “not yet.”
Tom warned, from a decade of boardrooms, that private-equity-backed companies bring a jaundiced eye to marketing and often go there first for cuts. Sheren pushed back hard from Splunk, where marketing was a genuine revenue generator, and noted that HR carries the same unfair label. Steve resolved it: the cynical view is often correct, but only because the words are loose. Brand spend out of cadence with growth marketing is lighting money on fire, while disciplined acquisition marketing fuels the company. Greg landed it, and it became a positioning line: “We're not a black hole. We're an enabler. We're a partner with sales, and it's all about revenue.” The exchange turned into a wedge rather than a disagreement. The functions boards suspect most are exactly the ones we make measured and defensible.
Norm leads the operating and financial model, working with Ken, Greg and Chris. Greg named the hard part twice: our rates vary widely, so the offering has to be engineered to blend them and still work commercially, and the strategy has to tether back to execution. This sets the baseline framework everything else depends on. The front door is a paid assessment. Ken's point: a free assessment achieves little because people read free as worthless, while a low-cost paid assessment earns real attention and functions as a partially paid sales cycle. David noted IG runs the same shape as audit, build, expand. Agatha gets documented before content interviews, at Henry's request.
“A free assessment usually doesn't achieve much, because people see it as free and not of value. But a low-cost assessment, entry-level type of thing, people are willing to pay for it, and they will listen. In some ways it's a partially paid sales cycle.”
Ken Crafford, on the commercial modelA safe haven (Sheren): this has to be the forum where ugly and beautiful ideas both get beaten up, before anything reaches a client. Trust them, like them, want to work with them (Godfrey's rule, via Steve): all three, or don't work together. Argue hard, then commit as one (Steve): he and Ken should be able to argue a strategy to the ground, decide what is best for the client, then go in with one voice. Do our homework before we quote (Norm): build a client profile and real intelligence first, so we never leave money on the table because we failed to understand the client.
“One of our principles should be that this has to be a safe haven where we can beat up all of these thoughts, ugly and beautiful, where we can figure this out here in this forum before we present it up.”
Sheren Bouchakian, August 28The session was introductions and draft principles, and the room did something better than the agenda asked. It reframed “principles” into two separate tracks, because we had been mixing them: how we operate as a bench, and our ethos, meaning the reason a client should choose us. Tom flagged that the six drafts on the board were apples and oranges, which is what triggered the split. The introductions themselves were the real content. Everyone told the story of the seat they hold and the scar that shaped how they hold it, and most of what now sits on the Persona & GTM playbook came straight out of this session.
Track A, how we operate: embedded operators from day one, a vetted bench behind every chair, a team sport where everyone hunts on behalf of all the chairs, and slow is smooth while smooth is fast. Track B, our ethos: do the right thing even when it costs us, balanced against running a real business; customer-first, because you cannot outsell poor retention; and trust through value.
“It almost should be the first principle, just do the right thing. To Ken's point, we'll have to do it in a fiscally responsible manner. Both things can and should be true, but the guiding North Star needs to always be, do the right thing.”
Greg Higham, August 25, in the principles discussion“Do the right thing” emerged as principle one, and it held through Session 2. Greg's segmentation became the operating matrix used on Friday: startups and SMB lean fractional, enterprise and carve-out lean interim. Two exercises did not get run and were carried over: what holding a chair actually means, and the dot-vote on principles. Sheren also introduced HBDI, a thinking-preferences assessment she used at Splunk, as a possible team baseline; she is scoping cost, so it stayed an information item rather than a deliverable.