CompoundCraft — What comes after twenty years inside companies

For whom

You've spent fifteen or more years inside companies.

Most recently at director or VP level. You've led teams, shipped work you're proud of, and built a reputation that extends beyond your current employer.

You might still be in the role, quietly asking what comes next. You might have been laid off — a lot of excellent people have been. You might have already left and be figuring out how to shape the next chapter. Or you might already be independent and trying to sharpen a practice that's still taking form.

CompoundCraft isn't a job search tool, and it isn't for people early enough in their career that the answer is another internal role. It's for people considering — or already in — work that doesn't fit inside a single org chart: consulting, fractional leadership, boards, expert networks, teaching, or some combination that becomes a career of its own.

What you get

Two buckets, because the founding cohort is part of what ships.

The first is what you have access to the moment you activate. The second is what the founding cohort is actively shaping during the beta.

Available when you activate

Pathway assessment and personalized analysis.

About twelve minutes in, a full analysis out. Seven independent pathways scored against your profile and situation, a bottom-line recommendation, the trade-offs that come with it, and a Field Guide read on where to start — across weighing, building, and engaging — with one illustrative way through.

Field Guide.

Pathway-by-pathway guidance on where to start and how to make progress — concrete techniques for moving from weighing a path to acting on one. The launch pathways are live; coverage expands across professional identities and pathways through the beta.

Vetted resource catalog.

More than a hundred platforms, communities, and tools — filtered for relevance to senior practitioners, not a scraped list. Organized by pathway, so you know where to look once you know what you're looking for.

Market intelligence for your professional identity.

Rates, demand signals, and competitive landscape across the seven pathways. Design has the deepest data at launch. Product, finance, operations, HR, and other identities expand as research publishes during the beta.

Champion Map.

A guided exercise to identify the fifteen to twenty people in your network most likely to generate your first engagement — not a list of everyone you know, a short list of who actually matters when you start reaching out.

Goals & Priorities.

Set what you're optimizing for — target income, time horizon, the shape of life you want — and see every pathway read against it, with a financial picture that updates as you log real income.

Building with the founding cohort

Peer cohort.

Small groups by professional identity — an intimate set of peers, not a community you lurk in. Forming as founding members join.

Independent pathway coaches.

One-to-one advice from practitioners who've actually built the pathway you're weighing — a vetted roster matched to you, not a directory to browse. Coming during the beta.

The founding cohort

Fifty practitioners, hand-invited during the beta.

The founding cohort is forming across professional identities — design, product, finance, operations, HR, and others.

Founding members get:

Twelve months of free platform access during the beta
Direct influence on the whole platform — everything here is an early draft, and founding member input shapes how all of it evolves, not just what's still to come
Preferential treatment when the beta ends and the platform opens more broadly

In return, I'm asking for honest feedback on what's working and what isn't, and — informally — that you forward this to two or three senior people in your network, ideally in professional identities different from your own.

Founding cohort forming across professional identities. Limited to the first fifty practitioners at this phase.

Why now

The last few years have been a disruption I can't look away from.

AI is reshaping the tech industry at a pace no one is ready for. “Efficiency” is the other word for it — sometimes synonymous with AI, sometimes just cover for companies cutting costs to juice the stock price. Either way, rounds of layoffs keep landing on experienced people, and senior design leaders I respect are spending nine, twelve, eighteen months looking for their next role.

I've spent twenty years running DesignMap with my partners — a non-traditional path from the start. I've learned a lot about building a business, finding clients, and doing the work around the work. Most senior professionals I know have only ever been internal. The playbook for what comes next — consulting, a fractional role, a board seat, a quieter runway into semi-retirement — isn't one they've ever needed.

For many, this is the last chapter of work before retirement, and most people can't afford to fully retire when they'd planned to. Independent pathways can be a real option: a way to offer what you know, on your terms, for as long as you want to.

I'm building CompoundCraft while running DesignMap, and I'm exploring my own transition in parallel. It's genuinely a tool I'm building for myself and people like me.

Greg Baker
Co-founder, DesignMap
Substack →

What comes after twenty years inside companies.