Tech & Transformation

The technology is the easy part. It’s the humans that are messy.

We’ve been founders, CxOs, and operators through every major technology shift since dial-up, and we build with AI ourselves now. When a company faces a hard call, it’s usually one we’ve had to make too: what to build, who should lead it, how fast to move, what it does to the people.

What we do

Four ways companies bring us in.

Scope and lead AI work

We sit between leadership and engineering to figure out what’s worth building, then make sure the company has what it takes to ship it: the people, the data, the budget, and the cover to see it through.

Run the transformation

When a company needs more than advice, we embed as a fractional CTO or product leader and run the change ourselves — the technology, the team, and the way the organization makes decisions.

Oversee outside firms

When you bring in a consulting firm or vendor, we work from your side of the table: scoping the brief, then holding the firm to what it promised.

Coach the leaders through it

Every technology change lands on a few leaders who have to make the calls. We coach the founders, CEOs, and CTOs in that seat, including on the newer questions, like what it means to manage a team when half the work is being done by agents.

Who we work with

Two kinds of companies.

Some of the companies we work with were built before AI and now have to fold it into how they already run, without breaking the business that pays the bills. That work is mostly judgment and sequencing: what to adopt, what to ignore, what to change first, and how to bring along a workforce that didn’t ask for any of this.

Others are AI-native from the first day, where the old playbook doesn’t apply and the operating model is being invented in real time. That work is faster and stranger: small teams, new roles, and decisions with no precedent to lean on.

We spend time on both sides, and the line between them is disappearing quickly.

Most technology initiatives don’t fail for technical reasons. They fail in how people and organizations respond to the change — which is exactly where we come in.

Track record

We’ve done exactly this work.

As Co-CTOs of Goop, we ran the technology rebuild and the harder job underneath it: the people. We replatformed the team, rewired who got to decide what, and kept a nervous organization productive through eighteen months of change.

Before that, between us: founder, CEO, and CTO across digital agencies, software and hardware companies, e-commerce, and media. Our consultancy General Things sold to GoPro in 2013, where Nick became VP of Software and Services, and GoPro went public the next year. And we’re still building today.

CoachClaw

We build with AI ourselves.

AI runs through our own practice. We’re building CoachClaw, a private, persistent extension of your human coach that’s there in the 167 hours a week you’re not in session, in beta with our own clients now.

And a lot of the leaders we coach are building AI products themselves. Between their work and ours, we’re rarely talking about any of this in the abstract.