The people around you have never been where you need to go.

I work with software and SaaS CEOs on what the next version of the company has to be, what’s actually stopping it, and what closing that gap is worth. Then on who should build each part.

You can see the company this has to become. Getting there means decisions across product, systems, marketing and cost at the same time, and the people advising you have each only ever run one of those. So it keeps coming back as four plans instead of one, and none of them are priced.

Matthew Kantor. Head of Engineering at GrowthLoop while the company tripled. Product lead at Discovery Channel. Strategic advisor at Becht, fractional product lead at PerformLine, and working with AI since 2016. Different rooms, same job every time: move faster, make more money, get rid of work that shouldn’t exist.

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Two things show up in almost every software company this size.

  1. A roadmap for the product, none for the companyYou can tell me exactly what ships next quarter. What the business has to look like in two years is a conversation, not a document, and the two aren’t the same plan.
  2. A marketing function that never caught up with the productThe product got good. Distribution didn’t. Engineering has been the centre of gravity since the first line of code, and nobody in the building can tell you with a straight face which channel is actually working.

Every roadmap comes down to three questions.

The gap is never short of ideas. It’s short of a way to rank them. These are how I decide what earns a place and what gets cut.

  1. 1Where are we leaving revenue on the table?
  2. 2Where are we spending money, or human effort, unnecessarily?
  3. 3What can we do now that wasn’t economically or technically possible two years ago?

The third one is where most of the surprise is, and almost nobody has gone back to re-run the arithmetic.

Four things to look across. One thing to answer for.

Sometimes the answer is product. Sometimes it’s the systems nobody owns. Sometimes it’s marketing, or a piece of software that stopped earning its place. Sometimes it’s eliminating something entirely.

You’re not buying four capabilities. You’re buying the economic outcome. The four are how I go looking for it.

  1. ProductPerformLine. AI assistants had started answering consumers’ questions about financial products, and when the answer was wrong the exposure landed on the bank. Nobody was monitoring it. Four people made it a product category in under seventy days.
  2. MarketingA 77-year-old skincare brand. Their agency reported 11.7× on ad spend; reconciled against the bank, one “winning” campaign had made $918 on $600. We took marketing in-house and taught their team to run it with AI. Site conversion 0.97% to 2.73%, same traffic.
  3. SystemsA $30M experiential agency. Fifty placements per campaign, resized by hand in Photoshop, three to five days a time. Automated down to three hours, run by the same designers, no new headcount.
  4. AIPresent in all three. The reason for none of them. It compressed the research, held quality across a team of four, and made a process cheap enough to stop being a job. But take it away and the method still stands, and take the method away and no amount of it helps.

Two of the three companies are anonymised at their own request. Every number reconciles to the client’s reporting.

I read your numbers before I talk to anyone.

Not to grade you. To price the gap.

Ask people what’s holding the company back and you get people-shaped answers: a decision nobody made, a thing nobody owns. Start with what the business actually did (billings, cohorts, spend, every lost deal rather than a sample) and the roadmap comes back with numbers on it.

Which matters, because a roadmap without economics is a wish list. The point isn’t the finding. It’s knowing which three things to do first, and what each is worth.

  1. Where this has to get toThe next version of the company, in the CEO’s terms, not a framework’s.
  2. What’s in the wayAcross product, systems, marketing and cost, read from the numbers first.
  3. What closing it is worthEach move priced, ranked, and honest about confidence.
  4. Who builds each partYour people where they can. Hands I trust where they can’t. Never me.
Matthew Kantor

All three ended the same way: they own it and I left.

PerformLine’s team still builds on that platform. The skincare brand runs its own marketing. The agency’s designers run the automation themselves. I learned why that matters at Dow Chemical, who asked me to automate a process they couldn’t describe, so I built them a tool to change it themselves, and it became a corporate standard because I wasn’t standing next to it. A fix that needs me in the room forever isn’t a fix.

So your people run it, and I stay in as an advisor while it moves. Where nobody on your bench can run a part, I’ll point you at someone and take no fee for the introduction. Otherwise you couldn’t trust the name.

More about how I work

Know where this needs to go, and not how?

Twenty minutes. Tell me where you want this company to be in two years and I’ll tell you what I’d go look at first.

Start a conversation Field notes from active work