Advisory & Fractional GTM Leadership · $5M → $50M ARR

Charted water, not open ocean.

Founders can build the product; they can't always chart the go-to-market seas. Five to Fifty Growth is the operator who has run the $5M-to-$50M passage before — sitting in the boat, hand on the tiller, naming the hazards early and building the go-to-market engine that carries the company through the points where growth stalls.

Who I work with

CEOs and founders of technical software companies — DevOps and developer tools, data, AI/ML platforms, cybersecurity, and fintech infrastructure, open source included — at the points where growth stalls: when founder-led selling stops scaling, again around $10M ARR, and again near $25M. They want a guide who has been through those stalls, not a framework deck and nothing else.

Approach

How I work

Operator, not observer

Every recommendation comes with something I built to prove it works: a script, a dashboard, a sequence — not a framework deck and nothing else.

One signal at a time

Each engagement gets one priority to execute, not a stacked backlog. The next one waits until the first ships.

Depth over polish

Honest numbers, real artifacts. Nothing that looks like stock optimism.

Common questions

What this is, plainly

What is fractional GTM leadership?

Fractional go-to-market leadership is an experienced revenue executive working inside your company part-time — typically one to two days a week — owning the go-to-market the way a full-time CRO or VP would, but scoped to the stage you are actually at. You get the operating cadence, the sales process, and the accountability without carrying a full executive salary before the revenue supports it.

When should a company hire a fractional GTM leader instead of a full-time CRO?

When the go-to-market still has to be built rather than scaled. A full-time CRO is the right hire once there is a repeatable motion to run and a team to run it; before that, the job is diagnosis and construction — finding the constraint, building the sales process, and proving the motion works. Hiring a CRO to do that work is expensive, slow to correct if the profile is wrong, and often ends with the company's first CRO being its first CRO mistake.

What does the $5M to $50M passage mean?

It is the stretch where a technical software company replaces founder-led selling with a go-to-market engine that runs without the founder in every deal — and it rarely goes in a straight line. Growth tends to stall at predictable points: when founder-led selling stops scaling, somewhere around $5M ARR; again around $10M; and again near $25M. At each one, the same activity produces less predictable results, forecasting gets unreliable, and the company needs a commercial motion it has never had to build before. Five to Fifty Growth is named for that passage because it is the whole focus of the work.

Why technical software companies specifically?

Because the failure mode is particular to them. Whether the product is a developer tool, a data or AI/ML platform, cybersecurity, or fintech infrastructure, these companies usually have the opposite of a demand problem — real technical credibility, strong adoption with technical users, sometimes an engaged open source community — and still cannot convert it into predictable enterprise revenue. The work is not generating more interest; it is building the commercial motion that turns technical adoption into contracts. That is a different problem from the one most go-to-market advice is written for.

How is this different from a consultant or an agency?

A consultant hands you a recommendation and leaves; an agency executes a channel. This is an operator who has run the passage from the inside — early sales at MySQL AB, Enterprise sales through the Oracle acquisition, roughly 10x ARR at ScyllaDB, and the go-to-market build at Buf — sitting in the seat with you while the thing gets built. Every recommendation comes with something built to prove it works, not a framework deck and nothing else.

How does an engagement start?

With a diagnosis rather than a proposal. Most engagements open with the GTM Transformation Experience, a single executive working session that names the actual constraint on growth and ends with a straight recommendation on what should happen next — including the recommendation that nothing should. From there the path usually runs GTM Planning, then fractional leadership, though you do not have to start at the beginning.

Get in touch

Let's talk.

If you're leading a company through the five-to-fifty stretch and need growth leadership, a board partner, or just a second opinion — reach out.

Prefer email? rich@fivetofiftygrowth.com