AI Go-To-Market Team · B2B SaaS
Put the Wind in Your Sales.
SAILS turns what you already know about your business into a sales system your team can actually run.
How SAILS works
Founders Don't Have a Knowledge Problem. They Have a System Problem.
You've closed ten deals. Then twenty. Then fifty. You know exactly what works: the question that qualifies a prospect, the objection that kills a deal, the moment in a demo where they lean in.
None of that lives anywhere but your head. Your first hire fails trying to reverse-engineer it from watching you close. Six months later, you're still in every deal, because nobody else can run what only you know how to do.
Three ways founders solve this today
| Option | Cost | The catch |
|---|---|---|
| Guessing | Free | The most expensive of the three |
| A consultant | $15K to $25K | Eight weeks, then they leave |
| Hiring a VP of Sales too early | $200K+ | Most fail without a system to run |
See the full breakdown of what each option costs
SAILS turns what you already know into a system your team can actually run. Not generic frameworks. Not theory borrowed from a motion that doesn't match yours, the exact way you already sell, documented, taught, and built out by three AI agents.
Real pricing lands once the model is set. Join the waitlist and you'll be the first to know.
An AI Go-To-Market Team.
Not a Copilot.
Learn. Build. Arm. Three agents, one job each, always in that order.
That gap is worth $340K a year.
CRO: reads your business, sizes what it's costing you
Drop in a URL. It reads your positioning the way a buyer would, benchmarks you against segment norms, and puts a number on the gap, free, no email required.
VP of Sales: turns the diagnosis into a playbook
Section by section, it documents the exact way you sell, the qualifying questions, the demo flow, the objections and how you kill them, then reviews your team's work against it like a real pipeline review.
Join the waitlist for early access- One-pager
- Outbound sequence
- Sales deck
Enablement Lead: builds the assets your team runs on
Matched to your brand and the playbook above it, not generic templates: a one-pager, an outbound sequence, and a deck, ready to send.
Join the waitlist for early accessSAILS runs continuously, not on a clock. Change your ICP in month one, and messaging, discovery, sequences, everything downstream already knows. The agents are locked to your context, so they compound instead of repeating.
See the full breakdown of how the three agents work together
Who SAILS Is Built For
Two starting points. Same three agents.
Build Track or Scale Track
Build Track
Founder-led, no system yet. SAILS extracts what you already know and turns it into a playbook your first hire can run.
Scale Track
Reps in seat, uneven results. SAILS diagnoses the gap between your best rep and the rest, then rebuilds what isn't working.
More on Build Track vs Scale Track, and fit across SMB, mid-market, and enterprise
Common Questions
What is SAILS?
An AI go-to-market team for B2B SaaS: three agents that diagnose where revenue is leaking, teach you the framework, and build the assets your team runs on. It's software, not a consultant's calendar.
What happens to what I share with the CRO agent?
Nothing is saved beyond your session unless you join the waitlist. If you give a URL, it's read live to generate that one diagnosis, not stored. The conversation itself is never gated or sold, you get the full diagnosis whether or not you sign up for anything.
Is this a fit for my stage?
Built for B2B SaaS sales teams, whether you are founder-led with no system yet or have a team in place with uneven results. Ask the CRO agent (bottom right) for an honest read.
When is pricing available?
Not yet public. The pricing model is still being finalized. Join the waitlist and you'll be the first to hear when it's set.
What happens after I join the waitlist?
You'll hear from me directly as access opens. No spam, no drip sequence, just an update when there's something real to tell you.
Join the Waitlist
Early access, plus the full playbook from your diagnosis if you ran one.
Want Early Access?
SAILS is in build. Get on the list and I'll reach out directly when a spot opens.
Have a Question First?
Not ready for the diagnostic or the waitlist? Tell me what's on your mind and I'll get back to you within one business day.
Email directly: matt@sailsadvisory.com
Or write here. Same one-business-day reply.
