Traditional advisory
- Vague monthly retainer
- Broad advice
- Long discovery
- Strategy decks
- Unclear immediate output
Pineapple GTM sanity checks
Unlock the juicy path through the spiky GTM problems.
Focused working sessions for B2B SaaS and AI founders when the pitch, ICP, outbound, conference plan, enterprise call, sales hire, or UK entry decision is almost clear.
Bring the mess. Get the diagnosis, the sharper words, and the next practical move. No vague retainer. No bloated strategy deck.
Spiky problem
Useful next move
Founder-led GTM
Pitch / ICP / outbound / hiring / UK entry
The expensive almost
Founder-led GTM is spiky.
The hard part is rarely total confusion. It is the almost-working motion that keeps pulling founders into slow, expensive circles.
Your pitch is almost clear.
Your ICP is almost obvious.
Your outbound almost makes sense.
Your first sales hire almost feels like the answer.
Your conference plan is almost more than "networking."
That "almost" is where founders waste months.
Pineapple helps you cut through the sharp edges, pressure-test the assumptions, and leave with a practical next move.
Pick your slice
Pick the slice of GTM help you need.
Choose the problem in front of you. Send the context. Work through it live. Leave with decisions, edits, and next actions.
Most sessions are $300-$500.
No subscription. No monthly commitment. Book the slice you need when the problem is real.
Before the expensive mistake
Not every GTM problem needs a retainer.
Sometimes you need one strong working session before you make the wrong hire, send the wrong pitch, target the wrong ICP, waste a conference, or walk into a big customer call underprepared.
Pineapple sessions
- Specific GTM problem
- Focused working session
- Send context before
- Live decisions
- Clear next actions
Retainers can make sense later. But first, prove the value in one useful session.
Simple by design
How it works
Pick the problem
Choose the GTM session that matches the decision in front of you.
Send the context
Deck, outbound copy, target list, event plan, job spec, account notes, or messy thoughts.
Work through it live
A focused 90-120 minute session. Direct feedback. Practical pressure-testing. No theatre.
Leave with the next move
You get decisions, edits, priorities, and clear actions to take next.
Best place to start
Start with a GTM Sanity Check
If you are not sure which session fits, start here. Bring the mess. We will find the real issue and work through the highest-leverage next move.
Useful when:
- We are not sure who to sell to first.
- We have pipeline, but it feels fake.
- Our pitch is not landing.
- We are considering a first sales hire.
- We are going to an event and need a plan.
- We are entering the UK and need a second brain.
Free monthly slots
Founder GTM Office Hours
A few free sessions each month for founders working on interesting B2B SaaS or AI GTM problems.
This is for founders with a real GTM question: pitch, ICP, outbound, events, discovery, first sales hires, or UK entry. Apply with context. If it looks like I can be useful, I will offer a free session.
Fit check
Who Pineapple is for
B2B SaaS / AI founders
Especially founder-led sales, pre-seed to Series A.
Technical or product-led teams
You know GTM matters, but you do not want fluffy advice.
Mid-market or enterprise sellers
You need sharper discovery, qualification, messaging, and process.
Teams entering the UK
Useful for US, Israeli, or European SaaS founders testing UK GTM.
Before a high-stakes decision
Hiring sales, launching outbound, attending a conference, pitching, or entering a market.
Probably not for you if
- You want someone to "just do sales" while you avoid the customer.
- You want generic motivation.
- You are building a pure consumer app with no B2B sales motion.
- You have no product, customer hypothesis, or GTM question yet.
- You want a 40-slide strategy deck instead of a working session.
Operator-led
Built by an operator, not a deck factory.
I spent 10 years in SaaS sales and go-to-market, including helping build monday.com's UK new business motion.
I have sold, hired, coached, qualified, disqualified, built pipeline, worked with partners, sat in messy founder-style conversations, and seen what breaks when companies try to scale sales before the basics are clear.
Pineapple is for founders who want a practical GTM sparring partner for the specific decision in front of them - not a vague advisor call or a bloated consulting engagement.
10 years in SaaS GTM
Ex-monday.com UK new business
Founder-led sales
UK market entry
Next move
Got a spiky GTM problem?
Pick the slice of help you need now - or start with a GTM Sanity Check and we will find the real issue together.