Core session拢300
GTM Sanity Check
For messy problems where you are not sure which GTM lever matters most.
- Diagnosis of the real GTM issue
- Clearer priorities
- Practical next actions
GTM sanity checks for founder-led sales
Bring the spiky GTM problem. Leave with the next move.
Focused GTM working sessions for B2B SaaS and AI founders dealing with pitch, ICP, outbound, conferences, enterprise discovery, first sales hires, and UK market entry.
Our ICP is too broad
Outbound isn't working
Hiring sales too early?
Conference with no plan
Enterprise call next week
UK market entry?
Built for messy founder-led GTM moments: pitch 路 ICP 路 outbound 路 discovery 路 events 路 first sales hires 路 UK entry
The almost problem
Founder-led GTM is spiky.
Your pitch is almost clear. Your ICP is almost obvious. Your outbound almost makes sense. Your first sales hire almost feels like the answer.
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.
PitchAlmost clear
ICPAlmost obvious
OutboundAlmost working
ConferenceAlmost a plan
Ongoing support
GTM Coaching, on retainer.
For founders who want a standing GTM partner, not just a one-off session. A regular monthly or quarterly touchpoint, working through whatever's live for you right now: pricing, positioning, a hire, a board update, a stalled deal, the next segment to attack.
Scope stays open on purpose. A fixed-deliverable package doesn't fit an ongoing relationship. Think of this as a standing sparring partner who already knows your business, so every conversation starts from context instead of from zero.
Not fractional. Not a full-time embedded role. See current availability.
“Johnny is a rock star! … a strong commercial contributor… with his strong in-depth understanding of our customer needs.”
Or Offer, Founder & CEO, Similarweb (NYSE: SMWB)
Priced on request, based on cadence and scope.
New here? Start here
Not sure which session you need?
Answer one quick question and we'll point you to the right one.
What's going on right now?
Do you already have someone in the seat?
Intro services
Not ready for coaching? Start with one slice.
Choose the problem in front of you. Send the context. Work through it live. Leave with decisions, edits, and next actions — no retainer required.
Story拢300
Pitch Deck Tear-down
Find where the narrative breaks and sharpen the buyer or investor talk track.
- Slide-by-slide feedback
- Objection map
- Priority fixes
Targeting拢500
ICP Surgery
Pressure-test the market, buyer, pain, triggers, and the first segment to attack.
- ICP narrowing
- Trigger-event map
- Recommended first segment
Pipeline拢300
Outbound Roast
Review your list, message, sequence, CTA, and rebuild the logic behind the campaign.
- Targeting diagnosis
- Messaging critique
- Sequence feedback
Enterprise拢300
Big Deal Prep
Bring the account, contact, and context. Leave with the discovery plan.
- Account hypothesis
- Discovery question map
- Next-step strategy
Events拢350
Conference Pipeline Plan
Turn the conference into a targeted GTM campaign before you arrive.
- Target attendee strategy
- Outreach scripts
- Follow-up system
Hiring拢500
First Sales Hire Check
Decide whether to hire, what role you need, and how not to hire into chaos.
- Hire/no-hire recommendation
- Interview scorecard
- 30/60/90 expectations
Expansion拢500
UK GTM Check
For US, Israeli, or European SaaS founders considering the UK market.
- UK entry assumptions
- First 20-account strategy
- No-go signals
Mini-sprintFrom 拢3,500
Junior Rep Setup
Set up a junior rep with targets, messages, reporting, call review, and what good looks like.
- Target account definition
- Weekly activity model
- 30-day management rhythm
Most sessions are 拢300-拢500, one-off, no subscription. Want an ongoing relationship instead? See GTM Coaching →
No theatre
Not every GTM problem needs a full engagement.
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.
Coaching makes sense once the relationship is worth it. Until then, prove the value in one useful session.
Traditional advisory
- Vague monthly retainer
- Broad advice, no context
- Long discovery
- Strategy decks
- Unclear immediate output
Pineapple sessions
- Specific GTM problem
- Focused working session
- Context sent before
- Live decisions
- Clear next actions
The flow
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.
Start here
Start with a GTM Sanity Check.
If you're not sure which session fits, bring the mess. We'll find the real issue and work through the highest-leverage next move.
- We're not sure who to sell to first.
- We have pipeline, but it feels fake.
- Our pitch isn't landing.
- We're considering a first sales hire.
- We're entering the UK and need a second brain.
Free founder sessions
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'll offer a free session.
Fit
Who Pineapple is for
B2B SaaS / AI founders
Especially founder-led sales, pre-seed to Series A.
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.
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.
Next move
Got a spiky GTM problem?
Pick the slice of help you need now, or start with a GTM Sanity Check and we'll find the real issue together.