AI sales coaching for complex B2B deals

Stop guessing. Start winning more deals.

Every sales tool tracks activity, predicts pipeline, or records calls. None answer the question every seller asks at 9pm the night before a deal-defining meeting: "what should I do next on this deal?" WinCoach does. In ten minutes.

Standalone  ·  Assessment-driven  ·  Methodology-grounded  ·  No call recording  ·  No CRM required
Enterprise · Stage: Propose
Acme Holdings · Platform renewal
Close · Q2 · 42 days
£1.2m
ARR
67
Win %
Pillar signal
Pain
82
Economics
74
Champion
38
Decision
46
Competition
61
Priority actions
i. Confirm economic buyer's Q2 priority list — your champion thinks this is top-3, but hasn't tested that assumption with the CFO.
ii. Pressure-test the decision criteria — criteria as currently written favour the incumbent. Reshape before the short-list.
iii. Build a second coach in Ops — single-threaded on Engineering is a known stall pattern at this stage.
Section 01 · The problem

Complex deals keep slipping.
And coaching doesn't scale.

6–10
stakeholders in a typical B2B buying group — more veto, more stalls Source · Gartner
~20%
average B2B win rate in 2025, down from 29% the year before Source · Ebsta × Pavilion
73%
of sales managers spend under 5% of their time coaching Source · LinkedIn State of Sales

The judgement that wins complex deals used to be transferred seller-to-seller, manager-to-rep, apprentice-style over years. That system broke when pipelines grew and the most experienced leaders moved on. The methodology still exists. It just isn't where the seller is, when the deal needs it.

Section 02 · Who it's for

Three people. Three jobs. One product.

Persona i.
The Seller
What you're doing today
Gut-feel next steps, ad-hoc ChatGPT, MEDDPICC spreadsheets that get filled in the morning of pipeline review.
What WinCoach gives you
A structured, 10-minute answer to "what should I do next on this deal?" — for every deal, every week.
Try it with
One stuck deal.
Start free →
Persona ii.
The Sales Manager
What you're doing today
Running weekly pipeline reviews that produce optimism, not clarity. No time to coach every rep on every deal.
What WinCoach gives you
Every rep showing up to pipeline review already coached. You spend the hour on judgement, not triage.
Try it with
Three reps on your team.
Book a team walkthrough →
Persona iii.
The Sales Leader
What you're doing today
Watching win rate decline while your coaching headcount stays flat. Methodology rollouts that never stick.
What WinCoach gives you
Methodology that actually gets used because sellers opt in — it helps them, not just you. Measurable win-rate lift in one quarter.
Try it with
One pilot cohort, on a monthly contract.
Talk to us about a pilot →
Section 03 · What it does

Assess. Coach. Act.
Built for the way complex deals actually move.

01  ·  Assess
Assess
Answer a stage-adaptive assessment on your live deal. 28 dimensions across 7 winnability pillars, weighted by real-world influence on win probability. Starts at Prospect — not Qualify. Takes 10 minutes.
02  ·  Coach
Coach
Your weakest dimensions surface first. AI coaching grounded in senior practitioner knowledge — the specific questions to ask your buyer, the traps only obvious in hindsight, the moves that materially shift a pursuit. Chat with your coach on any dimension to go deeper.
03  ·  Act
Act
Priority actions ranked by impact on win probability. Purpose-built deal tools — stakeholder maps, champion plans, mutual action plans, win themes, competitor assessments — each one pre-populated from your assessment, coached by the AI. You never face a blank canvas.

The loop is the product. Most sales tools treat a deal as a static record that updates when the rep logs activity. WinCoach treats it as a live pursuit that deserves coaching every time something material changes.

THE LOOP ↻ Assess Coach Explore Plan Reassess
Section 04 · Why this is different

Everyone added AI in 2025.
We start with a different question.

By 2027 every sales tool will have a frontier model attached. The question is what the AI is grounded in. Every competitor grounds theirs in something else — and each grounding has a structural limit.

This product WinCoach Incumbent type Call-capture tools Incumbent type CRM-native coaches Incumbent type Enablement platforms Incumbent type The default today
Grounded in Practitioner Methodology Call recordings CRM history Vendor training content Spreadsheets + ChatGPT
Works at Prospect ✓ ✗ ✗ Partial Unstructured
No CRM integration ✓ ✗ ✗ Partial ✓
No call recording ✓ ✗ ✗ Varies ✓
Per-dimension coaching chat ✓ ✗ ✗ ✗ Generic only
Starts at £0 Enterprise contract Salesforce licence Quote-based Free, but no method

The AI is the conductor.
The framework, the knowledge base, and the tools are the orchestra.
Swap the model — the moat stays.

Section 05 · Built for regulated teams

The product you can adopt without Legal in the room.

Financial services. Healthcare. Legal. Government. EU regulated enterprise. Anywhere call recording is friction, forbidden, or foolish — WinCoach works. We capture no calls. Require no CRM integration. Run on zero-retention AI. GDPR-compliant by default.

Which is why mid-market teams adopt in days, not quarters. The buying committee is Sales Leadership, not IT, SecOps, CRM admin, and Procurement. That compresses the first deployment from 6+ months to 4–6 weeks.

GDPR compliant EU data residency Zero-retention AI SOC 2 Type II on roadmap
Section 06 · Pricing

Four tiers. Free forever to start.

Free
£0
Forever, no card
Up to 3 deals. Full assessment. Limited coaching.
The wedge that gets reps in
Coach
£29/mo
Per seller
Unlimited deals. Full 7-section coaching. Per-dimension chat.
The individual tier
Coach Plus
£49/mo
Per seller
Everything in Coach + live web intelligence on buyers and competitors.
The power-seller tier
Teams
£89/mo
Per seat + manager view
Everything + manager oversight, analytics, invitations, coaching annotation.
The ACV unlock
Budget line: Sales Enablement · RevOps · Sales Productivity.
Mid-market signatory is your sales manager — no procurement cycle required for the first 50 seats.
Start with one deal

Win the deals you're already working.
Starting with the one that's stuck.

Pick one live deal. Assess it in 10 minutes. See the coaching. Decide whether WinCoach earns its place in your stack. Free, no card, no IT approval.

Start free Book a 15-minute walkthrough