Sales · Deal Coaching

AI Deal Strategy Coach

92Building evidence

Generate Revenue

“I want to be able to ask 'what's wrong with this deal and what should I do next' at any moment — not just in my weekly pipeline review — and get a specific, honest assessment based on the actual deal data, not a gut feeling.”

At a glance

Cost

$100–300 /mo

Time saved

30–45 minutes of manager coaching time per deal per week — deal coaching available to reps 24/7

Difficulty

High

Steps

2 AI · 3 automation

What you end up with

An on-demand 7-section deal coaching assessment delivered via Slack: deal health score (1–10), MEDDIC gap analysis by element, stakeholder coverage map, discovery quality review, next-step risk score, a specific recommended play for the next 72 hours, and yellow/red flags — with executable action materials ready to use.

The pipeline · 5 steps

STEP 1

Salesforce

Provides the complete deal record including stage, contacts, activity log, and methodology fields

Automation

STEP 2

Gong

Surfaces the full conversation history with buyer engagement signals and risk indicators across all calls

Automation

STEP 3

Claude

Synthesizes all deal data into a structured coaching assessment with specific, actionable recommendations

AI decides

STEP 4

Claude

Translates the strategic recommendation into executable outreach copy and scripts

AI decides

STEP 5

Slack

Delivers the coaching assessment on-demand to the rep's Slack, decoupling coaching from the weekly 1:1 schedule

Automation

AI decides a model generates or judges hereAutomation runs mechanically, no judgment

How it runsamber = the model makes a judgment call

STEP 1

Provides the complete deal record including stage, contacts, activity log, and methodology fields · Salesforce

Automation

Salesforce executes this mechanically. No judgment call — it runs the same way every time.

STEP 2

Surfaces the full conversation history with buyer engagement signals and risk indicators across all calls · Gong

Automation

Gong executes this mechanically. No judgment call — it runs the same way every time.

STEP 3

Synthesizes all deal data into a structured coaching assessment with specific, actionable recommendations · Claude

AI decides

The model generates and decides here — output quality depends on the prompt and context you give Claude.

STEP 4

Translates the strategic recommendation into executable outreach copy and scripts · Claude

AI decides

The model here — output quality depends on the prompt and context you give Claude.

The honest readpros and trade-offs, side by side

What works

Available on-demand — reps don't wait until Friday 1:1 to get strategic clarity on a deal

MEDDIC gap analysis is evidence-based from actual call transcripts, not rep self-reporting

Honest deal health scoring replaces optimistic pipeline padding with grounded assessment

Scales coaching to every rep on the team, not just those with the most attentive managers

Yellow and red flags section surfaces uncomfortable truths reps often avoid stating themselves

The trade-offs

Gong transcripts must be linked to Salesforce opportunities — orphaned calls produce incomplete assessments

Deal health score calibration takes time — Claude's scoring needs to be validated against win/loss outcomes

High-quality assessments require high-quality deal data — reps who don't log activity get shallow coaching

Where people go wrong

The failure modes builders hit most often. Avoiding these is most of the battle.

01Asking for a deal assessment without providing Gong call history — Claude produces surface-level advice without conversation data

02Using assessment output in manager 1:1s without rep review — coaching should empower reps, not be used to judge them

03Not acting on the recommended play within 72 hours — the value is in execution speed, not just diagnosis

04Omitting the rep's own assessment — their context often adds crucial deal nuance that CRM data doesn't capture

Built for

Account ExecutiveEnterprise Sales RepSales ManagerVP of SalesRevenue Operations

Industries

SaaSEnterprise SoftwareB2B ServicesFinancial ServicesHealthcare TechProfessional ServicesManufacturing

Use cases

AEs seeking strategic clarity on a complex deal without waiting for a manager reviewSales managers getting a pre-1:1 deal brief for every rep automatically before the meetingVPs of Sales running deal reviews with an objective AI assessment as a baselineRevOps teams building a deal quality scoring system to improve forecast accuracyEnablement teams identifying systematic MEDDIC gaps across the entire pipeline

FAQ

How do I get deal coaching without waiting for my manager?

AI Deal Coach: Apex Financial Group — June 14, 2025 Deal Health Score: 5/10 MEDDIC Gap Analysis: - Metrics: Partially confirmed. Rep quantified time waste in discovery but no CFO-level financial target established. Risk: economic buyer has no number to justify to the board. - E

How do I use AI to identify MEDDIC gaps in my deals?

Deal coaching currently happens in weekly 1:1s, which means reps operate with strategic blind spots for 5–6 days at a time. By the time a manager spots a discovery gap or missing stakeholder, a week of deal time has been lost. Reps in high-volume pipelines also get less 1:1 time — the deals that need coaching most often get the least attention.

How do I assess deal health using Gong and Salesforce data?

Workflows, proven by builders

AI Deal Strategy Coach