How Well Is Your Sales Team Using AI?
Seventeen scored questions across six dimensions a sales leader actually controls — prospecting, conversation intelligence, forecasting, deal velocity, enablement, and tooling — produce a sales-specific AI leverage profile.
- A scored profile across 6 dimensions — see exactly where you're strong and where the gaps are.
- Your biggest opportunities, mapped to specific next moves.
- A personalized video walkthrough from Shawn (optional) — a real read on your results.
Most sales orgs don't lose ground on AI because the tools are bad — they lose ground because the leverage never compounds. Reps still do account research in browser tabs, calls aren't being captured, the CRM gets updated on Fridays, and proposals get rebuilt from scratch every deal. An honest read on sales AI leverage looks past the demos at what actually moves quota: how much of the rep day is reclaimed, how much of the pipeline is visible in real time, how fast deals move from verbal yes to signed contract, and whether the AI features your CRM already ships with are actually turned on.
This free assessment scores your sales org across six dimensions and returns a clear leverage profile in about six minutes. It's built from 27 years of technology leadership across Fortune 500 and growth-stage companies — the same lens a fractional Chief AI Officer would bring to your first conversation about prospecting velocity, conversation intelligence, forecasting accuracy, and rep adoption.
What sales AI leverage actually measures
Leverage is a profile, not a single number. The assessment scores six dimensions independently so you can see where AI is already paying off and where the gaps are: Prospecting & Pipeline Generation (is AI doing the research and personalization at the top of the funnel), Conversation Intelligence & Coaching (are calls captured, scored, and shaping coaching), Forecasting & Pipeline Hygiene (is the CRM clean enough and predictive enough to forecast without a spreadsheet war), Deal Execution & Proposal Velocity (do proposals and contracts move at the speed buyers expect), Enablement & Rep Productivity (do reps have AI in their workflow for content, role-play, and ramp), and Tooling & Integration (are the AI features you already pay for actually configured and adopted). The final question maps which sales workflows to automate first.
Why most sales AI investments underperform
The pattern is consistent across mid-market sales orgs: a sales engagement platform, a conversation intelligence tool, a forecasting tool, and a CPQ that don't talk to each other. Each one captures partial data; none of them roll up to a single trusted view of the deal. Reps double-enter information, managers pull conflicting dashboards, and the AI features inside the CRM stay turned off because no one owns them. The orgs that capture real value treat AI leverage as an integration problem first — connect two or three high-leverage workflows, prove the lift, and earn the right to roll out more. A leverage profile turns a vague AI ambition into a sequenced plan, and it tells you whether your constraint is tooling, integration, rep adoption, or decision speed.
What you get at the end
You'll see an overall Sales Team AI Leverage Score, a band that describes where you stand (from Pre-Foundation through Execution-Ready), a per-dimension breakdown, and a map of your highest-value automation opportunities across prospecting, conversation intelligence, forecasting, deal execution, enablement, and tooling. From there you can request a personalized video walkthrough — a short, recorded read on your specific results and what a fractional Chief AI Officer engagement would do for your sales motion. No generic sales deck.
Frequently asked questions
What is a sales team AI leverage assessment?
It's a structured evaluation of how much of your sales motion is being amplified by AI today and where the biggest unreclaimed leverage is. Rather than measuring AI knowledge, it measures the practical workflows — research, outbound, call capture, forecasting, proposal velocity, rep enablement, and tooling integration — that determine whether AI is moving quota or quietly sitting as shelfware.
How is this different from an AI readiness assessment?
A general AI readiness assessment looks at the whole company's preconditions. This one is scoped to the things a CRO or VP of sales actually controls and is measured on: pipeline generation, conversation intelligence, forecasting accuracy, deal execution speed, rep adoption, and the AI features inside the sales stack. The questions, scoring, and opportunity map are framed in the language of sales — pipeline, quota, ramp, forecast accuracy — not generic AI strategy.
How long does it take?
About six minutes. It's 17 scored questions across six dimensions, two short financial-context questions, and a final workflow-mapping question across prospecting, conversation, forecasting, execution, enablement, and tooling. Your progress auto-saves, so you can leave and resume without losing answers.
Who should take this?
CROs, VPs of sales, heads of revenue operations, sales enablement leads, and senior sales leaders weighing AI investment who want a clear-eyed read on where the leverage actually is — and what to fix first if the AI you've already bought isn't producing results. It's also useful for fractional CROs and PE operating partners scoping sales AI work for a portfolio company.
What do most sales orgs score?
Most sales orgs land in the Emerging Leverage or Pre-Foundation bands on the first run — usually because the AI features inside the CRM aren't turned on, conversation intelligence isn't tied to coaching, or the forecast is still a spreadsheet exercise. That's not a failing grade; it's a useful diagnosis, and it tells you where the next dollar of sales AI investment should go.