Autonomy AI — Internal Sales Playbook

The Paid Pilot
Sales Process.

From first discovery call to signed contract.
No free trials. No open-ended POCs. Just structured pilots that close.

Conversion rate 40–60% (paid pilot)
vs. free trial <10%
Pilot duration 60 days
The Model

Free pilots don't close.
They signal desperation.

<10% Conversion rate for free trials in enterprise SaaS
40–60% Conversion rate for structured paid pilots with written success criteria
3.2× More likely to convert when success criteria are written and signed before Day 1
"95% of AI pilots fail to deliver ROI — not because the tech doesn't work, but because no one managed the change. Your pilot includes change management. That's the difference."
Free trial
✕ No skin in the game
✕ No exec sponsor assigned
✕ No success criteria
✕ No urgency to evaluate
Paid pilot
✓ Committed budget → committed attention
✓ Named exec sponsor, attends kickoff
✓ Written success criteria, signed before Day 1
✓ Day 45 review = the close meeting
The Motion

Five stages. Sixty days.
One signed contract.

01
Discovery
Qualify the pain, find the sponsor
→
02
Qualification
ICP fit, deal sizing, budget confirmation
→
03
Pilot Agreement
Success criteria signed before Day 1
→
04
60-Day Pilot
Weekly check-ins, Day 45 sponsor review
→
05
Full Contract
Day 60 — annual commitment signed
Kill criteria
No exec sponsor named
Engineering leadership veto
No PMs or designers in scope
Procurement > 6 months
The non-negotiables
Written success criteria, signed
Named exec sponsor
Pilot fee paid before Day 1
Day 45 sponsor review on calendar
Pilot pricing rule
15–20% of anticipated ACV
100% credited to full contract
Keep under $20k/month (discretionary)
Invoice before kickoff
Stage 1 — Discovery

Five questions. One goal:
quantify the pain and find the sponsor.

1
"Walk me through how a feature gets from idea to production today."
Listen for: number of handoffs, wait times, who can unblock vs. who has to wait. Count the steps. That number is your first selling point.
2
"What's in your backlog right now — and how old is the oldest item?"
A backlog older than 6 months is organizational debt. Quantify it: 50 items × 2 weeks avg = 2 engineering years of deferred value sitting in a queue.
3
"What happens to a feature request your PM has today that an engineer is blocking?"
Surfaces the handoff frustration — spec rewrites, back-and-forth, the real cost of waiting. Let them vent. This is the emotional hook.
4
"If your PMs and designers could ship directly — no tickets, no handoffs — what would they build first?"
The answer to this question becomes the pilot's first project. Write it down exactly as they say it. It's also the vision and the emotional hook.
5
"Who has authority to approve a $15–30k pilot without a 3-month procurement process?"
Identifies your economic buyer and your procurement path. If nobody — reframe as 2 months at $10k/month to stay under discretionary limits.
Stage 2 — Qualification

Qualify fast. Walk away faster
from the wrong deals.

Signal
Green ✓
Yellow ~
Red ✕
Team size
10–200 people
5–9 or 200–500
<5 or >500
PM:Engineer ratio
1:3 to 1:6
1:2 or 1:8
1:1 (no need) or 1:10+
Backlog age
>3 months old
1–3 months
<1 month (not in pain)
Designer role
Blocked waiting for eng
Design team exists
No designers on team
Engineering attitude
Wants to work on harder problems
Neutral or skeptical
Hostile + has exec cover
AI maturity
"Experimenting with AI tools"
"Heard about it"
"We don't allow AI"
3+ green = proceed
Yellows = address in next call
Any red = disqualify or defer
Stage 2 — Pricing

Price the pilot at 15–20% of ACV.
Credit 100% on conversion.

// Pilot pricing formula Pilot fee = 15–20% of expected ACV Example: $10k/mo target ACV Annual ACV = $120,000 Pilot fee = $18,000–$24,000 Duration = 60 days Credit = 100% applied to Year 1 Net client pays: ACV - pilot_fee
Typical ranges
Small team (5–20 seats)$10–20k pilot
Mid-market (20–50 seats)$20–40k pilot
Enterprise (50+ seats)$50k+ pilot
Pilot scoping template
Client_______________
Duration60 days
Pilot fee$_______________
Expected ACV$_______________
Exec sponsor_______________
Pilot team___ PMs, ___ designers
First project_______________
Day 45 reviewOn calendar before signing
Stage 3 — Pilot Agreement

Success criteria are co-authored.
Never hand them a pre-filled version.

Speed
At least [N] features shipped by PMs or designers without an engineering ticket
Average lead time for PM/designer features: <[X] days (baseline today: ___ days)
Backlog
[N] items removed from engineering backlog because PM/designer shipped them directly
30–50% of backlog reclassified as PM/designer-owned by Day 45
Adoption
At least [N] PMs/designers actively using the platform ([X] sessions/week)
At least 1 PM/designer self-describes as "I can now build things I couldn't before"
Team Impact
Engineering reports [X]% reduction in spec review interruptions per week
First PM/designer-shipped feature has been used by [N] real users
The rule: If the criteria aren't signed before Day 1, the pilot doesn't start. No exceptions. Unsigned criteria = no shared definition of success = no conversion pathway.
Stage 4 — The 60-Day Pilot

Week by week. Your job
and their job, in parallel.

Week
Focus
Your Job
Client's Job
Wk 1
First Win
Hands-on setup, white-glove first build
PM ships first feature — even if small
Wk 2–3
Expand Scope
Identify 2nd and 3rd use case
2–3 more PMs/designers onboarded
Wk 4
First Review
Baseline vs. Week 4 data deck
Sponsor sees progress — show it up the chain
Wk 5–6
Backlog Attack
Help prioritize backlog items for PM ownership
Engineers see the shift — tension may surface
Wk 7
Change Mgmt
Address adoption friction, coach on org changes
Redesign sprint rituals, intake routing
Day 45
★ Close Meeting
Present success criteria scorecard + full contract
Exec sponsor attends. This is the conversion meeting.
The Day 45 review is scheduled before Day 15. If it's not on the calendar, get it there immediately.
Stage 5 — The Close

Day 45 is a business conversation.
Not a demo. Not a check-in.

// Open — get the quote before the numbers
"Before we get into the metrics — [Sponsor name], when [PM name] shipped [Feature X] in [N days] instead of [N weeks], what was your reaction?"
// Let them answer. That quote goes in your case study. Then pivot to data.
"Here's the scorecard against what we agreed." [Walk through criteria — green/yellow/red.] "We hit [N of N]. Here's what that means in dollar terms over a full year..."
// Present the ROI model. Annualized.
"The proposal in front of you is [X seats at $Y/month, annual commitment]. We've applied your full pilot fee as a credit. To move forward today, I just need [signature / PO / verbal commit so legal can start]."
// Then stop talking. The next person who speaks loses.
// If they don't sign same day — the Day 50 follow-up:
"We need to submit the contract to our provisioning queue by [date]. Is there anything blocking [Sponsor] from signing this week?"
Objection Handling

Five objections you'll hear.
Five responses that don't fold.

🔍
"We need to see more data before we commit."
"What specifically would make you more confident? Let's define it — we can extend 2 weeks if we name the criteria right now." Don't accept "more data" without pinning it to a metric.
🏛
"Procurement takes 3 months for any new vendor."
"Who's your procurement contact? Let's get them on a call this week — we can start legal review while the pilot wraps. Most of our contracts close in parallel with the last 2 weeks of the pilot."
⚙️
"Engineering is pushing back. They're not comfortable."
"Let's get [Eng Lead] in the room. In every case I've seen, the conversation changes when they understand the engineering partner role — they own the safety layer, not lose the work."
💰
"The price is too high."
"The pilot credit is already applied. I can offer a 12-month vs. 24-month option if total cash outlay is the constraint. What's the ceiling I need to fit under?"
🔄
"Can we do another pilot period before committing?"
"A second pilot without a contract is a free trial — and free trials don't get exec attention or change management support. What would need to be true to sign a 12-month agreement today?"
The Numbers That Justify the Sale

Use these benchmarks in
every discovery and close conversation.

3.2×
More likely to convert when pilot has written, co-authored success criteria signed before Day 1
Forrester
40–60%
Paid pilot conversion rate vs. <10% for free trials in enterprise SaaS
Industry benchmark
95%
Of AI pilots fail to deliver ROI — not because the tech fails, but because no one managed the change
MIT Sloan 2024
$200–250K
Average fully-loaded engineer cost per year. 1–2 avoided hires = $200–500k in savings — exceeding the contract cost
US market average
3×
More features shipped per year when lead time drops from 8 weeks to 2 weeks
McKinsey 2025
40%
Of a typical engineering backlog is work PMs and designers could own directly with the right platform
Internal analysis
Deal Health

Use this checklist at every stage.
A stalled deal usually has an unchecked box.

Discovery & Qualification
Pain is quantified, not just acknowledged
Economic buyer identified and willing to meet
Engineering leadership is not a veto
ICP: 3+ green, 0 red
Pilot team named (specific PMs and designers)
Budget confirmed: pilot fee and expected ACV
Pilot Agreement
Success criteria signed before Day 1
Executive sponsor named and attending kickoff
First project scoped (not "TBD")
Pilot fee invoiced and paid
Pilot Execution
Week 1 win shipped by PM/designer
Weekly check-ins on calendar (all 8)
Day 45 sponsor review scheduled before Day 15
Week 4 metrics reviewed with sponsor visibility
Engineering partner role live and working
Backlog classification exercise completed
Conversion
Day 45 scorecard built and shared before meeting
Full contract proposal sent before Day 50
Procurement contact identified by Day 40
Signed by Day 60
The Bottom Line

Every week a feature sits in a backlog is a week of deferred revenue.

The paid pilot proves the model. The change management project makes it stick. The annual contract scales it. That's the full motion.

1
Qualify hard in discovery. Bad deals cost more than lost deals.
2
Get success criteria signed before Day 1. No criteria, no pilot.
3
Day 45 is the close meeting. Prep the scorecard. Bring the contract.
Autonomy AI — Internal Use — adir@autonomyai.io
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