Pilot-to-Paid Conversion Playbook
Compress the journey from free pilot to annual contract with a four-week cadence that combines evidence capture, risk controls, and executive storytelling.
MB
Max Beech
Head of Content
TL;DR
- 35 of 106 Athenic posts reference pilots, but few detail the hand-off to procurement (Athenic Content Audit, 2025).
- Map success metrics, governance triggers, and stakeholder roles on day one; capture proof using the customer evidence vault and organic growth data layer.
- Run a four-week close cadence that merges executive storytelling with compliance-ready documentation.
Jump to Alignment · Jump to Proof · Jump to Commercials · Jump to Close cadence
Pilot-to-Paid Conversion Playbook
Pilots are only useful if they become revenue. The work isn’t done once the customer says “let’s try it.” This pilot-to-paid playbook blends evidence capture, risk management, and executive storytelling so you leave no doubts when asking for the signature.
Key takeaways
- Don’t launch a pilot without a success charter that names metrics, risks, and signatories.
- Evidence beats anecdotes -log results and testimonials into the customer evidence vault with timestamps.
- Align pricing, legal, and security review before the executive pitch so procurement sees you as prepared.
How do you align on pilot success in week one?
- Success charter: Co-write a one-page charter covering scope, baseline metrics, target uplift, and risk controls. Share in
/app/app/projects. - Stakeholder map: Identify economic buyer, champion, technical evaluator, legal, and security. 62% of B2B deals stall because senior stakeholders join late (CIPS, 2024).
- Governance hooks: Plug into the AI escalation desk so any risky outputs escalate immediately.
| Stakeholder | Role | Success metric | Risk concern |
|---|---|---|---|
| Chief Product Officer | Economic buyer | Reduce research cycle by 40% | Data leakage |
| Head of Compliance | Security reviewer | Maintain audit trail | Regulatory exposure |
| Marketing Lead | Champion | Increase community replies | Brand voice drift |
Stat to monitor: Pilots appear in one-third of our content archive, but fewer than 10% contain procurement exit criteria (Athenic Content Audit, 2025). Surface exit criteria up front to avoid surprise.
What proof converts pilots into contracts?
- Quantitative evidence: Log usage metrics via the organic growth data layer -time saved, leads generated, errors prevented.
- Qualitative proof: Capture testimonials using the customer evidence vault. Timestamp quotes and attach consent.
- Risk management: Document approvals in
/app/app/approvalswith escalation metadata.
How do you guarantee trust in the evidence?
- Use dual attestation: champion + operations sign each proof point.
- Reference guidance from the Financial Reporting Council on trustworthy evidence (FRC, 2024).
- Export a read-only packet for procurement.
How do you build a deal that procurement approves?
- Commercial model: Calculate ROI using pilot data. Keep pricing simple -annual contract with quarterly opt-out if targets missed.
- Compliance packet: Combine security questionnaire, data processing agreement, and audit logs. Map to UK Digital Functional Standard (GOV.UK, 2024).
- Risk mitigation: Offer staged rollout with clear escalation triggers referencing the AI escalation desk.
What legal hooks should you prepare?
- Draft a mutual NDA upgrade to cover full deployment.
- Prepare a Data Protection Impact Assessment template (ICO, 2024).
- Align with CIPS pilot project guidance on handover readiness (CIPS, 2024).
What does the four-week close cadence look like?
Week-by-week flow:
- Week 1: Success charter locked, instrumentation live, intro call with procurement booked.
- Week 2: Evidence sprint -agents compile dashboards, humans validate quotes.
- Week 3: Commercial draft shared, legal and security review scheduled.
- Week 4: Executive readout, objections mapped within 24 hours, contract countersigned.
Expert review pending: [PLACEHOLDER for Commercial Lead sign-off]
How do you keep momentum between meetings?
- Send asynchronous video updates summarising progress and next steps.
- Provide micro-wins to the champion every three days.
- Use Athenic jobs to automate reminders and escalations.
Mini story: From £0 to £120k ARR in 28 days
During a pilot with a UK insurer, the team logged a 43% reduction in manual research time. The compliance lead co-signed every data point. On week four, the executive readout aligned ROI (4.7x) with compliance controls. The board approved a £120k ARR contract on the call, with expansion triggers already written into the SOW. Momentum stayed high because every objection already had evidence.
What post-signature steps lock in value?
- Transition to the founder community roadshow for customer storytelling.
- Feed telemetry into the AI experiment council backlog.
- Schedule a 45-day value review with finance.
Summary & next steps
- Draft the success charter template today and align stakeholders.
- Instrument evidence and risk controls by day five.
- Build the commercial packet in week three, then run the executive close in week four.
Next step CTA: Activate Athenic’s pilot-to-paid workspace to install success charter, evidence vault, and close cadence templates in minutes.
QA checklist
- Pilot coverage stats verified through repository analysis (Athenic Content Audit, 2025-05-20).
- External guidance consulted: CIPS pilot project handover guidance, Financial Reporting Council evidence expectations, GOV.UK digital functional standard, ICO DPIA guidance.
- Internal links tested:
/blog/organic-growth-data-layer,/blog/ai-escalation-desk-marketing,/blog/founder-community-roadshow,/blog/ai-experiment-council. - Style, legal, and compliance review scheduled: 3 June 2025.