Growth Stage: $2M Customer Compliance vs CEO Vision vs Marketing

RECOMMENDATION: Compliance Priority + Parallel Innovation Track

RATIONALE:
A $2M enterprise customer threatening churn represents critical revenue protection. At your current scale, losing this customer damages ARR metrics and investor confidence. The Q2 compliance deadline is firm and non-negotiable. With 10 engineers, you can run parallel tracks: compliance (6 engineers) and strategic bets (4 engineers split between AI and mobile exploration).

PRIORITIZATION FRAMEWORK (weighted for growth-stage revenue protection):

TRADE-OFF ANALYSIS:

THREE-TRACK APPROACH:

Track 1 - Compliance Team (6 engineers):

• Dedicated team for Q2 compliance delivery
• Weekly customer validation sessions
• All other work paused for this team until delivery

Track 2 - AI Exploration (2 engineers):

• Lightweight POC to validate CEO’s vision
• Month 1-2: ChatGPT/Claude API integration proof-of-concept
• Define success metrics (>40% user engagement)

Track 3 - Mobile Foundation (2 engineers):

• Core infrastructure and authentication
• Month 1-2: Basic user flows on mobile
• Evaluate traction before full commitment

STAKEHOLDER COMMUNICATION PLANS:

To $2M Enterprise Customer:
“I’m committing our best engineers (6-person dedicated team) to deliver full compliance by Q2. Here’s our roadmap:

• Month 1 (Jan): Requirements validation with your compliance team + audit logging prototype
• Month 2 (Feb): Role-based access control + data retention features
• Month 3 (Mar): Compliance reporting + third-party audit preparation
• April: Final validation and certification completion

Weekly progress updates every Friday at 2pm PT. Our VP of Engineering joins the kickoff meeting for technical alignment. No blockers - this is our #1 company priority.”

To CEO (AI Integration):
“I’m validating the AI integration vision with a lightweight proof-of-concept while protecting $2M revenue. Here’s the approach:

Months 1-2: 2 engineers build AI integration POC using ChatGPT/Claude APIs. Success metrics:

• 40% of users try AI feature

• 25% weekly active usage

• Qualitative feedback from 10 power users

Month 3: Decision point based on POC results:

• If POC validates (hits metrics) → Commit 4 engineers post-compliance for Q3 full build
• If POC underwhelms → Pivot to enterprise features that expand $2M customer relationship

This validates AI cheaply while protecting revenue. We’ll have data-driven confidence before committing major engineering resources.”

To Marketing (Mobile App):
“I’m running a mobile foundation sprint (2 engineers, Months 1-2) to validate demand before full commitment. This gives us:

• Month 1: Authentication + core navigation on iOS/Android
• Month 2: Key user flows (login, dashboard, primary action)
• End of Month 2: Beta with 50 users to measure engagement

Decision in Month 3:

• If beta shows >30% weekly active usage → Commit 4 engineers post-compliance for full build
• If beta shows <30% usage → Defer mobile and focus engineering on web product excellence

This prevents a 4-month mobile investment without validation. You’ll get data to justify the full build or pivot to other growth channels (SEO, partnerships, etc.).”

ROADMAP:

Q1 2025 (Jan-Mar):
Track 1 - Compliance (6 engineers):
├─ Month 1: Audit logging + requirements validation
├─ Month 2: Role-based access control + data retention
├─ Month 3: Compliance reporting + certification prep
└─ Outcome: $2M customer retained, enterprise credibility established

Track 2 - AI POC (2 engineers):
├─ Month 1: ChatGPT/Claude API integration
├─ Month 2: User testing with 50 beta users
└─ Outcome: Data on AI engagement (>40% try, >25% weekly use = success)

Track 3 - Mobile Foundation (2 engineers):
├─ Month 1: Authentication + navigation
├─ Month 2: Core user flows + beta testing
└─ Outcome: Data on mobile demand (>30% weekly active = success)

Q2 2025 (Apr-Jun):
├─ April: Compliance certification completion
├─ May-June: Decision-driven allocation of 10 engineers
│   ├─ If AI POC validated → 6 engineers on AI, 4 on mobile
│   ├─ If Mobile validated → 6 on mobile, 4 on enterprise expansion
│   └─ If both underwhelm → 10 engineers on enterprise product depth
└─ Outcome: Data-driven commitment to winning strategy

ESCALATION PREVENTION STRATEGY:

1. Pre-brief CEO (30-min 1:1 before announcement)

   • Share trade-off analysis
   • Get buy-in on POC approach for AI
   • Emphasize $2M revenue protection

2. Pre-brief $2M customer (executive sponsor call)

   • Show 6-engineer commitment
   • Provide detailed delivery timeline
   • Request compliance team point-of-contact

3. All-hands stakeholder alignment meeting

   • Present prioritization framework to entire leadership team
   • Show how all priorities fit over time (not just “no” but “when”)
   • Transparency on decision-making methodology

4. Stakeholder-specific roadmap views

   • Customer: Compliance timeline with milestones
   • CEO: AI POC experiment design
   • Marketing: Mobile validation metrics

5. Bi-weekly progress updates (every other Friday)

   • Track 1: Compliance progress vs. customer requirements
   • Track 2: AI POC engagement metrics
   • Track 3: Mobile beta user feedback
   • Proactive communication prevents escalation