Overview
You're the first RevOps hire at Warp, building the billing and deal execution function from the ground up. You'll own Stripe configuration, subscription management, contract workflows, and commission tracking for their AI-native HR/Payroll platform. You report directly to the CEO with full autonomy to design processes as they scale from 1,000+ customers toward Series B.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Revenue Operations Specialist (Billing + Deal Desk + Systems) |
| Sales Motion | Supporting B2B SaaS sales team (likely PLG-assisted given 1,000+ customers) |
| Deal Complexity | Transactional to Consultative (HR/Payroll requires implementation) |
| Sales Cycle | N/A (RevOps support role) |
| Deal Size | Unknown (likely SMB to Mid-Market given customer count) |
| Quota (est.) | N/A (operational excellence metrics, not quota) |
Company Context
Stage: Series A/B (91 employees, preparing for Series B per post)
Size: 91 employees
Growth: 1,000+ customers using the platform, first RevOps hire signals scaling phase
Market Position: AI-native entrant in crowded HR/Payroll space (competing against established players like Rippling, Gusto, Justworks)
What You'll Actually Do
Time Breakdown
Billing/Stripe Admin (35%) | Deal Desk Execution (30%) | Systems/Process (20%) | Commission Admin (15%)
Key Activities
- Stripe Configuration & Subscription Management: Setting up pricing plans, managing subscription changes, handling upgrades/downgrades, configuring payment methods, troubleshooting failed charges. You're the Stripe expert who handles all billing edge cases.
- Deal Desk Operations: Reviewing contracts before they go out, enforcing discount approval workflows, ensuring pricing consistency, managing PandaDoc workflows, tracking redlines and contract exceptions.
- Commission & Incentive Administration: Calculating monthly/quarterly commissions for the sales team, resolving payout disputes, maintaining compensation records, ensuring comp plans are executed correctly in systems.
- Revenue Data Integrity: Reconciling Stripe revenue with CRM bookings, maintaining audit-ready records, cleaning up data inconsistencies, ensuring MRR/ARR reporting is accurate for board meetings and investor updates.
- Tooling Stack Management: Maintaining integrations between Stripe, PandaDoc, and CRM (likely HubSpot or Salesforce), troubleshooting sync issues, configuring automations to reduce manual work.
The Honest Reality
What's Hard
- You're building in a vacuum: No playbook, no predecessor to ask questions. Every process decision is yours to make and defend. You'll second-guess yourself frequently in the first 6 months.
- Billing edge cases are endless: Customer wants to pause for 2 months, prospect needs custom payment terms, someone's credit card fails during renewal. You'll spend hours per week on one-off scenarios that don't fit clean workflows.
- Commission disputes are emotionally charged: Sales reps care deeply about their money. You'll have uncomfortable conversations when comp calculations don't match their expectations, even when you're right.
- You're juggling operational fires: Stripe integration breaks right before month-end close, sales team needs urgent contract approval while you're reconciling revenue data. Everything feels urgent.
- Limited resources: At 91 people, there's no dedicated finance team, no rev systems admin backup. If something breaks, you're figuring it out.
What Success Looks Like
- Commission runs on time every month with zero disputes
- Sales team can self-serve 80% of contract/pricing questions through documentation you created
- Revenue data matches perfectly between Stripe and CRM during board prep
- Billing errors drop to near-zero and customers stop contacting support about invoice issues
- You've documented repeatable workflows that can scale as the sales team doubles
Who You're Supporting
Primary Stakeholders:
- Sales team (AEs/AMs who need clean deal execution and accurate commission tracking)
- CEO (who needs confidence in revenue reporting and operational efficiency)
- Finance/Accounting (who rely on your data for revenue recognition and reporting)
What They Care About:
- Sales: Fast contract turnaround, no surprise commission deductions, clear pricing authority
- CEO: Audit-ready books, accurate revenue metrics for investors, no billing embarrassments with customers
- Finance: Clean data exports, consistent revenue categorization, documentation for audits
Requirements
- 1-3 years in RevOps, Billing Operations, or Deal Desk at a B2B SaaS company
- Deep Stripe Billing knowledge (not just surface-level familiarity—you understand subscriptions, proration, revenue recognition)
- Experience building processes from scratch in fast-growth environments (not just maintaining existing systems)
- Comfortable making judgment calls without approval chains—you report to CEO but own day-to-day decisions
- Detail-obsessed personality—billing errors genuinely bother you and you catch discrepancies others miss
- Strong Excel/Sheets skills for commission calculations and data analysis