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Salary: USD 210,000 - 225,000 / annual
UpKeep is the AI-first Computerized Maintenance Management System (CMMS) and Asset Operations Management platform, serving over 4,000 companies including Shell, Yamaha, Unilever, and Marriott. The company is backed by Insight Partners, Emergence Capital, and Y Combinator, and is positioned to lead a $30B category shift toward intelligent asset operations.
As Director, Revenue Strategy & Operations, you will own the analytical and AI infrastructure that drives visibility into the sales funnel, identifies performance drivers, and informs strategic decisions for Sales, Marketing, Customer Success, and Finance. This is a hands-on leadership role centered on full-funnel growth and revenue analytics—understanding drivers of new business, retention, expansion, pipeline health, conversion, and productivity.
You will lead a lean RevOps team including a Deal Desk Manager and Salesforce Administrator, with dotted-line partnerships across Sales Operations, GTM Engineering, and Marketing Operations. You report to the CFO. This role requires deep involvement in data analysis and problem-solving, not management through layers.
Key responsibilities include:
- Weekly inspection and analysis of pipeline creation, lead flow, funnel conversion, and rep-level productivity, translating findings into actionable recommendations for leadership
- Diagnosis of funnel breakdowns and outperformance drivers; assessment of opportunity and pipeline quality beyond face-value metrics
- Building AI-driven workflows for account prioritization, buying-signal detection, and automated GTM inspection to replace manual analysis
- End-to-end visibility from lead generation through new business, onboarding, retention, expansion, and churn; analysis of GRR, NRR, churn, and expansion tied to acquisition source and deal characteristics
- Cohort and segment performance analysis; identification of best-customer and closed-won deal patterns to sharpen ICP and targeting
- GTM capacity planning framework including headcount, productivity, quota capacity, and pipeline requirements; modeling ROI from incremental GTM investment
- Pressure-testing forecast assumptions and surfacing leading indicators in partnership with Sales Operations
- Ownership of GTM performance narrative for executives and the Board
- Setting priorities and governance for GTM systems, data architecture, reporting, and metrics to ensure reliable, decision-useful data
Requirements:
- 6–10+ years in Sales Strategy, Sales Operations, GTM Strategy, Revenue Analytics, Revenue Intelligence, Revenue Operations, or FP&A
- Career built through Sales Strategy, Sales Ops, Marketing Ops, or GTM Strategy (not primarily Salesforce administration)
- Experience at high-growth SaaS companies in the $30M–$150M ARR range, with hands-on data pulling, modeling, and CRM work
- Proven ability to independently diagnose performance problems and identify scaling opportunities
- Bachelor's Degree (or equivalent experience)
- Deep, practical AI experience—hands-on building, not just familiarity with AI tools
- Hands-on expertise with modern GTM stack: Salesforce, Gong, Clay, enrichment/intent data, SQL, dbt, or BI tools
- Strong full-funnel analytics: pipeline, conversion, segmentation, retention, expansion, cohort analysis, capacity modeling
- Strong Excel/Google Sheets modeling; SQL, BI, or data warehouse experience preferred
- Exposure to Salesforce Revenue Cloud/CPQ or similar quote-to-cash systems preferred (not a day-to-day admin role)
- Root-cause diagnosis across Marketing, BDR, Sales, and Customer Success
- Ability to communicate complex analytical findings clearly to executives
- Builder mentality: inquisitive, high-energy, low-ego, comfortable in small teams and in the details
