Director of Revenue Strategy & Operations, UpKeep

• You should be comfortable getting into the data, inspecting the funnel, building the analyses and models yourself, and sitting down with functional leaders to solve problems
• 6–10+ years across Sales Strategy, Sales Operations, GTM Strategy, Revenue Analytics, Revenue Intelligence, Revenue Operations, or FP&A
• A career built through Sales Strategy, Sales Ops, Marketing Ops, or GTM Strategy, rather than one centered primarily on Salesforce administration and systems ownership
• Experience at high-growth SaaS companies in the ~$30M–$150M ARR range, where you personally pulled the data, built the model, and worked directly in the CRM
• Proven ability to diagnose performance problems independently — and equally, to spot what is working and build the case for scaling it
• Bachelor's Degree with equivalent experience a plus
• Deep, practical AI experience — hands-on building, not familiarity with AI tools for drafting and content generation
• Hands-on with the modern GTM stack: Salesforce, Gong, Clay, enrichment and intent data, SQL, dbt, or BI tools
• Strong full-funnel analytics: pipeline, conversion, segmentation, retention, expansion, cohort analysis, and capacity modeling
• Strong Excel/Google Sheets modeling skills; SQL, BI, or data warehouse experience is a plus
• Exposure to Salesforce Revenue Cloud / CPQ or similar quote-to-cash systems is preferred; this is not a Salesforce implementation role, and you will not be the day-to-day administrator
• Root-cause diagnosis across Marketing, BDR, Sales, and Customer Success — demand, qualification, process, capacity, productivity, or execution
• Ability to communicate complex analytical findings clearly to executives and functional leaders
• Builder mentality: inquisitive, high-energy, low-ego, and comfortable working in a small team and directly in the details

Desirable

• As Director, Revenue Strategy & Operations, you will build the analytical and AI infrastructure that tells us what is happening in the funnel, why it is happening, what Sales and Marketing should do about it, and where Finance should allocate resources across the GTM function
• This is a hands-on role leading a lean RevOps function that supports Sales, Marketing, Customer Success, and Finance
• It is centered on full-funnel growth and revenue analytics — understanding the drivers of new business, retention, expansion, pipeline, conversion, and productivity, and translating those insights into clear decisions about where the company should focus
• Handed a pipeline export, your instinct should be to find the problem, and to find what is working well enough to scale
• This role reports to the CFO. You will lead and develop the RevOps team, including the Deal Desk Manager and Salesforce Administrator, and work in dotted-line partnership with the Sales Operations Manager, GTM Engineering, and Marketing Operations
• Own the weekly inspection of pipeline creation, lead flow, funnel conversion, and rep-level productivity, and turn each week's findings into a short, specific list of actions for Sales and Marketing leadership
• Diagnose where the funnel is breaking and where it is outperforming, and make sure both get acted on
• Assess opportunity and pipeline quality directly, rather than taking stage and amount at face value
• Use AI to inspect pipeline at scale — opportunity quality, deal risk, and forecast credibility — rather than sampling manually
• Build AI-driven workflows for account prioritization, buying-signal detection, and weekly GTM inspection, replacing recurring manual analysis with automated reporting that leadership can trust
• Partner with GTM Engineering and functional leaders to identify and implement high-value AI use cases
• Deliver end-to-end visibility from lead generation through new business, onboarding, retention, expansion, and churn, including the analytical view of GRR, NRR, churn, and expansion tied back to acquisition source, segment, and deal characteristics
• Analyze conversion, velocity, pipeline health, cohort and segment performance, and revenue leakage; identify what our best customers and closed-won deals have in common and sharpen ICP, targeting, and segmentation around it
• Own the analytical framework for GTM capacity planning — headcount, productivity, quota capacity, pipeline requirements, and segment opportunity — and model the expected return from incremental GTM headcount, programs, and channels in partnership with Finance on annual planning
• Pressure-test forecast assumptions and surface leading indicators before they show up in reported results, partnering with the Sales Operations Manager, who owns the weekly forecast process, deal-level scrutiny, and sales operating cadence
• Own the GTM performance narrative for executive leadership and the Board, anticipating the questions before they are asked
• Set priorities and requirements for core GTM systems, data architecture, and reporting, and govern GTM definitions, metrics, and data quality so that Salesforce and other systems produce reliable, decision-useful data