VP of Customer Success

📣 ROLE SUMMARY We're hiring a VP of Customer Success to own the full post-sale customer journey. You'll be accountable for retention, expansion, and the end-to-end experience from activation through renewal. You'll lead and grow a multi-sub-function org spanning Customer Support, Customer Success, and Expansions, and partner as a peer with Sales, Product, Marketing, RevOps, and Engineering. This is a key leadership hire: you'll set the multi-year CX strategy, own Net Revenue Retention as a board-level metric, and represent the voice of tens of thousands of small business owners inside the company. ⚡ WHAT YOU'LL DO - Own NRR as a company KPI: Forecast it, explain it, defend it, and present it to the board quarterly. Drive Gross Revenue Retention, expansion-sourced ARR, and activation/time-to-value as the supporting levers. - Build the CX team: Hire, develop, and retain strong sub-function leaders across Customer Support, Customer Success (CSM), and Expansions. - Define the customer operating model: Set segmentation, service tiers, and the high-touch vs. tech-touch service model. - Build proactive retention and expansion motions: Continue pushing on our focus to move CX from reactive to proactive through churn prediction, renewal motion, expansion motion, and win-backs. - Lead CX tooling strategy: Partner with RevOps to revamp our end to end tech stack across GTM (leveraging AI across the stack) - Revamp CX reporting: ops-level, leadership-level, and manager-level coaching dashboards, in partnership with RevOps and BizOps. - Represent voice-of-customer to the LT and Company: Bring structured, prioritized customer insight into Product roadmap, pricing, GTM, and company strategy decisions. - Partner cross-functionally: Product (activation, adoption), Sales (handoff, expansion, renewal), Marketing (lifecycle, references, advocacy), Data (health scoring, churn prediction), Engineering/BuildOps (customer-facing reliability). - Integrate AI deeply into the CX motion: Build on the existing first-line AI triage and push aggressively on agent tooling, summarization, and CSM productivity. - Own the CX annual plan, headcount model, and tooling budget. 🎯 WHAT WE'RE LOOKING FOR - Proven VP-level CX ownership at a high-velocity SMB SaaS company: accountable for a company-level retention/expansion metric (NRR) and company KPIs - Multi-sub-function leadership experience: Direct experience scaling and managing a CX org spanning Support and Success through managers. - Systems and metrics fluency: Can speak fluently to activation definitions, retention cohorts, expansion attribution, and how CX data should be modeled. - Expansion ownership: Demonstrated ability to drive expansion-sourced ARR. - Strong peer partnership with Sales on post-sale handoff, renewal, and expansion motion design. - Modern CX tech stack experience: Have set up or rationalized a CSP, ticketing, dialers, and CX BI stack at scale. - People leader: Have hired and developed strong first- and second-line CX managers. - AI-native operator: Have meaningfully integrated AI agents into a CX motion (first-line triage, summarization, deflection, CSM productivity). - Startup pace: Comfortable in ambiguity and quickly evolving teams. - In-office presence: Excited to be in the NYC office 5 days a week with the team. 🤗 WHO YOU ARE - A builder with executive range: You're energized by setting strategy and getting into the queue to understand what's actually happening on the frontline. - Outcome-obsessed: You measure your success by what the company-level retention and expansion numbers actually do, not by activity or org size. - A customer-first operator: You instinctively orient every decision around the customer and you've built mechanisms that force the rest of the company to do the same. - Comfortable disagreeing well: You bring healthy dissent to the LT and disagree-and-commit when the call goes the other way. - Low-ego, high-bar: You hold a high standard for your team and yourself...