VP of Customer Success

Role Summary We're hiring a VP of Customer Success to own the full post‑sale customer journey. You will be accountable for retention, expansion, and the end‑to‑end experience from activation through renewal. You will lead and grow a multi‑sub‑function organization 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 will 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 supporting levers. Build the CX team: hire, develop, and retain strong sub‑function leaders across Customer Support, 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: push the 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 the 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 the voice of the customer to the leadership team and the company: bring structured, prioritized customer insight into product roadmap, pricing, GTM, and company strategy decisions. Partner cross‑functionally with Product, Sales, Marketing, Data, Engineering/BuildOps, and others to integrate AI deeply into the CX motion. 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 company‑level retention/expansion metrics. Multi‑sub‑function leadership experience spanning Support and Success through managers. Systems and metrics fluency, able to discuss activation definitions, retention cohorts, expansion attribution, and CX data modeling. 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: set up or rationalized a CSP, ticketing, dialers, and CX BI stack at scale. People leader: hired and developed strong first‑ and second‑line CX managers. AI‑native operator: integrated AI agents into a CX motion (first‑line triage, summarization, deflection, CSM productivity). Comfortable in startup pace: handling ambiguity and rapidly evolving teams. In‑office presence: willing to be in the NYC office five days a week. Who You Are A builder with executive range, energized by setting strategy and understanding frontline realities. Outcome‑obsessed, measuring success by company‑level retention and expansion numbers. A customer‑first operator, orienting decisions around the customer and building mechanisms that enforce this across the company. Comfortable with healthy dissent, bringing constructive disagreement to leadership and committing when the decision differs. Low‑ego, high‑bar: setting high standards, communicating directly and warmly, and uplifting others rather than avoiding collaboration. Calm in ambiguity, thriving in fast‑moving, lightly defined environments where the playbook is created, not inherited. Enthusiastic about AI as a force multiplier, not threatened by it. Aligned with Topline Pro’s values and excited to help small business owners win. Benefits Competitive cash compensation and meaningful equity package. Full medical, dental, and vision health coverage. Computer and workspace enhancements. Monthly stipend for mental and physical health. 401(k) plan (non‑matching). Unlimited vacation, nine company holidays including election day, and one personal volunteer day a year. A seat on the leadership team, board exposure, and the chance to define a function from the ground up at a Series B inflection point. The opportunity to take significant ownership in scaling a product that materially changes the lives of home‑service professionals. #J-18808-Ljbffr Topline Pro