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.

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).
• Own the CX annual plan, headcount model, and tooling budget.

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.
• Calm in ambiguity: You thrive in fast-moving, lightly-defined environments where the playbook is something you'll write, not something you'll inherit.
• 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, communicate with directness and warmth, and bring others along rather than working around them.
• AI-native operator: You have meaningfully integrated AI agents into a CX motion (first-line triage, summarization, deflection, CSM productivity).

Hiring Process

• Recruiter Screen
• Hiring Manager Screen — Nick Ornitz (CEO)
• People Screen - Maya Alperin
• Onsite Live Case Study, Lunch with Team + XFN 1on1 Interviews — Multiple XFN LT members
• Co-Founder Final - Shannon Kay (COO & Co-Founder)
• References

What We Offer

• Competitive cash compensation + meaningful equity package (VP-level)
• 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, 9 company holidays including election day, and 1 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 pros

About Topline Pro

We're building an AI-powered Shopify for service businesses. We help service pros (e.g., roofers, landscapers, painters, cleaners) acquire direct business, fast. Up and running within minutes using Gen AI, our digital storefront products help pros get discovered, trusted, and booked repeatedly. Topline Pro was co-founded by Nick Ornitz (CEO) and Shannon Kay (COO), with an excellent team of 120+ rockstars and plans to expand further in 2026. We serve thousands of local service businesses and were named one of the top 50 Tech Companies building for SMBs in 2023 and 2024. We're YC-backed and well-funded, with several years of runway, and we've experienced rapid growth over the past year. We're in a phenomenal position to scale, with the financial foundation, product-market fit, and momentum to go big. You'll be joining at an inflection point, where the groundwork is laid, and the path to massive impact is clear. We believe "great candidates" do not come about simply from a check mark next to past experience. We believe in hiring people, not just skills. Even if you do not check every box but find excitement at the prospect of working with us in this capacity, please apply. Topline Pro is committed to building an inclusive workplace and assembling a team from diverse backgrounds. We ensure that individuals with disabilities receive reasonable accommodation throughout the application and interview process. We strongly encourage applications from underrepresented candidates and those from nontraditional backgrounds.