VP of Customer Success

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.

• 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.
  

• 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.
  

• 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, communicate with directness and warmth, and bring others along rather than working around them.

• Calm in ambiguity: You thrive in fast-moving, lightly-defined environments where the playbook is something you'll write, not something you'll inherit.

• Energized by AI as a force multiplier, not threatened by it.

• Aligned with Topline Pro's values and excited to help small business owners win.
  

• 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

• 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

• No Bullsh*t: We create meaningful results for our customers and drive growth for our team — ensuring progress and impact are felt every day. Our focus, both internally and externally, is on delivering genuine value rather than superficial solutions or benefit without purpose.

• Think Big, Learn Fast: We move quickly, acting on data to uncover insights and solutions. We embrace risks, knowing every experiment fuels growth — even when it doesn't go as planned.

• One Team, One Dream: We tackle challenges together with creativity, and an open mind — always seeking solutions and embracing fresh ideas to win as a team.

• Empower Every Voice: We welcome diverse perspectives and bold ideas, creating space for authenticity and respect — because great ideas come from everywhere.

• Be an Owner: We take responsibility for outcomes, act in the company's best interest, and treat every dollar as our own. We move with urgency, think long-term, and take pride in driving impact.

• Boom!: We take time to celebrate each other's achievements, big and small — at work and in life — because shared success fuels lasting momentum. And we end all team meetings in a "Boom!"

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.