VP of Customer Success

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.

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, 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.

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

Our Values

• 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