VP of Customer Success

Topline Pro • New York, NY

3d • Onsite

About The Position

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.

Requirements

• 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.

Nice To Haves

• 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.

Responsibilities

• 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.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed