Head of Customer Success

What You’ll Do

• Drive retention and expansion: Own the motions, renewal forecast, risk management, and day-to-day execution that protects and grows the base.
• Hire, develop, and retain the team: Lead and grow the CS team — managing both individual contributors and a manager. Define career paths, performance standards, and coaching rhythms.
• Be the senior escalation point: Step in decisively with customers to reset expectations, unblock the team, and drive to resolution.
• Run the operating model: Design and refine escalation paths, staffing plans, workload distribution, success plans, QBR cadences, and renewal and expansion motions.
• Instrument the function: Build the reporting and tooling that give leadership clear visibility into account health, risk, and expansion opportunities.
• Own the team’s knowledge base: Keep best practices, tooling and product enablement, configuration preferences, and playbooks current.
• Deliver measurable outcomes: Help customers reduce DSO, deepen automation adoption, and realize clear ROI.
• Carry the voice of the customer: Bring sharp, specific feedback to Product and Engineering.
• Partner across the company: Own the interface between CS and Implementation, Sales, Support, Product, and Engineering on handoffs, renewals, expansion, and escalations.

Who You Are

• Operator at heart: energized by systematizing what works and iterating relentlessly.
• Comfortable balancing IC work with team leadership: running a team while staying hands-on with key accounts.
• Deep fluency in finance and accounting workflows.
• Thrive in a fast, high-ambiguity environment.
• Earn credibility with every audience — CFOs, controllers, AR teams, engineers, and your own team.
• Distill complexity into clarity; let data drive decisions.

Requirements

• 8–12+ years in customer success or post-sale roles, with 5+ years leading and managing teams.
• Track record of building or leading CS teams in high-growth B2B SaaS or fintech, consistently delivering against retention and expansion targets.
• Proven ability to hire well, coach directly, and hold a high bar without micromanaging.
• Process-builder: design systems that scale.
• Strong accounting and technical fluency.
• Knowledge of ASC 606 revenue recognition, order-to-cash workflows, and ERP integrations (NetSuite, QuickBooks, Sage) and CRMs (Salesforce, HubSpot) is a plus.
• Comfortable operating cross-functionally with Sales, Product Delivery, Support, Implementation, Product, and Engineering.
• Excellent communicator with high customer EQ.
• Background in accounting or finance software is a strong plus; CPA or Big Four experience welcome.
• Based in New York City, available to work 5 days per week in office at our Soho HQ.

Nice-to-Haves

• CPA or Big Four experience.
• Knowledge of ASC 606, order-to-cash, ERP (NetSuite, QuickBooks, Sage), CRMs (Salesforce, HubSpot).

Compensation and Benefits

• Competitive compensation and equity (base salary range $216,000 - $276,000).
• Unlimited PTO.
• Up to 100% employer covered monthly healthcare premium (medical, dental, vision).
• Lunch provided via Sharebite, plus dinner for late office days.
• Parental leave up to 12 weeks.
• Tax free commuter and parking benefits.
• Voluntary insurances (Life, Hospital, Critical Illness, Accident).
• Employee Assistance Program.
• Free One Medical Membership.
• 401k.