Head of Technical Support

Tabs • New York, NY

90d

About The Position

We’re hiring our first Head of Technical Support to build and lead a world-class, customer-obsessed support organization. You’ll own the strategy, team, tooling, and day-to-day operations that keep our customers (we call them “merchants”) running—while turning support insights into product improvements. This is a high-leverage leadership role for a builder who has scaled multi-tier support teams in a fast-growing B2B SaaS environment and knows how to balance speed, quality, and empathy.

Requirements

• 8–12+ years in technical support/customer support for B2B SaaS, including 3–5+ years leading managers and multi-tier teams.
• Proven experience building and managing a sizable team (10 people) in a high-growth startup; adept at org design, hiring, and coaching.
• Strong technical depth: comfortable with APIs/logs, ERP/finance systems (NetSuite, QuickBooks), and payments (Stripe); able to triage and guide L2/L3 issues.
• Expert in support operations: SLAs, queue management, incident response, RCAs, postmortems, and executive escalations.
• Fluency with support/ticketing tools (Pylon/HubSpot/Intercom), Omni, Jira, knowledge bases, and analytics; able to build dashboards and make data-driven calls.
• Stellar written and verbal communication—clear, calm, and customer-friendly—and a knack for simplifying complex concepts.
• Bias to action, thrives under pressure, and comfortable in ambiguity; you balance speed with quality and know when to loop in Engineering/Product.

Nice To Haves

• Experience with RevRec/ASC 606 or finance SaaS.
• SQL for ad-hoc analysis.

Responsibilities

• Build & Lead the Org: Hire, coach, and scale a high-performing multi-tier support team (L1/L2/L3), setting clear SLAs and escalation paths.
• Scale Strategy: Grow headcount relative to ARR and merchant acquisition by leveraging technology and AI.
• Drive Operational Excellence: Own KPIs (FRT, TTR, SLA attainment, CSAT), and build self-service resources (including Knowledge Center) to reduce ticket volume.
• Own Incidents & Escalations: Lead Sev1/Sev2 response, executive-level comms, and postmortems; partner with Engineering/Product to prevent repeat issues.
• Optimize Tools & Automation: Select and manage the support stack (Pylon/HubSpot, Jira, KBs, analytics), Integrate AI for ticket triage, resolution, and proactive merchant support.
• Be the Voice of the Customer: Translate recurring trends into actionable insights, shaping product roadmap and improving customer experience.
• Partner Cross-Functionally: Collaborate with Implementations, Success, and Solutions to ensure seamless onboarding, feature adoption, and customer outcomes.

Benefits

• Competitive compensation and equity
• 100% coverage for healthcare (Medical, Dental, Vision)
• Daily meal and coffee stipend for in-office days
• Tax-free commuter benefits
• Collaborative team environment with real ownership and growth
• Learn from a founding team with a track record of multiple IPO exits

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Number of Employees: 51-100 employees