Head of Support

Crunchafi (formerly LeaseCrunch) builds cloud-based accounting solutions that help CPA firms and financial professionals streamline lease accounting, data extraction, and cash flow forecasting. The Head of Support will lead and scale a customer-centric Support organization, establishing consistent service quality and predictable performance while acting as the voice of Support across the business. A major focus is evaluating, migrating, and rolling out a modern ticketing platform to improve routing, automation, insights, and operational efficiency.

• Lead the end-to-end Support function serving external customers and internal stakeholders.
• Design and implement a scalable tiered support model (Tier 1/Tier 2/Tier 3) with clear escalation paths and ownership.
• Hire, coach, and develop a high-performing team; define roles, coverage models, and on-call/escalation expectations.
• Establish support standards and a culture of urgency, accountability, and continuous improvement.
• Define, track, and manage core Support KPIs (CSAT, SLA attainment, first response time, time to resolution, backlog health).
• Create operating rhythms (daily/weekly triage, ticket QA reviews, trend analysis, cross-functional escalation meetings).
• Implement quality assurance standards, coaching processes, and ticket audits to improve consistency and resolution quality.
• Provide executive reporting on performance trends, risks, root causes, and improvement initiatives.
• Design scalable workflows for technical troubleshooting, billing requests, and product/accounting questions.
• Create escalation and handoff processes to Product/Engineering, Billing/Finance, Customer Success, and other internal teams.
• Build playbooks for categorization, severity levels, customer communication, and consistent resolution.
• Build a scalable self-service strategy (knowledge base, FAQs, standardized help content).
• Evaluate ticketing/support tooling; develop selection criteria aligned to customer and internal needs.
• Lead ticketing platform implementation (workflows, SLAs, routing rules, automation, macros, tagging, reporting structure).
• Drive rollout planning, change management, training, and adoption measurement across teams.
• Serve as the voice of Support in cross-functional planning and decision-making and advocate for customer experience improvements.
• Ensure customer-impacting incidents are escalated appropriately with clear internal communications.
• Collaborate with Product, Engineering, Billing/Finance, and Customer Success to drive measurable experience improvements.

• 3–5+ years of leadership experience scaling support teams, including hiring and performance management.
• Proven experience building support processes from the ground up (SLAs, tiering, escalation models, QA).
• Hands-on experience with modern ticketing ecosystems (e.g., Zendesk, Freshdesk, Intercom, Jira Service Management, ServiceNow, Help Scout).
• Demonstrated success replacing or modernizing a ticketing platform, including rollout and change management.
• Strong operational rigor and data fluency (dashboards, trend analysis, KPI-driven execution).
• Excellent communication skills with the ability to align stakeholders and drive decisions.

• Preferred:

  • Experience supporting subscription billing complexity (renewals, usage-based billing, credits).
  • Experience supporting accounting or compliance-adjacent workflows and customer questions.
  • Experience partnering closely with Product/Engineering via structured escalation and incident management processes.
  • Support Operations/CX Operations background; experience implementing automation or AI-assisted support tools.

• Competencies:

  • Builder mindset and systems thinking.
  • Operational excellence and process discipline.
  • Customer empathy paired with business judgment.
  • Technical fluency and structured problem-solving.
  • Change leadership and cross-functional influence.
  • Strong written and verbal communication.

• Type: Full time, salaried.
• Location: Remote with occasional travel requirements.
• Benefits: Health, dental, and vision insurance plans.
• Flexible time off.
• 401K retirement savings plan for US-based employees with 3% employer match.
• Incentive Equity Plan.
• Professional development opportunities.
• Dynamic, collaborative work environment with opportunities for growth.