Head of Support

Job Title: Head of Support  

Reports to: VP of Client Operations 

Type: Full time, salaried 

Location: Remote; with occasional travel requirements  

About Crunchafi 

Crunchafi (formerly LeaseCrunch) is revolutionizing the world of accounting with easy-to-use, cloud-based solutions designed to simplify complex financial data management. Our products empower CPA firms and financial professionals by streamlining lease accounting, data extraction, and cash flow forecasting, helping them deliver strategic value faster and more efficiently. Trusted by over 750 firms and more than 27,000 companies, Crunchafi combines cutting-edge technology with expert support to power the future of accounting. 

Our Team 

Crunchafi is made up of passionate, forward-thinking professionals committed to transforming the accounting industry. Our team is dedicated to providing innovative solutions that simplify accounting processes and provide actionable financial insights. We value collaboration, creativity, humor, and a shared vision of improving the accounting profession through technology. 

Why Join Us? 

We are looking for talented individuals to join our growing team and contribute to our mission of empowering CPA firms and financial professionals. At Crunchafi, you’ll be part of a dynamic, collaborative environment where your ideas are valued, and your growth is supported. We offer a rewarding work/life balance, opportunities for professional development, and a chance to make a real impact in the world of accounting. 

Position Overview 

We are seeking a Head of Support to lead and scale a fully functional, customer-centric Support organization. You will create the processes, reporting, and tooling required to deliver consistent service quality, predictable performance, and a best-in-class customer experience. 

A key component of this role is leading the evaluation, migration, and rollout of a modern ticketing platform, replacing legacy systems and improving routing, automation, insight, and operational efficiency. 

Key Responsibilities  

Lead and Scale a Modern Support Organization 

• Lead end-to-end Support function serving both external customers and internal stakeholders. 

• Design a scalable support model (e.g., 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 consistent support standards and a culture of urgency, accountability, and continuous improvement. 

Own Support Operations, Metrics, and Performance 

• Establish, track, and manage core Support KPIs including CSAT, SLA attainment, first response time, time to resolution, and 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 Support Processes Across Technical, Billing, and Accounting Questions 

• Define standard workflows for technical troubleshooting, billing requests (invoice/payment/credits), and product/accounting questions. 

• Create escalation and handoff processes to Product/Engineering, Billing/Finance, Customer Success, and other internal teams. 

• Build playbooks for issue categorization, severity levels, customer communication, and resolution consistency. 

• Partner with stakeholders to reduce friction and ensure support responsibilities and handoffs are clear and measurable. 

• Build a scalable self-service strategy including a knowledge base, FAQs, and standardized help content. 

• Evaluate ticketing and support tooling options; develop selection criteria aligned to customer and internal needs. Lead implementation, including workflows, routing rules and automation.  

• Lead platform implementation including workflows, SLAs, routing rules, automation, macros, tagging, and reporting structure.  

• Drive rollout planning, change management, training, and adoption measurement across teams. 

Cross-Functional Leadership and Customer Advocacy 

• Serve as the voice of Support in cross-functional planning and decision-making. 

• 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. 

Required Qualifications 

• 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, and KPI-driven execution. 

• Excellent communication skills with the ability to align stakeholders and drive decisions. 

• Preferred Qualifications  

• 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 and 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 

Benefits 

• Remote work-from-home environment 

• Competitive salary, health, dental and vision insurance plans  

• Flexible time off  

• 401K retirement savings plans for US-based employees, with 3% employer match  

• Incentive Equity Plan   

• Professional development opportunities  

• Dynamic and collaborative work environment with opportunities for growth