Head of Operations, PermitFlow

• 7–12+ years of experience in operations, with at least 3–4 years in a senior leadership role managing managers and large teams
• Strong operator who can balance strategy, systems design, and execution
• Experience scaling operational processes in a high-growth environment
• Comfortable working cross-functionally with product and engineering teams
• Proven track record scaling operations in a high-growth startup
• Experience managing teams at meaningful scale (100+ people)
• Strong commercial instincts you understand how operations connects to revenue, retention, and growth
• Data-driven decision maker who can define the right metrics, interpret them, and act on them
• Experience working alongside or within a product/engineering organization; comfort with technology and AI
• Excellent communicator and cross-functional partner; you can hold your own in a room with Sales, Engineering, Finance, and the executive team
• Experience in construction, real estate, permitting, or government services is a plus but not required

Desirable

• We’re looking for a Head of Operations to lead and scale the operational engine behind PermitFlow
• This role will oversee a large, multi-layered operations organization responsible for delivering permitting outcomes for customers, supporting new customer pilots, and ensuring excellent service that drives retention and growth
• The Head of Operations will work closely with Sales, Customer Success, and Product, Engineering, and Design to continuously improve operational workflows and help translate operational insights into product and AI-driven automation.
• Lead and scale PermitFlow’s core operations organization
• Manage a team of Operations Managers and Operations Leads
• Partner with Sales and Customer Success to onboard prospective and new customers and help convert them into long-term partnerships
• Own customer operations, ensuring customers receive reliable, high-quality service that drives retention and expansion
• Work closely with Product and Engineering to identify opportunities for AI agents and workflows
• Build systems, metrics, and processes that enable the operations team to scale efficiently as the company grows