Head of Operations

What You’ll Do

• Lead and scale PermitFlow’s core operations organization.
• Manage a team of Operations Managers and Operations Leads supported by a global workforce.
• 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 automation and AI-enabled workflows.
• Build systems, metrics, and processes that enable the operations team to scale efficiently as the company grows.

What We’re Looking For

• 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 or tech-enabled services company
• 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 as a core enabler of operational performance
• Excellent communicator and cross-functional partner; you can hold your own in a room with Sales, Engineering, Finance, and the executive team

Nice to have:

• Experience in marketplaces, services businesses, or tech-enabled operations.
• Experience implementing automation or AI in operational workflows.
• Exposure to construction, permitting, or real estate development.