Head of Operations

Role Overview

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.

What You’ll Do

• 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.

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.
• A 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).
• 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.

Nice to Have

• Experience implementing automation or AI.
• Exposure to construction, permitting, or real estate development.

Why This Role Matters

Operations is at the center of how PermitFlow delivers value to customers. This role will help build the systems that power thousands of permitting workflows while helping build scalable software and AI-driven solutions. You’ll play a key role in shaping how PermitFlow scales in the years ahead.

PermitFlow Provides

• Equal Employment Opportunity (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, gender expression, or family status, as protected by applicable law.
• Commitment to a diverse and inclusive workforce.
• Welcome people from all backgrounds, experiences, perspectives, and abilities.
• All employment decisions are based on merit, qualifications, and business needs.