Enterprise Sales Director

PermitFlow is redefining how America builds. We’re an applied AI company serving the nation’s builders, tackling one of the largest information challenges in the economy: understanding what can be built, where, and how. Our AI agent workforce helps the fastest-growing construction companies navigate everything from permitting and licensing to inspections and project closeouts – accelerating housing, clean-energy, and infrastructure development across the country.

Despite being a $1.6T industry, construction still suffers from massive delays, wasted capital, and lost opportunity. PermitFlow has already delivered unprecedented speed, accuracy, and visibility to over $20B in development, helping contractors reduce compliance time, de-risk projects, and scale with confidence.

As the U.S. enters a new capex supercycle across data centers, factories, housing, and renewables, joining PermitFlow means building the AI infrastructure at the core of every construction project driving the next wave of reindustrialization.

We’ve raised over $90M, most recently completing our Series B, from top-tier investors including Accel, Kleiner Perkins, Initialized, Y Combinator, Felicis, and Altos Ventures, with backing from leaders at OpenAI, Google, Procore, ServiceTitan, Zillow, PlanGrid, and Uber.

Why PermitFlow Wants You

We're looking for an Enterprise Sales Manager to lead a team of enterprise Account Executives that wins at the highest levels of construction-tech. Reporting to the Head of Enterprise Sales, you'll own day-to-day execution and revenue for your team and book of accounts, while helping execute the enterprise playbook in a massive, fragmented market.

This role requires creativity, grit, operational excellence, and a hands-on coaching style. You thrive in fast-growing environments disrupting an entire industry, you take a thoughtful approach to developing talent, and you lead from the front in complex, multi-stakeholder deals ($1M+ in scope).

This is a high-stakes, high-upside opportunity to help scale PermitFlow's enterprise motion.

What You'll Do

• Own revenue, forecasting, and day-to-day execution for your team of enterprise Account Executives and assigned accounts, leveraging data to inform tactics

• Report to the Head of Enterprise Sales and help execute the segment-wide strategy with a consistent, repeatable enterprise motion

• Recruit, lead, coach, and develop your team of enterprise Account Executives — driving performance management, career development, and a high-accountability, high-trust culture

• Help refine and reinforce repeatable, scalable sales processes that standardize PermitFlow's enterprise motion

• Lead and coach the team through complex, multi-threaded deals with executives, operators, and procurement across multiple business units and PE roll-up accounts

• Drive both net-new logo acquisition and expansion within existing roll-up and national accounts, converting pilots into multi-division, enterprise-wide partnerships

• Partner cross-functionally (Solutions, CS, Product, Marketing, SDR, RevOps) to scope solutions, align the sales process with customer success, and ensure successful outcomes

• Build and review ROI-driven business cases that resonate with C-suite and board-level stakeholders

• Maintain forecasting accuracy, pipeline hygiene, and deal visibility across long enterprise sales cycles

• Surface field and customer insights to the Head of Enterprise Sales and GTM leadership to inform the enterprise roadmap and go-to-market strategy

• Leverage automation, modern sales tooling, and AI-driven tools to streamline processes, optimize performance, and increase conversion

• Travel as needed for customer meetings, conferences (e.g. Pantheon), and roll-up HQ visits

Who You Are

• Emerging Sales Leader: 5+ years in enterprise SaaS sales, with 1–2+ years of management or team-lead experience (player-coach background a plus)

• Builder of Teams & Systems: Track record of scaling sales teams, building repeatable systems, and consistently exceeding ambitious revenue targets

• Strategic Seller: Skilled at navigating executive relationships, procurement, and multi-division rollouts; comfortable leading deals over $1M+

• Industry Knowledge: Construction-tech experience strongly preferred; experience with home services contractors, GCs, developers, or adjacent industries (PropTech, InsurTech, Field Service software) a plus

• Data-Driven Operator: Fluent in CRM systems, sales automation tools, and performance analytics; turns complexity into clear, actionable plans

• Problem-Solver & Storyteller: Surfaces operational pain points and builds compelling, ROI-backed business cases

• Cross-Functional Partner: Builds senior-level relationships quickly and effectively, especially with Product and Marketing

• Mission-Driven: Energized by transforming how infrastructure gets built and scaling technology in one of the largest industries in the world. Growth mindset, bias for action, and a love for innovation.

How Success Will Be Measured

• Your team's attainment against enterprise revenue and pipeline targets

• New logo acquisition and expansion within your assigned accounts

• Contribution to repeatable, scalable sales processes that inform PermitFlow's enterprise motion

• Strength of executive relationships and the team's ability to navigate PE roll-up strategies

• Hiring, retention, and development of a high-performing enterprise sales team

• Effective execution of the Head of Enterprise Sales' strategy across your team

What We Offer (Full-Time Roles Only)

• Competitive salary and meaningful equity in a high-growth company

• 100% company-paid base medical, dental, and vision coverage for employees + healthcare FSA

• 401(k) savings plan

• Unlimited PTO and paid family leave

• Home office & equipment stipend

• Daily in-office lunch and dinner provided

• Commuter benefits (pre-tax transit and parking)

PermitFlow provides equal employment opportunities (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.

We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities. All employment decisions are based on merit, qualifications, and business needs.

PermitFlow provides equal employment opportunities (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.

We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities. All employment decisions are based on merit, qualifications, and business needs.