CEO / Chief Executive Officer - Hybrid

Job Description: Chief Executive Officer (CEO)
Company: Pilot Policy
Location: Hybrid / Remote
Employment Type: Full-Time
Reports To: Board of Directors / Founders
Company Overview
Pilot Policy is a cutting-edge, niche SaaS platform transforming how the commercial construction, roofing, and insurance sectors handle asset management, policy analysis, and damage evaluation. Leveraging custom AI, automated drone payloads (including thermal imaging), and cloud-hosted enterprise integrations, Pilot Policy streamlines the technical inspection and claim processes for public adjusters, large-scale roofing contractors, and commercial property managers.
We bridge the gap between complex industry data and intelligent natural language solutions, offering both a scalable, recurring monthly subscription product and tailored, secure enterprise-level workspace deployments.
Role Purpose
As the Chief Executive Officer (CEO), you will hold the vision, steer the corporate strategy, and drive exponential revenue growth. You will be directly responsible for taking our Minimum Viable Product (MVP) and scaling it across two primary revenue engines: a high-volume B2B SaaS subscription model and high-ticket enterprise custom contracts.
The ideal candidate is an aggressive, relationship-driven closer with deep experience in enterprise software sales, corporate scaling, and a strong understanding of how cutting-edge technology (AI, drones, thermal analytics) solves real-world physical asset challenges.
Core Responsibilities
1. Strategic Leadership & Vision
* Define, execute, and iterate the company’s long-term commercial strategy, product roadmap, and market positioning.
* Protect and manage the company’s proprietary intellectual property, backend APIs, and secure architecture boundaries.
* Establish, monitor, and report on core SaaS growth metrics (MRR, LTV, CAC, Churn, and Net Revenue Retention).
2. High-Ticket B2B & Enterprise Sales
* Act as the primary "closer" for high-ticket corporate contracts, pitching custom, secure, private-workspace deployments to large commercial roofing firms and insurance agencies.
* Design and execute high-converting funnel strategies that turn low-friction, public AI touchpoints (like custom GPT store integrations) into premium website subscribers.
* Negotiate enterprise contracts, deployment fees ($5k $20k+), and long-term monthly data-maintenance retainers.
3. Product & Technology Oversight
* Collaborate with engineering to ensure seamless, secure infrastructure integration (e.g., Stripe Billing, OAuth authentication, cloud data privacy).
* Guide the technical product evolution, ensuring the software continually solves acute pain points like rapid hail/wind damage analysis, roofing asset management, and complex policy decoding.
* Ensure the product safely and scale-ably ingests drone, thermal, and spatial data feeds to deliver elite technical output.
4. Financial & Operational Excellence
* Manage corporate budgets, burn rates, resource allocation, and cash flow to ensure maximum profitability and runway.
* Build, inspire, and manage a lean, high-performing team across sales, engineering, and customer success.
* Transition the company culture from a transactional software mindset to a world-class, service-oriented enterprise partner.
Job Requirements & Qualifications
* Experience: 5+ years of executive leadership experience (CEO, VP of Sales, or Founder) within a B2B SaaS, InsurTech, PropTech, or commercial construction-tech landscape.
* Proven Track Record: Demonstrated success in scaling a software product from early-stage adoption to significant Monthly Recurring Revenue (MRR), with a proven history of closing five-figure enterprise B2B accounts.
* Industry Literacy: Strong understanding of commercial asset management, insurance adjusting processes, or advanced drone/thermal data applications is highly preferred.
* Tech Savvy: Comfortable commanding tech conversations involving APIs, secure OAuth data models, and the commercial application of Large Language Models (LLMs).
* Education: Bachelor’s degree in Business, Computer Science, Engineering, or a related field (MBA or equivalent practical experience preferred).
Competencies for Success
* The Ultimate Closer: A relentless drive to hunt down, pitch, and seal partnerships with massive industry players.
* Data-Driven Decision Maker: Ability to filter through user analytics, market trends, and financial metrics to pivot strategies instantly.
* Exceptional Communicator: Able to cleanly articulate deeply technical AI capabilities into simple, high-value ROI propositions for corporate boardrooms.