Regional Account Executive, Pennsylvania

Territory: Pennsylvania Type: Full-Time Work Arrangement: Remote Role Type: Outside Sales (80% in the field in your territory) This role is specifically responsible for building and growing Flai’s presence across Pennsylvania. The Regional Account Executive will regularly meet with dealerships throughout the state and should be comfortable traveling across the territory.

About Flai AI has transformed B2B SaaS but has struggled to reach many of the real-world industries that shape our lives. Flai is building the leading AI-native communications platform for automotive dealerships. Auto retail is a $1.3 trillion industry. Dealerships sell 96% of the 16 million new vehicles purchased each year, yet many still rely on outdated systems and manual processes. Dealerships spend approximately $36 billion annually on operations, creating a significant opportunity for Flai. We launched our first voice AI product a year ago. Since then, we have introduced multiple products across hundreds of dealerships throughout the United States. We have partnered with the country’s second-largest automaker and many leading dealership groups. Flai is backed by Toyota Ventures, First Round Capital, Y Combinator, Innovation Endeavors, SV Angel, and Liquid 2. We have grown rapidly with a small, scrappy team and continue to operate with that speed and ambition.

Role Overview We’re hiring a Regional Account Executive to own and grow Flai’s go-to-market presence across Pennsylvania. You will develop the territory strategy, build the prospecting motion, establish an in-person presence, and drive revenue across the state. You will work directly with the founders and help shape how Flai wins the dealership market.

What You’ll Do

• Own the full sales cycle: Prospect, book meetings, pitch, and close dealerships and dealer groups across Pennsylvania.

• Build and manage pipeline: Map priority accounts, identify decision-makers, and keep opportunities organized and moving forward.

• Sell in the field: Meet dealership leaders in person to build trust, understand their needs, and create momentum.

• Build the go-to-market motion: Shape the territory strategy, outreach approach, and field sales playbook alongside the founders.

• Strengthen the product feedback loop: Share market insights directly with Product and Leadership to influence our direction as we scale.

What We’re Looking For

• Proven sales execution: Experience owning and closing deals from prospecting through signature in a high-velocity or high-stakes environment.

• Automotive experience: Direct experience selling to dealerships or working inside one. You understand dealership organizations and how purchasing decisions are made.

• Strong communication skills: Clear, persuasive, and confident when presenting in person or remotely.

• Solution-oriented thinking: Able to understand dealer pain points and recommend the right solution instead of simply pitching a product.

• Comfort with field sales: Willing and able to travel throughout Pennsylvania to meet customers and prospects.

• A high-speed operating rhythm: Energized by a fast-moving, high-growth environment.

• Operational discipline: Comfortable maintaining CRM hygiene, managing a clean pipeline, and following structured, repeatable processes.

• A founder mindset: Self-directed, persistent, and motivated by ownership. You focus on outcomes and do not require extensive direction.