Regional Account Executive, Pennsylvania

Flai; Pennsylvania; Remote; USD 100,000 - 180,000; Full time

Job summary

Flai is hiring a Regional Account Executive to own and grow its presence across Pennsylvania. This role requires building the territory strategy, creating a prospecting motion, establishing an in-person presence, and driving revenue while collaborating with the founders.

You will travel across the state to meet dealerships, close deals, and shape how Flai wins the dealer market, leveraging automotive experience and a founder mindset in a fast-moving startup.

Qualifications

• Proven sales execution across prospecting to close.
• Automotive dealership sales experience preferred.
• Clear, persuasive communication in person or remote.
• Ability to understand dealer pain points and tailor solutions.
• Willingness to travel across Pennsylvania for field meetings.
• Thrives in a fast-paced, high-growth environment.
• Maintain CRM hygiene and structured sales processes.
• Self-directed, ownership-driven approach.

Responsibilities

• Own the full sales cycle: prospect, book meetings, pitch, and close dealerships in PA.
• Build and manage pipeline with priority accounts and decision-makers.
• Sell in the field: meet dealership leaders in person to build trust.
• Shape the territory go-to-market motion with founders.
• Provide market feedback to Product and Leadership as we scale.

Skills

Proven sales execution

Automotive experience

Strong communication skills

Solution-oriented thinking

Field sales experience

High-speed operating rhythm

Operational discipline

Founder mindset

Job description

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 Dealerships sell 96% of the 16 million new vehicles purchased each year, yet many still rely on outdated systems and manual processes.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.