Regional Account Executive, Indiana & Ohio

OpenKrill; United States; On-site; USD 90,000 - 130,000; Full time

Job summary

Flai is expanding its AI-native communications platform for automotive dealerships across Ohio and Indiana. As Regional Account Executive, you will own the end-to-end sales cycle, prospect, meet dealers, present tailored solutions, and close deals to grow Flai’s market presence across the territory.

You will build a robust pipeline, map priority accounts, and collaborate with the founders to shape the go-to-market strategy and field playbook.

Qualifications

• Proven sales execution, closing deals with speed and precision.
• Automotive dealership experience and understanding of purchasing processes.
• Clear, persuasive communication in person or remotely.
• Able to diagnose dealer pain points and tailor solutions, not just pitch.
• Willing and able to travel across Ohio and Indiana for meetings.
• Energetic, fast-moving in a high-growth environment.
• Maintain structured, clean CRM and sales processes.

Responsibilities

• Own the full sales cycle: prospect, meetings, pitch, close with dealers across OH and IN.
• Build and manage pipeline: identify decision-makers and move opportunities forward.
• Sell in the field: meet dealership leaders in person to build trust and momentum.
• Shape the go-to-market motion: define territory strategy and field playbook with founders.
• Provide market feedback to Product and Leadership to influence product direction.

Skills

Sales excellence

Automotive sales

Communication

Solution oriented

Field sales travel

CRM hygiene

Founder mindset

Tools

CRM software

Job description

Territory: Ohio & Indiana

Type: Full-Time

Work Arrangement: Remote

This role is specifically responsible for building and growing Flai’s presence across Ohio and Indiana. The Regional Account Executive will regularly meet with dealerships throughout both states 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 Dealerships sell 96% of the 16 million new vehicles purchased each year, yet many still rely on outdated systems and manual processes.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 Ohio and Indiana.

You will develop the territory strategy, build the prospecting motion, establish an in-person presence, and drive revenue across both states. 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 Ohio and Indiana.
• 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 Ohio and Indiana 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.