Location: Remote (US)

Type: Full-Time

Work Arrangement: Remote

About Flai

AI has transformed B2B SaaS, but it has struggled to reach the real-world industries that shape our lives. Flai is building the leading AI-native CRM for car dealerships.

Auto dealerships are a $1.3 trillion industry and sell 96% of the 16 million new cars sold each year. Yet they still run on outdated systems and manual processes, and they spend $36B a year on operations. That’s our opportunity.

Flai is live in many hundreds of dealerships across the U.S., including 20% of the top 50 dealer groups. We work closely with OEMs and distributors too, and are backed by Toyota Ventures, Gulf States Toyota, and the Findlay Automotive Group. We’ve raised over $33M, including our recent $27M Series A.

We’ve grown very fast with a small, scrappy team, and we keep moving at that pace.

Role Overview

We’re hiring a senior individual contributor to sell Flai’s AI-native sales CRM. You’ll help operators make a confident decision to replace their incumbent CRM.

You’ll work closely with the founders, sell to new dealership groups and expand relationships with dealers already using Flai for service. This is a remote role with travel for important customer meetings, pilots, industry events and group rollouts. Travel follows the deal; it is not a continuously on-the-road territory role.

What You’ll Do

• Prospecting, discovery, tailored demos, pilot design, commercial proposals, negotiation and close. Build your own pipeline and partner with customer success on expansion opportunities.

• Assess how a store handles lead response, appointments, sales follow-up, customer records, team activity and reporting. Connect the proposed CRM change to measurable business outcomes.

• Address incumbent contracts, adoption risk, data migration, integrations, change management and rollout sequencing with the right internal partners.

• Define clear stores, users, lead sources, human and AI responsibilities, success measures, owners and decision dates. Build a path from the first store to a group rollout.

• Keep HubSpot pipeline and forecasts accurate. Maintain concrete next steps, identify risk early and hand signed customers to implementation and customer success with clear commitments.

• Bring customer and competitive feedback to product and the founders. Help build the sales playbook as the CRM business grows.

What We’re Looking For

• Automotive CRM sales experience: Direct experience personally selling automotive sales CRM, either currently or within the past 12 months.

• A proven dealer track record: A record of closing deals with dealerships and dealer groups. You can explain your quota, attainment, new-logo versus expansion mix, self-sourced pipeline, deal size, sales cycle and individual contribution.

• Dealership fluency: Deep knowledge of dealership sales and BDC workflows, with experience earning trust across store leadership and group stakeholders.

• Strong commercial judgment: Strong discovery, demos, objection handling and commercial judgment. You can sell a replacement and manage adoption concerns without promising capabilities or delivery dates you cannot support.

• A founder mindset: The discipline to run a remote sales process, the willingness to travel when it advances a deal, and the initiative to prospect and build in an early-stage environment.

Typically, this background includes three or more years in a quota-carrying automotive CRM sales role. Dealership operating experience, multi-rooftop rollouts, competitive displacement wins and a strong dealer network are valuable additions.