Weekend Cold Case Foundation Jobs in Kentucky (NOW HIRING)

Pay range is a good-faith estimate for this role and may vary based on experience and leveling.

Job Description

Founding Account ExecutiveAbout Proaction

Proaction is building the modern alternative to expensive, opaque fleet management. Our AI-native platform brings fleet programs, workflows, costs, and reporting into one place, with managed services available wherever customers want help executing the work.

We recently raised $4.2 million to help fleets replace fragmented tools and legacy providers with a more flexible, visible operating model. We're a small team tackling a massive industry—and we're hiring the first Account Executive to help us define how Proaction wins it.

Until now, sales at Proaction has been founder-led. We're looking for the person who can take what's working, run alongside our CEO, and turn it into a repeatable enterprise sales motion.

This is not a role for someone who wants to inherit a mature pipeline, manage a large team, or operate from an established playbook. You'll open doors, build relationships with fleet leaders, run complex opportunities from first conversation through close, and help us sharpen how we position Proaction.

The bar is straightforward: if our CEO is on a plane and one of our most important prospects calls, we should trust you to take the meeting—and move the opportunity forward.

What You'll Own

• Own the complete sales cycle across large mid-market and enterprise fleet accounts: account selection, prospecting, discovery, solution design, business case, pilot, procurement, negotiation, and close.
• Build trusted relationships with fleet, operations, finance, and executive leaders.
• Create pipeline directly while partnering with our growth and business-development team.
• Segment opportunities by high, medium, and low fit, then concentrate time on the accounts with the strongest need, urgency, and alignment.
• Learn Proaction's product and value propositions quickly enough to communicate them naturally - not from a script.
• Turn customer conversations into sharper positioning, stronger qualification criteria, and actionable product feedback.
• Partner with the CEO on our largest strategic opportunities while independently owning the rest.
• Build the practical parts of our early sales playbook: account plans, discovery frameworks, qualification standards, business cases, and deal reviews.
• Maintain disciplined pipeline visibility without introducing unnecessary process.
• Help identify and onboard future sales hires as the motion becomes repeatable - while remaining a hands-on seller.

We're Looking For

• A highly motivated, self-directed seller who creates momentum without waiting for a task list.
• A record of closing complex B2B software or technology-enabled-services deals with mid-market or enterprise customers. We need to know you can close deals with integrated payments alongside digital transformation.
• Experience in fleet management, mobility, telematics, transportation, logistics, field services, or another operationally complex industry—or compelling evidence that you can learn a new market unusually quickly.
• Early-stage startup experience, ideally helping a company move from founder-led selling toward a repeatable sales motion.
• Strong product instincts: you can understand a nuanced offering, isolate the value that matters to each buyer, and position it clearly.
• The credibility to speak with fleet operators and executives, ask incisive questions, and challenge established ways of working.
• Creativity and judgment. When something isn't working, you diagnose it, change the approach, and explain what you learned.
• A hunter's mindset: you notice opportunities, pursue them thoughtfully, and don't let promising relationships go cold.
• Comfort working in person with our team in San Francisco.

You May Not Be the Right Fit If

• You need a mature brand, predictable inbound pipeline, or extensive sales-enablement infrastructure to succeed.
• You're primarily looking to hire and manage a team instead of personally selling.
• You prefer to wait for direction rather than propose the next move.
• You optimize for pipeline volume instead of customer fit and closeability.
• Your best work happens inside a slow, highly structured sales organization.

What Success Looks Like

In your first 30 days, you understand Proaction's customers, culture, product, competitive landscape, and core value propositions. You can explain why customers buy and identify the accounts most likely to buy next.

Within 90 days, you are independently running customer conversations and active opportunities, building relationships in the market, and providing useful feedback on our ICP, messaging, and sales process.

Within 6-12 months, you have closed meaningful customer relationships, reduced the company's dependence on the CEO for every deal, and helped establish a repeatable foundation for the sales team that follows.

AI at Proaction

We're an AI-native company. Every team member receives a dedicated monthly AI token budget, and we expect you to use it. We believe the best work happens when people use AI as a daily collaborator - whether that's researching accounts, preparing for meetings, analyzing pipeline, creating business cases, or automating repetitive work.

If you're excited about working at the frontier of how AI changes the way teams operate, you'll fit right in.

Why Proaction

You'll join at the point where your work can materially shape the company. You'll work directly with the founders, carry real ownership, and help define how a new category of fleet management is sold.

Proaction offers comprehensive health coverage, flexible PTO, meaningful equity, a learning budget, excellent equipment, and a dedicated AI-tool budget.