Founding Account Executive

About Proaction

Proaction is building the modern alternative to expensive, opaque fleet management. Our AI-native platform brings fleet data, workflows, cost control, and reporting into one place, with managed Fleet Programs when customers want Proaction to execute alongside the software. We help operators spend less time wrestling with fragmented vendors and spreadsheets—and more time running a safer, more efficient fleet.

We recently raised $4.2 million to accelerate that mission. Now we are hiring our first dedicated Account Executive to turn founder-led wins into a repeatable enterprise sales motion.

About the Role

This is a net-new, full-cycle acquisition role for a hands-on seller who wants to help build the system while carrying the number. You will partner closely with the CEO and founders, inherit real customer proof and market insight, and take increasing ownership of pipeline creation, complex deal execution, and forecasting.

You will sell both software and technology-enabled fleet programs (managed services). That requires commercial judgment: understanding the value of recurring software, the operating realities and margins of managed programs, and when a deal is genuinely good for both the customer and Proaction.

What You’ll Own

• Build a focused target-account strategy and create pipeline directly through strategic outbound, referrals, events, partners, and founder networks.
• Lead the full sales cycle: account selection, prospecting, discovery, solution design, pilot scoping, proposal, commercial negotiation, procurement, and close.
• Run disciplined, multi-threaded opportunities across fleet, operations, finance, IT, security, procurement, and executive stakeholders.
• Translate operational pain into a defensible business case measured in cost, downtime, risk, and administrative workload.
• Build credibility equally with fleet operators doing the work and executives approving the investment.
• Coordinate Product, Marketing, Pricing, Legal, Security, Implementation, and Customer Success resources to move complex opportunities forward.
• Maintain accurate CRM hygiene, next steps, pipeline visibility, and forecasts without adding process for its own sake.
• Turn field learning into sharper ICP definitions, messaging, qualification standards, packaging, and deal-review practices.
• Deliver a complete, launch-ready handoff covering scope, economics, success criteria, stakeholder map, risks, commitments, and next steps.

Where Your Ownership Ends

You own the commercial process through signature and remain accountable for accurate scope, stakeholder alignment, kickoff, and a successful launch and handoff. From signature forward, Fleet Success and Operations lead implementation execution, enrollment, utilization, service delivery, and ongoing adoption. You remain an executive and commercial sponsor through a defined transition period; you do not become the long-term program operator, and this role does not carry an adoption quota.

What Success Looks Like

First 30 days

• Build fluency in Proaction’s customers, platform, Fleet Programs, unit economics, and competitive landscape.
• Shadow customer and prospect conversations, then form a point of view on the highest-priority accounts and buying triggers.
• Learn how software value, program scope, gross profit, and implementation risk affect deal quality.

First 90 days

• Run strong discovery and product conversations independently.
• Own a credible set of qualified opportunities, with clear stakeholders, business cases, next steps, and risks.
• Create reliable CRM and forecast discipline and close—or materially advance—early launch-ready opportunities.

Months 6–12

• Close meaningful new customers and reduce dependence on the CEO for day-to-day deal execution.
• Establish a repeatable enterprise qualification and sales motion that the next seller can inherit.
• Deliver against the approved ramped software target while protecting program economics and handoff quality.
• Turn recurring field insight into better positioning, product priorities, pricing, and customer proof.

What We’re Looking For

• A demonstrated record of closing complex, six-figure enterprise B2B software or technology-enabled-services deals.
• Experience navigating multi-stakeholder buying groups, financial buyers, procurement, security, legal review, and contracting.
• You are a hunter with evidence that you can create pipeline directly, not only work inbound leads.
• Commercial and financial fluency: you can build an ROI case, discuss pricing and margin, and recognize a bad deal.
• Credibility with both frontline operators and senior executives.
• Fleet, mobility, telematics, transportation, logistics, field-service, or adjacent experience.
• Comfortable operating on an early-stage team: limited brand awareness, evolving enablement, fast feedback loops, and no mature playbook to hide behind.
• Strong written communication, CRM discipline, forecasting judgment, and attention to commitments made during the sale.
• Practical fluency with AI tools and the judgment to verify their output.
• Ability to travel on-site to our San Francisco office as well as travel regularly to customers and industry events.

You May Not Be the Right Fit If

• You want a management seat, a large team, or a fully built sales machine on day one.
• Your experience is primarily renewals or relationship management rather than net-new acquisition.
• You expect inbound demand, SDR coverage, or a mature playbook to create your number for you.
• You delegate account research, CRM updates, follow-through, or forecast ownership.
• You are uncomfortable selling a solution that can combine software with operational services.
• You avoid customer sites, travel, or detailed conversations about how work actually gets done.

AI at Proaction

AI is part of how we work, not a slogan. You will use it to research accounts, prepare for meetings, test messaging, synthesize calls, improve follow-up, and make the team faster. We expect curiosity, strong judgment, respect for customer data, and ownership of the final output. It’s very important we avoid unreviewed AI slop.

Why Proaction

• Founding scope: meaningful influence over how the company defines its sales motion, qualification process, pricing strategy, and process iteration cycles.
• Meaningful equity in an early-stage company.
• Comprehensive medical, dental, and vision coverage for employees and dependents.
• A top-of-the-line laptop, monitor, and working setup.
• A high-trust, high-ownership team working on a large, operationally important market.

Compensation

• Base salary: $200,000.
• On-target-earnings expectation of $300,000 – $350,000.
• Additional uncapped commission upside for eligible software and services deals sold
• Meaningful equity, with the final grant based on experience and founding scope.

Location and Travel

This is a full-time role that can be remote or work from our San Francisco office. Expect regular monthly travel to customer locations, industry events, and other high-value in-person meetings.

Equal Opportunity and Accessibility

Proaction is an equal-opportunity employer. We consider qualified applicants without regard to legally protected characteristics and are committed to providing reasonable accommodations during the hiring process. Candidates who need an accommodation may contact Proaction through the application channel.

Apply

If interested, please submit your application through Proaction’s careers page.