Enterprise Account Executive

Responsibilities

Own enterprise pipeline and account strategy

• Own a named target account list, including research, entry strategy, account plans, and sequencing.
• Source the majority of your own pipeline while working across insurance, fleet management, transportation management, and fuel card segments.
• Qualify out early when a cycle will not close.
• Track qualified enterprise pipeline by segment, self-sourced pipeline, forecast quality, and account progression.

Run complex technical and executive sales cycles

• Multi-thread buying committees spanning executives, engineers, data scientists, and actuarial teams.
• Build business cases and equip champions to drive internal alignment.
• Coordinate Terminal executives and teams across engineering, operations, security, compliance, privacy, data governance, SOC 2, and procurement.
• Explain the economics of building in-house when prospects evaluate that option.
• Progress accounts through executive, technical, security, procurement, and commercial stages.

Own commercial terms, close, and activation handoff

• Structure usage-based commercial terms, negotiate commitments and minimums, and create credible ramps.
• Close net-new enterprise logos and transition accounts to post-sales while remaining involved through activation and early expansion.
• Co-author business cases, segment narratives, competitive positioning, and ROI models with product marketing.
• Measure booked value, activated usage, target-logo progress, and commercial ramp quality.

Requirements

• 8+ years of sales experience, including 5+ years selling to large enterprises.
• Track record of landing net-new enterprise logos and attaining comparable quotas across multiple years.
• Ability to reconstruct several enterprise wins, including entry strategy, relationship building, business case, obstacles, and resolution.
• Fluency selling technical products to technical buyers, including data, APIs, and integration architecture.
• Experience with usage-based or consumption pricing, commitments, minimums, and ramp forecasting.
• Exceptional written communication for one-pagers, follow-ups, and business cases.
• Strong judgment, initiative, attention to detail, and ability to qualify out weak opportunities.
• Located in Toronto and able to work from the office four days per week.
• Willingness to travel to the United States approximately six to eight times annually for conferences and customer onsite visits.

Nice to Have

• Experience selling to insurance companies.
• Experience selling to fleet management, logistics, or transportation technology companies.
• Background in telematics, IoT, or connected vehicle data.
• Experience selling APIs, data infrastructure, or other developer-facing products.

Compensation

• ATS-listed salary range: 260000–300000 CAD.