Strategic Account Executive

Overview

You'll own a book of PrePass's largest fleet accounts, working to expand their usage of weigh station bypass, toll management, and compliance tools. You're selling to transportation and logistics companies - think large trucking fleets, private fleets for retailers, and for-hire carriers. Your job is to deepen relationships, identify expansion opportunities, and land multi-year contracts worth $100K-500K+ annually.

Role Snapshot

Company Context

Stage: Mature / Established (325 employees)

Size: 325 employees

Growth: Expanding strategic account team - signal they're focused on deepening wallet share with existing enterprise customers

Market Position: Market leader in weigh station bypass and toll management - they're the incumbent with the largest network and most transponders installed

GTM Reality

Pipeline Sources:

• 70% Expansion within existing accounts - you're mining your book for upsell/cross-sell opportunities
• 20% Renewals that need active management - multi-year contracts coming up for renegotiation
• 10% Net-new strategic accounts - landing competitors' largest customers or breaking into new verticals

SDR/AE Structure: No SDR support - you're managing the full relationship and identifying your own expansion plays

SE Support: Likely shared technical resources for implementation support, but you're doing most product demos yourself

Competitive Landscape

Main Competitors: Drivewyze (weigh station bypass), Bestpass (toll management), integrated ELD/telematics providers trying to bundle similar features

How They Differentiate: Largest bypass network, most comprehensive coverage, deepest integrations with state weigh stations - they're selling scale and reliability

Common Objections: "We already have bypass through our ELD provider", "Bestpass is cheaper for tolls", "We're happy with our current setup"

Win Themes: Network coverage (more sites = more time saved), proven ROI data, integration with existing fleet systems, customer service/support quality

What You'll Actually Do

Time Breakdown

Account Management (40%) | Expansion Deals (35%) | Internal (25%)

Key Activities

• Quarterly Business Reviews: You run QBRs with your top 15-20 accounts, showing them usage data, ROI metrics, and identifying where they're leaving money on the table by not using certain features. You're building the business case for expanding from just bypass to full toll management or adding more trucks to the platform.
• Multi-Threading Relationships: You're talking to fleet managers about operational efficiency, CFOs about cost savings, safety directors about compliance tools, and procurement about contract terms. Deals stall when you're single-threaded, so you spend time mapping org charts and finding champions.
• Renewal Negotiations: You manage contract renewals 6-9 months out, which means pricing discussions, competitive threats, and proving continued value. Some customers will threaten to walk to negotiate better rates - you need to know when to hold firm and when to involve leadership.
• Product Roadmap Feedback: You're the voice of your strategic accounts internally, pushing product and engineering teams on feature requests and integration priorities. Your biggest customers want custom reporting, API access, or specific state coverage - you navigate what's possible and what's on the roadmap.

The Honest Reality

What's Hard

• Your largest accounts are often the most demanding - they'll have dedicated CSMs at competitors, tough procurement teams, and high expectations for service. One outage or billing issue can put a renewal at risk.
• ROI is measurable but can be argued - fleet managers will do their own math on fuel savings, time savings, and weigh station fines avoided. If fuel prices drop or their routes change, your value prop gets questioned.
• You're selling into a conservative industry with long decision cycles. Getting a fleet to switch toll providers or add new transponders means coordinating with operations, IT, drivers, and finance. Deals slip quarters regularly.
• Expansion requires finding budget that wasn't planned. You're often competing with other fleet priorities (new trucks, ELD upgrades, insurance costs) for the same dollars.

What Success Looks Like

• You grow your book of business by 20-30% year-over-year through expansion and retention
• 95%+ renewal rates on your strategic accounts - losing a big customer is a major hit
• You land 2-3 significant expansions per quarter (adding new product lines, bringing on more trucks, or extending contract terms)
• Your accounts become reference customers - willing to speak to prospects, provide case studies, or attend industry events with you

Who You're Selling To

Primary Buyers:

• Fleet Managers / Directors of Operations (day-to-day users, care about driver efficiency and operational simplicity)
• CFOs / Finance Directors (approval for large contracts, care about total cost of ownership and ROI)
• Procurement / Supply Chain VPs (negotiate terms, compare competitive bids, drive hard on pricing)

What They Care About:

• Measurable time savings (hours saved per truck per year bypassing weigh stations)
• Toll cost reduction and consolidated billing (simpler accounting, lower admin overhead)
• Driver satisfaction (less time stopped, smoother routes, easier compliance)
• Integration with existing systems (ELD, TMS, accounting software)
• Network coverage (does it work on their specific routes and states)
• Reliability and uptime (can't afford missed bypasses or billing errors)

Requirements

• 3-5 years in B2B sales, ideally selling to transportation, logistics, or fleet management buyers
• Experience managing large, complex accounts with multi-stakeholder deals
• Comfort with ROI-based selling and navigating procurement processes
• Understanding of fleet operations, trucking industry dynamics, or supply chain is a major plus
• Track record of hitting quota in a relationship-driven, expansion-focused role
• Willingness to travel occasionally for customer QBRs, industry events, or on-site meetings