Account Executive (Chicago area)

What we do

At Truckbase, we empower small and mid-sized trucking companies with an easy-to-use dispatch-centric platform that helps them grow. Whereas legacy trucking software is clunky and built for CFOs of large enterprises, Truckbase was built for the operators of asset-based trucking companies. We’re on a mission to ruthlessly eliminate friction, time, and cost for small fleet owners and their teams.

This role

Truckbase is looking for an experienced mid-market Account Executive who will join our growing sales team and help expand our outbound & field sales motion.

Strong candidates will have prior mid-market sales experience, ideally in a startup or growth-stage SMB/vertical SaaS company. Trucking-specific experience is not required, but the ideal candidate must be able to relate to the owners & operators of small & mid-sized trucking companies.

As an Account Executive at Truckbase, you will be at the frontline of our sales engine. You will be responsible for building a regionally focused sales motion, with a mix of outbound prospecting and inbound lead volume. This role offers the opportunity to work with modern, industry-leading dispatch, finance, and operations for the trucking industry.

Responsibilities

• Manage a full-cycle sales process with a focus on outbound/field sales for mid-sized trucking companies
• Understand and communicate value of a simple yet robust end-to-end product (e.g., configuration for various operating models, EDI integrations, etc.)
• Build rapport and find ways to surprise & delight high-value partners
• Partner with other members of the sales team to share best practices and develop repeatable, creative outbound strategies to generate ICP pipeline
• Leverage knowledge of our product, market, and customer to win deals through creative deal structures and Truckbase’s unique advantages

Qualifications

• Prior full-cycle sales experience with closing responsibilities and at least 25% of deals came from outbound and/or self-sourced deals
• Proven ability to drive sales processes and exceed quota selling complex products, ideally with family-owned enterprises in the lower mid-market
• Experience with sales travel & leading in-person sales meetings Willingness and comfort with traveling 50% of the time (focused regionally in the Midwest)
• Bonus points for prior experience in freight/trucking and/or SaaS
• Bonus points for bilingual candidates: Russian-speaking, Ukrainian-speaking, or Polish-speaking

Perks of working at Truckbase

• 100% remote workplace, equipment provided
• Competitive compensation package with base, commission, and equity
• Strong benefits with medical, dental, and vision insurance + 401k program
• Quick opportunities for career advancement
• Work directly with our CEO and founding team