At Truckstop, we have transformed the entire freight-moving lifecycle with our SaaS solutions. From freight matching to payments and everything in between, we are the trusted partner for carriers, brokers, and shippers alike. We lead this industry forward with our One Team mindset committing to principles such as assume positive intent, have each other’s back, and be your authentic self. Our drive for greatness produces high expectations, yet our regard for humans is even higher. Join a team of brilliant minds and generous hearts who care deeply about other's success.
In an effort to provide greater transparency, we are sharing the base salary range for this position. The position is also eligible for commission based on meeting monthly targets. The On Target Earnings for this position is $125,000 if all commission is earned.
Job Summary
The Sales Engineer is responsible for supporting Truckstop’s sales efforts within the oversized, overdimensional, and heavy haul freight segment by serving as a subject‑matter expert on both industry practices and Truckstop’s solutions. This role partners closely with Account Executives to engage customers in discovery conversations, lead product demonstrations, and provide technical and workflow guidance. The Sales Engineer brings deep, hands‑on experience in OD and heavy haul freight, allowing them to engage customers as a knowledgeable peer and translate complex operational challenges into practical solutions. This position works directly with carriers, brokers, and shippers to demonstrate how Truckstop addresses the unique demands of moving oversized and heavy haul freight.
Essential Job Functions
Customer-Facing Sales Engagement
· Join AE-led sales calls as the heavy haul and OD subject matter expert — leading discovery, handling objections, and building credibility with prospects who expect to talk to someone who knows the space.
· Deliver product demos and presentations grounded in the realities of OD freight — permits, routing, pilot cars, bridge laws, weight limits, and seasonal constraints.
· Act as a trusted advisor to prospects and customers, helping them connect their operational challenges to real solutions.
· Engage decision-makers across carriers, brokers, and shippers specializing in heavy haul and OD, leveraging existing relationships to open and advance deals.
· Drive opportunities from discovery through close — translating customer needs into solutions and keeping deals moving.
Industry Expertise & Segment Authority
· Serve as Truckstop's internal authority on the heavy haul and OD market — bringing real-world context to sales conversations, product discussions, and go-to-market strategy.
· Stay current on regulatory changes, permitting requirements, market trends, and competitive dynamics in the OD and heavy haul space.
· Represent Truckstop at relevant industry events and trade shows, building relationships and brand presence in the segment.
· Feed customer insights and market feedback back to the product team to help shape how Truckstop's solutions evolve for this segment.
AE Partnership & Pipeline Development
· Partner with the Account Executive team to identify and prioritize heavy haul and OD opportunities across the existing customer base and new logos.
· Help AEs navigate the sales motion in this segment, where industry credibility is a prerequisite to earning trust.
· Surface new opportunities through industry contacts, referrals, and a clear understanding of where unmet needs exist in the market.
· Collaborate with support, onboarding, and product teams post-sale to ensure customers activate and get to value quickly.
· Keep Salesforce records accurate and current — pipeline, activity, and forecasting.
Tools & Execution
· Use Salesforce to maintain pipeline visibility and forecast accurately.
· Run structured outreach cadences via Salesloft or equivalent tools.
· Use Gong to review calls, sharpen messaging, and share what's working with the team.
At Truckstop we are dedicated to creating a workplace that is equitable, inclusive, and inspiring for every employee. In an effort to provide greater transparency, we are sharing the base salary range for this position. The position is also eligible for commission based on meeting monthly targets. Final salary is based on a number of factors including market location, job-related knowledge, education/training, certifications, key skills, experience, internal peer equity as well as business considerations.
The above description covers the most significant duties performed but does not include other related occasional work that may be assigned or is completed by the employee.
Truckstop provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.
Truckstop participates in the E-Verify program. Learn more about the E-Verify program here: https://www.e-verify.gov/
Truckstop Privacy Policy
Skills Required
- Experience in heavy haul and oversized freight industry
- Strong sales skills and technical aptitude
- Able to engage with decision-makers and translate operational challenges
- Proficiency in Salesforce and sales productivity tools
- Ability to work collaboratively with Account Executives
Truckstop Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Truckstop and has not been reviewed or approved by Truckstop.
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Healthcare Strength — Comprehensive medical, dental, and vision options, mental-health support, and wellness incentives are prominently offered. Company-paid portions for employee-only coverage and additional protections like life and disability insurance reinforce perceived value.
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Leave & Time Off Breadth — Unlimited PTO for exempt staff, substantial accruals for non-exempt, paid holidays, sick days, and volunteer time support time away. Remote-first flexibility further enables work-life balance.
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Strong & Reliable Incentives — Commission plans in sales roles can yield excellent earnings when quotas are met, complemented by performance and referral bonuses. High earners in sales can achieve strong outcomes under these structures.
Truckstop Insights
What We Do
At Truckstop, our One-Team mindset has transformed big dreams into epic success. We commit to principles such as assume positive intent, have each other’s back, and be your authentic self. This results in a feeling of connectedness, so no one feels isolated in a remote work world. Together, we build technology that determines the future of freight. Partners make the impact. We call our employees partners because we are interdependent upon each other to achieve greatness. From day one, we empower our partners with the freedom to innovate, take smart risks, and voice bold ideas. This autonomy allows our partners to think big and make an impact. Imagine greatness and own it. Imagine a place where you are equipped to drive your career – where exploration is encouraged, and opportunities present themselves to the curious. This is Truckstop.com. Our TLC (Truckstop Learning Center) and AI Talent Marketplace are examples of tools that help our partners develop new and critical skills. We are committed to empowering our partners to own their greatness. Flexibility to help you balance. We encourage our partners to embrace the richness of North America like the trucker who drives its highways. Whether seaside, countryside, or citified, wherever our partners draw inspiration from is where we want them to be. If it’s in an office or working from home, we set them up with the resources they need to excel. The best of two worlds. After 25 years of steady growth and profitability, Truckstop.com caught the eye of tech investor ICONIQ Capital. They saw how our breakthrough SaaS solutions impact an $800 billion industry. Our partners enjoy the stability of historical success yet are primed for exponential growth.
Why Work With Us
We are creating a culture of brilliant minds and generous hearts who care deeply about other's success. Our drive for greatness produces high expectations, yet our regard for humans is even higher.
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