Sales Engineer

Truckstop•Chicago, ID

4d•$100,000 - $100,000

About The Position

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.

Responsibilities

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.
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.
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.
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.