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 $150,000 if all commission is earned.
The Sales Engineer is responsible for supporting Truckstop’s sales efforts within the financial technology space by serving as a subject matter expert on both fintech industry practices and Truckstop’s solutions. This role partners closely with Account Executives to engage prospects in discovery conversations, lead product demonstrations, and provide technical and workflow guidance.
The Sales Engineer brings deep, hands-on experience in financial services and fintech platforms—such as payments, risk, fraud, lending, compliance, or financial operations—allowing them to engage customers as a knowledgeable peer and translate complex financial and technical challenges into practical, scalable solutions. This position works directly with customers and partners to demonstrate how Truckstop’s fintech solutions improve financial workflows, reduce risk, and support growth.
Essential Job FunctionsCustomer-Facing Sales Engagement- Join AE-led sales calls as the fintech subject matter expert—leading discovery, handling objections, and building credibility with financially sophisticated buyers.
- Deliver product demos and presentations grounded in real-world financial workflows, such as payments processing, reconciliation, underwriting, compliance, risk management, or financial reporting.
- Act as a trusted advisor to prospects and customers, helping them connect operational and financial challenges to practical, technology-driven solutions.
- Engage decision-makers across finance, operations, risk, and leadership teams, tailoring messaging to both technical and business audiences.
- Drive opportunities from discovery through close by translating customer requirements into clear solutions and supporting deal momentum.
- Serve as Truckstop’s internal authority on the fintech domain, bringing market and operational context into sales conversations, product discussions, and go-to-market strategy.
- Stay current on financial services trends, regulatory considerations, and competitive dynamics relevant to fintech (e.g., payments, fraud, compliance, lending, or financial infrastructure).
- Represent Truckstop at relevant industry events, conferences, and customer meetings, strengthening credibility and brand presence.
- Provide ongoing customer and market feedback to product teams to help shape the evolution of Truckstop’s fintech offerings.
- Partner closely with Account Executives to identify, qualify, and advance fintech opportunities across both existing customers and new logos.
- Support AEs in navigating complex sales cycles where trust, security, and financial impact are core decision drivers.
- Surface new opportunities through industry knowledge, customer insights, and awareness of unmet financial or operational needs.
- Collaborate post-sale with onboarding, support, and product teams to ensure smooth implementation and early customer value.
- Maintain accurate Salesforce records including pipeline status, activities, and forecasts.
- Use Salesforce to manage pipeline visibility, opportunity tracking, and forecasting.
- Run structured outbound and follow-up cadences using Salesloft or equivalent tools.
- Leverage Gong or similar conversation intelligence tools to review calls, refine messaging, and share best practices across the team.
The above description covers the most significant duties performed but does not include other related occasional work that may be assigned or completed by the employee.
Position Requirements- 5+ years of experience in fintech, financial services, or financial technology platforms (e.g., payments, lending, fraud/risk, compliance, financial operations, or B2B SaaS).
- Strong understanding of financial workflows and systems, including how technology supports compliance, risk management, and operational efficiency.
- Experience working with or selling into finance, operations, risk, or executive stakeholders.
- Proven ability to engage customers in a consultative or pre-sales role and translate complex financial and technical concepts into clear business value.
- Excellent communicator and presenter, comfortable with both technical discussions and executive-level conversations.
- Self-directed and accountable, with the ability to manage multiple opportunities in a remote environment.
- Highly collaborative, with a strong partnership mindset toward Account Executives and cross-functional teams.
- Experience using Salesforce, Salesloft, Gong, or similar sales tools preferred.
- College degree preferred; equivalent industry experience considered.
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/
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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.
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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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