Enterprise Customer Success Manager

About the Company: Highway is the fastest-growing freight tech provider in North America. We serve the largest freight brokers in the industry, solving one of their biggest pain points: who is really hauling their freight. We answer the question of Carrier Identity, protecting brokers’ networks, preventing fraud and increasing transparency. Serving and protecting our customers is our top priority, and we are proud that our best marketing is our customer referrals and testimonials. FLSA Status: Exempt Location: Dallas, TX (This is an onsite position) Reports to: Director, Customer Success Status: Full-time About the Company Highway is the fastest-growing freight tech provider in North America. We serve the largest freight brokers in the industry, solving one of their biggest pain points: who is really hauling their freight. We answer the question of Carrier Identity, protecting brokers’ networks, preventing fraud and increasing transparency. Serving and protecting our customers is our top priority, and we are proud that our best marketing is our customer referrals and testimonials. Role Description: The Enterprise Customer Success Manager is a technical solutions expert who bridges Solutions and Customer Experience post-sales activities, enabling customers to understand the value of Highway and successfully adopt our platform. This role spans the entire customer journey—from evaluating our product fit through implementation and expansion. Your Role: Navigate customers through pre-integration decision frameworks and assess full platform adoption readiness Participate in implementation kickoff calls for Tier 1 customers and select Tier 2 accounts Translate technical requirements and collaborate with Technical Solutions Engineers (TSEs) to define comprehensive implementation plans to ensure customer success Conduct solution definition and implementation planning sessions, including understanding customers' current solutions and providers Lead monthly planning meetings with Business Unit Sales Leaders and Solutions Consultants to identify and plan expansion sales opportunities (e.g., Load Compliance, Capacity Solutions) Evaluate and present the pros and cons of current TMS integrations and demonstrate the ROI of migration to our platform Deliver technical demonstrations to prospects, answering detailed product and integration questions Align with SE Leadership on solution components and ensure all deliverables are properly scoped Develop deep technical understanding of how customers interact with our platform at the API level Define strategic customer goals (e.g., feature adoption, mandate optimization) that Customer Success Managers will drive forward Attend quarterly business reviews (QBRs) for key accounts, including pre-meeting alignment with CSMs on blockers and next steps Provide prescriptive recommendations on customer journey progression and expansion opportunities Product Adoption: Drive successful onboarding and feature adoption among assigned accounts ARR Conversion: Accelerate the conversion of booked customers to billed recurring revenue Customer Satisfaction: Maintain strong technical credibility and account relationships Solution Quality: Ensure implemented solutions match promised functionality and deliver expected ROI Qualifications: 6+ years of experience in customer experience, solutions architecture, and/or technical sales support Deep technical knowledge of TMS platforms, transportation software, or SaaS solutions Strong understanding of API integrations and technical implementation processes Excellent communication skills with the ability to translate technical concepts for business stakeholders Ability to travel up to 30% of the time Experience working cross-functionally with sales, customer success, and engineering teams Preferred: Background in transportation, logistics, or supply chain software Experience with customer journey mapping and expansion selling Knowledge of product roadmapping…

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