VP of Engineering
About the Role:Breakthrough is looking for a VP of Engineering who loves building world-class engineering organizations. Someone who gets energized by making teams ship consistently, developing people into leaders, and building teams that own their outcomes. We're a 170-person freight tech company at an inflection point. You'll own delivery execution, people development, and engineering excellence partnering closely with our Chief Technologist. This role requires someone who drives results by developing capability in teams and leaders.About Breakthrough:Breakthrough is a strategic transportation partner empowering shippers with data, technology, and market knowledge to reduce cost, improve efficiency, and decarbonize transportation. Our flagship product, Fuel Recovery, is the industry's only market-based fuel reimbursement solution, replacing outdated national average fuel surcharges with precise, lane-level calculations based on real-time wholesale fuel prices. Backed by $32B+ in annual freight spend data and recognized on FreightWaves' FreightTech 25 list of leading freight technology companies, we're transforming how Fortune 500 shippers manage their transportation networks. As a profitable, growing company, we invest heavily in technology as a core part of our strategy.Location:Green Bay, WI (preferred) or Remote within the US - Midwest preferred. Our team is concentrated in Northeast Wisconsin with significant presence across greater Wisconsin and Chicagoland. For remote candidates, expect monthly visits to Green Bay plus additional trips as needed. Relocation assistance available for the right candidate.What You'll OwnTeam Enablement & DeliveryBuild autonomous teams that own their delivery outcomes. You're accountable for creating the systems and capability that make this possibleCreate clarity around decision rights, accountability, and escalation pathsEnable teams through coaching, unblocking, and removing organizational frictionEstablish when to engage directly vs. when teams have what they need Engineering Excellence & EffectivenessEstablish SLAs, metrics, and engineering standardsImprove engineering effectiveness: deployment frequency, lead time, quality, velocityCreate structure that scales from 40 to 60+ engineers while maintaining high performanceBuild systematic practices that enable scale without slowing teams down People & Leadership DevelopmentDevelop engineers, engineering managers and directors into confident, capable leadersCoach managers to make strong decisions independentlyDrive performance reviews, promotions, and career developmentExpand capacity for technical mentorship and creative problem-solving developmentFoster a culture of experimentation where teams take calculated risks aligned with product strategyHelp shape the culture and define what high-performing engineering teams look like here Delivery & GrowthAccountable that engineering ships predictably and meets roadmap commitmentsBuild recruiting infrastructure that attracts self-directed, senior talentDesign org structure that supports autonomous teams with clear boundaries and minimal dependenciesImplement onboarding that builds capability quicklyGrow the engineering team while maintaining team quality and culture QUALIFICATIONSExperience:10+ years in engineering leadership roles5+ years leading engineering teams of 30+ engineersProven track record scaling engineering organizationsExperience developing engineering managers and leadersDemonstrated success implementing engineering metrics, SLAs, and operational excellence practicesLeadership:Track record of hiring and building high-performing teamsExperience coaching managers to operate autonomouslyHistory of creating systems and processes that enable team independenceComfortable operating in ambiguous, fast-growing environments Technical:Strong technical background with hands-on engineering experience (not required to code daily, but must understand technical trade-offs)Experience with modern software development practices (CI/CD, DevOps, Agile)Understanding of SaaS architecture and scalability challenges Nice to Have:Experience in B2B SaaS or logistics/supply chain technologyBackground scaling remote or distributed engineering teamsPrevious experience at companies going through similar growth stages (50-200 people) Education:Bachelor's degree in Computer Science, Engineering, or related field (or equivalent practical experience) You're a Great Fit If:You've scaled an engineering org by building strong, autonomous teamsYou take full ownership. Delivery, hiring, team health are YOUR outcomesYou proactively identify and solve systemic problemsYou measure success by team outcomes, not your direct involvementYou love operational excellence. Metrics, SLAs, effectiveness improvements energize youLearn more about Breakthrough's tech team and our culture here. You're NOT a Fit If:You need to be involved in most decisions to feel effectiveYou prefer directing work rather than developing capabilityMetrics and operational excellence feel like secondary concerns= Team structure:5 product teams with strong execution autonomyEngineering managers/directors paired with staff/tech leads