Vice President, Engineering; Breakthrough

POSITION SUMMARY

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 Our flagship product, Fuel Recovery, is the industry’s only market‑based fuel reimbursement solution, replacing outdated national average fuel surcharges with precise, lane‑level calculations based on real‑time wholesale fuel prices.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 Freight Waves’ Freight Tech 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.

• Build autonomous teams that own their delivery outcomes. You’re accountable for creating the systems and capability that make this possible
• Create clarity around decision rights, accountability, and escalation paths
• Enable teams through coaching, unblocking, and removing organizational friction
• Establish when to engage directly vs. when teams have what they need

• Establish SLAs, metrics, and engineering standards
• Improve engineering effectiveness: deployment frequency, lead time, quality, velocity
• Create structure that scales from 40 to 60+ engineers while maintaining high performance
• Build systematic practices that enable scale without slowing teams down

• Develop engineers, engineering managers and directors into confident, capable leaders
• Coach managers to make strong decisions independently
• Drive performance reviews, promotions, and career development
• Expand capacity for technical mentorship and creative problem‑solving development
• Foster a culture of experimentation where teams take calculated risks aligned with product strategy
• Help shape the culture and define what high‑performing engineering teams look like here

• Accountable that engineering ships predictably and meets roadmap commitments
• Build recruiting infrastructure that attracts self‑directed, senior talent
• Design org structure that supports autonomous teams with clear boundaries and minimal dependencies
• Implement onboarding that builds capability quickly
• Grow the engineering team while maintaining team quality and culture

• 10+ years in engineering leadership roles
• 5+ years leading engineering teams of 30+ engineers
• Proven track record scaling engineering organizations
• Experience developing engineering managers and leaders
• Demonstrated success implementing engineering metrics, SLAs, and operational excellence practices

• Track record of hiring and building high‑performing teams
• Experience coaching managers to operate autonomously
• History of creating systems and processes that enable team independence
• Comfortable operating in ambiguous, fast‑growing environments

• 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, Dev Ops, Agile)
• Understanding of SaaS architecture and scalability challenges

• Experie…