About the JobPosition Name: Head of EngineeringCompany Name: T3 TMSPosition: 1099 - Independent Contract / Full TimeSalary Range: $120,000 - $150,000The Opportunity:This is a founding engineering leadership hire. As Head of Engineering at T3, you won't be inheriting a mature org - you'll be building it. You'll work directly with the CPO to shape how the engineering function operates: hiring and developing the team, establishing engineering culture and process, and owning the technical delivery of a complex, domain-rich product.
The right person for this role is an experienced engineering leader who is still close enough to the work to have strong opinions about architecture and quality - and who thrives in the ambiguity of an early-stage company with real customers and a hard deadline.
What You'll Own:Engineering leadership & team building:- Own the engineering org: hiring, onboarding, and developing engineers and QA as the team grows through 2026 and into 2027.
- Set engineering culture - code quality standards, review practices, incident response, on-call norms, and how the team works day-to-day.
- Be a player-coach: hands-on where needed, especially early, while building toward a team that executes independently.
- Partner with the CPO on roadmap planning, sprint sequencing, and resourcing decisions.
Technical delivery & architecture:- Own delivery of the T3 TMS platform from architecture through production - brokerage core, billing module, document management, and ERP integrations.
- Make and defend key architectural decisions: API design, data modeling, integration patterns with NetSuite, QuickBooks, and Triumph Pay.
- Establish and enforce engineering standards that support a Q1 2027 go-live with AiLO Logistics without accumulating unsustainable technical debt.
- Drive the build-vs-outsource evaluation for the accounting module integrations and own execution of that decision.
Process & cross-functional execution:- Define how engineering works with product and design: sprint cadence, ticket lifecycle, definition of done, and release process.
- Establish a structured intake and prioritization process for external customer requests (AiLO Logistics) so the team can execute with confidence and without constant context-switching.
- Own engineering roadmap visibility: keep the CPO, exec team, and stakeholders informed on progress, risks, and tradeoffs.
Quality & reliability:- Partner with the QA engineer to build a testing culture - automated, integration, and performance testing coverage that scales with the product.
- Own uptime, incident management, and production reliability as the platform moves toward full commercial use.
What We're Looking For:Required:- 7+ years of software engineering experience, with at least 3 years in an engineering leadership role.
- Proven track record of leading engineering teams at an early-stage or growth-stage SaaS company.
- Strong technical depth - you can review code, weigh in on architecture, and debug hard problems when needed.
- Experience owning complex integrations (ERP, payments, third-party APIs) in a production environment.
- Excellent cross-functional communication - you can translate between technical and non-technical stakeholders clearly and without losing nuance.
- Experience hiring and developing engineers; you have a point of view on what good engineering culture looks like.
Nice to Have:
- Experience in freight, logistics, TMS, or supply chain software.
- Familiarity with NetSuite, QuickBooks, or Triumph Pay integrations.
- Experience leading a team through a major product go-live or launch milestone.
- Background working with external enterprise customers on product delivery timelines.
- Exposure to outsourced or contract development teams - you know how to scope work and manage delivery without direct control.
What We Offer:- Competitive salary and meaningful equity at an early stage.
- Hybrid work arrangement with flexibility.
- A genuine leadership seat - you'll report to the CPO and have a direct line to the executive team.
- The chance to build an engineering org from the ground up, with budget approved and the mandate to hire.
- A product with real customers, real revenue, and a clear 12-month milestone to build toward.
