Head of Engineering

About the Job

Position Name:
Head of Engineering

Company Name: T3 TMS

Position: 1099 - Independent Contract / Full Time

Salary Range: $120,000 - $150,000

About T3 TMS:

T3 TMS is a modern Transportation Management System built for freight brokers and carriers. We're building the platform that powers how freight moves - from load assignment and driver scheduling to billing, compliance, and ERP integrations with Net Suite and Quick Books. We're at an exciting inflection point: our product is live and in use, our flagship customer AiLO Logistics is targeting a full go-live in Q1 2027, and we're now building the leadership team to scale execution through that milestone and beyond.

AiLO Logistics is an affiliated company with T3 TMS, this position is a 1099 Independent Contractor opportunity with T3 TMS.

The 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 Net Suite, Quick Books, 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 Net Suite, Quick Books, or Triumph Pay integrations.
• Experience leading a team through…