Lead the engineering function and remain hands-on while building an AI-powered freight billing platform. Own architecture, data infrastructure, AI/ML validation, enterprise integrations, security, CI/CD, observability, testing, and scalability. Partner with Product and Data Science to automate invoice validation, discrepancy detection, exception handling, and auditability. Build and mentor distributed engineering teams, establish technical direction, and deliver rapid MVP iterations for enterprise adoption.
Company Overview:
Groundtruth, a Vantora (formerly UP.Labs) portfolio company is hiring a hands-on Head of Engineering. Groundtruth is building an AI-powered platform focused on freight billing, revenue integrity, and cash-flow automation.
Freight billing today is fundamentally broken. Complex contracts, fragmented systems, and manual, error-prone workflows lead to disputes, revenue leakage, delayed payments, and significant overhead. This company exists to change that by unifying fragmented data into a single source of truth, validating invoices automatically, and identifying discrepancies in real time, turning revenue chaos into predictable outcomes.
As the first engineering leader, you will own the technical foundation end-to-end: architecture, data infrastructure, AI integration, and team building. You’ll stay hands-on early, build from first principles, and define the long-term technical direction as the platform scales to enterprise adoption.
You’ll also have access to the UP.Partners ecosystem, a world-class team across product, engineering, design, analytics, marketing, legal, talent, finance, and venture capital - to help accelerate execution.
In This Role, You Will:
- Lead and grow the engineering function, balancing hands-on development with technical leadership and team building.
- Architect and own the core platform, including:
- Data ingestion and normalization pipelines
- AI/ML and rules-based validation layers
- Scalable, secure enterprise infrastructure
- Build and maintain deep integrations with enterprise systems such as TMS, ERP, billing platforms, and other operational data sources.
- Partner closely with Product and Data Science to translate complex, real-world billing workflows into intelligent, automated solutions.
- Design systems that support invoice validation, discrepancy detection, exception handling, and auditability.
- Establish best practices around security, CI/CD, observability, testing, and documentation suitable for enterprise finance and operations teams.
- Define the technical vision for AI-driven automation, explainability, and closed-loop resolution workflows.
- Manage and mentor distributed contributors (including nearshore/offshore teams), building a high-trust, high-output engineering culture.
- Deliver rapid MVP iterations while laying a durable foundation for enterprise scale and reliability.
Who You Are:
- A technical leader who thrives at the intersection of data, AI, and enterprise SaaS.
- Deeply hands-on comfortable writing code, reviewing PRs, and making architectural tradeoffs.
- Experienced integrating complex, messy enterprise systems and normalizing inconsistent data.
- Fluent in building platforms that combine data infrastructure, applied machine learning, and workflow automation.
- A collaborative partner who works seamlessly with product, data science, and business stakeholders.
- Comfortable operating in ambiguity and scaling systems and teams from 0→1 and beyond.
You Should Have:
- 8+ years of software engineering experience, including 4+ years leading small, high-impact teams.
- Strong backend or full-stack background with the ability to remain hands-on.
- Proven experience building and scaling B2B SaaS platforms with complex data pipelines and system integrations.
- Deep knowledge of cloud architecture, CI/CD pipelines, observability, and distributed systems.
- Experience working with AI/ML systems (e.g., LLMs, rules engines, optimization or validation models).
- Familiarity with enterprise finance, billing, or revenue systems is a strong plus.
- Experience leading or managing distributed (nearshore/offshore) engineering teams.
- Background in logistics, supply chain, or fintech is helpful but not required.
Why Join:
- Solve a high-impact, revenue-critical problem for logistics operators using AI and automation.
- Build a category-defining platform at the intersection of logistics, finance operations, and applied AI.
- Own the technical foundation from day one with real influence over architecture and strategy.
- Work closely with top enterprises, operators, and investors through the UP.Labs model.
- Meaningful equity ownership in a high-growth venture with enterprise-scale potential.
About Vantora:
Vantora builds high-growth technology startups that enable faster, cleaner, and safer movement of people and goods.
Our platform is unique in three ways:
- Risk: We reward our team and partners with meaningful equity.
- Technology: We build and launch scalable technology products from day one.
- Industry Focus: We stay deeply focused on the underlying fabric of mobility and logistics.
Similar Jobs
27 Minutes Ago
Easy Apply
Easy Apply
Cloud • Information Technology • Security • Software • Cybersecurity
Leads strategic relationships with private equity firms, developing joint go-to-market plans, originating portfolio company opportunities, structuring commercial deals, and driving adoption of Zscaler’s security platform. The role partners with PE leaders, sales teams, business value specialists, and technical experts to quantify value, improve EBITDA, mitigate cyber risk, support M&A transactions, and advance digital transformation across portfolio companies.
Top Skills:
Ai/MlCybersecurityDigital TransformationEbitdaIrrNetwork SecurityQbrsRoiSales ForecastingSaseTcoZero Trust Exchange
Artificial Intelligence • Cloud • HR Tech • Information Technology • Productivity • Software • Automation
Drive net-new business growth within a strategic enterprise technology account. Identify expansion opportunities, build business cases and solution roadmaps, develop relationships from IT teams through C-suite executives, coordinate cross-functional sales and partner teams, and close new solution areas while achieving license, renewal, professional services, and annual sales targets.
Top Skills:
Artificial IntelligenceCustomer Service ManagementHr Service DeliveryIt Operations ManagementIt Service ManagementSecurity OperationsServicenow
Artificial Intelligence • Fintech • Insurance • Marketing Tech • Software • Analytics
Handles inbound calls and warm leads to understand customers’ insurance needs, recommend appropriate Property & Casualty coverage, and convert prospects into policyholders. The role includes paid licensing and training, customer consultation, sales closing, brand representation, and maintaining a reliable remote work environment. Employees must work four weekdays and one weekend day, meet home-office and internet requirements, and remain in their resident state for at least one year.
Top Skills:
PcWired High-Speed Internet
What you need to know about the Boston Tech Scene
Boston is a powerhouse for technology innovation thanks to world-class research universities like MIT and Harvard and a robust pipeline of venture capital investment. Host to the first telephone call and one of the first general-purpose computers ever put into use, Boston is now a hub for biotechnology, robotics and artificial intelligence — though it’s also home to several B2B software giants. So it’s no surprise that the city consistently ranks among the greatest startup ecosystems in the world.
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories
