Director, Data & AI
Company shown to members 🔒 · Remote · US only
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First recorded by Psst: 12 October 2026. Your first 3 jobs are free to apply to (the first right away, 2 more with your email). After that, the company and the apply link are for Psst members, from $4.99 for 7 days.
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The 20-second read
- Experience
- Senior
- Where you can live
- US only
- Skills and tools
- forecasting, machine learning
- Job type
- Full-time
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Job details
- Where you can work
- United States
- Employment type
- Full-time
- Advertised pay
- $220K–300K/yr
- Experience
- Senior
- Employer publication date
- 24 September 2026
- First recorded by Psst
- 12 October 2026
- Last checked at the source
- 10 November 2026
About the job
The role
The company is building the network and software that move the world’s goods with speed, intelligence, and trust. We're looking for a Director of Data — an AI-forward leader who owns the company's data end to end, from the analytics that steer the business to the machine learning that ships into the product.
This is not a reporting-and-dashboards role. You'll set the data and ML roadmap, partner with product and engineering to turn data into shipped features, and build the team and platform that make the company smarter with every delivery.
What you'll own
Roadmap & product impact
- Own the data and machine learning roadmap, and tie it directly to product outcomes and company metrics.
- Partner with product, engineering, and operations to turn data into shipped features — smarter routing, batching, deadhead reduction, pricing, and ETA accuracy.
- Bring an AI-forward point of view: identify where machine learning and modern AI make the product materially better, and drive those bets from concept to production.
Machine learning
- Lead the strategy for machine learning in the company product — routing and optimization, demand forecasting, pricing, and delivery intelligence.
- Move models from prototype to production and own their performance, monitoring, and iteration in the real world.
- Make build-vs-buy calls on models, tooling, and AI infrastructure.
Analytics & decision-making
- Own the analytics function that steers the business — the metrics, dashboards, and analyses leadership relies on.
- Drive data-informed decision-making across the company, from GTM to operations to finance.
- Deepen the company's understanding of customers and lanes — penetration, expansion, and delivery economics.
Platform & foundations
- Own the data platform and warehouse (Snowflake), including modeling, semantics, and quality.
- Set the standard for data governance, reliability, and trust so the whole company can build on it.
- Ensure the pipelines and infrastructure scale with the company's growth.
Team & leadership
- Build, hire, and mentor a high-performing data and ML team.
- Set the bar for craft, and establish the analytical foundations and best practices as the team grows.
What you need to have
- 8+ years in data and/or ML, including 3+ leading teams at a high-growth company, with a track record of product impact.
- Genuine depth in machine learning: you've shipped models into production and owned their outcomes.
- Fluency with a modern data stack (Snowflake or equivalent) and the judgment to build the right foundations.
- Strong product and business instincts, with a history of connecting data work to measurable outcomes and influencing a roadmap alongside product and engineering leaders.
- A builder's bias and clear communication, comfortable going hands-on early while scaling a team, and able to earn trust from both executives and engineers.
Bonus points for
- Logistics, marketplace, or operations-heavy domain experience.
- Experience standing up an AI-native / agentic approach to data and internal tooling.
- Our headquarters are in Ventura, CA, and we have a strong preference for candidates in the Ventura and greater Los Angeles area. Relocation assistance is provided.
What is in for you
- A dual mandate that's rare: own the analytics that runs the business and the ML that powers the product.
- Real, physical outcomes — your models move trucks, not just pixels.
- Early enough to shape the function, resourced enough to ship.
- Competitive salary, equity compensation, and comprehensive benefits (health, dental, vision, 401K).
- A high-growth, mission-driven environment where your work has direct and measurable impact.
Who are we?
We are the company, and our mission is to build the network and software that move the world’s goods with speed, intelligence, and trust. The company provides on-demand, last-mile logistics for construction and adjacent industries with our nationwide fleet of cars, trucks, and flatbeds.
Founded in 2018 and part of the YC S19 Batch, we’re solving the massive inefficiencies that exist in the construction industry. Our headquarters are in Ventura, CA. Learn more at the company [link for members]
The company is an equal opportunity employer and complies with all applicable federal, state, and local fair employment practices laws. All qualified applicants will receive consideration for employment. We don't discriminate based on race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.
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