Director, Data Engineering

WHO WE ARE

SQUIRE is the leading business management system designed for the needs of barbers, shop owners, and their communities. We believe the pursuit of artistry and autonomy should not be restricted by the complexities of running a business. With SQUIRE, we provide custom-branded tools, resources, and guidance to help barbers of all stages and experience levels attract and retain more customers, efficiently manage their shop operations, and increase their revenue.

Founded in 2015, SQUIRE is trusted by more than 30,000 barbers across 5,000+ shops in more than a thousand cities worldwide. From streamlined booking and opening new shops to real-time earning dashboards and building lasting customer relationships, SQUIRE supports shop owners in seamlessly bridging the gap between their personal craft and business goals. SQUIRE enables barbers everywhere to unlock their full potential both as artists and as entrepreneurs.

For more information, please visit or download the SQUIRE app from the App or Play Store.

ABOUT THE ROLE

At SQUIRE, trusted data turns information into action - powering everything from company-wide reporting and automation to the AI capabilities shaping our next chapter. We're hiring a Director, Data Engineering to build and lead our Data organization through a player-coach model, spending approximately half your time hands-on in the code and the other half developing engineers, setting technical direction, and owning the organization’s strategy. You’ll own SQUIRE’s long-term data architecture and lead a growing team spanning Data Engineering, Machine Learning Engineering, and Analytics.

Success in this role means building a data foundation the company trusts by default, with reliable pipelines, clear standards, and scalable systems. You'll have the authority and accountability to make architectural and organizational decisions needed to move the function forward while helping the team grow in both capability and impact. As SQUIRE continues to scale, your work will directly enable more confident decision-making, stronger automation, and AI use cases that power our next phase of growth.

Reports To: Chief Product and Technology Officer
Location: Remote - US or Canada
Type: Full-Time
Compensation: Base ($200,000 - $230,000) + Bonus (15%)

YOUR CRAFT (Job Duties & Responsibilities)

• Design, build, and debug the highest-impact pipelines, connecting our business systems, including CRM, billing, and internal platforms to our Snowflake warehouse, in both directions
• Own the data strategy and architecture across a multi-year horizon, while maintaining deep, hands-on familiarity with the systems and their edge cases
• Establish technical direction and standards for pipeline design, data modeling, and data quality across the org; personally build and ship the highest-risk or most ambiguous work
• Build, structure, and lead a growing Data organization of 5+ across Data Engineering, ML Engineering, and Analytics
• Own headcount planning, hiring strategy, and budget for the Data organization
• Partner with the Chief Product and Technology Officer and cross-functional leaders to translate company strategy into data contracts and platform investments
• Lead audits of existing integrations and automations, and determine what should be replaced and how that work should be prioritized
• Champion AI and automation enablement company-wide, ensuring agents and LLM use cases are built on a trusted data foundation, while remaining hands-on in building select enablement capabilities

YOUR FOUNDATION (Experience & Skills)

• 8+ years in data or software engineering, including 4+ years managing engineers
• Experience building and leading a multidisciplinary data organization (data, ML, analytics, software) of 5+ people
• Advanced SQL and Python skills, along with strong MDM fundamentals, with the technical depth to lead by example
• Hands-on experience with Snowflake (or equivalent), dbt, and an orchestration tool such as Airflow, Dagster, or Prefect, beyond just an architectural understanding
• Direct experience setting AI and LLM enablement strategy and building with LLM tooling
• Comfortable operating at Director scope (owning budgets, advocating for roadmaps, and translating technical tradeoffs for non-technical stakeholders) while remaining directly involved in technical execution

EXTRA CUT (Nice to Haves)

• Experience building AI agents with LLMs (wired models into real systems with tool use, retrieval, and orchestration) and with the ability to guide others doing similar work
• Backend engineering experience (ideally in JS/TS) with sufficient depth to effectively evaluate architecture
• Strong ML and MLOps knowledge, with the ability to set direction, assess technical tradeoffs, and support ML Engineering Leads
• Experience with Salesforce, Stripe, Gong, or reverse ETL (Polytomic), and data governance / PII handling at a company-wide policy level

Don’t let this list stop you from applying - If you are interested in the role, we’d love to hear from you!

WHY SQUIRE?

As a Director, Data Engineering, you’ll have real ownership over a function the whole company depends on, a mandate to develop its leadership structure, and the charter to define the data foundation for SQUIRE's AI future — with the authority to turn that strategy into a lasting practice.

WHAT WE OFFER

• Base Salary ($200,000 - $230,000) + Bonus (15%)
• New hire stock grant
• 100% employer-paid medical/dental/vision insurance for you and your dependents
• 401K plan with company contribution
• Generous PTO and Parental Leave policies