Director of Data Engineering & AI Platform

SQUIRE; Ontario (CA); Remote; USD 200,000 - 230,000; Full time

Benefits offered by this job

New hire stock grant

Employer-paid medical/dental/vision

401K plan with company contribution

Generous PTO

Job summary

SQUIRE seeks a Director of Data Engineering to build and lead our Data organization, blending hands-on coding with people leadership. You’ll shape long-term data architecture, own the data strategy, and guide a growing team across Data Engineering, ML Engineering, and Analytics.

Reporting to the Chief Product and Technology Officer, this fully remote role supports US or Canada-based candidates, with base pay of $200,000–$230,000 plus a 15% bonus and equity.

Qualifications

• 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.

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

Skills

SQL

Python

MDM fundamentals

Data architecture

AI/LLM enablement

Director scope

Hands-on coding

Cross-functional leadership

Tools

Snowflake

dbt

Airflow

Dagster

Prefect

Job description

SQUIRE seeks a Director of Data Engineering to build and lead our Data organization, blending hands-on coding with people leadership. You’ll shape long-term data architecture, own the data strategy, and guide a growing team across Data Engineering, ML Engineering, and Analytics.

Reporting to the Chief Product and Technology Officer, this fully remote role supports US or Canada-based candidates, with base pay of $200,000–$230,000 plus a 15% bonus and equity.