Director, Data Engineering

 

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%)

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

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

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!

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

SQUIRE is committed to working with and providing reasonable assistance to individuals with physical and mental disabilities. If you are an individual with a disability requiring an accommodation to apply for an open position, please email your request to recruiting@getsquire.com and someone on our team will respond to your request.

SQUIRE provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.

This applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

SQUIRE will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. However, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge, (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by the employer, or (c) consistent with the contractor’s legal duty to furnish information.