Director, Data Science Engineering

SQUIRE is the leading business management system designed for the needs of barbers, shop owners, and their communities. 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. com

or download the SQUIRE app from the App or Play Store.
SQUIRE is the leading business management system designed for the needs of barbers, shop owners, and their communities. 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. com or download the SQUIRE app from the App or Play Store.
At SQUIRE, trusted data turns information into action - powering everything from company-wide reporting and automation to the AI capabilities shaping our next chapter. Were 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. Youll 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
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
~ Direct experience setting AI and LLM enablement strategy and building with LLM tooling
~ 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

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 SQUIREs AI future — with the authority to turn that strategy into a lasting practice.

Base Salary ($200,000 - $230,000) + Bonus (15%)
~ New hire stock grant
~100% employer-paid medical/dental/vision insurance for you and your dependents
~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 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.
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.
Below are a few important details about our hiring practices and policies.
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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

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.
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.
AI in the Hiring Process
SQUIRE may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. If you would like more information about how your data is processed, please contact us.