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 getsquire.com 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)
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)
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
Interview Accommodations
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
[email protected] and someone on our team will respond to your request.
Equal Employment Opportunity
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.
Pay Transparency Nondiscrimination Provision
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.
