Director, Analytics & Insights

Role Description

As SQUIRE continues to grow, so does the need for clean, well-defined, and trustworthy data on how the business is performing. As the Director, Analytics & Insights , you will define the standards, taxonomies, and requirements in our core source systems needed for data to flow and report information properly for the business. Based on the data captured, you will consolidate and uncover the drivers behind churn, retention, and conversion, then apply that same rigor to product telemetry and marketing analytics, and bring those insights directly to the leaders who can act on them.

Success in this role means the company operates from one consistent and trusted set of metrics built on quality source system data, with leaders able to approach important decisions with a clear understanding of the factors behind them. Your work will directly influence business outcomes with a clear understanding of what matters most, rather than simply report on them. As SQUIRE expands its use of AI, you will bring a thoughtful perspective on where it can add the most value in analytics and ensure our data is prepared to support that work. This role, above all, is central to how SQUIRE makes informed decisions to move faster and scale with confidence.

• Reports To: SVP, Operations
• Location: Remote - US or Canada
• Type: Full-Time
• Compensation: Base ($200,000 - $230,000) + Bonus (15%)

Qualifications

• 10+ years of experience in an analytics or data function, including 4+ years of people management.
• Demonstrated experience translating data into insights that influence leadership decisions and measurable business outcomes.
• Experience building analytical models, systems, and practices that create lasting organizational value beyond individual dashboards.
• Technical fluency across SQL, data modeling, statistics fundamentals, dbt or similar transformation tools, and Looker.
• Strong leadership and communication skills, with the ability to develop a team and translate complex analytical concepts for executive audiences.

Requirements

• Proactively analyze business performance to identify what is changing and why across churn, retention, conversion, unit economics, funnel performance, product adoption, product telemetry, and marketing analytics.
• Translate complex data into clear insights and recommendations for the leaders and teams positioned to act on them.
• Define and lead the multi-year strategy for SQUIRE’s analytical data, including how it is modeled, structured, and governed to support accurate analysis for scalable business growth and future AI capabilities.
• Partner closely with Data Engineering to develop scalable and reliable analytical models.
• Set the strategy for AI-driven analytics, keeping our data clean and AI-ready.
• Lead Looker as SQUIRE's primary business intelligence platform, including dashboard strategy, reporting improvements, platform cleanup, and self-service reporting.
• Establish the metric definitions, quality standards, and governance practices needed to maintain trust in the company's data.
• Lead the company's OKR process and performance readouts, including the cadence, measurement, and reporting used to create visibility and accountability.
• Lead and grow the analytics function by hiring and developing a team known for quality and reliability across analytics engineering, business intelligence, and analysis.

Benefits

• 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