Director, Data & AI (Hybrid)

Hi, Future Homie!

At Homebase, you’ll join a team that’s bold, fast-moving, and obsessed with helping small businesses thrive. We build with empathy, act with urgency, and take big swings that drive real-world impact. Here, every Homie shows up to raise the bar, support one another, and celebrate wins as a team.

We’re not just building an app—we’re building unstoppable teams. So what do you say, are you in?

Your Impact Starts Here

We’re looking for a Director, Data & AI to lead our Data Engineering, Data & ML Platform, Data Science, and Applied AI teams. You'll own the strategy, execution, and people leadership for a 20+ person org that powers everything from our data platform and analytics infrastructure to production ML models and AI-powered product experiences.

This is a high-impact leadership role at the intersection of data and AI. You'll set the technical vision for how Homebase uses data as a product—trustworthy, consistent, and accessible—while driving applied AI initiatives that directly shape customer outcomes. You'll partner closely with Product, Engineering, and GTM leadership to ensure data and AI capabilities accelerate Homebase's growth strategy.

These are the key ways you’ll contribute and create impact in this role:

• Own the Data & AI strategy. Define and execute the technical roadmap across data engineering, data platform, data science, and applied AI. Align priorities to Homebase's product and business goals.

• Lead and grow a 20+ person org. Manage managers and senior ICs across four sub-teams. Recruit, develop, and retain top talent. Build a culture of velocity, ownership, and craft excellence.

• Drive data platform and infrastructure. Own the reliability, scalability, and governance of Homebase's data stack (Databricks, Unity Catalog, Airflow, dbt). Ensure data is a trusted, self-serve asset across the company.

• Accelerate applied AI and ML in product. Partner with Product and Engineering to ship AI-powered features—from LLM-based assistants to recommendation systems and intelligent automation. Own the MLOps lifecycle from experimentation to production.

• Drive data science rigor. Build experimentation frameworks, guardrail metrics, and evaluation pipelines that drive confident product decisions. Ensure models are reliable, fair, and cost-effective.

• Champion AI fluency org-wide. Coach your leaders to enable their teams with AI tools and workflows. Drive adoption of AI-assisted development practices (agentic coding, AI-augmented analytics). Measure and share impact.

• Set governance and standards. Define org-wide standards for data quality, model monitoring, data contracts, and responsible AI use. Be the authority on data architecture and AI governance.

• Partner cross-functionally. Work with Product, Growth, GTM, Finance, and CX to understand their data and AI needs. Enable a hub-and-spoke model where your team empowers the entire org to work with data effectively.

The Foundation for Success - These are the experiences and strengths that will set you up for success in this role:

• 10+ years in data and/or AI/ML , with at least 5 years leading teams of 8+ across data engineering, data science, or applied AI.

• Director-level leadership experience. You've managed managers, built orgs, and driven technical strategy at a company with real scale.

• Deep technical fluency across the modern data stack (warehousing, orchestration, transformation, BI) and applied ML/AI (production ML systems, LLMs, experimentation platforms).

• Strong product instincts. You connect data and AI work to customer outcomes and business metrics, not just technical milestones.

• AI-first mindset. You actively use AI to improve your own workflows and have led teams that ship AI-powered products. You stay current on frontier developments (LLMs, agentic systems, multimodal AI).

• Excellent communication. You translate complex technical concepts for non-technical stakeholders and build trust across the org.

• Experience with modern data platforms such as Databricks, Snowflake, or similar. Familiarity with Unity Catalog, Airflow, dbt, and ML platforms (MLflow, Baseten, or equivalent) is a strong plus.

• Hybrid commitment. You're based in or willing to relocate to the Toronto area and are energized by in-person collaboration Tues/Weds at our Toronto hub.

• Bonus points if you bring:

  • Experience building data and AI orgs at a SaaS or marketplace company serving SMBs.

  • Background in establishing data-as-a-product disciplines (data contracts, semantic layers, data mesh concepts).

  • Experience with experimentation platforms and causal inference at scale.

AI Fluency - We're an AI-first company. That's not a buzzword here—it's how we build. At the Director level, you are expected to:

• Push the boundaries of what's possible with AI across the organization, from production ML systems to agentic workflows, and lead a high-impact team that does the same.

• Enable teams and coach AI strategy. Ensure your managers and ICs are actively using AI to improve their workflows, and measure the impact.

• Drive adoption of AI-assisted engineering practices across Data & AI and the broader engineering org.

• Champion responsible AI use—set guardrails, evaluation standards, and governance frameworks.

• Stay current on frontier AI developments and translate them into Homebase's product and technical strategy.

The Homie Way - These principles guide everything we do—from how we work and make decisions to how we show up for each other.

• Be Customer Obsessed – Solve problems with empathy and creativity.

• ⚡ Move Fast, Learn Fast – Experiment, take action, and grow every day.

• Own Your Impact – Think big, focus on what matters, and make decisions you stand behind.

• Master Your Craft – Excellence fuels impact—show up, step up, and make your mark.

• Win Together – Put goals over roles, lead with trust, and connect to our mission and each other.

What We Offer

• Ownership & Savings: Stock options + TFSA/RRSP with 4% company match

• Health & Wellness: Comprehensive medical, dental, and vision for you and your dependents

• ⏰ Paid Time Off: Flexible PTO + company holidays + designated focus periods

• AI access, for real: We invest in builders and believe that curiosity shouldn't have a paywall. That means you'll have access to paid AI tools with minimal restrictions, so you can build, experiment, and level up your craft.

• Family Support: Maternity/Parental Leave EI top-up support offered (after 6 months of service)

• Work Your Way: Work From Anywhere Month + meeting-free weeks yearly

• ️ Protection Plans: Life insurance + short/long-term disability coverage

• ️ Workspace Perks: Meals provided, team offsites, and Customer Days

• Our Hybrid Rhythm: We believe collaboration drives impact. That’s why Tuesdays and Wednesdays are our required in-office days —a time to move faster as a team, build deeper connections, make better decisions, and build together.

What to Expect During the Interview Process

• Meet the Talent Acquisition team. Mavel W.

• Meet the Hiring Manager, Andrea C.

• Meet with Engineering Leadership

• Participate in a Technical Deep Dive

• Meet Cross-functional Partners

• Meet with the Chief Development Officer, Ankit B.

• Background Check + Offer Stage

• Welcome to the team, Homie

Belonging at Homebase - We're committed to fostering a welcoming space where every Homie can be their full self. Experience comes in many forms—so if you're excited about this role, even if you don’t meet 100% of the qualifications, we encourage you to apply! 

Homebase will consider qualified applicants with criminal histories in a manner consistent with the San Francisco Fair Chance Ordinance.

Hey, We’re Homebase

Homebase is the everything app for hourly teams—built to simplify the day-to-day and superpower local businesses. With tools for scheduling, time clocks, payroll, communication, HR, and more, we help teams stay connected and in control. Today, over 150,000 small (but mighty) businesses rely on us to make work radically easier. Together, we’ve tracked over a billion hours for 2M+ workers—and we’re just getting started.

At Homebase, we celebrate diversity and are proud to be an equal opportunity employer. We welcome all candidates and do not discriminate based on any legally protected status. If you need accommodations during the hiring process, please let us know—we’re committed to ensuring fair and equitable access for all.