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Toronto, Ontario, Canada
Hybrid
Purpose in Every Position
Pebl puts a world of talent at your fingertips. With our AI-powered Global Work Platform™, companies can hire, pay, and manage employees in 185+ countries—removing risk, red tape, and guesswork from global growth. Backed by more than a decade of compliance leadership and local expertise, Pebl helps businesses move fast, stay compliant, and scale with confidence. With Pebl, companies everywhere can hire great talent anywhere.
Where Your Work Moves the Needle.
At Pebl, every team member drives our success. Joining us means more than filling a role—you’re accountable for results and impact. Our values guide how we operate, execute, and collaborate across borders. By putting them into action, you’ll help us scale faster, compete harder, and lead the future of global work.
What Makes You a Great Fit
We are seeking a highly technical, deeply analytical, and aggressively innovative Director of Data to lead our data strategy, infrastructure, and AI integration. You will not just be managing a team; you will be the chief storyteller for our data and the evangelist for our "AI Everywhere" initiative.
Based out of our Palo Alto office, you will sit at the intersection of R&D and our core business functions—specifically Marketing, Sales, Operations, Finance, and Legal—ensuring that Pebl’s vast repository of global employment and compliance data is secure, accessible, and actionable.
In-office collaboration is required at our Toronto office Monday through Wednesday.
How You'll Make An Impact:
1. Architect the Future (Technical & Hands-On Data Engineering)
Own the vision and execution of Pebl’s modern data infrastructure.
Serve as the ultimate technical authority on data engineering, ensuring highly scalable, performant, and reliable data pipelines.
Champion strict data security, privacy, and governance protocols to protect our global payroll, HR, and compliance data.
2. Drive Actionable Business Insights (Analytical Powerhouse)
Transform complex datasets into clear, actionable strategies across all departments.
Partner with Marketing and Sales to optimize our growth funnel, CAC, and conversion rates.
Collaborate with Operations, Finance, and Legal to improve billing accuracy, payroll speed, and compliance tracking.
3. Champion "AI Everywhere" (AI Native Operations)
Lead the charge to make Pebl a truly AI-native company.
Bring AI capabilities to our R&D offerings, such as enhancing our compliance assistant, Alfie.
Engage directly with Marketing, Sales, Operations, Finance, and Legal to embed AI into their daily workflows, driving massive internal efficiency.
4. Bridge the Gap (Communication & Storytelling)
Act as the ultimate translator between deep technical R&D work and overarching business objectives.
Master the art of data storytelling to present complex insights to the executive team and the board in a compelling way.
5. Build and Foster the Team (Leadership)
Lead the Charge: Be a hands-on, execution-oriented leader who ensures delivery of strong business results.
Be the NBA Coach: Recruit top-tier talent and assemble a high-performing team of data engineers, analysts, and AI specialists.
Be the Gardener: Foster a culture of continuous learning and psychological safety to cultivate a data-driven mindset across the entire company.
Let's Connect If You Have:
Extensive Technical Background: 15+ years of experience in data engineering, data science, or analytics, with at least 5 years in a senior leadership role.
Modern Stack Mastery: Deep, hands-on expertise orchestrating our specific modern data infrastructure stack: Snowflake, Fivetran, Atlan, Looker, and Monte Carlo.
AI/ML Track Record: Proven experience deploying LLMs, machine learning models, and AI tools for both production products and internal operational workflows.
Cross-Functional Business Acumen: Demonstrated ability to collaborate with Marketing, Sales, Operations, Finance, and Legal to tie data initiatives directly to top-line growth and bottom-line efficiency.
Exceptional Communication: A track record of weaving data into compelling business narratives for non-technical stakeholders.
Work Style: Ability to work from our Palo Alto office Monday through Wednesday to collaborate directly with the executive and R&D teams.
Our Commitment to You
At Pebl, we’re committed to supporting our team with comprehensive rewards and benefits designed to meet diverse needs across roles and locations. Our core offerings include:
Flexible Time Off – Take the time you need to recharge.
Parental Leave – Support for growing families.
Health and Dental Insurance – Where applicable, to cover you and your loved ones.
Retirement Savings + Employee Incentive Plan – Plan for the future while sharing our success.
Please visit our career page for more information.
Pebl is an Equal Opportunity Employer.
We power global teams and believe diverse perspectives drive innovation and impact. Employment decisions at Pebl are based on qualifications, merit, and business needs. We do not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, or gender identity), national origin, age, disability, genetic information, veteran status, or any other status protected by applicable law. We’re committed to fostering an inclusive culture where every teammate can thrive and do the best work of their career—anywhere in the world.