Senior Director, Compliance & Platform (AI)

Location: Remote (United States)

Salary: 214,000–268,000 USD per year (US National), plus eligibility for an annual bonus.

Company

HR technology company providing secure software for employee leave and accommodation management.

What you will do

• Own the strategy, roadmap, and results for the compliance engine and enterprise-scale platform, including retention, expansion, and win-rate outcomes.
• Consolidate product strategies across product managers and domain experts into a unified plan.
• Extend coverage of leave and accommodation laws across jurisdictions as regulations change.
• Set direction for configuration, identity and access, integrations, APIs, and data, including how enterprise customers adopt and extend the platform.
• Build, coach, and develop product managers, domain experts, and managers while raising standards for product craft, delivery speed, and AI-enabled work.
• Partner with Engineering, Legal, Customer Experience, Sales, Marketing, Finance, executive leadership, the board, and customers; maintain applicable security and compliance controls.

Requirements

• 15+ years in product management, including 5+ years leading product managers and experience leading managers or multiple product areas simultaneously.
• Proven experience owning a compliance, regulatory, or rules-engine product at enterprise scale in RegTech, tax, payroll, benefits, healthcare, fintech, or HR compliance.
• Proven experience owning a multi-tenant enterprise platform, including identity and access, configuration, integrations and APIs, or data.
• Track record of shipping complex products on committed dates for demanding enterprise customers, with clear personal contribution to delivery commitments.
• Experience shipping AI features into production in an accuracy-critical domain with rigorous evaluation and governance.
• Demonstrated ability to set product strategy that improved ARR, retention, or win rate, supported by measurable results.
• Enterprise B2B SaaS experience with strong data fluency, including scaling a product from mid-market to enterprise.
• Strong bias for action and speed in decision-making and delivery; clear and authoritative communication with senior customer stakeholders.
• Ability to work autonomously in ambiguity, learn alongside subject-matter experts, prioritize customers and product quality, and develop high-performing product leaders and teams.

Nice to have

• Experience in leave and absence, benefits, employment law, or HR technology.
• Experience working directly with legal and regulatory experts to translate requirements into products.
• Experience in a high-growth, scaling SaaS environment.

Culture & Benefits

• Remote-first, results-driven work environment with flexibility and trust.
• Learning resources, leadership programs, and opportunities for expanded responsibility.
• Comprehensive benefits, performance-based bonus program, and equity opportunities.
• Flexible time off, paid holidays, and flexible leave programs.
• Inclusive culture focused on innovation, collaboration, accountability, measurable outcomes, and diverse perspectives.