Senior Director, Compliance & Platform

Accountabilities:

Own the product strategy, roadmap, and business outcomes for compliance and platform solutions, driving customer retention, expansion, and competitive win rates.
Collaborate with product managers and domain experts to develop a unified product strategy, empowering individual leaders to own their respective areas while aligning priorities across the broader portfolio.
Expand and maintain regulatory compliance coverage across jurisdictions, ensuring products evolve alongside changing leave, accommodation, and employment-related legislation.
Define and execute the enterprise platform strategy, encompassing configuration, identity and access management, integrations, APIs, and data infrastructure, while enabling customers and partners to adopt and extend the platform effectively.
Lead, mentor, and develop high-performing product teams, including product managers, domain experts, and people managers, fostering strong product practices, faster delivery, and AI-enabled workflows.
Partner closely with Engineering to deliver complex products on schedule, maintain high quality standards, and integrate AI capabilities with rigorous accuracy, evaluation, and governance practices.
Collaborate with Legal, Customer Experience, Sales, Marketing, and Finance to align product priorities with customer needs, commercial objectives, and regulatory requirements.
Represent compliance and platform initiatives with executive leadership, board members, enterprise customers, and other key stakeholders.
Support the maintenance of organizational security, risk management, and compliance controls within the scope of the role and department.
Undertake additional responsibilities as required to support business priorities.
Requirements:
Extensive product leadership experience: 15+ years in product management, including at least five years leading product managers and demonstrated experience managing managers or overseeing multiple product areas simultaneously.
Regulatory and compliance expertise: Proven experience owning an enterprise-scale compliance, regulatory, or rules-engine product. Relevant industries include RegTech, tax, payroll, employee benefits, healthcare, fintech, and HR compliance. This experience is essential for the role.
Enterprise platform leadership: Demonstrated ownership of a multi-tenant enterprise platform, including capabilities such as identity and access management, configuration, integrations, APIs, and data infrastructure.
Enterprise product delivery: A strong track record of delivering complex products to demanding enterprise customers against committed timelines, with clear personal accountability for execution and results.
AI product experience: Experience bringing AI-powered features into production within accuracy-critical environments, supported by rigorous evaluation processes, governance, and quality controls.
Commercial impact: Proven ability to develop and execute product strategies that improve annual recurring revenue (ARR), customer retention, or win rates, supported by measurable business results.
B2B SaaS expertise: Significant experience in enterprise B2B SaaS, strong data literacy, and a demonstrated ability to scale products from mid-market customers to enterprise organizations.
Preferred domain knowledge: Experience in leave and absence management, employee benefits, employment law, or HR technology, as well as direct collaboration with legal and regulatory experts to translate complex requirements into product functionality.
Scaling experience: Previous experience in a high-growth SaaS business where adaptability, operational discipline, and continuous improvement are essential.
Leadership and communication: Strong decision-making skills, a bias for action, and the ability to communicate clearly and confidently with senior stakeholders, including CHROs, General Counsel, and CIOs.
Strategic autonomy: Ability to navigate ambiguity, establish direction with minimal guidance, and balance strategic thinking with hands-on execution.
Customer focus and product quality: A strong commitment to understanding customer workflows, learning directly from users, and delivering intuitive, reliable, high-quality products.
Team development: Proven ability to coach, empower, and develop product leaders while building collaborative, accountable, and high-performing teams.
Benefits:
Competitive compensation: Annual salary ranging from $214,000 to $268,000 USD, depending on relevant experience, skills, education, and geographic location.
Performance-based rewards: Eligibility for an annual bonus and equity opportunities.
Comprehensive healthcare and benefits: Access to a comprehensive employee benefits package.
Remote-first flexibility: Work remotely from anywhere in the United States, with a results-driven culture built on trust and autonomy.
Flexible time off: Flexible paid time off, paid holidays, and leave programs designed to support different life circumstances.
Professional development: Access to learning resources, leadership development programs, and opportunities to expand responsibilities and career impact.
Meaningful impact: The opportunity to shape technology that helps employers navigate complex workplace situations and improve the employee experience.
Inclusive culture: A collaborative environment that values diverse perspectives, encourages shared ownership, and celebrates collective success.
Innovation-driven workplace: The opportunity to influence product strategy, explore AI-enabled ways of working, and continuously improve solutions for enterprise customers.