Director, Product — Compliance and Configuration

At AbsenceSoft, we’re transforming the employee experience. Our secure, intuitive technology helps employers bring humanity, certainty, and efficiency to some of the most complex moments in the workplace. Built by HR professionals for HR professionals, we’re proud of where we’ve been and even more excited about where we’re going.

The Director, Product - Compliance and Configuration is responsible for leading the strategy, roadmap and execution of AbsenceSoft’s compliance platform; the engine that encodes 200+ statutory leave and accommodation laws (FMLA, ADA, PWFA, state paid-leave programs) and keeps that content accurate as regulations change. This individual contributor role reports directly to the Chief Product Officer, and partners with a team of product managers and compliance domain experts and collaborates cross-functionally with Legal, engineering, design, and go-to-market to ensure compliance capabilities remain accurate, current, and market-competitive. The Director plays a pivotal role in advancing how AI and automation are applied to regulatory complexity, and in maintaining AbsenceSoft’s reputation for getting the law right.

• Define and execute the product vision and strategy for AbsenceSoft’s compliance platform.
• Partner with, mentor, and grow a team of product managers and compliance domain experts.
• Own the roadmap for the engine encoding 200+ statutory leave and accommodation laws (FMLA, ADA, PWFA, state paid-leave programs).
• Ensure compliance content stays accurate and current as laws change across supported jurisdictions.
• Advance the use of AI and automation to keep the platform ahead of the regulatory landscape.
• Exercise clear judgment on where automation adds value and where accuracy must be protected.
• Partner with Legal and compliance domain experts to translate regulatory requirements into scalable product capabilities.
• Partner with engineering, design, and go-to-market to ensure timely, high-quality delivery of compliance features.
• Drive go-to-market readiness for compliance capabilities in collaboration with Sales and Customer Experience.
• Instrument what you ship and and track outcomes against clear metrics.
• Present the compliance roadmap to executive leadership and to customers’ compliance and legal leaders.
• Represent the voice of the customer and their compliance and legal stakeholders across the product lifecycle.
• Monitor the regulatory landscape to identify emerging risks and opportunities.
• Participate in a highly compliant environment, assisting to maintain company controls and security within your role.
• Assist in maintaining applicable organizational security and compliance controls within your department and role.
• Other duties as assigned.

What’ll Set You Up for Success

Required Skills:

• Minimum 10 years of experience in product management, including time leading a product area end to end and managing or building a team of PMs.
• Demonstrated success setting product direction, aligning teams, driving measurable business outcomes, and shipping complex products on time.
• Direct experience owning a compliance, regulatory, or rules-engine product (RegTech, tax, legal, benefits, healthcare, fintech, or HR compliance). This is the core of the role.
• Proven ability to translate regulatory requirements into scalable product features.
• Proven experience shipping AI or LLM-powered products, with the evaluation rigor to keep quality high in accuracy-critical domains.
• Enterprise B2B SaaS experience with strong data fluency.

Preferred Skills:

• Domain experience in leave and absence, benefits, employment law, or HR tech preferred.
• Experience in a high-growth, scaling environment preferred.

Key Skills & Behaviors:

• Strategic thinking with the ability to connect product decisions to business outcomes.
• Strong working partnership with domain experts, legal, and regulatory SMEs.
• Presence to hold a room with compliance and legal leaders, internally and with customers.
• Decisive operator with a bias toward shipping and learning.
• Customer-obsessed approach with deep instincts for product quality.
• Clear, confident communicator who presents effectively to executive leadership.
• Sound judgment on where automation adds value versus where human review is required.
• Ability to translate complex regulatory requirements into clear product direction.
• Resilience and adaptability in a fast-changing regulatory environment.

Why join us

At AbsenceSoft, we LEAD with our values:

Lead with Innovation - We create meaningful change through intelligence, focus and passion.  We embrace curiosity, data, and insight to shape the future of our industry. Always innovating, learning and evolving.

Elevate Every Voice - Every perspective matters. We listen, learn, and build a culture where diversity of thought and experience drives better solutions and smarter decisions. 

Achieve Together - The customer fuels everything we do. We share knowledge, collaborate, celebrate wins, and face challenges as one team because success is always a collective achievement.

Drive Outcome - Every action we take delivers measurable value to our teams, our customers, and the employees they support. Accountability is non-negotiable. We honor our commitments, take responsibility for results, and see every success and setback as a chance to grow stronger.

We offer:

• Impact that matters. You’ll do work that shapes the future of the modern workplace
• Flexibility and trust. We’re remote-first and results driven. You’ll have the freedom and flexibility to do your best work, wherever you do it best.
• Growth and development. We believe the best work happens when people are growing. You’ll have access to learning resources, leadership programs, and real opportunities to take on new challenges and expand your impact.  
• Competitive rewards. We offer comprehensive benefits, a performance-based bonus program, and equity opportunities – because when we grow, you should too.
• Time for life. Recharge and reconnect with flexible time off, paid holidays, and flexible leave programs designed to support every season of life.
• Belonging and balance. We’re building an inclusive culture where every voice is valued, collaboration is celebrated, and success is shared.

We’re committed to building a team as diverse as the customers we serve. If your experience doesn’t align perfectly with every qualification, we still encourage you to apply you might be exactly what we’re looking for. If this sounds like a fit, apply today, we’d love to meet you!

Final compensation is determined based on a candidate's relevant experience, skills, education, and geographic location. This position is also eligible for annual bonus.