Director – Benefits

Director – Benefits

Requirements

• At least 10 years of progressive experience in benefits, including strategy development, program design, administration, and compliance.
• Experience transition and managing a self-funded plan – Ensuring compliance with insurance regulations and managing the associated risk, including working closely with legal, vendors, and brokers to ensure proper reporting and auditing for the US.
• Proven leadership experience with a track record of managing a team and driving results in a fast-paced, high-growth environment.
• Deep expertise in 401(k) plan management and a thorough understanding of benefits compliance (e.g., ERISA, ACA, IRS regulations).
• Strong experience with Workday and benefits administration systems.
• Excellent analytical skills with proficiency in Excel (pivot tables, vlookups, conditional formatting, etc.).
• Strong communicator with the ability to influence and engage at all levels of the organization, including C-suite executives.
• Ability to think strategically and creatively, balancing both employee needs and business goals.

Responsibilities

• Oversee the entire benefits function, including but not limited to: medical, dental, vision, life insurance, Flexible Spending Accounts (FSA), commuter benefits, retirement plans, voluntary & supplemental benefits, and wellness programs.
• Lead the Benefits team, providing mentorship, guidance, and strategic direction to team members.
• Take ownership of Datadog’s 401(k) plan, ensuring it aligns with our overall benefits strategy and remains competitive and compliant.
• Continuously assess and enhance the design and delivery of benefits programs to ensure they meet the needs of our diverse employee base. Use data-driven insights to make recommendations that promote adoption and satisfaction.
• Champion effective communication of our benefits offerings, ensuring employees understand the value of the programs available to them and driving higher engagement and utilization.
• Ensure all benefits programs comply with state, federal, and international regulations. Work closely with legal, benefits brokers, and vendors to ensure accurate reporting, filing, and audit responses (e.g., ACA reporting, 5500 filings, IRS and DOL compliance).
• Partner with senior leadership and key stakeholders to align benefits strategies with company goals and employee needs, ensuring our programs support Datadog’s growth and retention initiatives.
• Lead regular program assessments and audits to optimize cost management and ensure benefits are aligned with employee preferences and market trends.

Preferred Qualifications

• Certifications such as PHR, SPHR, or CEBS are a plus.
• Experience in a high-growth, global company, ideally in a tech or SaaS environment, is highly desirable.
• A service-oriented mindset with a passion for employee well-being and creating positive workplace cultures.
• Maintains a strong professional network across the Benefits space to stay ahead of emerging trends, legislative changes, and innovative vendor solutions.
• Leverages external networks and partnerships to pull relevant benchmark data, ensuring our programs are competitive, market-aligned, and tailored to evolving employee needs.
• Experience managing benefits in Mexico, Brazil and Canada