Director, Benefits

The Team:
At Datadog, the People team is more than just human resources—it’s a data-driven team dedicated to constantly improving the way we hire, develop, and support our most valuable asset: our people. Our People team are strategic problem solvers who work closely with leadership and employees to ensure that Datadog continues to scale smoothly and remains a great place to work.

The Opportunity:
We are seeking a Director, Benefits to lead and evolve our benefits function. This senior leadership role will not only manage and mentor the Americas Benefits team, it will also play a key role in driving the strategic vision for benefits at Datadog. The Benefits Director will be responsible for overseeing and enhancing the benefits programs, including the management of our 401(k) plan, while ensuring they align with Datadog’s overarching goals for talent attraction, retention, and well-being. This role offers a unique opportunity to make a substantial impact on the employee experience across multiple countries.

You will collaborate closely with senior leadership and cross-functional teams to ensure our benefits programs are competitive, inclusive, and aligned with Datadog’s culture and values. As a key decision-maker, you will be responsible for ensuring operational excellence, compliance, and driving employee engagement with our benefits offerings. You’ll lead a high-performing benefits team and foster a culture of continuous improvement to deliver value to our employees.

At Datadog, we are a hybrid workplace, allowing our Datadogs to create a work-life harmony that best fits their needs, while contributing to our culture of collaboration, creativity, and shared success.

What You’ll Do:

• Lead and Innovate: 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.
  
  
• Strategic Leadership: Lead the Benefits team, providing mentorship, guidance, and strategic direction to team members.
  
  
• Drive 401(k) Management: Take ownership of Datadog’s 401(k) plan, ensuring it aligns with our overall benefits strategy and remains competitive and compliant.
  
  
• Program Design & Optimization: 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.
  
  
• Employee Engagement: Champion effective communication of our benefits offerings, ensuring employees understand the value of the programs available to them and driving higher engagement and utilization.
  
  
• Compliance & Risk Management: 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).
  
  
• Partnership with Leadership: 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.
  
  
• Data-Driven Decision Making: Lead regular program assessments and audits to optimize cost management and ensure benefits are aligned with employee preferences and market trends.
  
  

Who You Are:

• 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 strategical