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Senior Director, Total Rewards

Milestone Technologies

Dallas, TX · Posted November 4, 2026

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How AI is used in this kind of work

AI use among compensation and benefits managers is little observed so far. Measured exposure for compensation and benefits managers: 0% (little observed).

Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.

Check how this applies to your own job

Milestone Technologies has filed 6 layoff notices in the last twelve months, covering 390 workers, most recently October 2026. These are public filings with state labor departments, and an open role can sit alongside them. See the filings

Skills this job asks for

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  • Excel
  • Onboarding
  • Workday
  • HIPAA
  • M&A

About the job

Milestone Technologies is seeking a dynamic and visionary Head of Total Rewards and People Analytics to lead and inspire our global compensation and benefits team, serving 16 diverse countries worldwide. This is a unique opportunity to shape and elevate our Total Rewards strategy, ensuring it successfully reflects our Employee Value Proposition while meeting the evolving needs of a global, high-performing workforce. As a strategic leader, you will drive innovation, operational excellence, and exceptional employee experiences in a competitive and fast-paced environment. Reporting directly to the Chief People Officer, you will play a key role in influencing business success through people-centric rewards and insights.

Please note: We will consider candidates in Texas, Colorado, Illinois, Virginia and Georgia locations.

How You Will Make an Impact:

As the leader of our global Total Rewards strategy, your strategic vision and strong execution ability is needed to build equitable, competitive, and valuable rewards that meet the needs of our diverse global workforce—while maintaining financial stewardship by balancing cost with employee value.

• Collaborate effectively within the People Experience organization as well with other organizations to effectively drive the development and analysis of compensation programs, including base and variable pay while driving change on an organization-wide scale.

• Oversee all processes associated with compensation programs, including roll-out strategies and communications as well as training.

• Manage the job costing function, collaborating with Sales and Service Delivery, for pricing roles for customer RFP responses and contract renewals.

• Provide expertise, guidance, and education to leaders and managers on our compensation programs.

• Perform ad-hoc analysis and manage special projects (e.g., job architecture and leveling, organizational planning, compensation strategy, retention).

• Drive continual improvement in our compensation and benefits programs, practices and policies.

• Develop and drive an effective Benefits communication strategy to ensure employee understanding of benefits plan offerings and policies.

• Design and ensure delivery of an optimal employee experience for Benefits related processes and events (e.g. Open enrollment, life events, onboarding, etc).

• Manage vendor relationships to ensure optimal execution of benefits programs. Lead negotiations and annual contract renewals with our carriers globally and assess fit for future needs as we scale.

• Leverage collaborative partnerships with our benefits and retirement administrators to maintain compliance with US federal and state regulations (ERISA, HIPAA, FMLA, COBRA, ACA, etc).

• Oversee the management of global benefit programs in accordance with market practices and statutory regulations.

• Build meaningful people analytics for use within People Experience and for use by Executives, managers, and other organizations with a need for workforce data.

• Inspire employee confidence with a strong customer service focus.

What You Will Need to Succeed:

• Bachelor’s degree in business administration, Human Resources, or related field.

• 15+ years relevant compensation, benefits, and leadership experience.

• Broad experience with strategic compensation and benefits programs to attract, develop and engage the workforce.

• Workday experience with compensation and analytics modules is required as well as a high level of proficiency with process design/efficiency and systems.

• Expertise with job costing and burden rate calculations for global contingent workforce is required.

• Advanced proficiency in Microsoft Excel (can perform complex functions) and qualitative analysis.

• High level of competency in leading a team and maximizing capabilities.

• Experienced with Radford Global Technology Survey or similar market survey providers.

• Strong collaborative, interpersonal, verbal, and written communication skills.

• Strategic planner with sound business skills, analytical ability, good judgment, with strong operational focus.

• Familiarity with M&A a plus.

• Intense focus on employee experience.

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