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Head of Total Rewards Strategy & Operations
Head of Total Rewards Strategy & OperationsZinnia • Old Greenwich, CT, US
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Head of Total Rewards Strategy & Operations

Head of Total Rewards Strategy & Operations

Zinnia • Old Greenwich, CT, US
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Head Of Total Rewards Strategy & Operations

Zinnia is the leading technology platform for accelerating life and annuities growth. With innovative enterprise solutions and data insights, Zinnia simplifies the experience of buying, selling, and administering insurance products. All of which enables more people to protect their financial futures. Our success is driven by a commitment to three core values : be bold, team up, deliver value.

Who You Are

The Vice President of Total Rewards will serve as a strategic and hands-on leader responsible for developing, executing, and evolving the company's global compensation and benefits programs. Reporting directly to the CHRO, this role will be central to driving both immediate operational excellence and long-term transformation, leveraging technology, AI-enabled insights, and modernized systems to reshape how the business manages, rewards, and retains its talent. The ideal candidate will thrive in a PE-backed environment where scale, speed, and rigor are critical, while also acting as a "player / coach" - capable of rolling up their sleeves to execute and deliver results today, while building the strategy, infrastructure, and team that supports the workforce of the future. This leader will know what great looks like, have the patience and stamina to chart the right sequencing of change, and deliver programs that make Zinnia an attractive, competitive place to work.

What You'll Do

  • Partner with the CHRO and executive team to design and implement a forward-looking Total Rewards strategy aligned with business priorities, growth objectives, and evolving market demands.
  • Lead the transformation of compensation and benefits programs into a technology-powered, AI-enabled platform that drives efficiency, scalability, and business insight.
  • Reimagine the Total Rewards operating model to balance immediate needs with long-term innovation.
  • Present insights, recommendations, and data-driven perspectives to the Board of Directors and Executive Leadership, helping shape decisions that influence the company's ability to manage and enable talent globally.
  • Oversee design, governance, and administration of global compensation structures, including base pay, incentive programs, equity, and executive compensation.
  • Implement scalable job architecture, pay-for-performance frameworks, and data-driven benchmarking practices.
  • Partner with Finance and business leaders to align compensation programs with company performance, talent strategy, and investor expectations.
  • Lead the strategy, design, and management of comprehensive benefits offerings (healthcare, retirement, wellness, leave, recognition, etc.) across diverse employee populations.
  • Maximize the effectiveness of existing third-party partners in payroll, benefits administration, and other services; evaluate future needs and recommend when to expand or transition providers.
  • Build innovative programs that address workforce wellbeing and engagement.
  • Modernize the rewards infrastructure by introducing AI-enabled tools, automation, and analytics platforms to deliver real-time insights and improve decision-making.
  • Ensure robust data governance and compliance in all aspects of compensation and benefits.
  • Drive continuous improvement and scalability in processes, systems, and tools.
  • Build, lead, and mentor a high-performing team of Total Rewards professionals, fostering a culture of accountability, innovation, and collaboration.
  • Serve as both strategist and hands-on operator, ensuring seamless execution of day-to-day operations while advancing transformational initiatives.
  • Collaborate with HR, Finance, Legal, and business leaders to ensure rewards programs are integrated, well-communicated, and effectively executed.

What You'll Need

  • 15+ years of progressive experience in Total Rewards, with at least 5 years in a senior leadership role overseeing both compensation and benefits in complex, multi-site or global organizations.
  • Proven experience in a private equity-backed environment strongly preferred; ability to operate with rigor, speed, and investor-focused discipline.
  • Demonstrated success leading large-scale transformational initiatives (technology enablement, operating model redesign, AI-driven insights, automation, etc.).
  • Strong background in partnering with third-party vendors to maximize value, service quality, and innovation.
  • Adept at presenting to Boards and Executives, with strong executive presence and ability to translate complex data into actionable insights.
  • Strong analytical acumen with the ability to leverage data, metrics, and insights to inform strategy and drive outcomes.
  • Excellent leadership and team-building skills; proven ability to inspire, develop, and retain high-performing teams.
  • Hands-on, "player / coach" mindset with a willingness to roll up sleeves and execute as needed.
  • Exceptional communication and influencing skills, with the ability to engage stakeholders at all levels of the business.
  • Bonus Points

  • Transformational Mindset : Able to envision and implement innovative, tech-enabled approaches to Total Rewards.
  • Hands-On Operator : Balances strategic thinking with operational execution; comfortable being in the details.
  • Business Orientation : Understands financial levers and PE-backed performance expectations.
  • Data-Driven Decision Maker : Uses analytics to drive insights, action, and continuous improvement.
  • Change Leader : Comfortable leading through ambiguity and guiding organizations through major transitions.
  • Patient Strategist : Knows how to sequence actions effectively for maximum impact, with the resilience and stamina to drive sustainable change.
  • What's In It For You?

    Zinnia offers excellent career progression and competitive compensation. We offer great benefits, including health / dental insurance, parental leave, 401(k), incentive / bonus opportunity, tuition reimbursement, and so much more. The expected salary range for this position is $200,000 - $250,000, dependent on skills and location. We're looking for the best and brightest innovators in the industry to join our team. At Zinnia, you collaborate with smart, creative professionals who are dedicated to delivering cutting-edge technologies, deeper data insights, and enhanced services to transform how insurance is done.

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    Head Of Strategy • Old Greenwich, CT, US

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