Sr Director, People Operations & Total Rewards (Oak Brook)

Sr. Director, People Operations & Total Rewards

Job Summary

The Sr. Director, People Operations & Total Rewards is a senior HR leader responsible for designing and leading RedSail’s compensation, benefits, and HR operations strategy. This role sits at the intersection of total rewards strategy, HR operations excellence, and business partnership, ensuring RedSail has the scalable people infrastructure, competitive rewards programs, and leadership advisory support needed to enable growth. Reporting to the Chief People Officer, this leader ensures RedSail's pay and benefits programs are competitive, equitable, and sustainable, while building scalable HR operations infrastructure that supports a growing organization. The Sr. Director also serves as an HR Business Partner to assigned senior leaders and functions, develops HR talent, and partners closely with Finance, Payroll, Legal, and senior HR leadership to align total rewards strategy with business objectives. This individual also serves as a trusted advisor to the CPO and executive team.

Key Duties

Total Rewards

• Own the enterprise compensation strategy, including salary structures, job leveling, and incentive programs that ensure internal equity and market competitiveness.
• Lead annual compensation planning cycles and ongoing market benchmarking and pay equity analysis, partnering with Finance and business leaders to keep pay practices competitive, defensible, and compliant.
• Own the design, vendor management, and cost strategy for health & welfare and retirement (401(k)) benefits programs, including annual open enrollment.
• Evaluate benefits plan performance, cost trends, and utilization, recommending plan design changes that balance employee experience with cost management.

People Operations and Compliance

• Own the People Operations function, including HRIS strategy, payroll partnership, HR compliance and data integrity across the employee lifecycle.
• Identify and lead HR technology, workflow, and process improvements that increase efficiency, strengthen data quality, and improve the employee and leader experience.
• Establish and maintain HR operations and total rewards metrics, dashboards, and reporting routines that provide visibility into service levels, compliance, cost trends, employee experience, and program effectiveness.

HR Business Partnership

• Serve as the HR Business Partner to assigned senior leaders and functions, providing proactive counsel on organizational design, workforce planning, and complex employee relations matters.
• Advise business leaders on compensation structuring for new roles, promotions, and organizational changes, ensuring decisions align with both business needs and total rewards strategy.
• Represent the human capital perspective in business planning discussions, serving as a bridge between business strategy and HR program delivery.

Team Leadership & HR Talent Development

• Lead, develop, and inspire a team of People Operations and Total Rewards professionals, building a high-performing, service-oriented team culture.
• Build team capability and future HR leadership bench strength through individual development plans, stretch assignments, mentorship, and clear performance expectations.
• Lead change management and communication planning for total rewards, HR operations, HR technology, and compliance initiatives to drive adoption, minimize disruption, and ensure leaders and employees understand what is changing and why.
• Serve as a senior thought leader across the HR pillar, contributing to enterprise HR strategy alongside the CPO and peer HR leaders.
• Ensure programs and practices are equitable, legally compliant, and aligned with RedSail's values and policies.
• Support HR diligence and integration activities for acquisitions.
• Performs other duties as assigned.

Education/Training

• Bachelor's degree in Human Resources, Business, Finance, or a related field required; Master's degree or relevant certification, such as CCP, CEBS, or SHRM-SCP, preferred.
• Ten or more years of progressive HR experience, including significant depth in compensation, benefits, or HR operations, with at least five years in a senior leadership role managing teams and programs at an enterprise level.

Required Work Experience/Skills

• Demonstrated expertise in compensation design, benefits strategy, and HR operations, with a track record of building programs that are competitive, compliant, and scalable.
• Executive presence and the ability to build credibility with and influence senior leaders, including C-suite stakeholders.
• Experience partnering with Payroll, Finance, and Legal on complex compensation, benefits, and compliance matters.
• Proven ability to lead, develop, and inspire high-performing teams in a fast-paced, growth-oriented environment.
• Strong vendor management skills, with experience negotiating and managing broker, carrier, and HRIS vendor relationships.
• Demonstrated ability to lead cross-functional process improvements that simplify workflows, increase operational efficiency, and improve stakeholder experience.
• Excellent communication and consultative skills, with the ability to explain complex concepts clearly to employees and leaders at all levels.
• Strong proficiency with HRIS platforms, compensation management tools, and Microsoft Office applications.

Discretionary Judgment

• Regularly exercises high-level independent judgment on sensitive, complex, and confidential matters involving compensation, benefits, and HR compliance.
• Uses good judgment and possesses ethical work values; models integrity and discretion in all aspects of the role.

Physical Demands, Working Conditions, and General Employment Guidelines

• Moderate or high levels of stress may be experienced in the performance of the job
• Position is performed in a general office environment, home office, or approved remote workspace where physical work includes, but is not limited to, sitting, standing, reaching, kneeling, bending, and lifting to 25 lbs.

Equipment

• Must have high speed internet access and suitable home office setup in order to work a hybrid schedule.

Safety to Self and Others

• Little responsibility for safety of others. Job is performed in an office setting where there are no hazardous materials or equipment.

Working Conditions/Hazards

• Position is performed in an open office environment or approved remote work location.

Compensation & Total Rewards

• The anticipated base salary range for this position is $160,000-$180,000 annually.
• This position is also eligible for an annual target bonus of 15-20%. Actual compensation will be determined based on factors including relevant experience, skills, qualifications, and geographic location.
• Benefits include paid time off, medical, dental, and vision insurance, a 401(k) with a 5% company match, a fitness bonus, professional development opportunities, and programs that support overall well-being.

Work Location

• Near any RedSail office.

Equal Opportunity Employer
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