AVP, Total Rewards
SageSure
| Company | SageSure |
| Category | Finance |
| Location | Chicago |
| Remote | On-site (inferred) |
| Employment | Not stated |
| Level | Not stated |
| Salary | Not stated by the employer |
| Posted | 15 Jun 2026 |
| Last verified | 6 Aug 2026 |
| Source | Employer ATS (greenhouse) |
Description
Overview
If you're looking for the stability of a profitable, growing company with the entrepreneurial spirit of a startup, we’re hiring. SageSure , a leader in catastrophe-exposed property insurance, is seeking an Assistant Vice President (AVP) of Total Rewards . This role is ideal for a seasoned Total Rewards leader with private equity experience , strong operational rigor, and the executive presence to partner effectively across the organization.
As the AVP, Total Rewards, you will own both the strategy and execution of SageSure’s Total Rewards roadmap—shaping compensation, benefits, equity, payroll, and HR systems to attract, retain, and motivate a geographically distributed workforce. This role is equally tactical and strategic , requiring deep hands-on expertise alongside the ability to influence senior leaders and guide change at scale.
You will play a critical role in ensuring our programs are compliant, competitive, scalable, and aligned with the expectations of a private equity–backed environment , while leading and developing a high-performing remote team .
Non-Negotiables
Private Equity–Backed Company Experience Direct experience operating within a private equity–backed organization, including administering and evolving Total Rewards programs in a PE environment with strong governance, pace, and accountability.
Equity & NSO Expertise Hands-on experience designing, administering, and educating stakeholders on equity programs, including Non-Stock Options (NSOs) and other private-company equity vehicles, with a strong understanding of tax and compliance implications.
Operationally Strong Total Rewards Leader Demonstrated ability to operate at both a strategic and highly tactical level, with deep ownership of day-to-day execution across compensation, benefits, equity, payroll, and HR systems.
Remote Workforce Leadership Proven success leading and developing a remote or highly distributed team, with the ability to drive accountability, performance, and engagement across geographies.
Multi-State Workforce & Payroll Tax Mastery Deep experience managing a workforce across 45 states, with expert-level knowledge of payroll tax nuances, compliance requirements, and risk mitigation.
HRIS Transformation Experience Demonstrated success r eplacing, significantly upgrading, or optimizing legacy HRIS and People systems to support scale, reporting, compliance, and improved employee experience in a growing organization.
Audit & Compliance Experience Strong background in auditing compensation, benefits, equity, and payroll practices, with a rigorous focus on compliance, internal controls, and regulatory adherence.
Change Management Leadership Proven ability to lead and execute enterprise-level change, including systems implementations, program redesigns, and process improvements, while effectively influencing stakeholders at all levels.
Executive Presence & Leadership Partnership Clear executive presence with the ability to serve as a trusted partner to senior leaders, influence decision-making, and confidently represent Total Rewards strategy at the executive and board level.
What You’d Be Doing
Develop and execute a comprehensive Total Rewards strategy aligned with business objectives and private equity expectations, including compensation, benefits, equity, and payroll programs.
Lead the design, administration, and management of compensation and equity plans for a large, diverse employee population in a private company environment, ensuring accurate eligibility management, lifecycle administration, employee education, and compliance.
Lead the stabilization, redesign, and scaling of Total Rewards operations, addressing legacy processes and systems that can scale with organizational growth and complexity
Oversee payroll strategy and execution for a fully remote workforce spanning 45 states , ensuring acc