AVP, Total Rewards

SageSure•Chicago, IL

12h•Remote

About The Position

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.

Requirements

Bachelor’s degree in Human Resources, Business Administration, or a related field (required).
12+ years of progressive Total Rewards experience, including compensation, benefits, payroll, equity, and HR systems.
Hands-on experience in administering complex equity and long-term incentive programs within a private equity-backed organization, including managing multiple plan structures concurrently.
Hands-on experience in administering complex equity and long-term incentive programs within a private equity-backed organization, including managing multiple plan structures concurrently.
Demonstrated experience administering equity programs, including non-stock options (NSOs) and long-term incentive plans for private companies.
Proven ability to operate effectively in a highly operational, hands-on role while also setting strategic direction.
Extensive experience managing multi-state payroll, including complex states such as California.
Deep expertise in payroll taxes, compliance, and regulatory nuances across multiple jurisdictions.
Demonstrated experience replacing or significantly upgrading legacy systems that no longer meet the needs of a maturing organization.
Workday experience strongly preferred.
Experience successfully leading and managing remote teams.
Strong background in auditing and compliance, with a proactive, detail-oriented approach to risk management.
Experience leading and supporting change management initiatives across systems, processes, or organizational growth phases.
Track record of managing annual merit, bonus, LTIP, and deferred compensation payout processes for a private company.
Experience working in a multi-site, multi-state environment.
Experience with profits interest plans and K-1 tax treatment (preferred).
Strong understanding of HR technology platforms and systems implementation/optimization (e.g., UltiPro, Carta, DOMO).
Advanced analytical skills with the ability to translate data into insights and recommendations.
Exceptional communication skills and executive presence, with the ability to influence and partner with senior leaders and cross-functional stakeholders.

Nice To Haves

Advanced degree (Master’s or higher) in Human Resources, Business Administration, or related field.
Professional certifications such as CCP, CEBS, SHRM-SCP, SPHR, or similar.
Significant leadership experience designing and managing sophisticated Total Rewards programs within a private-equity backed organization.
Experience designing and administering complex benefits programs within a non-public company environment.

Responsibilities

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 accuracy, timeliness, and compliance with state-specific wage, hour, and tax regulations.
Oversee benefits administration across multiple legal entities and plan structures, ensuring compliance, consistency, and operational alignment across the organization.
Serve as the organization’s subject-matter expert in payroll taxes, multi-state payroll nuances, and regulatory compliance.
Lead and support internal and external audits, with a strong focus on compliance, controls, and risk mitigation across payroll, equity, and benefits programs.
Partner closely with Finance and FP&A on equity modeling, benefits cost modeling, budgeting, forecasting, and reconciliation related to annual compensation cycles, promotions, and incentive payouts.
Provide clear education and guidance to executives, managers, and employees on Total Rewards programs, equity mechanics, and payroll-related matters.
Drive change management initiatives related to Total Rewards, payroll, equity, and HR systems, ensuring smooth adoption and minimal disruption.
Lead large-scale HR system transformations, including requirement definitions, vendor partnerships, data migration, testing, change management, and post-launch stabilization.
Optimize and oversee People systems and data, ensuring data integrity, reporting accuracy, and operational efficiency.
Build foundational Total Rewards reporting and analytics capabilities, establishing reliable data, metrics, and insights.
Manage vendor relationships across compensation, benefits, payroll, and equity administration, including contract negotiation and cost management.
Stay current on evolving federal, state, and local regulations impacting Total Rewards programs (e.g., ACA, FLSA, COBRA, HIPAA, payroll tax law).
Act as a trusted advisor with executive presence, partnering effectively with leaders at all levels of the organization.
Assess, develop, and, where necessary, redesign the Total Rewards operating model to meet the demands of a growing, complex organization, setting clear performance expectations and accountability.