AVP, Total Rewards (Chicago)

OverviewIf 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-NegotiablesPrivate Equity–Backed Company ExperienceDirect 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 ExpertiseHands-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 LeaderDemonstrated 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 LeadershipProven 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 MasteryDeep experience managing a workforce across 45 states, with expert-level knowledge of payroll tax nuances, compliance requirements, and risk mitigation.HRIS Transformation ExperienceDemonstrated success replacing, significantly upgrading, or optimizing legacy HRIS and People systems to support scale, reporting, compliance, and improved employee experience in a growing organization.Audit & Compliance ExperienceStrong background in auditing compensation, benefits, equity, and payroll practices, with a rigorous focus on compliance, internal controls, and regulatory adherence.Change Management LeadershipProven 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 PartnershipClear 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 DoingDevelop 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 complexityOversee 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.We’re Looking for Someone Who HasBachelor’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.Highly PreferredAdvanced 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.About SageSure:Named among the Best Places to Work in Insurance by Business Insurance for four years in a row (2020-2023), SageSure is one of the largest managing general underwriters (MGU) focused on catastrophe-exposed property in the US. Since its founding in 2009, SageSure has experienced exceptional growth while generating underwriting profits for carrier partners through hurricanes, wildfires, and hail. Available in 16 states, SageSure offers more than 110 home, flood, and commercial products on behalf of its highly rated carrier partners. Today, SageSure manages more than $3.2 billion of inforce premium and helps protect more than 970,000 policyholders.   We have more than 1,000 employees in a distributed workforce environment across 12 offices—Fairfield, CA; Mountain View, CA; Cheshire, CT; Jacksonville, FL; Tallahassee, FL; Tampa, FL; Chicago, IL; Jersey City, NJ; Marlton, NJ; Cincinnati, OH; Houston, TX; Sheboygan, WI—who are tackling the industry’s toughest challenges.     SageSure is a proud Equal Opportunity Employer committed to building a workforce that reflects the spectrum of perspectives, experiences, and abilities of the world we live in. We recognize that our differences make us strong, and we actively seek out diverse candidates through partnerships with organizations, institutions and communities that represent various backgrounds. We champion belonging and inclusion for all identities, including, but not limited to, race, ethnicity, religion, sexual orientation, a