HR Generalist
The Opportunity
As our HR Generalist, you’ll build the core of our People Operations for a fast-moving insurtech team. You’ll own multi-state compliance for a Hybrid and Remote workforce, partner with our benefits broker, lead onboarding/offboarding, support employee relations, and keep policies and our handbook current—while driving programs that strengthen culture, engagement, and inclusion.
Your main role responsibilities will include the following:
HR Operations & Compliance
- Own multi-state employment compliance for a remote/hybrid team: wage/hour, time-off, pay transparency, posters/notices, meal/rest, final pay rules.
- Maintain the compliance calendar and filings: EEO-1, ACA, CA Pay Data, I-9/E-Verify, COBRA notices, harassment training, and handbook acknowledgments.
- Manage HRIS administration (employee records, org changes, workflows, audits, reporting).
- Audit and maintain our Employee Handbook annually to ensure compliance.
Benefits, Payroll Liaison & Comp Support
- Serve as day-to-day point of contact with our benefits broker; drive open enrollment, qualifying life events, and employee education. Ensure benefits offerings are market competitive while maintaining a financially sound cost structure.
- Partner with Finance/Payroll on benefits deductions, reconciliations, and audits; resolve employee inquiries.
- Support compensation processes (market benchmarking, annual review cycle tooling, equity/grant comms in partnership with Finance/Legal).
Employee Relations & Manager Support
- Provide first-line ER guidance (coaching, performance documentation, investigations triage) and escalate appropriately.
- Enable managers with templates, toolkits, and training (goal setting, feedback, corrective action).
Onboarding, Offboarding & Talent Ops (HR-specific)
- Own end-to-end onboarding (pre-boarding, background checks, I-9/E-Verify, systems access, orientation, 30/60/90 surveys).
- Run offboarding (checklists, access removal, exit interviews, final pay coordination, asset return).
- Partner with Hiring Leaders and Talent Acquisition resources on headcount planning, interview process development, candidate experience and (scorecards, training, bias-aware process).
- Develop and maintain Employer Branding that markets Understory as a Top Employer in the Madison area and broadly within the InsurTech category.
Culture, Engagement & Communications
- Be the culture catalyst: design and deliver programs that build community (buddy program, recognition, wellness/volunteer initiatives, ERGs/interest groups).
- Run employee engagement surveys and onboarding NPS; analyze insights and drive action plans with leaders.
You're exactly the role model we're seeking if you:
- Are excited about a Hybrid schedule in our Madison, WI office 2-3 days per week.
- 3–6+ years progressive HR/People Ops experience.
- Demonstrated expertise in multi-state remote compliance and leave administration.
- Strong benefits and broker management experience; comfort partnering with Payroll/Finance.
- Solid employee relations judgment; credible partner to managers and employees.
- HRIS and ATS proficiency; HRIS selection and implementation experience is a plus.
- Exceptional communication, discretion, and documentation skills.
- SHRM-CP/SHRM-SCP or PHR/SPHR preferred.
Compensation includes:
- Competitive base salary commensurate with experience + annual corporate bonus.
- Comprehensive benefits package including health, dental, and vision insurance, plus a 401(k) plan.
- Unlimited PTO
About Understory
Understory is a leading provider of insurance solutions built for the era of climate change. The company's global network of Dot weather stations powers the world's most sophisticated weather risk model. By combining mutualized, optimized risk structures with precision weather technology and modeling, Understory develops affordable, stable property insurance solutions.
Traditional insurance is no longer fit for purpose. Natural catastrophes driven by the volatility of climate change is increasing rates and restricting coverage. Insurance and reinsurance companies are pulling out and leaving 76% of global assets unprotected. Transformation is inevitable, and disruption is coming to a $1T market. Understory cracked the code, and our approach is the only way to close this gap.
Comprising a compact yet fiercely dedicated & passionate remote team, Understory is a mission-centric, results-driven start-up that thrives on relentless adaptability and resilience. We cherish accountability and push the limits at breakneck speeds, always backed by the unwavering support of our colleagues. To sustain our drive, we place significant emphasis on work-life harmony, nurturing our families, and fostering our communities.