Head of Employment & Risk

Proper Hospitality is hiring a senior, operationally focused employment and risk leader to own the areas of the business where legal exposure is real, frequent, and expensive if mishandled.Position OverviewThis role sits close to the operators. As the Head of Employment & Risk, you will work directly with GMs, People & Culture, and department heads across the portfolio to guide decisions in real time and prevent issues before they become claims.This is not a back-office legal role. The expectation is clear judgment, direct guidance, and the ability to build systems that allow the company to scale without increasing legal risk.You will also support a defined lane of routine commercial contracts across the business, while partnering with outside counsel and senior leadership on more complex or strategic matters.What You OwnEmployment & Labor (Primary Focus)Own California wage and hour compliance across all properties: timekeeping, meal and rest breaks, overtime, final pay, and related practicesMaintain proactive compliance practices across California wage and hour obligations, Advise on discipline, terminations, accommodations, and leave management Lead workplace investigations from intake through resolution in partnership with People & CultureDraft and maintain employee handbooks, policies, and manager-facing guidanceSupport labor relations matters in coordination with outside counselRisk Management & ClaimsServe as the internal lead on employment-related claims and disputesManage outside employment counsel on active mattersPartner with leadership on litigation strategy and risk mitigationOversee coordination with insurance carriers on EPLI and related coverageOperational IntegrationPartner closely with SVP People & Culture; serve as a thought partner, not a back-end reviewerEstablish clear intake and escalation frameworks so issues are identified and addressed earlyWork directly with GMs and department heads to guide real-time decisionsBuild practical playbooks so operators can handle common issues without unnecessary escalationDesign and deliver training for managers on key compliance and risk areasStandard Contracts (Defined Secondary Lane)Review, draft, and negotiate routine, standardized agreements including NDAs, vendor contracts, and basic commercial agreementsBuild and maintain a library of templates and fallback positions to increase speed and consistencyEstablish contract review workflows and approval thresholdsIdentify when agreements fall outside standard parameters and should be escalated to outside counsel or senior leadershipSystems & ProcessBuild scalable workflows for investigations, documentation, and approvalsUse AI tools to support documentation, policy management, and contract review where appropriateCreate visibility into risk trends across the portfolio and proactively address patternsHelp define how legal work flows through the organization so the function scales without becoming a bottleneckWhat This Role Is NotNot the primary owner of complex real estate transactions, HMAs, or acquisitionsNot the default reviewer of every contract across the companyNot a back-office legal function removed from operationsQualificationsJD with active California Bar membership8+ years of experience with deep focus on California employment lawStrong experience in wage and hour, PAGA, investigations, and labor relationsExperience supporting multi-unit, operational businesses (hospitality strongly preferred)Demonstrated ability to guide non-legal operators clearly and directly in real-world situationsExperience building processes, templates, and scalable systemsComfortable using AI tools in day-to-day legal workflowsHow This Role WorksYou own employment and risk across the companyYou partner closely with People & Culture, operations, and leadershipYou handle standardized, repeatable contract work and build systems to streamline itYou escalate complex or specialized matters to outside counsel as appropriateYour success is measured by reduced risk, faster decision-making, and stronger operational consistencySalary$200,000-240,000Proper Perks & BenefitsCompensation & RecognitionCompetitive Salary + Bonus: Rewarding exceptional talent and performance across all levels.Recognition Programs: Celebrating achievements big and small through company-wide appreciation and milestone rewards.Annual Performance Reviews: Regular opportunities for feedback, growth, and advancement.Culture of Growth & BelongingCulture of Growth: A collaborative, design-forward environment that values creativity, intelligence, and curiosity — where learning and excellence are a daily practice.Guided Skills Development: Access to training, leadership programs, mentorship, and cross-property mobility to encourage achievement and discovery.Diversity, Equity, Inclusion & Belonging: We honor individuality while fostering a culture of respect and belonging across all teams.Community Engagement: Opportunities to give back through local volunteerism, sustainability, and charitable partnerships.Health & WellnessComprehensive Health Coverage: Medical, dental, and vision plans through Aetna, designed to fit a range of personal and family needs.Wellness Access: Company-subsidized memberships with Equinox and ClassPass, plus wellbeing workshops and mental health resources.Employee Assistance Program (EAP): Confidential support for emotional wellbeing, financial planning, and life management through Unum.Time Off & FlexibilityPaid Time Off: Flexible PTO plus 11 paid holidays each year for corporate team members.Paid Parental Leave: Paid time off for eligible employees welcoming a new child through birth, adoption, or foster placement.Flexible Work Practices: Hybrid schedules for eligible roles and an emphasis on work-life balance.Financial Wellbeing & Core Protections401(k) Program: Company match of 50% of employee deferrals, up to the first 4% of eligible compensation.Employer-Paid Life & Disability Insurance: Core protections with optional additional coverage.Financial Education: Access to planning tools and workshops to support long-term stability and growth.Lifestyle & Travel PerksHotel Stay Benefits: 75% off BAR (floor of $100) across the Proper portfolio.Design Hotels Partnership: 50% off participating Marriott Design Hotels.Dining Discounts: 75% off food & beverage at all Proper Hospitality outlets.Lifestyle Perks: Complimentary or subsidized parking, cell phone reimbursement, and exclusive hospitality and retail discounts.Why Join Proper HospitalityAt Proper, we build experiences that move people — and that begins with the team behind them. As a best-in-class employer, we’re committed to creating one of the Best Places to Work in hospitality by nurturing a culture where creativity, excellence, and humanity thrive together.Everything we do is grounded in the belief that hospitality is more than a profession - it’s an opportunity to care for others and make lives better. Guided by the Pillars of Proper, we show up with warmth and authenticity (Care Proper), strive for excellence in everything we do (Achieve Proper), think creatively and resourcefully (Imagine Proper), and take pride in the style and culture that make us who we are (Present Proper).We believe our people are our greatest strength, and we invest deeply in their wellbeing, growth, and sense of belonging. From comprehensive benefits to meaningful development programs, Proper is designed to help you build a career, and a life, that feels as inspiring as the experiences we create for our guests.Our Commitment: Building the Best Place to WorkOur Best Place to Work initiative is a living commitment — a continuous investment in our people, our culture, and our purpose. We listen, learn, and evolve together to create an environment where everyone feels empowered to imagine boldly, achieve confidently, care deeply, and present themselves authentically.At Proper, joining the team means more than finding a job — it means joining a community that believes in building beautiful experiences together, for our guests and for one another.