Director, People Operations

🔥 4 minutes ago

🇺🇸 United States – Remote

💵 $212k - $265k / year

⏰ Full Time

🔴 Lead

👥 People Operations

👻 Ghost score 0%

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Headway

WebsiteLinkedInAll Job Openings

501 - 1000 employees

Founded 2019

🏥 Healthcare

🏪 Marketplace

☁️ SaaS

💰 $100M Series D - Headway on 2024-07

Healthcare • Marketplace • SaaS

Headway is a healthcare technology company (Therapymatch, Inc. ) that operates an insurance-native marketplace connecting people with licensed mental health providers — therapists and psychiatrists — for in-person and online care. Headway matches users with providers by specialty, location, and insurance coverage, handles insurance verification and billing, and offers tools for providers (provider portal and an insurance-native EHR) to reduce administrative burden. The platform partners with 100+ insurance plans, supports many languages, and emphasizes affordable, in-network mental health care.

📋 Description

• Own Headway's benefits strategy end-to-end, including funding model assessment and refreshed strategy implementation • Redesign employee support for leave, carrier and claims issues, benefits questions, and immigration • Ensure accurate and timely payroll delivery compliant across all states where Headway operates • Lead an overhaul of employee policies and streamline employee recordkeeping • Set the strategic roadmap for People Systems, primarily Workday • Partner with Human Intelligence and People Analytics to build agentic, self-service capabilities • Rebuild contingent worker lifecycle operations across onboarding, offboarding, extensions, and conversions using automated and AI-native workflows • Drive change adoption through training, documentation, and enablement • Measure reductions in manual effort, escalations, and workflow impact over time • Coach and develop a high-performing team of Managers and Associates • Partner closely with Finance and Legal • Report to the Director of Total Rewards and Operations

🎯 Requirements

• 10+ years of experience in People Operations or Total Rewards • At least 5 years managing and developing an exceptional team • Experience rebuilding People workflows and support systems on automated foundations • Experience eliminating meaningful manual effort, reducing error rates, or improving SLAs through automation • Fluency in modern data and automation tooling • Understanding of AI in the infrastructure layer of People programs • Ability to translate ambiguous business needs into a sequenced roadmap • Ability to communicate clearly across audiences • Experience managing workflows and data for thousands of employees and handling rapid scaling • Proven track record managing complex, cross-functional projects with diverse stakeholders • Familiarity with HR technology platforms such as Workday and Ashby, including integration and API capabilities is an advantage • Must be authorized to work in the United States

🏖️ Benefits

• Equity / meaningful ownership opportunities • Robust health and wellness benefits • Retirement savings • Remote work arrangement • Reasonable accommodations for persons with disabilities