Leave Specialist - Contractor

Grow Therapy is on a mission to serve as the trusted partner for therapists growing their practice, and patients accessing high-quality care. Powered by technology, we are a three-sided marketplace that empowers providers, augments insurance payors, and serves patients. Following the mass increase in depression and anxiety, the need for accessibility is more important than ever. To make our vision for mental healthcare a reality, we’re building a team of entrepreneurs and mission-driven go-getters. Since launching in February 2021, we’ve empowered more than ten thousand therapists and hundreds of thousands of clients across the country and insurance landscape. We’ve raised more than $328Mm in funding, including our Series D, at a $3B valuation from Sequoia Capital, Transformation Capital, TCV, SignalFire, Menlo Ventures, Goldman Sachs Alternatives, and others.

Employment Type: 1099 Contractor
Hours: Approximately 25 to 40 hours per week, with flexibility based on leave volume
Duration: Initial 3 to 6 month engagement, with potential for extension
Compensation: $50 to $70 per hour, depending on experience.

As we continue to grow, we're looking for an experienced Leave Specialist to independently own the day to day administration of our leave of absence program.

This contractor will serve as Grow's primary leave administration expert, partnering closely with employees, managers, People Operations, Employee Relations, Payroll, and our third party leave administrator to deliver a compliant, seamless, and compassionate leave experience.

As our Leave Specialist, you'll own the end to end administration of employee leaves of absence, ensuring an exceptional employee experience while maintaining compliance with federal, state, and local leave laws.

Responsibilities include:

• Serve as the primary point of contact for employees navigating leaves of absence, providing timely, compassionate, and knowledgeable guidance.

• Manage the full lifecycle of employee leaves from intake through return to work, including medical, parental, family care, personal, military, and other protected leaves.

• Partner closely with our third party leave administrator (Sparrow) to ensure accurate case management, documentation, and employee support.

• Review leave documentation and coordinate next steps while ensuring compliance with applicable federal, state, and local regulations.

• Coordinate accommodations and return to work processes in partnership with Employee Relations and People Business Partners, including fitness for duty documentation and workplace accommodations where applicable.

• Partner with Payroll and People Operations to ensure accurate pay, benefits, and employment status throughout each leave.

• Maintain accurate records and documentation within Rippling and other internal systems.

• Respond to employee and manager questions regarding leave policies, eligibility, timelines, and processes.

• Monitor active leave cases and proactively manage key milestones, deadlines, and required communications.

• Identify opportunities to improve workflows, documentation, templates, and automations that increase efficiency and enhance the employee experience.

• Support reporting, audits, and compliance activities related to leave administration.

• 5+ years of dedicated leave administration experience supporting U.S. employees.

• Experience independently managing end to end leave administration for a multi state employer.

• Strong working knowledge of FMLA, ADA, CFRA, PWFA, USERRA, state paid family and medical leave programs, and other applicable leave laws.

• Experience partnering with third party leave administrators such as Sparrow, Sedgwick, Lincoln Financial, The Hartford, or similar vendors.

• Strong understanding of the intersection between leave administration, payroll, benefits, and HR operations.

• Excellent organizational skills and attention to detail with the ability to manage multiple concurrent leave cases.

• Exceptional written and verbal communication skills with a high degree of empathy and professionalism.

• Ability to exercise sound judgment while handling confidential and sensitive employee information.

• Comfortable working independently in a fast paced, high growth environment.

• Experience supporting organizations with 500+ employees.

• Experience using Rippling or a similar HRIS.

• Experience improving leave processes, documentation, or operational workflows.

• Experience partnering closely with Employee Relations teams on complex leave and accommodation cases.

Within your first 90 days, you'll:

• Independently manage Grow's leave administration program with minimal oversight.

• Deliver a timely, compliant, and high quality leave experience for employees and managers.

• Maintain accurate documentation and ensure all leave cases are managed proactively.

• Build trusted partnerships across People Operations, Employee Relations, Payroll, and our external leave vendor.

• Recommend and implement process improvements that strengthen compliance, improve efficiency, and create a better employee experience.

At Grow Therapy, we're building thoughtful, scalable people programs that support our employees through every stage of their journey. This role is an opportunity to have a meaningful impact during some of the most important moments in an employee's experience while helping us continue to build best in class people operations.

PLEASE NOTE: This is a 1099 contract position, and as such, does not include benefits provided to full-time employees.

Full Time Employee Benefits:

• Comprehensive Health Coverage: Medical, dental, and vision insurance, plus life and disability coverage.

• Parental Leave & Family Support: Up to 18 weeks paid leave and a new child stipend.

• Financial Wellness: 401(k) program and equity opportunities.

• Meals & Home Office Support: Stipends for home office setup and ongoing funds for meals, with tailored perks for both remote and in-office employees.

• Time Off to Recharge: Flexible PTO, 12 paid holidays, and a full winter break week.

• Wellness & Development: Annual stipends to put towards personal & professional growth.

• Mental & Physical Health Support: No-cost access to therapy through the Grow platform, weekly flexible hours for self-care (“Mental Health Mornings/Afternoons”) and memberships to leading wellness apps (such as One Medical, Headspace, and Talkspace).

• Extra Perks: Pet insurance discounts, commuter benefits, and global travel assistance.

Research shows that some groups hesitate to apply unless they meet every qualification. If you’re excited about this role but don’t check every box, we encourage you to apply. At Grow, we value diverse experiences, transferable skills, and the unique strengths each person brings.

Grow Therapy is proud to be an equal opportunity workplace and is an affirmative action employer. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements.

Use of AI Tools: We use certain AI and automated tools to support recruitment. These tools help our team review applications, organize interviews, detect potential application integrity issues, and maintain interview records; they do not make final hiring decisions.

Application Review: Ashby's AI-Assisted Application Review helps review application materials against role-specific criteria and may flag potential fraud or integrity issues for recruiter review. All advancement decisions are made by our human recruiting team after independent review. See Ashby's AI Bias Audit Report.

Interview Recording: We use BrightHire to record interviews, supporting note-taking and consistency across candidates. Learn more. Interviews are confidential; you may ask your interviewer to stop recording anytime, or opt out in advance. Choosing not to be recorded will not, by itself, affect your candidacy.

AI-Assisted Recruiter Screen: For select roles, BrightHire's AI features may help structure initial recruiter screens and organize interview notes. All responses are reviewed by our recruiting team; no hiring decisions are made by AI alone.

State-specific notices: Depending on your location, you may have additional rights. Illinois: If AI analyzes a video interview, we'll provide notice, explain how it works and what it evaluates, and obtain consent beforehand. New York City: Where required, we'll provide at least 10 business days’ notice before using an automated employment decision tool and explain how to request an alternative process. Maryland: We do not use facial recognition to create facial templates during interviews unless required notice and written consent are obtained.

Questions, accommodation requests, requests for an alternative selection process, objections to recording, or concerns about AI use? Contact [email protected]. We’re happy to help or offer an alternative way to participate.