Headway
Headway Compensation & Benefits
Headway Employee Perspectives
Headway invests in employee well-being through a comprehensive benefits package that supports healthcare, family needs, financial protection and professional development. Employees benefit from expanded parental leave, fertility and family-forming support, employer contributions toward healthcare coverage and insurance benefits. Flexible paid time off, work-from-home and telecommunications stipends, professional development funding and commuting reimbursements further support employees both inside and outside the workplace.
“Headway expanded our family leave policy from 13 to 16 weeks, introduced a partnership with Carrot which offers fertility and family forming benefits, increased our employer contribution to healthcare premiums for family plans and rolled out employer-paid life insurance and disability insurance.
In addition, we expedited benefits eligibility for new hires to ensure they have coverage on day one of employment versus having to wait until the following month.
Other ways that Headway invests in our employees is by offering flexible PTO, an annual work-from-home stipend, a monthly telecommunications stipend, an annual professional development stipend and a monthly commuting reimbursement for our two offices in New York and San Francisco.”
What People Are Saying About Headway
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Healthcare Strength: Medical, dental, and vision are offered with multiple plan options, and the employer is described as covering a majority of premiums. Life and short- and long-term disability coverage further reinforce the core health package.
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Parental & Family Support: Up to 16 weeks of fully paid parental leave for eligible employees is highlighted as a standout policy. Family-forming benefits through Carrot add further support for fertility and related needs.
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Wellbeing & Lifestyle Benefits: Therapy-cost reimbursement of roughly $2,100 per year, an EAP, and remote-first flexibility with home-office stipends are emphasized. These perks extend the package beyond basics to everyday wellbeing and work setup.
Headway's Benefits
Offers company equity
At Headway, we see every Headwegian as an owner. Equity is included as a part of the total compensation package, allowing employees to directly share in both Headway’s mission and financial growth.
Provides home-office stipend for remote employees
Headway offers two workspace allowance programs: (1) a one-time $500 allowance for new hires and (2) an annual $150 allowance for existing employees.
Offers generous parental leave
Headway offers up to 16 weeks of full salary or wages to eligible full-time regular employees to care for and bond with a newborn child or newly adopted or newly placed foster child.
Provides family medical leave
Headway provides leave according to the Family and Medical Leave Act of 1993 (FMLA), which provides for unpaid, job-protected leave to covered employees in certain circumstances.
Provides fertility benefits
Headway partners with Carrot Fertility to offer inclusive fertility, hormonal health, and family-forming benefits.
Offers dental insurance
Headway provides employees with the flexibility to choose from 3 Cigna Dental Plans, as well as covers a majority portion of premiums.
Offers Flexible Spending Account (FSA)
Headway offers a Healthcare FSA, allowing employees to pay for qualified healthcare expenses with pre-tax dollars. We also offer a Dependent Care FSA.
Offers health insurance
Headway provides employees with the flexibility to choose from 4 Cigna Medical Plans, as well as covers a majority portion of premiums.
Offers mental health benefits
Headway offers an HRA that reimburses employees for eligible mental health copays and therapy session costs, up to $2,100 per year. In addition, we offer an Employee Assistance Program (EAP).
Offers pet insurance
Offers transgender health care benefits
Offers vision insurance
Headway provides employees with the flexibility to choose from 2 Cigna Vision Plans, as well as covers a majority portion of premiums.
Offers 401(K)
Headway offers 401(k) and Roth plans to empower employees to proactively prepare for their future. Employees can choose the investment mix that aligns with their risk tolerance and financial goals.
Offers disability insurance
Headway offers Short-Term Disability (STD) and Long-Term Disability (LTD) coverage.
Offers life insurance
Headway covers Basic Life Insurance of 100% of an employees’ annual salary up to $500,000.
