Benefits at Headway

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.

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.

Commuter benefits

Headway offers a Commuter Benefits Flexible Spending Account (FSA) that helps pay for work-related parking and transit expenses using pre-tax dollars, as well as a $30 weekly commuter reimbursement.

Free snacks and drinks

Headway provides lunch for employees at our New York, San Francisco, and Seattle offices on Tuesday, Wednesday, and Thursday, as well as available snacks throughout the week.

Some meals provided

Headway provides lunch for employees at our New York, San Francisco, and Seattle offices on Tuesday, Wednesday, and Thursday, as well as available snacks throughout the week.

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.

Continuing education stipend

Headway provides a $500 professional development stipend to all full-time employees annually. This can cover courses, books, seminars, conferences, etc.

Promote from within

Dental insurance

Headway provides employees with the flexibility to choose from 3 Cigna Dental Plans, as well as covers a majority portion of premiums.

Disability insurance

Headway offers Short-Term Disability (STD) and Long-Term Disability (LTD) coverage.

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.

Health insurance

Headway provides employees with the flexibility to choose from 4 Cigna Medical Plans, as well as covers a majority portion of premiums.

Life insurance

Headway covers Basic Life Insurance of 100% of an employees’ annual salary up to $500,000.

Pet insurance

Vision insurance

Headway provides employees with the flexibility to choose from 2 Cigna Vision Plans, as well as covers a majority portion of premiums.

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).

Transgender health care benefits

Diversity manifesto

Mean gender pay gap below 10%

Diversity employee resource groups

Headway believes that an essential part of building the best startup team is to build a diverse, equitable, and inclusive team. We have 6 ERGs, as well as community-based Slack channels.

Hiring practices that promote diversity

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.

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.

Fertility benefits

Headway partners with Carrot Fertility to offer inclusive fertility, hormonal health, and family-forming benefits.

Generous PTO

Headway offers a generous PTO policy to give employees greater versatility to meet their personal needs.

Paid holidays

Paid sick days

Headway provides all full-time employees with 56 hours, or 7 days of sick time at the beginning of each calendar year or at the time of hire.

Bereavement leave benefits

Open office floor plan

Remote work program

Headway employees work remotely across the US, with the option to work from offices in New York City, San Francisco, and Seattle.

Team based strategic planning

OKR operational model

Employee resource groups

Employee-led culture committees

Quarterly engagement surveys

In-person all-hands meetings

Employee awards