Headway

HQ
New York, New York, USA
Total Offices: 3
819 Total Employees
Year Founded: 2019

Headway Benefits Overview

Compensation + Benefits

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 life insurance

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

Offers disability insurance

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

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 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 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 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 transgender health care benefits

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 pet insurance

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).

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 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.

Company Culture

Provides 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.

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.

Provides 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.

Has a diversity manifesto

Offers diversity-based 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.

Mean gender pay gap is below 10%

Hiring practices promote diversity

Open office floor plan to encourage communication and collaboration

Uses an OKR operational model to clearly define goals and priorities

Implements team-based strategic planning

Hosts in-person all-hands meetings

Offers a 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.

Quarterly engagement surveys to gauge employee satisfaction

Established employee awards to honor work and contributions

Career Growth + Development

Provides 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

Work-Life Balance + Wellbeing

Offers generous PTO

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

Provides 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.

Provides paid holidays

Provides bereavement leave

Offers Employee Resource Groups

Has employee-led culture committees

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