Headway
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).
Offers immediate health care coverage on employee start date
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
Documented operating principles
Promotes a people-first, social culture
Prioritizes real-world impact of work in decision-making processes
Leadership encourages open, transparent debate
Implements team-based strategic planning
Hosts in-person all-hands meetings
Defined values and mission statements
Prioritizes mission-driven work in decision-making processes
Policies promote a low-ego, team-driven culture
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
Managers offer consistent feedback loops
Provides resources to build team camaraderie
Encourages autonomy and ownership from employees
Employee feedback used to shape policies and strategy
Established employee awards to honor work and contributions
Company or teams have recognition rituals for individual work
Provides modern technology across teams
Managers give public shoutouts and celebrate employee milestones
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.
Supports employee-driven initiatives, not just top-down priorities
Defines roles and sets expectations for success
Provides formal manager training and leadership development
Provides opportunities to take on expanding responsibilities
Encourages knowledge sharing and cross-functional collaboration
Provides training support and resources for AI adoption
Managers hold regular development check-ins
Promote from within
Documented path to leadership development
Documented career progression frameworks
Encourages lateral mobility to expand skills and impact
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
