Culture

Our Culture at Windward.

An opportunity at Windward is more than just a job, it’s a career. We strongly believe the reason we’re successful—and will continue to be—is our people.

Why work for Windward?

At Windward, we believe that great work happens when talented people feel supported, valued, and empowered. Our culture isn’t defined by ping-pong tables or slogans — it’s grounded in real human experience, professional growth, and collaboration that drives impact.

We’re a remote-first team of thinkers, doers, and problem-solvers who are passionate about solving complex IT and operational challenges for global enterprises and government partners. Being remote-first doesn’t mean distant — it means intentional connection, thoughtful communication, and flexibility so you can do your best work wherever you are.

People First

We hire exceptional team members who bring curiosity, integrity, and a service mindset to everything they do. Our shared values — collaboration, accountability, and a drive for excellence — shape not only how we work, but how we grow together.

Remote-First, Connected Always

Whether you’re in Virginia, Texas, or working across time zones, Windward prioritizes meaningful connection: regular team touchpoints, leadership AMAs, virtual cohorts, and in-person meetups that help us build trust and camaraderie.

Growth & Development

We invest in your success. From professional training to mentorship and internal opportunities, Windward is a place where curiosity is encouraged and advancement is supported.

Leadership That Listens

Our leadership team is deeply invested in helping each person thrive. We value open dialogue, transparent decision-making, and a culture of empowerment where feedback becomes opportunity.

Balance With Purpose

Work-life balance isn’t a buzzword — it’s a priority. We encourage flexible schedules that recognize the full lives our team members lead outside of work. Whether accommodating family needs, personal goals, or continued education, we trust our people to bring their best selves to their roles.

United by Mission & Values

At Windward, culture is more than perks — it’s a shared commitment to delivering outcomes that matter, supporting each other through challenge and success, cultivating an environment where every voice contributes to who we are, and building a workplace where people feel seen, respected, and empowered to excel.

Windward strives to attract and retain the best individuals and provide an environment where they can all grow professionally and build a rewarding career. We continually strive to create an environment that balances work life and offers benefits that will enhance the compensation package. We offer Medical, Dental, Vision, Flexible Spending Accounts, Short Term Disability, Long Term Disability, Life Insurance and AD&D, as well as the option to purchase additional Life Insurance and AD&D, Paid Time Off, Personal Leave, Holidays, 401(k) plan with company match.

Windward is proud to be an Equal Opportunity Employer.

Applicants are considered for all positions without regard to race, color, religion, sex, national origin, age, disability, sexual orientation, ancestry, marital or veteran status.