People are our point of differentiation.

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.
Windward Connectivity

Why work for Windward?

We work to build an environment that provides an optimal work-life balance, as well as one that strives for high employee engagement. We create a culture where employees can thrive, innovate and be an active participant in the community. 

An opportunity with Windward is more than just a job, it’s a career. At Windward you will be a member of the A-Team where you will be joining other A-players. As a remote-first Company, we provide an integrated set of guidelines, tools, and environmental conditions to allow our team members to communicate effectively, simply, and securely, anywhere in the world. We believe this approach leads to a highly productive A-Team with an optimal work-life balance.

Want to learn more about our A-Team attitude?

Focus on Learning and Growth:

We offer unlimited paid training and certifications to our employees. We focus on supporting our employees short and long term goals. As well as providing tuition reimbursement.

Lifestyle Benefits:

We are a remote first company that provides 3 weeks of Paid Time Off. Coupled with Medical, Dental, Vision coverage as well as a 401K plan. We provide team activities in the form of Virtual Happy Hours that include a live musician, a virtual escape room, a mixologist and a magician. We strive to maximize productivity of our employees while providing a work life balance.


The Windward Foundation helps fund innovative programs that support family caregivers to those with Alzheimer’s disease. We also support the community with programs such as Toys for Tots, Canned Food Drive and donation to the Salvation Army. In addition to supporting new causes that are brought to us from our employees that are important to them.

“Whether working with a client on a tight timeline or utilizing company resources with prudence and foresight, we always look for opportunities to innovate. Working with what we’ve got. Finding possibilities where others threw their hands up. Problem solving for the highest gains. That’s what sets us apart from the pack.”
- Bill Driscoll, Consulting Director

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.