Fearless Digital Careers

Join Fearless Digital, our tech division.


At Fearless, we take a holistic approach to supporting our customers. This means we solve problems by addressing the technology, people, and organizational structure of their challenges. Our digital division focuses on building good tech, while our guides division specializes in people and organizational enablement.

Fearless Digital builds tech that makes a difference. We design, engineer, and deliver digital solutions to solve problems. By delivering intuitive and responsive technology, we help set the stage for tech to work better for people.

Fearless Digital Benefits

People do their best work when they're happy and healthy, so in our Digital division, we not only provide our team members with competitive healthcare and paid time off, we also offer fun perks like tech and wellness budgets. Our benefits package reflects the changing needs of our workforce, and it's designed to support our team (and their families) as they grow. We keep an open dialogue with everyone on the team to find ways to improve our benefits package each year.

Life-friendly schedules

Life doesn't contain itself to the hours after 9am and before 5pm. As long as you meet the core hours your team agrees to work together, you typically have a lot of freedom in setting your own schedule.

Paid leave

We believe in taking time off to be well and thrive. That's why we offer 14 days of PTO, 8.75 days of sick leave, 11 federal holidays, your birthday, jury duty, and bereavement.

Modern office and remote work options

For folks that like working from an office, our Fearless HQ in Baltimore has you covered. With automated sit/stand desks and reservable treadmills, our kiddo and pet-friendly space is designed to support you in doing your best work. And for those who prefer working from home, we offer fully remote options for roles that don't require an in-person presence. Because no matter how you work, you deserve to do it well.

Family and Medical leave

We believe in supporting our people in caring for themselves and their families. That's why we offer up to 12 weeks of fully paid Family and Medical leave for welcoming a new child into your family, caring for an immediate family member with a serious health condition, or caring for your own serious health condition.

Education and training

We're invested in your personal and professional growth. Team members get a budget of up to $1,500 each year to put towards classes, travel, conferences, and materials, plus unlimited access to LinkedIn Learning and discounts on certain programs at the Maryland Institute College of Art.

Tech

Everyone gets a yearly budget of up to $400 for tech that helps them do their best work. Whether they use their allowance on software subscriptions, a smartwatch, or their cell phone plan, we help our team members take advantage of the tech and innovations that help them grow.

Wellness budget

To encourage and support your wellbeing, Fearless Digital offers 100% reimbursement on a variety of wellness activities and products, up to $250/year.

Apparel

A lot of us live in our Fearless gear, and our moms have even asked for it. Every new hire gets a $200 Fearless Sports credit to load up on our purple apparel. It's another reminder to keep the purple spirit alive in our day to day.

Housing

For aspiring homeowners, we also participate in Baltimore City's Live Near Your Work program and the Maryland Mortgage Program's House Keys 4 Employees initiative.

401K

To help you plan for your future, we match up to 4% of your salary in a Safe Harbor 401k Matching Plan.

Insurance

We cover 100% of your premium for our medical HSA plan + the deductible portion of HSA contributions, 80% of your premium for our HMO or PPO plans, and offer competitive dependent coverage. We cover 100% of dental and vision premiums for you and your dependents and offer medical and dependent care FSA options. We also offer life insurance, short- and long-term disability coverage, and legal planning and support insurance.

Employee assistance

We offer an Employee Assistance Program through Inova Employee Assistance that gives our people access to confidential counseling, legal services, financial services, identity theft services, and other services and resources.

Referral bonus

Bring your friends! If someone you refer is hired, you’ll get a bonus of $6–12k!

Total Pet Plan

We have a lot of pet parents at Fearless, which is why we offer a Total Pet Plan through Pet Benefit Solutions. It includes discounts on pet products, prescriptions, and vet care, as well as telehealth and lost pet recovery.

Think Fearless Digital might be a good fit?

We're always in the market for fresh and exciting talent. If you want to join a team of people passionate about doing work differently, check out our open positions.

The process

After you apply for a position in Fearless’ digital division, we’ll screen your resume and reach out if we think you’d be a good fit to begin our interview process. We get excited about applicants who believe in our purpose and values because we know that passion drives our success. That’s why — in addition to our technical and business interviews — we also perform peer interviews. These interviews happen right off the bat to give you a chance to get to know the people that you'd be working with every day.

Don't have much real-world experience? Our internship program might be a good fit! Through it, we give college students and recent graduates the opportunity to get real-world experience working in the digital services industry.

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