Remote IT Project Manager

We are Skyward.
That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and unified; creative and collaborative; a collection of complementary, not competing talents. And though on the surface we remain relaxed, beneath, a torrent of energy links us to our civic tech mission.
We stand by our values, and we won’t compromise on any of them.
Integrity:

We’re conscientious, intentional, and empathetic. Our words and actions align. That’s our character. Please don’t ask us to play another part, we’re poor actors.

Compassionate:

If we may borrow a quote from Theodore Roosevelt: “No one cares how much you know until they know how much you care.” Because our team is thoughtful and supportive, caring deeply for each other, our clients, and our work, this comes naturally.

Inquisitive:

We remain students by failing openly and turning lessons into solutions.

Unconventional:

For us, life isn’t what happens outside of work. Work happens inside of life and our culture erases the line often dividing the two.

Authentic:

Made possible only because we embody the values listed above. We’re relaxed and fun yet intensely curious and driven. Team members are placed with thought, care, and precision to ensure that Trust, Truth, and Transparency continue to represent our brand.
Because of that, we continue Onward, Upward, and Skyward.
We need a Project Manager.

Do you listen to understand before formulating a response? Pick up on what’s left unsaid? Have a tight grasp on context? Write well? To be clear, we’re not looking for an author, but you should enjoy writing strategic plans, schedules, project requirements, and deliverables. And then writing new plans to follow up on those original plans. If we just described you, hit the apply button, like, now.
Lets go Skyward together.

What youll do:

Support the Department of Transportation’s Office of the Chief Technology Officer where you’ll ensure they are using the most cost-effective and efficient technology to meet current and future information needs.
Ensure the alignment of IT investments with the office’s strategic goals and objectives.
Guide project teams and other project managers, coordinating efforts with contractor teams and federal teams.
Create, update, and maintain a modernization plan for existing IT systems that includes scope, an implementation strategy, schedule, results-oriented goals, and measures.
Conduct analyses of previously implemented systems, ensuring each system is meeting customer and business needs, and identify areas for innovation.
What wed like you to have:

At least 6 years of experience planning and executing projects.
1-3 years of experience managing federal IT projects that includes web, enterprise or cloud-based applications.
Bachelor’s degree and PMP certification.
Agile certification (i.e., PMI-ACP, Certified Scrum Master, Certified Product Owner).
Experience with one or more different agile methodologies, including Scrum, Lean, or SAFe.
Experience managing matrixed teams.
Experience documenting and writing things. (Did we mention this already?)
Experience using Jira and Confluence (you know, to document).
What would blow us away:

Your entire project management experience has been supporting various federal agencies.
You eat, sleep, and breathe IT project management methodologies.

Even if you don’t meet 100% of the qualifications, we encourage you to apply. At Skyward, we’re focused on hiring individuals with the right skills and passion to grow, not just checking off every box.

And now the important part. What we offer you:

Medical, dental, vision insurance (fully paid for employees)
15 days of paid leave
7 days of sick leave
2 days bereavement leave
11 paid Federal holidays
Up to 40 hours for jury duty
401K with 4% employer contribution (and no vesting period)
Up to 4 weeks of paid paternity and maternity leave
Company provided laptop
$5,000 per year for professional development
$600 per year for technical supplies and equipment
$2,000 referral bonus
Life and disability insurance
HSA and FSA
Legal Shield and ID Shield Voluntary Benefits
Opportunity to work in a collaborative, motivated team focused on modernizing government services with cutting-edge technology and innovative solutions. Who says government work cant be exciting!
$110,000 - $120,000 a year

We believe great work deserves great pay. That’s why we ensure our compensation is not only competitive but also fair and transparent, as required by Maryland law. Expect a salary that matches your skills, experience, and the value you bring to the table — because you’re worth it!

At Skyward, we are committed to creating an environment where everyone, regardless of gender, race, ethnicity, sexual orientation, disability, or background, can thrive. We support flexible working hours and remote opportunities to help maintain a healthy work-life balance for all employees, including caregivers and those with unique needs.

Offers of employment with Skyward are contingent upon acceptable results of a background investigation.

Applicants must have the ability to obtain and maintain a Public Trust security clearance due to the nature of our work as a government contractor.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.