The Role
Lead IT modernization for the DOT CTO: align IT investments with strategy, create and maintain system modernization plans (scope, schedule, metrics), analyze existing systems for effectiveness and innovation, and support cost-effective, cloud-based solutions across software development projects.
Summary Generated by Built In
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 Senior 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.
Let's go Skyward together.
What you'll do:
- Support the Department of Transportation (DOT) 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.
- 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 we'd like you to have:
- At least 8 years of experience planning and executing software development projects.
- 2-4 years of experience managing federal IT projects that include 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 and regularly working with senior IT leadership.
- 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.
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 can't be exciting!
At Skyward, we support flexible working hours and remote opportunities to help maintain a healthy work-life balance for all employees.
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.
Skills Required
- At least 8 years of experience planning and executing software development projects.
- 2-4 years of experience managing federal IT projects that include cloud-based applications.
- Bachelor's degree.
- PMP certification.
- Agile certification (PMI-ACP, Certified Scrum Master, Certified Product Owner).
- Experience with agile methodologies (Scrum, Lean, SAFe).
- Experience managing matrixed teams and regularly working with senior IT leadership.
- Strong written documentation skills (creating strategic plans, schedules, requirements, deliverables).
- Experience using Jira and Confluence.
- Ability to obtain and maintain a Public Trust security clearance; employment contingent on acceptable background investigation.
- Experience supporting various federal agencies.
- Deep passion for and continual practice of IT project management methodologies.
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The Company
What We Do
Skyward IT Solutions, LLC is a technology services provider specializing in AI-driven government services and digital modernization for federal and public sector operations. Founded in 2013, the company delivers secure, scalable, and user-centered solutions including custom AI agents, cloud engineering, and agile software development, focusing on improving service delivery and operational efficiency for agencies such as CMS and the SBA.
