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.
Does “5,000 users, one hard vendor deadline, and an SSO integration that’s ‘almost done’” sound less like a nightmare and more like a Tuesday? Are you the person who knows exactly why the MDM push is taking three weeks, and can explain it to a stakeholder in two sentences flat? You build the schedule, you shepherd the security gates, and you somehow get thousands of people genuinely excited (or at least not grumpy) about a new tool.
If you can take AI tools from pilot to production and bring every last user along for the ride, please apply.
Let’s go Skyward together.
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.
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.
What you'll do:
Own the portfolio. Run the AI Tools project portfolio for the Centers for Medicare and Medicaid Services’ (CMS) end to end: HHS enterprise tools, externally hosted SaaS pilots, internal platform and integration projects, and ad hoc requests from CMS application teams.
Run the pilot playbook. Shepherd each tool through a defined lifecycle, from intake and approval to proof of concept (up to 25 licenses), pilot, and the big expand, right-size, or sunset decision, then carry approved tools through a separate path to production.
Master the dependencies. Build and maintain integrated schedules that account for everything: Security Impact Analysis, SecOps review, Section 508 accessibility testing, MDM deployment, SSO and identity integration, SaaS governance review, and ServiceNow updates.
Make change management real. Own the unified AI Tools change management plan and put it into practice for every rollout using a structured model like ADKAR or Prosci, so CMS sees implementation, not just a document.
Bring thousands of people along. Plan and run communications campaigns for audiences of 900 to 5,000+ users: draft the copy, coordinate agency communications office review, segment distribution lists, and time reminders against hard vendor deadlines.
Keep the help desk happy. Coordinate training, office hours, and a champion network of power users, and keep Tier 0 self-help content current so the IT Service Desk and our Tier 2 and Tier 3 teams aren’t absorbing avoidable tickets.
Measure what actually matters. Define and report business impact metrics for each tool (usage volume and time saved, not just logins), segment users into power, regular, light, and dormant tiers, and track operations and maintenance burden as a KPI.
Make ownership crystal clear. Write RACIs for each tool so CMS, HHS, partner teams, and our own pods know exactly who owns change management, technical integration, analytics, and support.
Always have a plan B. Maintain contingency plans for tools at risk of contract or vendor change, complete with cost comparisons and decision deadlines for leadership.
Keep the board moving. Run a Kanban cadence for the AI Tools team in Jira, keep status current in Confluence and program reporting tools, and prepare status, risk, and lessons learned briefings for CMS leadership.
Be the hub. Serve as the single point of coordination with CMS business owners, agency partner teams, and HHS, so our technical lead can stay focused on engineering and oversight.
What we'd like you to have:
7+ years of project or program management experience, with at least 3 years managing IT infrastructure, DevOps, cloud, or enterprise software deployment projects.
A track record of rolling out enterprise SaaS or desktop applications to 1,000+ users, including communications, training, and adoption tracking.
Hands-on organizational change management experience with a recognized framework (ADKAR, Prosci, Kotter, or similar), plus examples of plans you wrote and then actually executed.
Working knowledge of the infrastructure behind a rollout: SSO and identity providers (SAML, Okta, Entra ID), MDM (Intune, Jamf), cloud environments (AWS preferred), and test and staging environments.
Experience coordinating federal security and compliance gates such as ATO, SIA, Section 508, and privacy reviews.
Comfort with Agile delivery (Kanban in particular) and with Jira, Confluence, and ServiceNow.
Clear, concise writing that lands with both technical teams and executive audiences.
What would blow us away:
You’re Prosci certified (or hold an equivalent change management credential), so “ADKAR” is a framework you’ve actually used.
You’ve got PMP, PMI-ACP, or SAFe after your name, and you earned every letter.
You’ve already worked at CMS, HHS, or another big federal civilian agency, so agency comms review, security gates, and the IT service desk hold no surprises for you.
You’ve rolled out or administered AI tools like Claude, Gemini, ChatGPT Enterprise, Notion, Fireflies, or Wispr Flow, and lived to tell the tale.
You’ve built a pilot governance process from scratch, with real decision gates and success criteria. No vibes-based go/no-go calls here.
You build adoption dashboards (Power BI or similar) that prove a tool is earning its keep, not just that people logged in once and wandered off.
You’ve grown a champion network of power users who spread the good word so you don’t have to do it alone.
You know your way around tiered support and ServiceNow knowledge bases, and you believe a great Tier 0 article is a gift to everyone.
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
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!
