Help Desk Support Lead

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.

• Lead support for CMS’s enterprise AI services, keeping high-profile users productive and happy.
• Own the support queue, set the standard for response and quality, and keep the team’s rhythm tight.
• Provide white-glove support to CMS stakeholders, up to the Administrator’s office, with polish and discretion.
• Mentor support staff, build playbooks, and raise everyone’s game.
• Channel feedback from leadership back to the product, AI, and engineering teams.
• Maintain SOPs and knowledge base articles and support UAT and post-deployment smoke testing.

What we’d like you to have: