Internal IT Team Lead

Sorry, this job was removed at 02:25 p.m. (CST) on Tuesday, Feb 17, 2026
Hiring Remotely in Chicago, IL, USA
In-Office or Remote
Artificial Intelligence • Information Technology • Software • Business Intelligence
The Role

About Cuesta Partners
Cuesta Partners is a boutique consulting firm specializing in technology strategy, data, AI, and M&A execution. We work with PE-backed companies and growth-stage organizations who need fast, pragmatic advisory support and hands-on execution. Our culture values autonomy, craftsmanship, and a bias toward action.

Role Overview
We are building an IT Team responsible for the internal technology backbone of Cuesta Partners, supporting our fast-growing business. As the Lead, you will be the senior-most member of this team—owning our Microsoft environment, core business applications, identity/access, security posture, and operational processes. You will have direct responsibility to hire the remaining staff and develop a vision for how technology will catalyze and unlock firm growth. You’ll also collaborate directly with leadership on strategic projects, vendor evaluations, and ongoing company improvements.

This role is ideal for someone who enjoys both hands-on technical problem-solving and designing the systems and workflows that scale a professional services firm.

Key Responsibilities

  • Develop and manage strategic internal IT roadmap for Cuesta, including AI and efficiency initiatives.

  • Own, administer, and continuously optimize our Microsoft 365 / Entra ID / SharePoint / Intune environments.

  • Manage the service desk experience, ticketing workflows, and escalation practices.

  • Lead onboarding/offboarding processes across apps, identity, access, and hardware procurement.

  • Oversee vendor and SaaS application management (Salesforce, Rippling, Slack, Kantata, etc.).

  • Partner with finance, HR, and operations on back-office enablement and automation.

  • Guide security initiatives in coordination with our cyber program (endpoint, MFA, monitoring).

  • Drive cross-functional improvements across business apps and workflows.

  • Mentor and provide direction to team members (including LATAM).

  • When relevant, support client-facing diligence or cyber assessments (light involvement).

Experience & Skills

  • 5–8+ years hands-on experience in Microsoft 365 / Azure AD / SharePoint / Intune administration.

  • Demonstrated ability to create structure and process in fast-moving or high-growth environments.

  • Strong troubleshooting and problem-solving orientation.

  • Familiarity with security frameworks, MFA enforcement, device management, and identity governance.

  • Experience improving back-office workflows across business systems is a plus.

  • Comfortable working cross-functionally with leaders and non-technical stakeholders.

Personal Attributes

  • Pragmatic. Operationally minded. Calm troubleshooting approach.

  • Communicates clearly, proactively, and respectfully.

  • Enjoys ownership and autonomy rather than rigid process.

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The Company
HQ: Chicago, Illinois
119 Employees
Year Founded: 2019

What We Do

We believe in the power of technology to create sustained, differentiated advantage. Our firm helps organizational leaders understand and use emerging digital solutions to drive value across their business. Technology has become an accelerating source of competitive divergence – Cuesta helps companies capitalize on this opportunity with a pragmatic, hands-on approach. Our team has scaled and operated companies across several industries, launching technology solutions focused on delivering business value. We believe the truth is in the details and projects are successful when the work is done the right way. At Cuesta, we are building the firm where we always wanted to work. We challenge convention, work efficiently, and seek ongoing personal growth. Our team supports each other and laughs together. We value diversity, creativity, humility, and perseverance.

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