Senior Delivery Manager, Team Lead

66degrees · Chicago, IL · Other

Posted 2026-08-25

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Overview of Role

As a Senior contributor and Team Lead to the Delivery Management team at 66degrees, you will be responsible for managing the complete project / program life cycles of large complex enterprise projects, with a strong emphasis on leveraging agile delivery while actively leading, mentoring, and developing a team of delivery professionals. An ideal candidate will thrive in our fast-paced, collaborative culture at 66degrees, and believe in delivering innovative solutions that shape the future of work for our clients through effective project execution and exemplary people leadership.

Responsibilities:

Project Delivery and Execution

Manage enterprise projects from initial communication to project completion leveraging agile principles.

Lead cross-functional engagements (cloud, data, analytics, AI, application development, digital experience, strategy) and teams to maintain customer momentum driving project success.

Serve as the key intermediary between our customers and technical leadership to gather requirements, estimate work, define project milestones, and evaluate risks ensuring clear project scope.

Lead standups, scrum ceremonies, and project status meetings championing agile practices.

Facilitate the swift resolution of customer concerns and act as an escalation point for issues ensuring project progress.

Develop domain and technical knowledge to understand technical implementations to facilitate conversations that inform project decisions.

Responsible for project scope, finances, schedule and expectations of all parties, meticulously managing project deliverables.

Provide regular status updates to stakeholders and executive management, maintain effective communication with leadership to keep them aware of critical issues and action plans throughout the project lifecycle.

Own project retrospectives and related reporting, driving continuous improvement in project delivery.

Maintain an organized project using project management tools (e.g., FinancialForce, JIRA, Asana).

Build and maintain client relationships through project delivery and proven value.

Confidence in self-organization and a tenacity to deliver results for clients.

People Leadership and Mentorship

Facilitate 1:1 Meetings: Hold regular, scheduled one-on-one check-ins with each team member on a consistent cadence.

Provide Ongoing Feedback: Offer constructive, timely, and specific feedback to help your team members grow in their roles. Review individual goals and accountabilities on a regular basis.

Support Employee Growth: Take an active interest in your team members' career aspirations and help them identify opportunities to develop new skills and gain new experiences.

Foster a Positive Team Culture: Proactively build a supportive and inclusive team environment where all members feel valued, respected, and psychologically safe.

Manage Performance: Participate in the performance review process for your team members, providing comprehensive input that reflects their contributions and helps set clear goals for the future.

Qualifications:

8+ years of relevant experience working as an Engagement Manager or equivalent experience with technology implementations including significant experience successfully leading large engagements and programs for enterprise clients.

Proven experience mentoring, coaching, or formally leading a team (2+ years strongly preferred).

Prior experience working as a consultant and communicating with executives is required.

Strong technical background with a good understanding of software development and cloud technologies (GCP is a plus).

Unmatched analytical and communication skills, and demonstrated ability to translate client requirements to system functionality and project outcomes.

Technical aptitude and ability to understand technical designs, challenges, and risks

Proven ability to manage multiple projects at a time while paying close attention to detail

Solution-focused and ability diffuse high stake situations

Scrum/Agile Certification and knowledgeable about large enterprise delivery frameworks such as SAFe, Waterfall, etc with a strong preference for agile project work. Familiarity with agile software management and collaboration tools (JIRA, Google Workspace, Mavenlink, Asana).

Interest in building out regional delivery management teams focused on effective project delivery.

Capacity to travel to client sites as needed and requested (<25%)

A commitment to embodying the 66degrees culture of leadership, mentorship, and continuous learning.

A Bachelor’s degree in Business, Management, Engineering, or related or equivalent work experience required.

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