Transformation Scrum Master - Contact Center AI

Post Date

Jul 14, 2026

Location

Hartford,
Connecticut

ZIP/Postal Code

06105
US
Sep 20, 2026 Insight Global

Job Type

Contract-to-perm

Category

Project Manager

Req #

CHI-d39384e8-c43c-4f1f-b271-4d535699f877

Pay Rate

$40 - $50 (hourly estimate)

Job Description

This role is ideal for a Technical Scrum Master with enterprise-wide transformation experience and Contact Center AI initiatives. They will drive Agile ways of working, leading organizational change, optimizing value streams, and ensuring measurable business value realization across Contact Center AI and cross-functional strategic technology product programs.

The Transformation Scrum Master is responsible for driving organizational change and ensuring the successful realization of business value across strategic transformation initiatives. This role supports Contact Center AI programs, cross-product initiatives, and portfolio-level coordination efforts by facilitating agile practices, coaching teams and leaders, and helping the organization adopt new ways of working. The individual acts as a change agent, enabling alignment between business objectives, product outcomes, and enterprise transformation goals.
Key Responsibilities
• Lead and facilitate agile delivery practices across multiple teams and transformation programs.
• Drive organizational change initiatives and support adoption of new processes, technologies, and operating models.
• Facilitate Program Increment (PI) Planning, dependency management, and cross-team coordination.
• Partner with product, business, and executive stakeholders to align strategy, priorities, and outcomes.
• Coach teams, leaders, and stakeholders on Agile principles, Lean thinking, and continuous improvement practices.
• Monitor and track benefits realization, ensuring initiatives deliver measurable business value.
• Optimize value streams and identify opportunities to improve efficiency, flow, and customer outcomes.
• Manage portfolio-level dependencies and coordinate activities across multiple product and business groups.
• Develop and communicate transformation progress, risks, and outcomes to executive audiences.
• Support AI enablement initiatives within Contact Center operations and business transformation programs.

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to HR@insightglobal.com.To learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/.

Required Skills & Experience

• 5+ years of Scrum Master experience supporting technical product engineering teams.
• Healthcare or insurance claims domain expertise required.
• Strong understanding of Agile and SAFe methodologies with SAFe certification.
• Experience managing large-scale technology modernization initiatives with delivery metrics, risk and gap analysis, documentation, and coordination.
• Proven ability to coordinate cross-functional teams and third-party vendors.
• Expertise with JIRA and Rally.
• Strong communication, facilitation, and stakeholder management skills.
• Technical Domain Knowledge
○ Understanding of AI-enabled tools and emerging technologies.
○ Strong experience leading Agile transformations or enterprise-scale change initiatives.
○ Knowledge of Contact Center / CCaaS operations and AI-enabled business solutions.
○ Understanding of Lean Portfolio Management principles and practices.
○ Experience working across multiple teams, products, and organizational functions.
○ Familiarity with organizational change management methodologies and transformation frameworks.

Benefit packages for this role will start on the 1st day of employment and include medical, dental, and vision insurance, as well as HSA, FSA, and DCFSA account options, and 401k retirement account access with employer matching. Employees in this role are also entitled to paid sick leave and/or other paid time off as provided by applicable law.