Agile Coach

Post Date

May 18, 2026

Location

Sun Prairie,
Wisconsin

ZIP/Postal Code

53596
US
Jul 18, 2026 Insight Global

Job Type

Contract

Category

Insurance

Req #

MKE-e44b0a11-6b17-4b5b-9f82-88f2930ae178

Pay Rate

$68 - $85 (hourly estimate)

Job Description

Responsibilities
Strategic Alignment & Architecture Integration
• Work seamlessly with Strategy and Architecture teams to ensure new pipeline initiatives are aligned with departmental and organizational strategic direction.
• Translate strategic objectives into coherent, prioritized roadmaps that balance regulatory, risk, and value driven change across EDSR.
Roadmap & Portfolio Ownership
• Own and maintain EDSR roadmaps, ensuring alignment with approved strategies, interdependencies, funding horizons, and the broader enterprise change portfolio.
• Ensure roadmaps remain current and actionable as priorities, capacity, and risk profiles evolve.
Business Case & Readiness Assurance
• Drive the creation and refinement of business cases by ensuring that:
o The problem statement, scope, risks, dependencies, and intended outcomes are clearly defined
o Business readiness, operational impact, and change/adoption considerations are explicitly assessed at a proportionate level
• Provide assurance that business cases are decision ready and support sound, evidence based investment decisions.
• Partner with business and change management leaders to ensure initiatives are supported by appropriate adoption, communication, and readiness plans, enabling sustainable change and value realization.
Portfolio Prioritization
• Own backlog governance and prioritization, providing end to end assurance of the EDSR change portfolio, together with the PMO from intake through delivery and closure.
• Establish and operate a portfolio planning cycle to evaluate new demand post intake and confirm what initiatives should enter the portfolio based on strategic alignment and value
Agile & Incremental Delivery Enablement
• Promote and enable the effective use of agile and iterative delivery approaches across initiatives.
• Ensure initiatives are appropriately scoped to deliver incremental value, minimum viable outcomes, and early benefits realization.
• Support the definition, implementation, and oversight of the benefits realization framework to track intended and realized value across the EDSR change portfolio, ensuring initiatives deliver measurable strategic and business outcomes.
Executive Stakeholder Management & Decision Support
• Establish early executive level accountability for initiatives, including clear ownership, sponsorship, and decision rights.
• Act as a trusted advisor to senior stakeholders by:
o Facilitating trade off discussions and scenario analysis
o Providing portfolio level insights, options, and strategic recommendations
Enterprise Governance & Forums
• Coordinate the submission of business cases, roadmaps, and supporting materials to the Enterprise Technology Office and other relevant governance forums.
• Ensure governance discussions are outcome focused, decision led, and aligned to strategic priorities.
Work Experience:
Preferred Work Experience includes:
• Safe, Scrum, Kanban, XP, Design Thinking, Coaching education
• Proven Agile program delivery experience
• Proven results leading complex scale change to agile ways of working using Safe, Scrum and Kanban
• Experience of building agility into traditionally structured organizations
• CV Limit

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

Responsibilities
Strategic Alignment & Architecture Integration
• Work seamlessly with Strategy and Architecture teams to ensure new pipeline initiatives are aligned with departmental and organizational strategic direction.
• Translate strategic objectives into coherent, prioritized roadmaps that balance regulatory, risk, and value driven change across EDSR.
Roadmap & Portfolio Ownership
• Own and maintain EDSR roadmaps, ensuring alignment with approved strategies, interdependencies, funding horizons, and the broader enterprise change portfolio.
• Ensure roadmaps remain current and actionable as priorities, capacity, and risk profiles evolve.
Business Case & Readiness Assurance
• Drive the creation and refinement of business cases by ensuring that:
o The problem statement, scope, risks, dependencies, and intended outcomes are clearly defined
o Business readiness, operational impact, and change/adoption considerations are explicitly assessed at a proportionate level
• Provide assurance that business cases are decision ready and support sound, evidence based investment decisions.
• Partner with business and change management leaders to ensure initiatives are supported by appropriate adoption, communication, and readiness plans, enabling sustainable change and value realization.
Portfolio Prioritization
• Own backlog governance and prioritization, providing end to end assurance of the EDSR change portfolio, together with the PMO from intake through delivery and closure.
• Establish and operate a portfolio planning cycle to evaluate new demand post intake and confirm what initiatives should enter the portfolio based on strategic alignment and value
Agile & Incremental Delivery Enablement
• Promote and enable the effective use of agile and iterative delivery approaches across initiatives.
• Ensure initiatives are appropriately scoped to deliver incremental value, minimum viable outcomes, and early benefits realization.
• Support the definition, implementation, and oversight of the benefits realization framework to track intended and realized value across the EDSR change portfolio, ensuring initiatives deliver measurable strategic and business outcomes.
Executive Stakeholder Management & Decision Support
• Establish early executive level accountability for initiatives, including clear ownership, sponsorship, and decision rights.
• Act as a trusted advisor to senior stakeholders by:
o Facilitating trade off discussions and scenario analysis
o Providing portfolio level insights, options, and strategic recommendations
Enterprise Governance & Forums
• Coordinate the submission of business cases, roadmaps, and supporting materials to the Enterprise Technology Office and other relevant governance forums.
• Ensure governance discussions are outcome focused, decision led, and aligned to strategic priorities.
Work Experience:
Preferred Work Experience includes:
• Safe, Scrum, Kanban, XP, Design Thinking, Coaching education
• Proven Agile program delivery experience
• Proven results leading complex scale change to agile ways of working using Safe, Scrum and Kanban
• Experience of building agility into traditionally structured organizations
• CV Limit
o Most Qualified - 3 to 5 CVs

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.