Delivery Expert

RedMane Technology • Norridge, IL

2d • Hybrid

About The Position

The Delivery Expert is a senior practitioner and trusted advisor working across RedMane’s portfolio of projects and clients. The role helps teams start well, navigate difficult situations, prepare for critical milestones, and continuously improve delivery. It is not a compliance role or an additional layer of project management; instead, the Delivery Expert brings broad technical and delivery experience, identifies gaps and unintended consequences, connects work across teams, and helps leaders make pragmatic decisions while preserving creativity and innovation.

The role supports project direction and governance, advises teams through complex delivery challenges, strengthens delivery practices without imposing a single methodology, builds integrated expert teams, and leads or supports readiness assessments for releases, deployments, go-lives, and stabilization. It also contributes to strategic client discussions and selected pursuits, estimates, solution reviews, and project transitions. The position is Chicago-based and involves an expectation of 20–30% travel to client sites in North America.

Requirements

• Substantial hands-on experience delivering complex software or technology-enabled transformation programs; no specific number of years is stated.
• A hands-on technical foundation, preferably including software development or coding experience.
• Direct experience working with end users and client decision-makers on requirements, process, and solution design.
• Technical design and architecture experience sufficient to evaluate trade-offs, dependencies, complexity, and long-term consequences.
• Project or program management experience, including firsthand exposure to project controls, schedules, financials, risks, obstacles, and the results of decisions.
• Demonstrated success guiding large implementations through planning, delivery, deployment, go-live, and stabilization.
• Experience working with executive client sponsors and multidisciplinary project teams.
• Exceptional judgment and the ability to identify underlying issues.
• Ability to see the whole system and enough detail to spot gaps and unintended consequences.
• Ability to set direction early, build alignment, and adapt when evidence supports a different path.
• Strong facilitation, communication, coaching, and conflict-resolution skills.
• Ability to balance delivery discipline, technical quality, speed, financial responsibility, simplicity, and innovation.
• Confidence to challenge leaders and teams constructively while maintaining trust.
• Ability to turn experience into reusable insight without treating past practice as the only answer.
• Curiosity, collaboration, willingness to listen before prescribing, and ability to improve outcomes through influence, expertise, and judgment rather than hierarchy.

Nice To Haves

• Experience delivering large public-sector technology implementations.
• Experience in health and human services, child welfare, Medicaid, eligibility, workforce programs, or related government modernization initiatives.
• Experience across agile, iterative, hybrid, and phased delivery approaches.
• Consulting or advisory experience in complex client environments.

Responsibilities

• Help teams establish clear objectives, practical governance, decision rights, delivery plans, and project controls.
• Align client sponsors, project leaders, technical leaders, and workstreams on consequential choices, including simplicity versus customization.
• Identify assumptions, dependencies, and risks inherited from pursuits, proposals, contracting, and solution design.
• Encourage modular, phased approaches that build momentum and reduce risks associated with comprehensive big-bang delivery.
• Advise teams facing complex technical, delivery, organizational, financial, or client challenges.
• Identify gaps, conflicting decisions, hidden dependencies, and issues across workstreams.
• Facilitate candid conversations, clarify choices, and help teams move from analysis to practical action.
• Lead directly when needed while preserving project leaders’ accountability and development.
• Capture and share lessons, patterns, tools, and practices that improve team effectiveness without creating rigid rules.
• Help teams distinguish meaningful risk-management practices from low-value process and encourage pragmatic, simple, innovative solutions.
• Assess team strengths and gaps, ensure critical responsibilities are covered, and encourage collaboration across technical, functional, data, testing, change, operations, and client workstreams.
• Coach delivery leaders and emerging leaders in judgment, communication, and early issue resolution.
• Lead or support readiness assessments for major releases, deployments, go-lives, and stabilization periods.
• Evaluate readiness across architecture, requirements, design, development, testing, data, training, cutover, operations, staffing, finances, and client decision making.
• Check that workstream plans form a coherent end-to-end outcome and ensure significant risks have owners, mitigation plans, and appropriate sponsor visibility.
• Participate in strategic client discussions and help sponsors understand consequential choices, trade-offs, dependencies, and required support.
• Provide delivery and implementation insight during selected pursuits, estimates, solution reviews, and project transitions.
• Help ensure company commitments are realistic and executable while allowing teams room to innovate.
• Use delivery expertise, candor, and practical problem solving to build lasting client confidence and relationships.

Benefits

• Flexible work environment with hybridized locations and schedules.
• Frequently catered lunches in the office.
• Market-based compensation and a comprehensive benefits package, including medical, dental, vision, 401(k), and short- and long-term disability insurance.
• Professional training and mentoring to support career growth.
• Employee wellness program with access to professional fitness coaches, structured dietary and nutrition plans, weekly Pilates classes in the office, and fitness events.
• Opportunities to give back to the community through the RedMane Community Impact Team and charitable activities.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed