Delivery Expert

Full time | RedMane Technology | United States

Posted On 11/10/2026

Job Information

Work Experience 5+ years

City Chicago

State/Province Illinois

IT Services

60656

Job Description

Delivery Expert

Help Great Teams Solve Difficult Problems

At RedMane, we help clients solve complex, meaningful problems through technology, deep expertise, and creative thinking. Our work supports public-sector agencies and mission-driven organizations responsible for health and human services, child welfare, public assistance, workforce development, and other programs that affect millions of lives.

The way we deliver matters. We believe disciplined delivery and innovative thinking reinforce each other. We use experience, proven practices, and sound project controls to see the whole picture and avoid preventable problems. But we are not formulaic, overly process driven, or interested in asking talented people to follow a playbook blindly. We expect our teams to think, challenge assumptions, simplify complexity, and develop the right solution for each client.

We are looking for a Delivery Expert who can help RedMane preserve that balance as we grow: enough structure to keep teams aligned and risks visible, and enough freedom for smart people to solve hard problems creatively.

About the Role

The Delivery Expert is a senior practitioner and trusted advisor who works across RedMane's portfolio of projects and clients. The role helps teams start well, navigate difficult situations, prepare for critical milestones, and continuously improve how RedMane delivers.

This is not a compliance role and it is not another layer of project management. The Delivery Expert does not impose a single method on every engagement or replace the accountability of project leaders. Instead, this person brings broad technical and delivery experience, asks the questions that reveal gaps and unintended consequences, connects work across teams, and helps leaders make pragmatic decisions without limiting creativity or innovation.

The strongest candidate will be equally comfortable in a technical design discussion, a client sponsor conversation, a project financial review, or a working session with a team facing a difficult delivery problem.

What You'll Do

Help Projects Start with Clear Direction

• Help teams establish clear objectives, practical governance, decision rights, delivery plans, and project controls without creating unnecessary bureaucracy.
  
• Ensure early alignment among 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 create momentum and reduce the risk of comprehensive big-bang delivery.
  

Guide Teams Through Difficult Delivery Problems

• Serve as a trusted advisor when teams encounter complex technical, delivery, organizational, financial, or client challenges.
  
• Look across workstreams to identify gaps, conflicting decisions, hidden dependencies, and issues that may fall between the cracks.
  
• Help teams understand the consequences of decisions beyond their immediate area and keep the overall client outcome in view.
  
• Facilitate candid conversations, clarify choices, and help teams move from analysis to practical action.
  
• Lead from the front when direct involvement is needed, while preserving the accountability and development of project leaders.
  

Strengthen Delivery Without Making It Formulaic

• Capture and share lessons, useful patterns, tools, and practices that make teams more effective without turning them into rigid rules.
  
• Help teams distinguish practices that manage real risk from process that adds little value.
  
• Promote pragmatism over perfection, simplicity over unnecessary complexity, and innovation over tradition for its own sake.
  
• Create space for teams to challenge established approaches when a better solution is available.
  
• Use experience and evidence to improve judgment across the company, not to mandate one-size-fits-all delivery.
  

Build Integrated, Expert Teams

• Understand the strengths and weaknesses of a team, recognize who is succeeding and who needs help, and ensure critical responsibilities are covered.
  
• Encourage collaboration across technical, functional, data, testing, change, operations, and client workstreams.
  
• Help teams avoid siloed decision making while retaining clear ownership and room for specialized expertise.
  
• Coach delivery leaders and emerging leaders to exercise judgment, communicate clearly, and address issues early.
  
• Favor strong, expert teams with clear accountability over simply adding more people.
  

Prepare for Critical Milestones

• 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.
  
• Test whether individual workstream plans add up to a coherent end-to-end outcome.
  
• Ensure significant risks have clear owners, practical mitigation plans, and appropriate sponsor visibility.
  

Partner with Clients and Support Growth

• Participate in strategic client discussions where independent delivery and technical judgment can add value.
  
• Help client sponsors understand consequential choices, trade-offs, dependencies, and the support required from them.
  
• Provide delivery and implementation insight during selected pursuits, estimates, solution reviews, and project transitions.
  
• Help ensure RedMane commitments are realistic and executable while leaving room for teams to innovate.
  
• Turn strong delivery, candor, and practical problem solving into lasting client confidence and relationships.
  

• You are curious, highly collaborative, and willing to listen before prescribing a solution.
  
• You expect excellence and hard work, with appropriate balance, and you model both.
  
• You know when consistency is essential and when a team should depart from convention.
  
• You make complexity understandable and favor practical progress over theoretical perfection.
  
• You see connections across technical, functional, organizational, financial, and client dimensions.
  
• You challenge constructively, make difficult issues open for discussion, and build trust while doing it.
  
• You improve outcomes through influence, expertise, and judgment rather than hierarchy.
  

Experience and Perspective

• Substantial hands-on experience delivering complex software or technology-enabled transformation programs. We value the depth and range of your experience more than a specific number of years.
  
• 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.
  
• Sufficient technical design and architecture experience 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 both good and poor decisions.
  
• Demonstrated success guiding large implementations through planning, delivery, deployment, go-live, and stabilization.
  
• Experience working with executive client sponsors and multidisciplinary project teams.
  

Capabilities

• Exceptional judgment and the ability to identify the issue behind the issue.
  
• Ability to see the whole system while understanding enough detail to spot gaps and unintended consequences.
  
• Ability to set direction early, build alignment around it, and adapt when evidence supports a better 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 translate personal experience into reusable insight without treating past practice as the only answer.
  

Preferred Experience

• 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.
  

• Projects: make better decisions earlier and avoid preventable delivery problems.
  
• Teams: remain creative and empowered while operating with clear direction, connected plans, and visible risks.
  
• Work streams: collaborate as one team and understand how their decisions affect the overall solution and client outcome.
  
• Delivery leaders: become stronger and more confident rather than dependent on the Delivery Expert.
  
• RedMane: develops useful shared practices without becoming rigid or bureaucratic.
  
• Clients: experience RedMane as thoughtful, candid, technically credible, and focused on solving the right problem.
  

Most organizations respond to delivery challenges by adding more management or more process. RedMane takes a different approach.

Our Delivery Expert helps smart, talented people do their best work. The role provides perspective, challenge, and coordination without replacing judgment with rules. It helps teams use experience and proven practices without becoming constrained by them. And it protects innovation by making sure creative decisions are informed by the full picture, not made in isolation.

You do not have to own the project to improve its outcome.

RedMane is a solutions company focused on helping clients achieve better outcomes through technology, expertise, and innovation. Headquartered in Chicago, with offices across North America, we partner with government and commercial organizations to solve complex challenges that matter.

Our culture is collaborative, entrepreneurial, and grounded in quality, integrity, and doing the right thing. We believe the best solutions come from talented people who combine deep expertise, independent thinking, and a genuine commitment to helping clients and colleagues succeed.

We Offer You

RedMane has an environment that offers challenging and interesting work. A place where you can have fun and express your talent and creativity. You will be working side by side with like-minded peers in a non-bureaucratic environment where sharing knowledge is the norm. Everyone at RedMane shares a passion for making a real difference for individuals, communities, and the world.

Additionally, we believe you should have fun and enjoy growing your career; we provide the supportive and empowering environment to make it happen. RedMane is very proud to offer employees professional and personal perks that include:

• A flexible work environment that includes hybridized locations and schedules with frequently catered lunches in the office.
  
• Market based compensation with a full range of benefits including medical, dental, vision, 401(k), short and long-term disability insurance, etc.
  
• A culture that promotes and fosters career growth through professional training and mentoring.
  
• An employee wellness program that includes free access to professional fitness coaches, structured dietary/nutrition plans, weekly Pilates classes in the office, and events that range from 5k's to triathlons.
  
• Opportunities to give back to the community through our RedMane Community Impact Team which organizes events like Feed My Starving Children, Toy Drives, and other charitable activities.
  

Chicago-based with expectation of 20-30% travel to client sites in North America.

Type

Full-Time

Reports To

Compensation

Competitive salary and comprehensive benefits package.