Contract Remote Pattern Maker Jobs in Chicago, IL

Job Type: FTE
Level: Senior
Department: Engagement Management Office (EMO)
Location: Remote (US or Canada)
Rate: $120,000-$150,000 USD (rates vary in Canada)
Position Overview
Cyclotron is seeking a senior-level Project Manager with a strong background in IT services consulting to join our Engagement Management Office (EMO). This role blends traditional project delivery rigor with a high degree of engagement and relationship management. The ideal candidate is a trusted client partner who can lead complex Microsoft-focused initiatives end-to-end, translate business needs into executable plans, and proactively manage stakeholders, risks, and outcomes. This role emphasizes ownership of the overall engagement. Not just schedules and tasks. Ensuring projects deliver measurable value, strong client experiences, and long-term partnership success.
Responsibilities
Engagement & Stakeholder Management

• Serve as the primary point of accountability and escalation for client engagements, owning the overall success of the relationship.
• Build and maintain strong, trusted relationships with client stakeholders, delivery teams, and senior executives.
• Act as a trusted advisor to the client, providing guidance throughout the project lifecycle-not just execution updates.
• Demonstrate a deep understanding of the client's business context, objectives, and "why" behind the project.
• Drive business development by identifying upsell and cross-sell opportunities within existing accounts.

Project & Delivery Leadership

• Plan, initiate, and manage complex Microsoft-centric projects from initiation through closure.
• Develop and maintain detailed project plans covering scope, milestones, resources, budget, and dependencies.
• Lead and coordinate cross-functional delivery teams to meet contractual commitments around scope, schedule, and budget.
• Serve as the liaison between business and technical teams, ensuring clarity of requirements and alignment on delivery.
• Maintain a complete and current understanding of project scope and proactively manage change.

Risk, Quality & Financial Management

• Identify, assess, and proactively mitigate risks and issues throughout the lifecycle of the engagement.
• Monitor progress against plans, standards, and cost targets; adjust approach as needed to drive successful outcomes.
• Ensure deliverables meet quality expectations through review, validation, and continuous improvement.
• Understand project funding milestones and contractual requirements; track progress and support billing and proof-of-execution activities.
• Partner with resourcing and delivery teams to validate capacity, monitor actuals, and ensure alignment with contract assumptions.

Continuous Improvement & Leadership

• Apply sound project management methodology and judgment to lead teams, resolve conflicts, and remove blockers.
• Mentor delivery team members and, where appropriate, client stakeholders.
• Evaluate project outcomes against defined objectives and KPIs.
• Conduct post-project reviews to capture lessons learned and identify process improvement opportunities.
• Contribute as a thought leader within the EMO, bringing a growth mindset and continuous improvement focus.

Qualifications

• 8+ years of experience in strategic consulting and project management within an enterprise client-facing role.
• Proven track record managing complex projects involving multiple stakeholders, cross-functional teams, and executive audiences.
• Strong understanding of the Software Development Lifecycle (SDLC) and modern project delivery methodologies (Agile, Hybrid, Waterfall).
• Solid technical foundation, including experience with Microsoft technologies and cloud-based solutions.
• Experience managing project financials, including budgets, forecasting, and milestone-based funding.

• Demonstrated strength in client engagement management, including expectation setting, executive communication, risk mitigation, and issue resolution.
• Excellent verbal and written communication skills with audiences at all organizational levels.
• Ability to translate complex technical and business concepts into clear, actionable plans and insights.
• Confident decision-maker with strong analytical and problem-solving skills.
• Highly organized, detail-oriented, and capable of managing multiple concurrent engagements.
• Collaborative leadership style with strong interpersonal and conflict-resolution skills.

Additional Knowledge & Skills

• Proficiency with Microsoft Office tools and Microsoft Project.
• Bachelor's degree preferred.
• PMP, PRINCE2, Agile certification, or equivalent project management education preferred.
• Prior experience delivering Microsoft Cloud projects or working with Microsoft funding programs is a plus.

About the Company
Cyclotron is a Microsoft Solutions Partner focused on the modern workplace, data, and AI. We are dedicated to empowering clients to streamline operations and achieve their business goals. The company fosters a collaborative and inclusive environment, encouraging continuous learning and professional growth for its employees. Cyclotron's mission is to deliver reliable, forward-thinking technology solutions that drive success for clients across various industries.
What We Can Offer
Cyclotron offers a comprehensive benefits package designed to support our employees' well-being and professional growth in a fully remote work environment. We provide competitive health, dental, and vision insurance, and we cover 100% of employee medical premiums. Our team members benefit from generous and flexible paid time off (PTO), retirement plan options, and ongoing training opportunities. Additionally, Cyclotron promotes work-life balance with flexible work arrangements and robust wellness programs, creating a rewarding and supportive workplace for all.
Cyclotron relies on diversity of culture and thought to deliver on our goals. To ensure we can do that, we seek talented, qualified employees to join our team, regardless of race, color, sex/gender, including pregnancy, gender identity and expression, national origin, religion, sexual orientation, disability, age, marital status, citizen status, veteran status, or any other protected classification under applicable law. We are proud to be an Equal Employment Opportunity/Affirmative Action Employer.
We also provide reasonable accommodation for qualified individuals with disabilities and for sincerely held religious beliefs in accordance with applicable law.
Cyclotron is an Equal Opportunity Employer. Cyclotron values diversity, equity and inclusion, and aims to practice DE&I in all that we do.