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Principal Program Manager
Chicago, IL (Hybrid) - preferred; remote available in WI & MI · Full-Time
ABOUT ALEYSIAN
Aleysian is a B2B technology consulting firm that designs and builds the revenue foundation connecting selling, quoting, billing, and fulfillment into a single structural system. We work at the intersection of quote-to-cash and digital commerce, engaging at the C-suite level to architect around your revenue model — not just implement tools. The result is infrastructure built to hold under the weight of growth, across every channel, at scale.
THE ROLE
The Principal Program Manager owns the full lifecycle of client engagements, from initiation through closure, keeping delivery on scope, on time, and on budget. The ideal candidate is the client's primary point of contact, building the relationships and trust that drive satisfaction and program success. Our Program Managers work across executive leadership, project teams, and client stakeholders to align goals, manage risk, and control budgets on every engagement. They combine delivery rigor with technical credibility, translating complex enterprise systems and integration challenges into clear execution plans that drive measurable business outcomes.
WHAT YOU'LL DO
Program & Project Delivery
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Manage the full lifecycle of projects, from initiation through planning, execution, and closure, ensuring delivery within scope, time, and budget.
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Monitor project performance, conduct regular reviews, and implement quality control measures to ensure high-quality solutions.
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Lead formal testing, validation, and production readiness activities (system testing, UAT, integration validation) to ensure solutions are operationally sound before and after go-live.
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Manage go-live execution and hypercare/stabilization, ensuring smooth transition to operations and addressing issues in real time.
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Design governance structures and reporting cadences from kickoff, tailored to engagement complexity and stakeholder needs; own steering meetings and executive updates.
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Reset expectations proactively when project conditions shift; present stakeholders with options and impact assessments rather than just flagging changes.
Technical Partnership & Execution
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Work confidently with architects, engineers, and technical teams to understand system design, integrations, performance requirements, and technical constraints.
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Translate complex technical concepts into clear priorities, dependencies, and roadmap decisions that align business needs with technical feasibility.
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Understand systems, integrations, and data flows; anticipate downstream impacts and dependencies across the broader platform ecosystem.
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Interpret data models, object relationships, and technical trade-offs between configuration and customization; explain technical concepts clearly to non-technical stakeholders.
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Pressure-test technical estimates with relevant questions; identify scope creep risks in technical and functional conversations.
Client Partnership & Account Growth
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Serve as the main point of contact for clients, build strong relationships, understand their needs, and ensure their satisfaction throughout the project.
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Collaborate with key internal and external stakeholders — including executive leadership, project teams, and client representatives — to ensure alignment on goals, expectations, and timelines.
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Identify scope creep early and convert it into formal change orders with clear impact assessments; manage scope discussions without always escalating to leadership.
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Connect delivery performance to business outcomes; monitor account health and surface expansion or renewal opportunities to the account executive.
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Contribute to RFP responses and new business proposals, leveraging your delivery credibility and domain expertise to strengthen pursuits.
Resourcing & Team Leadership
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Oversee resource planning and allocation, ensuring project teams are effectively staffed and utilized while balancing workload across multiple projects.
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Lead, mentor, and support project teams, fostering a collaborative environment and promoting professional development.
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Identify opportunities for individual, team, and artifact development.
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Build and maintain high-performing teams; identify development needs proactively and create stretch opportunities for junior team members.
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Navigate team conflicts and maintain morale during high-pressure periods; facilitate planning sessions and retrospectives that drive continuous improvement.
Risk, Budget & Governance
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Identify, assess, and mitigate risks across the project or program, proactively addressing issues that may affect success and providing solutions to keep projects on track.
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Identify technical risks early (capacity, latency, integration gaps, system dependencies) and drive mitigation strategies before they impact delivery.
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Surface risks with context and resolution options, not just flags; manage escalations independently when possible to avoid unnecessary leadership involvement.
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Manage project budgets, including forecasting, tracking, and reporting on financial performance to ensure profitability while controlling costs.
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Implement governance structures to monitor project health, report on progress to stakeholders, and ensure adherence to program objectives and compliance standards.
WHAT YOU BRING
Required
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8+ years of experience in program or project management within a consulting environment.
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Experience leading technical programs or initiatives involving enterprise systems, integrations, platform implementations, or infrastructure modernization.
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Recognized for delivery excellence: requested by name for future engagements, with a track record of meeting commitments on time and at quality.
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Comfortable using AI tools to work more efficiently — from scoping and status reporting to research and QA — and expected to bring that same fluency to how programs are run for clients.
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Results-oriented, with the ability to be accountable for tasks and achieve objectives with minimal guidance.
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Ability to handle multiple priorities in a fast-moving environment.
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Excellent oral and written communication skills.
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Strong organizational skills, including experience with program management tools.
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Attention to detail and strong problem-solving skills.
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Ability to work well both individually and within a team.
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Comfort working in a small company atmosphere at a fast pace.
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Deep expertise in one or more delivery disciplines (e.g., Agile, large-scale program delivery, release management); recognized internally or externally as a subject matter expert.
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Eligible to work in the United States without limitation.
COMPENSATION & BENEFITS
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Base salary $140,000–$160,000, commensurate with experience.
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Full medical, dental, and vision insurance, and 401(k) with company match.
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Short-term and long-term disability coverage.
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Unlimited PTO.
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Home internet and mobile phone reimbursement.
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Flexible schedule, hybrid from our downtown Chicago office.
HOW TO APPLY
Send your resume and a short note on a program you've delivered under pressure to [email protected].
Aleysian is an equal opportunity employer. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.
We architect the revenue foundation. Then we build it.
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