Senior Program Manager Full Time Remote Jobs in Chicago, IL

The Senior Program Manager leads complex, enterprise-level initiatives that sit at the intersection of product strategy, software development, and business transformation. This role is responsible for driving high-visibility programs from concept through delivery, ensuring alignment between product vision, engineering execution, and organizational priorities. Unlike traditional project management roles, this position focuses on end-to-end ownership of strategic programs, including roadmap alignment, dependency management across teams, and measurable business outcomes. The role acts as a key connector across Product, Engineering, Operations, and Customer-facing teams to ensure initiatives deliver both technical success and business value.

• Own and deliver large, cross-functional programs tied to product innovation, platform enhancements, and company-wide strategic priorities.
• Translate high-level business objectives into structured, executable program plans with clear success metrics
• Partner with Product leadership to manage product lifecycle efforts from concept through launch, adoption, and ongoing optimization, ensuring initiatives align with roadmaps, release cycles, long-term strategy, and measurable business value
• Serve as the primary program partner to Product Managers and Engineering leaders, supporting portfolio trade-off and prioritization decisions across planning, delivery, and release stages by bringing clarity to scope, value, dependencies, risks, and resource constraints
• Leverage AI, process improvements, tooling, and scalable program management practices to streamline workflows, improve visibility, strengthen collaboration, and support consistent execution across teams
• Drive readiness for major releases, launches, and platform changes through the commercialization process to ensure alignment between technical delivery and customer/business outcomes, not just milestone completion
• Support Agile execution by aligning program-level milestones with team-level delivery frameworks (Scrum, SAFe, etc.)
• Lead simultaneous initiatives with varying complexity, ensuring consistent execution standards and visibility across programs
• Establish and maintain program structures including timelines, milestones, risks, and dependencies
• Proactively identify delivery risks and implement mitigation strategies after impact occurs
• Manage program governance, including status reporting, executive updates, escalation management, and clear stakeholder communication around program goals, progress, risks, and decisions
• Act as a central point of coordination across Product, Engineering, Customer Success, Sales, and Operations
• Track and communicate program success using defined KPIs and outcome-based metrics
• Incorporate feedback from internal teams and customers to refine future initiatives

• Bachelor’s Degree
• 6+ years of experience in program management, product development, or software delivery environments
• Scrum (Preferred)
• Project Management Certifications (Preferred)
• Certification in Six Sigma with documented execution of at least one Six Sigma project in a real business/production environment
• Proven experience managing large, complex initiatives involving Product and Engineering teams
• Experience in SaaS, platform, or technology-driven organizations strongly preferred

• Deep understanding of product development lifecycle and Agile delivery models
• Ability to operate at both strategic and execution levels, connecting vision to delivery
• Strong stakeholder management skills with the ability to influence across all levels
• Excellent communication skills, including experience delivering executive presentations and program reporting
• Advanced organizational and prioritization skills in fast-paced environments
• Strong analytical and problem-solving capabilities.
• Demonstrates proficiency using AI tools (e.g., Claude, ChatGPT, Copilot) to accelerate delivery, with hands-on experience applying them to program management work

• Uses independent judgment and discretion based upon the employee’s experience in the position and knowledge of the products, equipment, and services.
• Uses good judgment and possesses ethical work values.

• Moderate stress levels may be experienced in job performance.
• Position is performed in a general office environment, home office, or approved remote workspace where physical work includes lifting and carrying equipment and various other items weighing up to 50 lbs. at customer sites and trade shows.
• Ability to travel 25%

• Daily use of the Microsoft Teams (phone), computer, printer, and other routine office equipment
• Must have high-speed internet access

• Little responsibility for the safety of others. The job is performed in an office setting where there are no hazardous materials or equipment.

• Position is performed in an open office environment or approved remote work location.

• The anticipated base salary range for this position is $130,000 - $140,000 annually. This position is also eligible for an annual target bonus of 4%. Actual compensation will be determined based on factors including relevant experience, skills, qualifications, and geographic location.
• Benefits include paid time off, medical, dental, and vision insurance, a 401(k) with a 5% company match, a fitness bonus, professional development opportunities, and programs that support overall well-being.

• Hybrid at a RedSail Office