Freelance Remote Senior Program Manager Jobs in Chicago, IL

Rithum™ is the world's most trusted commerce network, accelerating how brands, suppliers, and retailers work together to deliver seamless e-commerce experiences. We provide an unmatched platform for brands and retailers, enabling them to accelerate growth, optimize operations across channels, scale product offerings and enhance margins.
Today, more than 40,000 companies trust Rithum to grow their business across hundreds of channels, representing over $50 billion in annual GMV. Using our commerce, marketing, and delivery solutions, our customers create optimized consumer shopping journeys from beginning to end.
Overview
Across all roles, employees are expected to leverage AI to move faster, work smarter, and create scalable patterns that improve execution and business outcomes.
As a Senior Strategic Program Manager you are responsible for leading execution across high-priority strategic initiatives, including mergers and acquisitions (M&A), corporate development, AI transformation, and enterprise operational priorities. Serving as a strategic partner to executive leadership, you will drive cross-functional coordination, program governance, executive reporting, and operational execution across a complex portfolio of initiatives. This role combines strategic program management, business transformation, and operational leadership to ensure initiatives remain aligned, risks are proactively managed, and programs move from strategy through execution with speed, accountability, and transparency. Success in this role requires strong executive presence, operational rigor, analytical thinking, and the ability to leverage AI-enabled tools to improve visibility, efficiency, and decision-making.
Responsibilities
Strategic Program Leadership

• Lead execution and coordination of complex strategic initiatives, including M&A integration activities, AI transformation programs, and enterprise operational priorities
• Partner closely with executive leadership to translate strategic priorities into actionable plans, timelines, milestones, and governance structures
• Drive accountability across cross-functional stakeholders to ensure initiatives remain aligned to business objectives and execution commitments
• Identify dependencies, risks, resource constraints, and escalation points across multiple concurrent initiatives
• Support strategic planning, prioritization, and operational alignment activities tied to corporate objectives and organizational transformation efforts

Corporate Development & Transformation Support

• Coordinate integration workstreams across functional areas to support acquisition onboarding, operational alignment, and post-merger execution
• Monitor integration milestones, issue resolution, organizational dependencies, and readiness activities across acquired entities and strategic initiatives
• Support due diligence, operational assessments, integration planning, and transformation readiness activities as needed
• Assist with organizational change management and communication efforts tied to strategic transformation initiatives
• Support operational optimization and continuous improvement initiatives that improve scalability and organizational effectiveness

Executive Operations & Business Management

• Support executive leadership in managing strategic priorities, operating rhythms, leadership meetings, action tracking, and cross-functional follow-through
• Prepare executive-level presentations, dashboards, status updates, business reviews, and strategic communications for leadership audiences
• Develop scalable reporting frameworks, KPI tracking, and executive visibility mechanisms to improve decision-making and organizational alignment
• Facilitate planning processes, prioritization discussions, governance reviews, and operational cadences across stakeholder groups

AI-First Operations & Process Optimization

• Leverage AI-enabled tools, automation, and scalable workflows to improve program execution, reporting, operational efficiency, and decision-making
• Identify opportunities to streamline manual processes and create repeatable operating mechanisms across strategic initiatives
• Partner with teams to improve adoption of AI-first ways of working and operational best practices
• Utilize analytics, reporting, and AI-assisted insights to support executive recommendations and business decisions

Qualifications
Minimum Qualifications

• 8+ years of experience in program management, strategic operations, business operations, consulting, corporate strategy, corporate development, PMO, or related functions with 5+ years in a SaaS company or technical e-commerce role
• Proven experience leading complex cross-functional initiatives with significant organizational visibility and executive stakeholder engagement
• Experience supporting corporate development initiatives, organizational transformation programs, or enterprise strategic initiatives
• Strong project and program management skills with demonstrated ability to manage multiple priorities simultaneously in fast-paced environments
• Demonstrated hands-on experience and AI fluency including Claude Chat, Cowork or Code to improve operational effectiveness and decision-making in a business environment
• Strong analytical, organizational, and problem-solving capabilities with attention to detail and operational rigor
• Experience building executive-level presentations, dashboards, reporting frameworks, and strategic business updates
• Exceptional communication, facilitation, and stakeholder management skills with the ability to influence across functions and leadership levels
• Strong proficiency with project management and collaboration tools such as Jira, Asana, Monday.com, Smartsheet, or similar platforms
• Ability to work standard business hours (8am - 5pm) either East Coast or Central Time

Preferred Qualifications

• Bachelor's degree in Business, Finance, Operations, Management, or related field; MBA or advanced degree preferred
• PMP or similar project/program management certification
• Experience supporting executive leadership within fast-paced, high-growth technology organizations
• Experience within e-commerce, retail technology, marketplace, SaaS, or commerce enablement industries
• Experience supporting board-level reporting, strategic planning, investor-related operational initiatives, or executive business operations
• Prior experience within consulting, strategy, corporate development, business transformation, or operational excellence environments

Travel Required
Up to 10%
Other Duties
Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities required of the employee for this job. Duties, responsibilities, and activities may change at any time with or without notice.
What it's like to work at Rithum
When you join Rithum, you can expect to work with smart risk-takers, courageous collaborators, and curious minds.
As part of the Rithum team, you are valued, supported, and included. Guided by a transparent culture and accessible, approachable leadership, we offer career opportunities aligned to your ambitions and talents. To ensure work and life balance works for you, we also offer an array of resources to support you and your families, including comprehensive benefits and wellness plans.
At Rithum you will:

• Partner with the leading brands and retailers.
• Connect with passionate professionals who will help support your goals.
• Participate in an inclusive, welcoming work atmosphere.
• Achieve work-life balance through remote-first working conditions, generous time off, and wellness days.
• Receive industry-competitive compensation and total rewards benefits.

We believe in transparency and fairness in our compensation practices.
For this position, the expected base pay range is: $145,000-$195,000 per year.
This range represents the base pay for the role across all U.S. locations and is determined based on market data, internal equity, and experience. Final compensation may vary depending on geographic location, skills, and relevant experience.In addition to base pay, we offer a discretionary bonus for non-sales roles, a comprehensive benefits package, and, where applicable, sales incentives.
For this position, the expected discretionary bonus is 12% of the annual base salary.
Benefits

• Medical, dental and vision benefits: Affordable health care plans and company HSA contributions, starting on Day 1
• A 6% 401(k) match
• Competitive time off package with 20 days of Paid Time Off, 9 Company-Paid holidays, 2 paid floating holidays, 7 paid sick days, 2 Wellness days, and 1 Paid Volunteer Day; at 3 years of service PTO increases to 22 days, and at 5 years it increases to 25 days
• 12 weeks primary caregiver leave & 4 weeks secondary caregiver leave
• Accident, critical illness, and hospital indemnity insurance
• Pet insurance
• Legal assistance and identity theft insurance plans
• Life insurance 2x salary
• Access to the Calm app and the Employee Assistance Program
• $65/month Remote work stipend for internet
• Culture and team-building activities
• Tuition assistance
• Career development opportunities
• Charitable contribution match up to $250 per year

Rithum is an equal opportunity employer. We are committed to providing an environment of mutual respect where equal employment opportunities are available to all applicants and teammates without regard to race, religion, color, sex, gender identity, sexual orientation, age, non-disqualifying physical or mental disability, national origin, veteran status or any other protected characteristic. All employment is decided on the basis of qualifications, merit, and business need.
We're committed to providing reasonable accommodations in accordance with the law for qualified applicants. If you require assistance during the interview process due to a medical condition or need support accessing our website or completing the application process, please reach out to us by completing the Accommodations Request Form. Your comfort and accessibility are important to us, and we're here to ensure a seamless experience as you explore opportunities with our team.