Senior Strategic Program Manager

This is a fully remote position, open to applicants in Illinois.

📋 Description

• Oversee the execution and coordination of intricate strategic initiatives, which include M&A integration activities, AI transformation programs, and enterprise operational priorities.

• Collaborate closely with executive leadership to convert strategic priorities into actionable plans, timelines, milestones, and governance frameworks.

• Foster accountability among cross-functional stakeholders to guarantee that initiatives stay aligned with business objectives and execution commitments.

• Recognize dependencies, risks, resource limitations, and escalation points across multiple simultaneous initiatives.

• Assist in strategic planning, prioritization, and operational alignment activities connected to corporate objectives and organizational transformation efforts.

• Coordinate integration workstreams across various functional areas to facilitate acquisition onboarding, operational alignment, and post-merger execution.

• Track integration milestones, issue resolution, organizational dependencies, and readiness activities across acquired entities and strategic initiatives.

• Aid in due diligence, operational assessments, integration planning, and transformation readiness activities as required.

• Support organizational change management and communication initiatives linked to strategic transformation efforts.

• Contribute to operational optimization and continuous improvement initiatives that enhance scalability and organizational effectiveness.

• Assist executive leadership in managing strategic priorities, operating rhythms, leadership meetings, action tracking, and cross-functional follow-through.

• Create executive-level presentations, dashboards, status updates, business reviews, and strategic communications for leadership audiences.

• Develop scalable reporting frameworks, KPI tracking, and executive visibility tools to bolster decision-making and organizational alignment.

• Facilitate planning processes, prioritization discussions, governance reviews, and operational cadences among stakeholder groups.

• Utilize AI-enabled tools, automation, and scalable workflows to enhance program execution, reporting, operational efficiency, and decision-making.

• Identify opportunities to refine manual processes and establish repeatable operating mechanisms across strategic initiatives.

• Collaborate with teams to promote the adoption of AI-first methodologies and operational best practices.

• Employ analytics, reporting, and AI-assisted insights to support executive recommendations and business decisions.

⛳️ Requirements

• 8+ years of experience in program management, strategic operations, business operations, consulting, corporate strategy, corporate development, PMO, or related fields within a SaaS or technical e-commerce context.

• Demonstrated experience in leading complex cross-functional initiatives with considerable organizational visibility and executive stakeholder engagement.

• Background in supporting corporate development initiatives, organizational transformation programs, or enterprise strategic initiatives.

• Strong project and program management abilities with a proven track record of managing multiple priorities simultaneously in fast-paced environments.

• Hands-on experience and fluency in AI tools including Claude Chat, Cowork, or Code to enhance operational effectiveness and decision-making in a business setting.

• Excellent analytical, organizational, and problem-solving skills, with a keen attention to detail and operational rigor.

• Experience in creating executive-level presentations, dashboards, reporting frameworks, and strategic business updates.

• Outstanding communication, facilitation, and stakeholder management skills, with the capability to influence across functions and leadership levels.

• Strong proficiency in project management and collaboration tools such as Jira, Asana, Monday.com, Smartsheet, or similar platforms.

• Availability to work standard business hours (8am – 5pm) either on the East Coast or Central Time.

🏝️ Benefits

• Medical, dental, and vision benefits: Affordable healthcare plans and company HSA contributions starting from Day 1.

• A 6% 401(k) match.

• Competitive time off package including 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 of primary caregiver leave and 4 weeks of secondary caregiver leave.

• Accident, critical illness, and hospital indemnity insurance.

• Pet insurance.

• Legal assistance and identity theft insurance plans.

• Life insurance at 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 matching up to $250 per year.