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[Remote] Principal Program Manager

Remote Full-time Now Hiring

Note: The job is a remote job and is open to candidates in USA. Wintrust Financial Corporation is a financial institution providing community and commercial banking, specialty finance, and wealth management services. The Principal Program Manager leads strategic business initiatives, operational priorities, and cross-functional programs while serving as a strategic partner to the Senior Vice President. The role coordinates executive priorities, resource planning, governance, process improvements, and enterprise projects across business, technology, finance, compliance, and operations teams.

Responsibilities

  • Develop proactive relationships with senior leaders of supported business units that are built on trust, transparent communication, and a spirit of collaboration
  • Forecast IT resource requirements and equipment needs based on business units; pipeline of planned projects
  • Support executive communications, leadership presentations, board materials, and strategic planning activities
  • Partner with Risk, Compliance, Finance, and Operations to ensure adherence to organizational policies, regulatory requirements, and governance standards
  • Partner with the Senior Vice President to translate strategic priorities into actionable business plans, business cases, and measurable outcomes
  • Represent the business line’s priorities across the organization, ensuring stakeholders remain informed, engaged, and aligned throughout strategic initiatives and operational projects
  • Partner with business leaders and cross-functional teams to remove operational roadblocks, improve processes, and accelerate high-priority business initiatives

Skills

  • Bachelor's degree in business or technology
  • 10+ years working in a financial services environment with special emphasis on coordinating large cross functional programs and stakeholder management
  • 8+ years of management experience in which one or more of the following has occurred:
  • Demonstrated high competency in the prioritization of various competing deliveries of efforts
  • Demonstrated competency in strategic thinking and leadership with strong abilities in relationship management
  • Experience in managing resources to meet goals across multiple projects
  • Experience in leading multidisciplinary, high-performance work teams/groups
  • Demonstrated competency in developing efficient and effective solutions to diverse and complex business operations
  • Working knowledge of general IT and business operations
  • Must possess exceptional leadership, time management, facilitation, and organizational skills

Benefits

  • Award-winning culture
  • Discretionary or incentive bonus eligibility
  • Medical insurance
  • Dental insurance
  • Vision insurance
  • Life insurance
  • Accidental death and dismemberment insurance
  • Short-term and long-term disability insurance
  • Parental leave
  • Employee Assistance Program (EAP)
  • Traditional and Roth 401(k) with company match
  • Flexible Spending Account (FSA)
  • Employee Stock Purchase Plan at 5% discount
  • Critical illness insurance
  • Accident insurance
  • Transportation and commuting benefits
  • Banking benefits
  • Pet insurance
  • Promote from within culture

Company Overview

  • Wintrust Financial Corporation delivers sophisticated financial capabilities with a community bank personality across its businesses in banking, specialty finance, and wealth management. It was founded in 1995, and is headquartered in Rosamond, Illinois, USA, with a workforce of 5001-10000 employees. Its website is http://www.wintrust.com/.
  • Company H1B Sponsorship

  • Wintrust Financial Corporation has a track record of offering H1B sponsorships, with 12 in 2026, 26 in 2025, 15 in 2024, 19 in 2023, 27 in 2022, 10 in 2021, 7 in 2020. Please note that this does not guarantee sponsorship for this specific role.