About The Position

At bswift we’ve been transforming benefits administration since 1996, making it simpler, smarter, and more human. Our state-of-the-art, cloud-based technology and services empower employees to understand, manage, and love their benefits. From downtown Chicago, and remotely across the country, we serve thousands of companies and millions of people nationwide, reducing administrative burdens and freeing HR teams to focus on creating thriving, people-first workplaces. We’re looking for motivated and goal-driven individuals who share our passion for delivering excellence and creating solutions that make a difference. The reward is a fun, flexible and creative environment with ample opportunity for professional and personal growth. If you love the bswift values of pursue excellence, embrace accountability, deliver superior service, and be a great place to work, we want to hear from you! We are seeking a dynamic Senior Program & Project Manager to lead enterprise-wide strategic programs and complex projects that drive transformation and growth. This role combines program-level vision with hands-on project execution, ensuring alignment with organizational priorities and delivering measurable business outcomes. The ideal candidate thrives in a fast-paced environment, excels at cross-functional collaboration, and builds strong partnerships with executive leadership.

Requirements

  • Bachelor’s degree required; advanced degree strongly preferred.
  • 8–12 years of experience in program and project management, with a focus on enterprise-level strategic initiatives.
  • Proven ability to influence and collaborate with executive leadership and cross-functional teams.
  • Expertise in Agile, Scrum, and Waterfall methodologies; PMP or PgMP certification preferred.
  • Exceptional communication, negotiation, and stakeholder management skills.
  • Proficiency in Smartsheet, Jira, and enterprise portfolio management tools.

Responsibilities

  • Strategic Program Leadership: Drive large-scale initiatives that support enterprise growth, operational excellence, and innovation.
  • Project Management Excellence: Manage multiple projects within strategic programs, ensuring scope, schedule, and budget adherence.
  • Executive Partnership: Serve as a trusted advisor to senior leadership, aligning program and project objectives with corporate strategy.
  • Cross-Functional Collaboration: Coordinate efforts across technology, operations, finance, and client-facing teams to achieve shared goals.
  • Governance & Reporting: Establish governance structures, reporting frameworks, and decision-making processes for programs and projects.
  • Stakeholder Engagement: Communicate effectively with executives, sponsors, and key stakeholders to provide transparency on progress, risks, and outcomes.
  • Methodology Expertise: Apply advanced program and project management methodologies (Agile, Scrum, Waterfall) for disciplined execution.
  • Risk & Change Management: Anticipate challenges, manage dependencies, and implement change strategies to minimize disruption and maximize impact.

Benefits

  • Comprehensive Health Benefits: Access to health, dental, and vision plans to support your wellness and that of your family.
  • Competitive Compensation: A compensation package that recognizes your skills, experience, and contributions, including performance-based incentives for most roles.
  • Remote first, Office friendly environment! No time to commute? No problem!
  • Retirement Savings Plans: Options to help you plan for a secure financial future with employer-sponsored retirement savings programs.
  • Professional Development: Opportunities for career growth, including training and access to resources to support your career progression.
  • Supportive Culture: A work environment that encourages collaboration, open communication, and creative problem-solving, where your voice and ideas are valued.
  • Employee Wellbeing Initiatives: Programs focused on mental health, financial planning, and wellness resources to help you thrive inside and outside of work.
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