Pegeen Reilly

Chief of Staff l Strategy & Operations l Program Management l Performance Management l 25+ years at LinkedIn, eBay, PayPal, ActBlue l Open to full time and fractional roles

Omaha Metropolitan Area

About

What makes my work different — and frankly rarer than it should be — is that I can both design a process and run it. A lot of strategy and operations leaders can do one or the other. I've spent 25+ years doing both. I've led strategy, business operations, program management, and Chief of Staff work at PayPal, eBay, LinkedIn, and ActBlue. The breadth has been intentional: I've partnered with engineering and product teams (technical program management, Agile, SDLC), with GTM and customer functions (operations, service quality, enablement), and with people and talent organizations (performance management, calibrations, talent planning, learning and development). The scale has ranged from a focused fintech team to LinkedIn's 19,000-person global workforce. What I'm strongest at: • Launching new functions from scratch — building strategy, operating cadence, measurement systems, and the team • Operationalizing executive strategy into recurring rhythms that actually run • Running complex cross-functional programs across engineering, product, and GTM • Performance management, calibrations, and talent planning at scale • Running Chief of Staff organizations or acting as Chief of Staff during periods of transition, growth, or high-stakes change. Colleagues describe me as thoughtful, low ego, steady under pressure, and trusted across functions. I'm equally comfortable in a room of executives shaping strategy and in a working session walking a team through a new process. I'm currently open to Director, Senior Director, or Chief of Staff roles in strategy & operations, talent & learning operations, or program management at growth-stage SaaS companies. I'm also taking on selective fractional Chief of Staff and interim BizOps engagements while I look for the right full-time fit. Based in Omaha; remote or hybrid; open to travel. Best way to reach me: [email protected].

Experience

  • Strategy Deployment Principal at Hyland
    Jun 2026 - Present · 2 mos

    Leads cross-functional execution of Hyland's most business-critical corporate strategy initiatives, partnering across product, finance, and go-to-market to shape and deliver programs that drive company growth and performance. Translates strategy into action through initiative roadmaps, KPIs/OKRs, and operating models; drives alignment across business leaders and functional partners and surfaces progress, risks, and dependencies through executive-ready reporting.

  • ActBlue (2 yrs)
    • Principal, Program and Operations Management
      Apr 2025 - Mar 2026 · 1 yr

      • Plan and execute strategic, cross-functional initiatives spanning Legal, M&A, new product development, and organizational change; act as change leader ensuring initiatives are implemented smoothly and the organization is prepared for resulting impact. • Partner with leaders across Finance, Legal, Operations, Product, Marketing, and People & Culture to drive planning integration, resource alignment, and follow-through on key initiatives; provide structured governance, business reporting, and tracking for complex portfolios of work.

    • Interim Strategic Initiatives Lead
      Apr 2024 - Apr 2025 · 1 yr 1 mo

      Guiding Executive Leadership Team through roadmap and execution planning for new product development and strategic initiatives, including technology/architecture transformation, business strategy development and KPI creation, capacity planning, process/toolkit development, and coaching.

    • Interim Chief of Staff
      Sep 2024 - Nov 2024 · 3 mos

      Leading the Office of the Chief Executive (OCE) during a senior leader's absence by directly supporting the CEO and the OCE team, overseeing operational cadences, building key program management and operational governance processes, and ensuring no gap in coverage or performance during the interim period; Includes guiding the Executive Leadership team through strategic planning, defining key initiatives, setting clear measurement strategies, and building operational plans for the upcoming cycle.

  • Consultant: Program/Technical Program Management, Strategy and Business Operations at Self-employed
    Feb 2023 - Aug 2024 · 1 yr 7 mos

    • Led strategic transformational programs for senior executives in the software industry, focusing on Agile transformations, building program management practices and toolkits aligned with SDLC, and talent transformation programs for Product and Engineering. • Designed and facilitated leadership summits to drive organizational change. • Implemented career frameworks and enablement programs to enhance team performance and drive business growth.

  • LinkedIn ()
    • Director, Talent Management - Performance, Strategy and Integration
      Mar 2022 - Jan 2023 · 11 mos

      Head of Performance Management at LinkedIn. I own and lead our current midyear and annual review process for our ~19k employees across the world. As we continue to grow and accelerate our mission to create economic opportunity for every member of the global workforce, we realize we also need to rethink how we manage performance. I am currently creating a new approach rooted in our culture and values and designed to help every LinkedIn employee focus on their impact and growth.

    • Director, Member & Customer Readiness and Enablement
      Jun 2020 - Mar 2022 · 1 yr 10 mos

      Led global learning and performance functions, including product education, onboarding & skills development, global learning programs, and service quality teams, supporting ~1300 employees in our Global Customer Operations and Member & Customer Experience organizations. Built and launched a redesigned service quality program to drive Value Enhancement (vs. just issue resolution), creating global Readiness measurements, and introducing new ways of working to improve capacity management, prioritization and execution.

  • Layoff/position eliminated at Career Break
    Jan 2020 - May 2020 · 5 mos

    Left eBay in December 2019 as part of a restructuring of the organization. Had intended to take a 2 month break and then do a short term consulting engagement March - May 2020 before starting permanent work in late Spring, but COVID extended my time off through May. In June I started at LinkedIn.