Ryan Cleaver

About Ryan Cleaver

I am a service delivery leader who believes great outcomes start with strong teams, clear communication, and trust. I currently serve as a Senior Manager of AIA Program Management at Five9, where I lead and support Program Managers delivering AI and automation solutions for our customers.Throughout my time at Five9, I have worked across implementation delivery, pre-sales support, financial forecasting, escalation management, and mentoring. While my roles have evolved, my approach has remained consistent. Listen first. Create stability. Set clear expectations. Support people so they can do their best work, especially in complex or high-pressure environments.I am particularly motivated by developing people. I enjoy coaching Program Managers through growth moments, helping them navigate challenges, and giving them the confidence and space to lead their projects effectively. I focus on explaining the “why” behind decisions, not just the “what,” and I aim to build teams that feel safe, supported, and accountable.I am an avid learner by nature and I enjoy staying curious, especially as technology and AI continue to evolve. Much of that curiosity is fueled by life outside of work as well. I am a parent to two young kids who ask endless questions, which has reinforced my appreciation for learning, patience, and perspective.Outside of work, I am a big sports fan, following both professional and college football, basketball, baseball, and hockey. Chicago sports loyalty included. Go Bears.I value humility, consistency, and thoughtful leadership, and I am grateful for the opportunity to build meaningful relationships with teammates, partners, and customers as we continue to grow and evolve.What I’m known for:• Creating stability in fast-changing organizations• Developing and mentoring Program Managers• Calm escalation management and executive communication• Translating complex delivery challenges into clear action• Building trust across Sales, Engineering, and Services teams

Experience

1. Senior Manager, Aia Program Management

   Five9

   Dec 2025 — Present · Lake Forest, IL, US

   Lead and develop a team of Program Managers responsible for delivering Five9’s AI and Automation solutions, including IVA and Agent Assist. Partner closely with AIA Engineering, Sales, Professional Services leadership, and cross-functional stakeholders to ensure successful customer outcomes, team stability, and operational excellence. • Directly manage and coach AIA Program Managers, focusing on performance, growth, engagement, and long-term career development • Serve as an escalation point for complex AI delivery challenges, working collaboratively with technical leadership and customers to drive resolution • Support AI pre-sales efforts by bringing delivery perspective, setting expectations, and helping teams align solutions to customer needs • Focus on creating stability, trust, and psychological safety for a team that has experienced significant change • Drive alignment between AIA delivery teams and broader Five9 Professional Services practices

Education

• Michigan State University

  Bachelor of Business Administration (B.B.A.), Business Management

  1999 — 2003

Skills

• Leadership
• Management
• Requirements Analysis
• Business Analysis
• Cross-Functional Team Leadership
• Integration
• Program Management
• New Business Development
• Project Management
• Account Management
• Analysis
• Professional Services
• Customer Service
• Solution Selling
• Business Development
• Business Intelligence
• Vendor Management
• Project Planning