Stephen Deflumeri

About Stephen Deflumeri

I’ve spent my career in software, mostly at early and growth-stage companies where things move fast and roles are fluid, which is exactly what I love about them. I’m passionate about building products that solve real problems and making sure customers have a great experience along the way. I’ve worked across sales, delivery, customer success, product, and go-to-market, so I’m used to jumping between teams and keeping the feedback loop tight. Big fan of collaboration, staying scrappy, and finding clarity in the chaos.

Experience

1. Account Executive

   Checkly

   Dec 2025 — Present · MA, US

   Checkly helps DevOps, SRE, and Platform Engineering teams catch issues 10x faster with code-first synthetic monitoring.Built for modern engineering teams, Checkly brings monitoring into the development workflow with Monitoring as Code and Playwright, so teams can monitor APIs and real user flows directly from their CI/CD pipelines instead of relying on clunky UI-driven tools. That means fewer blind spots, clearer alerts, and a lot less time spent firefighting.Teams use Checkly to validate critical workflows, reduce MTTR, and move away from expensive legacy monitoring without sacrificing reliability or control.

Education

• Rollins College

  Bachelor's Degree

Skills

• Microsoft Office
• Leadership
• Microsoft Word
• Microsoft Excel
• Powerpoint
• Teamwork
• Social Media
• Public Speaking
• Organization
• Project Analysis
• Sales Prospecting
• Salesforce.com
• Zoominfo
• Marketo
• Microsoft Sharepoint
• Business Analysis
• Business Planning
• Presentation Skills
• Social Networking
• Time Management
• Business Development
• Sales
• Team Leadership