Bill Stapleton

Revenue Growth Leader | Cybersecurity • Observability • SaaS

New York, New York, United States

About

As a sales leader with over two decades of experience, I specialize in driving revenue growth, securing strategic partnerships, and empowering teams to exceed targets. At Dynatrace, I led a high-performing sales team to achieve 130% of quota, expanded the pipeline by $20M, and collaborated with technical teams to significantly reduce client MTTR by 90%, delivering measurable ROI to enterprise clients. My career spans leadership roles in SaaS and cybersecurity, where I have consistently delivered impactful results. At Synack, I spearheaded a regional revenue expansion from $2M to $37M, secured multimillion-dollar contracts, and transitioned clients to advanced penetration testing models. I am committed to leveraging strategic vision, teamwork, and a data-driven approach to deliver sustainable value and foster growth in the financial services and technology sectors.

Experience

  • AVP Sales at Semperis
    Sep 2025 - Present · 11 mos

    Semperis is the pioneer of identity-driven cyber resilience for cross-cloud and hybrid environments. The company provides cyber preparedness, incident response, and disaster recovery solutions for enterprise directory services—the keys to the kingdom. Semperis’ patented technology for Microsoft Active Directory protects over 40 million identities from cyberattacks, data breaches, and operational errors. Semperis is headquartered in New York City and operates internationally, with its research and development team distributed between San Francisco and Tel Aviv.

  • Regional Director of Sales at Dynatrace
    Apr 2022 - Apr 2024 · 2 yrs 1 mo

    • Directed a high-performing team of 5 enterprise sales professionals, achieving 130% of quota for Full Stack Observability solutions. • Secured key accounts, including Ally Bank and Truist, contributing to $20M pipeline expansion. • Partnered with technical teams to cut client MTTR by 90%, delivering measurable ROI for enterprise clients.

  • Vice President of Sales East & Canada at Synack, Inc.
    Jan 2017 - Apr 2022 · 5 yrs 4 mos

    • Expanded regional revenue from $2M to $37M, closing $16M+ in enterprise contracts with clients like Morgan Stanley and Navy Federal. • Enhanced conversion rates by 32% through data-driven sales strategies and educational campaigns. • Transitioned financial services clients to continuous penetration testing models, reducing vulnerabilities and preventing fraud.

  • RSA Security (9 yrs 1 mo)
    • Global VP Sales & Sales Engineering
      Jan 2015 - Jan 2017 · 2 yrs 1 mo

      • Achieved 203% of sales targets by reinvigorating the fraud and risk intelligence business post-acquisition. • Closed multimillion-dollar agreemenrs with Barclays and ANZ, generating $8.5M+ in recurring revenue. • Launched a UK-based SWAT team that saved $10M annually through fraud detection optimization for top-tier banks.

    • AVP Sales (Americas)
      Jan 2014 - Jan 2015 · 1 yr 1 mo

      • Led 5 Regional Sales Leaders & 35 Sales Representatives to achieve over 100% target • Successfully reduced team headcount in the Americas by 50% while exceeding goals for 5 consecutive quarters

    • Regional Sales Manager & Global Account Manager
      Jan 2008 - Jan 2014 · 6 yrs 1 mo

      • Exceeded sales goals for Legato and Documentum solutions, earning recognition for outstanding performance. • Achieved 300% quota attainment as a Global Account Manager, securing over $9M in new business. • Recognized as Global Account Manager of the Year for exceptional contributions to RSA Security.