Ryan Staley
Career profile

Ryan Staley

Founder & CEO, Whale Boss | Demystifying AI Agents | Helping revenue leaders 2x team results through AI Led GTM | Trusted by $50M-$20B PE-backed and Publicly Traded Companies | AI ROI for your team in 60 days

Greater Chicago Area

Career path.

  1. Whale Boss

    Founder and CEO

    6 yrs 3 mos
  2. OpenAI

    Forum Member

    1 yr 9 mos
  3. The Scale Up Show

    Podcast Host

    6 yrs
  4. Pavilion

    Executive Member, Former CRO & Enterprise Sales GTM School Lecturer

    6 yrs 6 mos
  5. Gartner

    Peer Ambassador: B2B Sales, Sales Leadership & Enterprise GTM

    3 yrs 1 mo
  6. Sales Hacker, Inc.

    Founding Member

    1 yr 2 mos
  7. Flex Technology Group

    Vice President of Strategic Accounts

    2 yrs 2 mos
  8. Flex Technology Group

    Director of Strategic Accounts

    4 yrs 5 mos
  9. Flex Technology Group

    Director of Sales, Midwest Region

    1 yr 2 mos
  10. Flex Technology Group

    Regional Sales Manager

    1 yr 5 mos
  11. Pitney Bowes (Managed Services)

    Senior Sales Consultant

    1 yr 2 mos
  12. Antenna Software

    Director of Sales Midwest Region

    1 yr 10 mos
  13. Pitney Bowes (Managed Services)

    Senior Sales Consultant

    6 yrs 5 mos
  14. Marcus Evans

    National Sales Manager/Senior Sales Representative

    2 yrs 6 mos