Jenn Castillo

Community & Events @ Chili Piper 🌶 | Always bringing the #Jennergy

London, Ontario, Canada

About

My biggest passion right now? Strategizing about Community 🚀 I believe the future is Community. I love finding synergies and creating joint stories across organizations in order to be mutually beneficial in a GTM strategy. Passion, focus, trust, work ethic, enthusiasm. Those are the qualities that drive me everyday. I strive to find creative ways to create events and in the process build long lasting and genuine relationships.

Experience

  • Chili Piper (Permanent Full-time · 5 yrs 2 mos)
    • Head of Community & Events
      Jan 2026 - Present · 6 mos

    • Principal, Channel Partnerships
      Jul 2023 - Jan 2026 · 2 yrs 7 mos

      Chili Piper is the first all-in-one Demand Conversion Platform, helping you convert more inbound and outbound leads into qualified sales pipeline. It streamlines the handoff process in every inbound and outbound channel, consolidating many of the point solutions you use today. Form Routing, Chat, Lead Distribution, and Scheduling can now live in one platform with shared teams, routing rules, and reporting. That means easier maintenance and a much more complete picture of how you’re converting leads across the funnel. And the results speak for themselves. Teams are doubling their conversion rates, increasing show rates to 90%+, and saving 20+ hours per week distributing leads. Learn more at chilipiper.com

    • Senior Channel Partnerships Manager
      Oct 2022 - Jul 2023 · 10 mos

  • McCabe Promotional Advertising Inc (3 yrs 3 mos)
    • Account Executive
      Sep 2018 - Apr 2021 · 2 yrs 8 mos

    • Customer Service Representative
      Feb 2018 - Sep 2018 · 8 mos

  • Project Manager at Ripple Effect Marketing Canada
    Mar 2016 - Aug 2017 · 1 yr 6 mos

    • Effectively handled and led partnership with Pearson Airport public relations project. • Trained and led team on-site. • Coordinated through various strategy meetings the optimal ways of positively promoting Pearson Airport. • Created and featured in viral video for Pearson: https://www.facebook.com/torontopearson/videos/10154381732164663/.

  • Store Manager at GUESS?, Inc.
    Feb 2012 - Mar 2017 · 5 yrs 2 mos

    • Youngest store manager in Canada at the age of 19. • Achieved highest penetration of e-commerce sales in Canada. • Achieved 11% over target in Ontario - the highest increase. • Was able to beat previous year's profit by 9% with a 4% decrease in traffic during my first year as manager. • Developed and trained multiple teams to excel in customer service. • Traveled to different store locations in Southern Ontario to help optimize results