Tim Weber

Strategic Partnerships @ Hy.ly AI | Multifamily Technology | NAA 20 on the Rise ‘26 | US Air Force Veteran

Tampa, Florida, United States

About

Tim is a U.S. Air Force veteran whose leadership is rooted in authenticity, trust, and service. He’s established himself as a multifamily customer experience and partnerships leader, working closely with proptech suppliers to deliver transparency and strategy to operators. Known as a culture-builder, Tim leads with a mission mindset, a warm heart, and an extreme sense of ownership that fosters strong relationships. Beyond multifamily, he co-leads a Tampa nonprofit focused on ethically reducing the feral cat population, rescuing over 1,000 cats and generating more than $400,000 in community savings. His proudest accomplishment is his five years of sobriety.

Experience

  • Strategic Partnerships Manager at Hyly.AI
    Oct 2025 - Present · 9 mos

    Lead strategic partnerships to strengthen transparency and shared intelligence across multifamily. Hyly.AI helps multifamily operators scale smarter by automating their marketing, leasing, and operations workflows through AI-powered systems that connect people, data, and processes.

  • Senior Customer Success Manager at Flair
    Jan 2025 - Oct 2025 · 10 mos

    Built Flair’s customer success org from the ground up, serving as the first CS leader, reporting directly to the co-founders, and managing a team of five. Managed a portfolio of strategic multifamily clients, overseeing onboarding, pilots, and new business handoffs to ensure adoption and long-term value. Partnered with the product team on integrations and roadmap, translating customer feedback into priorities that improved outcomes for both clients and the business.

  • Peek (New York, New York, United States · Hybrid)
    • Senior Implementation Manager
      Feb 2024 - Jan 2025 · 1 yr

      Built and led Peek’s onboarding strategy and team, working closely with Top 50 NMHC owners and operators to deliver a best-in-class customer journey. Drove 4x ARR growth from seed to pre-series A by successfully onboarding more than 800 projects with zero churn and reducing customer time-to-value by 400%. Partnered cross-functionally with product and leadership teams to align customer insights with company strategy and accelerate multifamily adoption at scale.

    • Implementation Manager
      Mar 2023 - Feb 2024 · 1 yr

    • Technical Solutions Associate
      Jun 2022 - Mar 2023 · 10 mos

  • Military Crashpad (San Antonio, Texas, United States · Hybrid)
    • Associate Product Manager
      Jul 2019 - Dec 2020 · 1 yr 6 mos

      Analyzed industry trends and competitor behavior to design an adaptable product strategy and vision. Created and executed a go-to-market campaign that integrated new product workflows, streamlined guest onboarding, and increased annual occupancy rates by 40%. Led onboarding operations for more than 60 units, ensuring product strategy was executed successfully and long-term product vision was achieved.

    • Reservations Manager
      Oct 2018 - Jul 2019 · 10 mos

      Managed day-to-day reservations across 185 rental units in 10 states, maintaining occupancy rates above 90%. Led a small team of reservation agents while ensuring high service quality and operational consistency. Created and implemented a customer feedback program that improved product quality and generated 25% more five-star reviews.

  • United States Air Force (Spokane, Washington, United States · On-site)
    • Squadron Operations Coordinator
      Jan 2015 - Dec 2016 · 2 yrs

      Managed daily flight operations for 250 personnel, ensuring readiness and rapid deployment of squadron resources. Coordinated aircrews for Operation Noble Eagle, the U.S. Homeland Defense mission, while maintaining operational efficiency and compliance. Recognized as Airman of the Year in 2015 for leadership, performance, and contributions to mission success.

    • Boeing KC-135 Boom Operator
      Dec 2012 - Dec 2016 · 4 yrs 1 mo

      Safely transferred fuel between aircraft in flight, supporting global missions through precision and adherence to strict safety standards. Flew 120 combat air refueling missions in support of Operations Enduring Freedom, Freedom’s Sentinel, and Inherent Resolve. Led and graduated 52 trainees during Basic Military Training, earning Top Graduate honors and achieving promotion ahead of peers from E-1 to E-5.