Brandon Ciampanelli

GTM Performance @ ClickUp | 2025 Gong Enablement Leader of the Year Finalist | Sales Experience Design @ The SXD

Narragansett, Rhode Island, United States

About

I care about damn good design, smart systems, and helping others reach their peak potential. With over a decade of experience in tech sales + enablement and a background in design, I lead GTM performance at ClickUp, building AI-powered, rep-centered systems and programs that remove friction, boost adoption, and drive performance. My unique approach blends design thinking + systems thinking + sales execution. I treat enablement like a product: intentional, intuitive, and built to fit into how reps actually work. From training and toolkits to coaching systems and playbooks, I focus on creating experiences that feel seamless and get results. I didn’t take the traditional path here. I’m self-taught, shaped by curiosity, and grounded in what works in the real world. That perspective shows up in everything I build, thoughtful, clean, and always focused on making it easier for reps to grow and succeed. Outside of ClickUp, I run The Sales Experience Design (SXD), a space where I share ideas and consult at the intersection of design thinking and enablement. Through it, I help teams rethink how sales should feel, and how enablement can serve as a lever, not a layer. If you're passionate about building smarter systems, more human sales experiences, or just want to jam on how design makes things better, let's connect.

Experience

  • ClickUp (1 yr 7 mos)
    • Global GTM Performance Lead, Enterprise
      Oct 2025 - Present · 10 mos

      I design and engineer AI-powered performance systems and workflows for our global Enterprise GTM team (playbooks, embedded methodologies, and coaching programs) that close skill gaps, simplify execution, and create durable success to launch ClickUp into a billion-dollar business.

    • Senior Manager, Global GTM Enablement
      Jan 2025 - May 2026 · 1 yr 5 mos

      I led GTM Field Enablement, partnering with our global Commercial & Enterprise sales and solutions teams to improve how we bring ClickUp to market at scale.

  • Member | Speaker | Moderator at Modern Sales Pros
    May 2019 - Present · 7 yrs 3 mos

    I help GTM teams in the MSP community solve the toughest sales enablement problems, sharing forward-thinking strategies and tools for modern SaaS. As a speaker, I spark thought and challenge the norm. As a moderator, I create space for dynamic, meaningful conversations that push our profession to the next level.

  • Brex (3 yrs 1 mo)
    • Lead, GTM Enablement and Productivity Programs
      Jan 2024 - Dec 2024 · 1 yr

    • Senior Manager, GTM Productivity
      Dec 2021 - Jan 2024 · 2 yrs 2 mos

      I led the Enablement charge behind Brex’s massive transformation from a single-card product → full multi-product AI-powered Enterprise spend platform, helping fuel $200M+ in new SaaS revenue and a $5B exit. I architected many of the firsts that laid the foundation for scale: our global Sales Playbook and SaaS methodology, the enablement strategy for the milestone BrexPay + Navan partnership, and a coaching ecosystem embedded directly into tools like Highspot & Gong to drive rep adoption and GTM efficiency. This wasn’t "traditional" enablement. It was designing and delivering the infrastructure to scale revenue performance, simplify complexity, and power Brex’s next chapter of growth.

  • Learning and Engagement Consultant, Mid-Market Enterprise at LinkedIn
    May 2019 - Nov 2021 · 2 yrs 7 mos

    My area of expertise within LinkedIn was employee learning, development, and engagement. Forging client partnerships with Learning and Glint, I helped HR and L&D teams solve their biggest challenges. From retention and internal mobilization. Skilling, re-skilling, and productivity. To leadership, diversity, equity, inclusion, and belonging.

  • Founder at Surf Rhode Island
    Jan 2013 - Jun 2020 · 7 yrs 6 mos

    As a sole proprietor, I managed all aspects of business operations and e-commerce. This included concept, design, production, media, marketing, and finance. Unless, of course, the surf was up.