Zach Gilliland

About Zach Gilliland

I’ve always been driven by a restless curiosity—the kind that had me pulling things apart as a child just to see how they worked. Over the years, that insatiable “what if?” mindset evolved into a knack for invention and a unique way of learning: I jump in headfirst, ready to adapt on the fly.Over the years I’ve realized that my most valuable contribution is typically that I’m good at seeing what others can’t—recognizing hidden connections, mapping out complex problems, and envisioning future possibilities. I trust my instincts but never shy away from questioning them; I’ve learned that ego can be more obstacle than ally.Ultimately, I thrive when I’m helping teams or individuals communicate better, align their strengths, and push boundaries. I believe the best solutions often start with a bit of curiosity and a willingness to dive into the unknown.

Experience

1. Chief Revenue & Product

   Extendly For Highlevel

   May 2023 — Present

   As CRO & CPO at Extendly, I own both the strategic “what” (product vision, roadmap, market fit) and the operational “how” (team structure, processes, execution) to ensure our platform scales reliably for thousands of agencies and hundreds of thousands of end users.Key Responsibilities:Drive Product Consolidation & Platform StrategyLed the integration of ChatHQ, SupportOS, legacy widgets, and new AI modules into a unified ExtendlyOS.Oversaw the transition to organization-wide AI usage—embedding AI into support, success, onboarding, and engineering workflows.Partnered with engineering to design and launch Extendly SupportAI agents (multi-expert delegation, smart routing, human handoff).Spearheaded the launch of Extendly’s Enterprise Plan: defined target customer profile, feature requirements (dedicated support agents, custom insights), and go-to-market approach.Collaborated with Finance, Sales, and Customer Success to operationalize onboarding, SLAs, and success metrics for enterprise clients.Established a QA team from the ground up—hiring, defining test standards, and implementing CI/CD gating to improve release quality.Guided Customer Success, Support Services, and White-Label Onboarding teams through an Agile transformation—coaching Scrum practices, sprint planning, and retrospective frameworks.Conducted Strengths Assessments across the Extendly team to align roles with individual strengths, refine hiring profiles, and create clear ownership for each department.Facilitated regular cross-departmental workshops and executive planning sessions to align Product, Engineering, Sales, and Operations on quarterly priorities and KPIs.Managed due diligence for acquisitions, evaluating tradeoffs between building internally versus buying.

Skills

• Project Management
• Marketing
• Leadership
• Public Speaking
• Advertising
• Wordpress
• Product Management
• Management
• Brand Development
• Entrepreneurship
• Strategic Planning
• Software Documentation
• Social Media
• User Experience
• E-Commerce