Gresham L.

Go-to-Market Strategy & AI Transformation Leader | Building Scalable Systems That Connect People, Process, & Technology | Enterprise Growth | Revenue Architecture

United States

About

I take a future-focused approach to how organizations grow, scale, and create enterprise value in an AI-driven world. Throughout my career, I’ve helped companies navigate critical inflection points, moments where leadership alignment, strategic clarity, and forward-looking decision-making determine whether a business stalls or accelerates. My work centers on translating vision into systems and structures that strengthen investor confidence, support sustainable growth, and give executive teams the clarity they need to lead. At Zscaler, I lead the orchestration of the company’s go-to-market plan, bringing Sales, FP&A, People & Culture(HR), Sales Compensation, and IT into a unified, intelligence-driven operating model. My focus is on building planning frameworks that enhance predictability, improve resource allocation, and position the company to scale its multi-billion-dollar revenue engine with discipline and conviction. I work closely with senior leadership to anticipate challenges, model future scenarios, and ensure the organization is equipped for the next horizon of growth. Before Zscaler, I helped support one of the fastest expansion periods in cybersecurity at CrowdStrike. I shaped their territory, quota, and renewals motion for their Customer Sales group that became foundational to the company’s continued global growth. These experiences sharpened my ability to diagnose structural gaps, create frameworks that scale, and bring cross-functional teams into alignment around shared commercial objectives. Earlier in my career, I founded and scaled two ventures: experiences that shaped my leadership philosophy. I’ve raised capital, earned investor buy-in, guided teams through ambiguity, and built organizations in complex regulatory environments. Those chapters taught me how to communicate vision with credibility, make decisions under pressure, and look ahead to what the business will need long before it becomes urgent. I believe the next era of leadership belongs to those who can pair human judgment with AI-enabled insight. My goal is to help organizations harness this shift, plan further ahead, make stronger decisions, and create enduring value for customers, employees, and shareholders. Let’s connect.

Experience

  • Consultant, GTM Strategy & Planning and AI Transformation at Consultant
    2025 - Present · 1 yr 7 mos

    Advising organizations on AI-enabled GTM strategy, predictive planning, and enterprise-scale operating design to support durable revenue growth. Focus areas include strengthening leadership alignment, sharpening growth models, and building planning systems that enhance visibility, optimize resources, and build investor confidence. Work spans transformation strategy, scalability assessments, and development of intelligent frameworks that position companies for sustained market expansion.

  • Revenue Strategy & Operations at Zscaler
    2023 - Present · 3 yrs 7 mos

    Leading Zscaler’s global go-to-market planning function, shaping the operating blueprint that aligns Sales, FP&A, People & Culture (HR), Sales Compensation, and IT across a multi-thousand person GTM organization. My work focuses on building scalable planning systems, growth models, and cross-functional operating rhythms that strengthen collaboration , accelerate productivity, and support Zscaler’s multibillion-dollar revenue engine. Highlights: ➤ Re-architected the GTM Annual Operating Plan, creating scalable processes and governance models that improved alignment and shortened planning cycles. ➤ Drive the full GTM Planning cadence end-to-end, including segmentation, growth modeling, territory design, quota deployment, and application cutover. ➤ Enabled ARR expansion from $1.6BB to $2.7BB, including ~$120M in incremental value by accelerating territory assignments and fiscal-year cutovers. ➤ Guide a large Sales Operations organization through unified global planning and weekly cross-functional stakeholder alignment. ➤ Supported GTM integration for the Red Canary acquisition, aligning data, systems, and motions for day-one co-selling. ➤ Established planning standards and operating frameworks adopted across GTM, forming the foundation for future scale.

  • Team Lead, Sales Operations at CrowdStrike
    2021 - 2023 · 2 yrs

    Supported CrowdStrike’s Global Corporate Customer Sales organization during one of the fastest growth periods in cybersecurity. Co-led a global Sales Ops team responsible for strengthening renewals, territory design, and quota models to support consistent, scalable performance. Highlights: ➤ Designed a renewals quota model for the corporate segment that improved seller motivation, alignment, and revenue predictability. ➤ Built an accelerated territory-assignment system in SFDC ETM that improved rep ramp times, territory balance, and global performance consistency. ➤ Contributed to 60% YoY customer account growth by improving alignment across cross-sell, up-sell, and renewals teams. ➤ Promoted standards and best practices that became foundational to the group’s operational rhythm and growth trajectory.

  • Founder & CEO at First United Management
    2018 - 2021 · 3 yrs

    Founded and led a vertically integrated operation spanning real estate development, advanced manufacturing, and consumer packaged goods within a highly regulated environment. Oversaw strategy, capital planning, facility development, operations, and go-to-market execution. Highlights: ➤ Built and led an eight-person team; raised capital; directed full facility development for pharmaceutical-grade manufacturing. ➤ Implemented ERP systems, sales processes, brand development, and distribution strategies to enable scalable commercial growth. ➤ Navigated complex licensing, compliance, and regulatory requirements across multiple jurisdictions to achieve operational readiness.

  • Consultant, Enterprise Engineering - Infrastructure at Meta
    2016 - 2020 · 4 yrs

    Consulted for Meta’s Enterprise Engineering organization, designing the cloud compute infrastructure that supported R&D, machine learning, and content creation workloads. Highlights: ➤ Designed and supported proprietary compute systems used by 20+ global teams across ML, R&D, and content production. ➤ Increased compute efficiency by 800% through architecture redesign, automation, and improved provisioning workflows.