Kenneth Watson
Kenneth Watson

Enterprise AI Sales Director

Open to offers · Member since 1 Oct 2026
Location
New York, United States
Desired salary
Unspecified
Work preference
Remote Only
Experience level
Lead

About

Professional summary

I am an enterprise AI and customer-experience sales leader with more than 20 years of experience winning new business, growing strategic accounts, and leading complex go-to-market motions. My experience spans Generative AI, CCaaS, SaaS, data platforms, and enterprise technology.

I most recently led Gemini Enterprise AI growth pursuits at Google Cloud, managing $1M-$5M opportunities across Fortune 500 accounts. I guide deals from prospecting and business-case development through technical evaluation, commercial negotiation, and close.

I build trusted relationships with C-suite and board-level stakeholders by translating AI, analytics, API, and platform capabilities into measurable business outcomes. I also advise leaders on responsible AI adoption, regulatory considerations, and implementation roadmaps.

My background includes strategic-account leadership in financial services, healthcare, manufacturing, retail, media, telecommunications, and hospitality. I have delivered six- and seven-figure deals, expanded recurring revenue, exceeded enterprise targets, and secured major new enterprise logos.

I am experienced in designing repeatable GTM strategies, developing account plans, building pipelines, improving forecast discipline, and coordinating product, engineering, solution architecture, marketing, and sales teams. I also have a strong record of mentoring sales teams and leading executive-level commercial strategy.

Skills

28 capabilities

Experience

Career history

GECX Sales Specialist - Gemini Enterprise AI Google Cloud

Led full-cycle growth pursuits across strategic Fortune 500 accounts, including prospecting, pipeline creation, business-case development, deal structuring, negotiation, and closing.

Advanced seven-figure conversational AI and analytics opportunities averaging $1M-$5M. Advised C-suite stakeholders on Generative AI strategy, responsible deployment, and regulatory compliance while coordinating Product, Engineering, and Solution Architecture teams on adoption roadmaps and implementation plans.

Director, Enterprise Sales Here (formerly OpenFin)

Led enterprise sales into Fortune 500 financial-services organizations, securing enterprise browser platform contracts through complex, multi-stakeholder sales cycles.

Designed and executed financial-services GTM strategy for CCaaS solutions. Managed and mentored sales development representatives while owning executive relationships, target-account strategy, and coordinated pipeline creation.

National Account Executive LiveVox (CCaaS)

Owned a $12M strategic-account portfolio and led complex sales motions across multiple business units, with average deal sizes of $150K-$250K.

Expanded monthly recurring revenue from $25K to $150K through account planning, executive relationship development, and consultative expansion. Delivered against a $1M monthly recurring revenue quota through retention and growth programs.

Vice President, Sales & Marketing Teckst (SaaS)

Won 10 enterprise logos, including Disney and Madison Square Garden, in nine months by positioning omnichannel messaging SaaS as a C-suite priority with a clear ROI narrative.

Led sales, marketing, and strategic partnerships, aligning commercial execution and market positioning through the company's successful acquisition.

VP, Business Development & Marketing, North America Cxense (DaaS)

Reached 180% of enterprise sales target within the first 10 months and established partnerships including The Wall Street Journal.

Built C-suite relationships and navigated complex procurement processes to secure multi-year data-platform agreements with major media enterprises.

Founder & Principal Consultant CAYO Consulting

Founded and led a nine-year consulting practice serving enterprise clients including Verizon Wireless and Sodexo USA.

Advised clients on business development, CRM design, and digital go-to-market strategy. Designed and implemented end-to-end sales programs and GTM frameworks with direct accountability for commercial outcomes.

Global Account Manager, General Electric Xerox Corporation

Directed global account strategy for a $100M+ General Electric relationship spanning business units in 23 countries.

Coordinated cross-functional execution across regions, product lines, and executive procurement stakeholders. Led account governance and provided strategic direction to 1,000 sellers.

Education

Learning history

Thunderbird School of International Business

MBA

University of Virginia

BA

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