WORKPLAY

Fractional COO.
Team working together AI-native
operator.

Embedding with technology-driven companies at inflection points: deploying intelligent systems, clarifying the bets that matter, and executing where it counts.

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Trusted by

Amazon
Zappos
Etsy
PayPal
Google
Meta
Sunrun
Under Armour
eBay
Salesforce
EagleView
Qcells

About us

WorkPlay© exists at the intersection of building and thinking. I believe the best operators move fluidly between discipline and invention.

I partner with technology-driven companies navigating inflection points — embedding AI-native thinking into how they allocate capital, design products, and scale operations. Not as an observer. As an operator.

Fractional COO

Embedded operational leadership that scales teams, systems, and business operations.

Org DesignOKRsCapital AllocationBoard ReportingOperations

OpenClaw & AI Automation

Deploy AI agents that run your operations, from revenue tracking to customer workflows, so your team focuses on what only humans can do.

AI Agent DeploymentWorkflow AutomationOpenClaw SetupRevenue IntelligenceSystem Integration

M&A & Exit Advisory

Right-hand partner for founders navigating acquisitions, exits, and corporate development.

Exit ReadinessM&A ProcessDeal StructuringCorporate DevIntegration

GTM Execution

Go-to-market strategy and hands-on execution for new products and market expansions.

Launch PlanningPricing StrategyChannel StrategySales MotionMetrics

The operator behind the work.

Kyle Kelly

Kyle Kelly

Founder

Fractional COO · Advisor · Operator. I’ve worked across fundraising, GTM, M&A, and scaling operations for technology companies from Seed to Series B.

18+ YearsSeed → Series CAI-Native

WorkPlay is about leverage. Structured ambition. And the belief that building great companies should feel rigorous and inventive at the same time.