Robert Gray
Robert Gray is a veteran vertical-market software operator and former CEO of Wynne Systems who now leads OliveAI, an AI platform helping rental companies unlock 7–12% revenue growth through smarter pricing. With 5 pilot customers and 93 locations already committed, he’s building a category-defining SaaS company grounded in real industry needs and proven market demand.
Founder · Villa Park, CA, USA
Open to advisory
Customer acquisition · Product · Engineering & Tech · Leadership & Strategy
Makes warm intros to
5
Hours / month
About Robert
Robert Gray is a seasoned software executive and entrepreneur with deep expertise in the equipment-rental and construction-technology markets. He spent more than a decade at Wynne Systems—creators of RentalMan ERP—where he served as CRO and later GM/CEO, leading the business through significant product modernization, commercial expansion, and sustained organic growth.
Most recently, Robert operated at the intersection of vertical-market software, AI, and M&A. At Volaris Group (Constellation Software), he worked within the M&A team identifying, evaluating, acquiring, and scaling vertical SaaS companies across North America—giving him a unique vantage point on what drives durable value, high-margin growth, and long-term defensibility in niche software markets.
Robert founded OliveAI to solve one of the rental industry’s biggest and most persistent challenges: revenue leakage from suboptimal pricing and inconsistent fleet decisions. Leveraging his operator background, direct relationships across the RER100, and firsthand understanding of rental workflows, he built OliveAI as a practical, high-ROI AI engine that integrates seamlessly with rental ERPs and drives measurable revenue uplift.
Under his leadership, OliveAI has already secured 5 pilot customers representing 93 locations, validating both market demand and the platform’s immediate value. Robert’s differentiated perspective—operator + acquirer + founder—positions him to scale OliveAI into the category-defining pricing and fleet-intelligence platform for the $70B+ equipment-rental industry.
Company
OliveAI, LLC
oliveaiworks.com
OliveAI is an AI-driven revenue engine for equipment rental companies. We analyze utilization, rental events, seasonality, and local demand to automatically recommend the ideal rate for every asset, every day—delivering 7–12% revenue growth in the first year with a four-month payback. Unlike BI dashboards or static spreadsheets, OliveAI gives branch managers clear, actionable pricing recommendations they can trust. And with 5 pilot customers representing 93 locations already committed, the market has validated that OliveAI is solving a real, painful, industry-wide problem at scale.
Funding Stage
Pre-Seed
Funding Raised
None/Bootstrapped
Team Size
Just Me/Co-Founders
Annual Revenue
$100k to $250k
Founded
2025
Industry
Technology
Skills
Leadership
Held CRO, GM, and CEO roles; founded OliveAI, leading teams and strategic operations.
Equipment-Rental Industry
Extensive experience in equipment-rental and construction-technology markets, including leading product modernization and commercialization efforts.
Software Executive Leadership
Over a decade of experience leading software teams and companies, including roles as CRO and CEO at Wynne Systems.
Equipment-Rental
Over a decade of experience with Wynne Systems and founder of OliveAI, focusing on equipment-rental technologies.
Construction-Technology
Deep expertise in construction-technology markets, having led software development and integration for rental ERPs.
CEO Experience
Served as General Manager and CEO of Wynne Systems, leading significant modernization and growth efforts.
Vertical SaaS Strategy
Worked on acquiring and scaling vertical SaaS companies, contributing to understanding of value drivers in niche markets.
Entrepreneurship
Founded OliveAI, leveraging deep industry expertise to create a category-defining product.
Founder
Founded OliveAI, an AI platform for the equipment-rental industry, gaining pilot customers and market validation.
AI in Revenue Management
Developed AI-driven solutions for pricing optimization in the rental industry with OliveAI.
Business Strategy
Focused on durable value and high-margin growth in niche software markets.
Strategic Leadership
Extensive strategic leadership experience guiding companies through growth and M&A processes.
Product Management
Led product modernization and commercialization at Wynne Systems and developed AI solutions at OliveAI.
Mergers and Acquisitions
Experience with evaluating, acquiring, and scaling SaaS companies as part of the M&A team at Volaris Group.
Product Modernization
Led significant product modernization efforts at Wynne Systems, resulting in commercial expansion and growth.
Revenue Optimization
Focused on solving revenue leakage issues in the rental industry with OliveAI's AI engine.
AI Integration
Built OliveAI to seamlessly integrate with rental ERPs and provide real-time pricing intelligence.
Sales and Marketing
Experience in commercial expansion and securing customers with Wynne Systems and OliveAI.
Sales and Commercial Expansion
Led commercial expansion efforts at Wynne Systems, driving sustained organic growth.
Software Engineering
Involved in product modernization and development at Wynne Systems, enhancing ERP systems for rental companies.
AI
Developed AI-driven solutions for the rental industry with OliveAI.
Experience
job
General Manager/CEO
Wynne Systems
Led the business through product modernization, commercial expansion, and sustained growth.
Protected EBITDA and expanded commercial reach, contributing to sustained organic growth.
job
M&A Team Member
Volaris Group (Constellation Software)
Identified, evaluated, acquired, and scaled vertical SaaS companies across North America.
Gained insights into growth drivers and defensibility in niche software markets.
job
Founder/CEO
OliveAI, LLC
Developed and scaled AI-driven pricing and fleet-intelligence solutions for the equipment-rental industry.
Secured 5 pilot customers and validated market demand for the AI platform. Currently expanding market reach.