Rob Holland

Rob Holland is a serial software CEO and operating executive with over two decades of
experience building, scaling, and exiting technology, SaaS, and data businesses. As a Special
Operator in the NextLevel Operations talent ecosystem, Rob’s primary role is to accelerate
portfolio company growth by supporting their CEOs and commercial leaders in business
transformation, go-to-market strategy, organizational design, and strategic M&A.

Rob joined the Special Operators program in 2026, bringing a deep background in leading
sponsor-backed businesses through critical inflection points. Most recently, he served as CEO
of RedShelf, where he led a sponsor-backed transformation that returned the business to
profitability, accelerated growth, and culminated in its 2025 acquisition by VitalSource.
Previously, he served as CEO of Feedback Loop, leading a commercial and product
transformation that resulted in its acquisition by DISQO.

Earlier, Rob served as COO of Bluecore, helping scale the business from approximately $10
million to $35 million in ARR, and held senior general management roles at Oracle Data Cloud
and Datalogix, where he helped scale the consumer business from less than $1 million to
approximately $150 million in revenue before its $1.5 billion acquisition by Oracle.

Across his career, Rob has focused on businesses at critical inflection points, helping leadership
teams sharpen strategy, strengthen operating performance, and build organizations capable of
creating durable enterprise value.

Special Operators are independent contractors and are not employees or investment professionals of Level Equity.