Jason Romanosky is a revenue-focused CMO who combines the commercial discipline of a CRO with a product marketer’s command of positioning, pricing, and go-to-market strategy. He works with B2B software companies as a fractional CMO from Series A through growth stage, and as a fractional VP of Product Marketing for larger companies with an established marketing team.
In 18 years at Cisco, Jason designed the subscription and offer architecture behind Cisco Collaboration’s move to SaaS. His modular offer framework cut time to market by 50% and was adopted as Cisco’s company-wide software strategy. He launched Collaboration Flex Plan, which grew to 10% of Cisco’s Collaboration revenue, and built Cisco’s first volume purchase program, which booked more than $40 million. At Blackbaud, he simplified a complex portfolio of software and services, delivering the company’s largest increase in contractual ARR in two years.
As Chief Marketing Officer of Case Status, a B2B SaaS company serving the legal industry, Jason put product marketing, demand generation, sales development, business development, and pricing under one revenue target and grew ARR from $2 million to more than $10 million in three years. He built organic search into the company’s best-converting channel, with $1.9 million in attributed ARR at three times the conversion rate of paid search. He introduced the company’s first tiered pricing and packaging, raising average contract values and shortening sales cycles, and rebuilt marketing around AI-enabled workflows, cutting marketing’s cost base by 50% while holding pipeline contribution. Case Status made the Inc. 5000 in 2024, 2025 and 2026.
Jason also names new markets and builds the evidence behind them. At Case Status, he created the Intelligent Client Engagement category, supported by the legal industry’s first primary CX research study of 433 clients and 109 attorneys, now an annual publication. At ClaimAngel, he helped define Case Equity, a market far larger than traditional pre-settlement funding had reached, and built the marketing strategy to go after it.
At TechCXO, Jason helps companies find and fix what is holding back growth: unclear positioning, mispricing, inconsistent pipeline, and sales and marketing teams telling different stories. Engagements typically start with a fixed-scope diagnostic that delivers urgent fixes in the first two weeks, followed by an ongoing fractional role.
Jason holds an MBA from Duke University’s Fuqua School of Business, a product marketing certificate from the University of California, Berkeley, and certifications from Pavilion’s CRO School and the BCG Pricing Academy. He was named one of Pavilion’s 50 CMOs to Watch in 2025. He is based in Charleston, South Carolina.