ABOUT JIM
Jim is a seasoned SaaS and enterprise software executive with more than 30 years of leadership experience as both a Chief Revenue Officer and Chief Executive Officer. Throughout his career, Jim has built and led high-performing go-to-market organizations, driving profitable growth and delivering meaningful shareholder value.
Most recently, Jim has focused on scaling SaaS businesses through disciplined execution, strong culture, and clear strategy. As a two-time CRO, he has led all go-to-market functions—including sales, marketing, implementation, and customer success—while building elite teams and repeatable, scalable operating models. As a CEO, he has combined strategic vision with operational rigor to guide companies through critical growth and transformation phases.
Jim’s career highlights include transforming LivePerson’s go-to-market engine and scaling annual recurring revenue from $15M to $95M, as well as leading SundaySky from pre-revenue to a $100M+ acquisition by private equity. He is widely recognized for pioneering new market categories, achieving product-market fit, and optimizing sales models across both enterprise and high-velocity SaaS environments. His experience spans transitioning tech-enabled services for large enterprises into scalable SaaS offerings and improving the end-to-end customer journey across product, marketing, sales, and customer success.
At the core of Jim’s leadership philosophy is alignment—between customers, company objectives, and team members. He is deeply committed to operating with integrity, investing in the growth of others, and fostering cultures that inspire excellence, accountability, and innovation.
Jim’s professional passions include developing new markets, building world-class teams, leading change from the front, and selling value to smart, time-constrained senior executives at Fortune 100 companies. Outside of work, he enjoys stand-up paddleboarding.
EDUCATION
BS Electrical Engineering, Villanova University
Recent Articles from Jim Dicso
ABOUT JIM
Jim is a seasoned SaaS and enterprise software executive with more than 30 years of leadership experience as both a Chief Revenue Officer and Chief Executive Officer. Throughout his career, Jim has built and led high-performing go-to-market organizations, driving profitable growth and delivering meaningful shareholder value.
Most recently, Jim has focused on scaling SaaS businesses through disciplined execution, strong culture, and clear strategy. As a two-time CRO, he has led all go-to-market functions—including sales, marketing, implementation, and customer success—while building elite teams and repeatable, scalable operating models. As a CEO, he has combined strategic vision with operational rigor to guide companies through critical growth and transformation phases.
Jim’s career highlights include transforming LivePerson’s go-to-market engine and scaling annual recurring revenue from $15M to $95M, as well as leading SundaySky from pre-revenue to a $100M+ acquisition by private equity. He is widely recognized for pioneering new market categories, achieving product-market fit, and optimizing sales models across both enterprise and high-velocity SaaS environments. His experience spans transitioning tech-enabled services for large enterprises into scalable SaaS offerings and improving the end-to-end customer journey across product, marketing, sales, and customer success.
At the core of Jim’s leadership philosophy is alignment—between customers, company objectives, and team members. He is deeply committed to operating with integrity, investing in the growth of others, and fostering cultures that inspire excellence, accountability, and innovation.
Jim’s professional passions include developing new markets, building world-class teams, leading change from the front, and selling value to smart, time-constrained senior executives at Fortune 100 companies. Outside of work, he enjoys stand-up paddleboarding.
EDUCATION
BS Electrical Engineering, Villanova University
