With a track record of sales achievement across all sizes of companies, financial institutions and SaaS companies, Calvin Steinhoff joins Chief Outsiders as a fractional CSO to Grow Sales for SaaS and FinTech Clients.
CHICAGO, ILLINOIS – February 13, 2026 – Calvin Steinhoff, a seasoned SaaS sales leader with a record of success executing strategic initiatives to exceed goals, will now apply his SaaS and FinTech industry knowledge to take client sales to the next level as a Fractional CSO for Chief Outsiders. Recently, Steinhoff joined Chief Outsiders’ team of more than 100 Fractional Chief Sales Officers (CSOs) and Fractional Chief Marketing Officers (CMOs).
“An excellent communicator with exceptional interpersonal and leadership skills, Cal interacts effectively across all levels of the organization to build strong sales processes, sales pipelines and closed sales,” said Chuck Dushman, Central Managing Partner, Chief Outsiders. “We are excited to add his deep SaaS and FinTech experience to our team of battle-tested CSOs.”
According to the Chief Outsiders website, Steinhoff executes strategic, cross-functional initiatives to consistently build enterprise value. With a track record of sales achievement as both an individual contributor and executive leader, he excels in expanding product offerings and increasing sales in volatile, fast-growing markets. With strong experience in enterprise sales, team building, channel sales, account management, and strategic partners, he drives revenue growth.
SaaS Sales Leadership
At Chief Outsiders, Steinhoff works with the CEOs of PE-backed, early-stage, and mid-market SaaS and FinTech companies to accelerate sales growth. Whether delivering global revenue growth or building organizations for successful exit, his focus is on maximizing sales performance.
Prior to joining Chief Outsiders as Head of Sales, North America at GDS Link, he led a transformation of the sales team and sales process to enable rapid revenue growth. Prior to that as SVP Sales at Meridian Link, he led the sales teams for the recently acquired Small Business platform and marketing automation and background screening business lines and achieved 150% revenue growth.
Steinhoff’s executive sales leadership experience also includes roles as Head of Sales for Enova Decisions, a division of Enova International, SVP, Business Development at Mirador Financial. Additional prior roles include Vice President, Business Development at Paychex/SurePayroll, Vice President, Sales and Global Account Management for Ariba/Procuri.
To support his successful executive sales leadership career, Steinhoff completed the Executive MBA Program at the J.L. Kellogg School of Management at Northwestern University in Evanston, Illinois. He also earned a Bachelor of Arts degree in Liberal Arts from Loyola University in Chicago, Illinois.
About Chief Outsiders
Mid-sized companies unlock market potential and accelerate growth with top-tier talent and technology from Chief Outsiders, the nation’s leading provider of fractional sales and marketing services.
CEOs and business leaders drive sales and marketing strategy to make big things happen with instant access to the firm’s cohesive, battle-tested team of more than 100 fractional executives, a diverse pool of world-class expertise. Each brings the experience of VP Sales, VP Marketing, or higher at one or more operating companies, including many Fortune 500 firms.
Team OutsidersTM leverages this same expertise to deliver on-demand enterprise-grade execution to power growth with efficiency and flexibility. GrowthGears® OS supports faster, smarter, and less risky growth. The industry’s first AI-powered growth platform integrates both the comprehensive strategy of fractional executives and the precise execution of Team OutsidersTM. We built its transparent, client-friendly interface around Chief Outsiders’ proven Growth Gears® process.