How to Grow a Disruptive Software Company & Scale Globally Medallia President/CEO Leslie Stretch Shares Lessons from his 30-Year Career at the World's Biggest Tech Firms

Growing a software company, let alone scaling globally, is no easy feat. Get the inside scoop on how to do it from a true industry veteran with a storied 30-year career leading cloud software businesses. In the next episode of our Leadership Lessons series, host and Comparably CEO Jason Nazar speaks with Leslie Stretch, President/CEO of Medallia (NYSE: MDLA). As the pioneer and market leader in customer and employee experience and engagement, Medallia collects and analyzes user data and transforms them into actionable insights for company leaders. With over $477 million in annual revenue, and an enterprise value north of $4 billion dollars, Stretch led the San Francisco, Calif.-based SaaS platform to a successful IPO in July 2019. Prior to Medallia, he delivered a 25x increase in value in the public markets during his time as President/CEO of CallidusCloud, culminating in the company’s acquisition by SAP for $2.6 billion in 2018. Stretch will share his most valuable leadership lessons -- from his executive positions at Sun Microsystems and Oracle to his CEO roles. Other topics include:

  • Listening to the voice of the customer
  • How to scale operations in global markets
  • Preparing to go public
  • Patent-pending methods for hiring + performance predictions
  • Best practices for motivating high-performance sales teams

Leslie Stretch is President/CEO of Medallia, and is a technology industry veteran and innovation leader with over 30 years of experience growing disruptive cloud and software companies. Stretch led Medallia’s IPO in 2019, and has overseen the company’s emergence as a category leader in the employee and customer experience and engagement space. Before joining Medallia, Leslie served as President/CEO of CallidusCloud, transforming the company into a successful, enterprise software company, acquired for $2.5 Billion in 2018. Prior to Callidus, Stretch held several executive sales roles at Sun Microsystems and Oracle where he was responsible for scaling operations in global markets. 

 
Jason Nazar brings 15 years of experience as a serial entrepreneur, investor, and advisor to his role as co-founder/CEO of Comparably, a leading workplace culture and compensation monitoring site. Previously, he was co-founder/CEO of Docstoc (acquired by Intuit in 2013), one of the most visited content sites in the world for SMBs. Jason was named one of the “Most Admired CEOs in L.A.” by the Los Angeles Business Journal and appointed “Entrepreneur in Residence for the City of Los Angeles” in 2016-2018 by Mayor Eric Garcetti. 
 

Upcoming Webinar

Marketing

How to Build a Personal Brand That Grows Your Business

In this live session, discover how our guest built a personal brand that fueled a near-$100M acquisition, then leveraged that same trust to launch his next venture into 1,400+ stores. Register now!

Running a Business

5 Leadership Strategies from Someone Who Rescued His Business from the Brink of Collapse

Join us for this free webinar to learn how to lead a company through turbulence and find success on the other side.

Marketing

How to Use Press & PR to Grow Faster Without a Big Budget

Get a step‑by‑step playbook for turning press coverage into one of your most powerful growth channels—without relying on a big ad budget. In this live session, Pace PR founder Annie Scranton breaks down exactly how to win earned media, boost credibility, and drive customers using the same strategies top brands use every day.​

Running a Business

How Recent Tax Changes Create New Opportunities for Solopreneurs and Small-Business Owners

Join us for a free webinar with Lisa Greene-Lewis, Principal Communications Manager and tax expert at Intuit TurboTax.

Running a Business

How Restaurant Owners Can Win Back Profits in 2026

Learn how successful restaurant owners are adapting and thriving, using strategies ranging from menu overhauls to new marketing tactics to technology-driven dining experiences that give a competitive edge.

Starting a Business

On Demand: How a Restaurant is Made

Opening a restaurant? Get insights and advice from chefs Rasheeda Purdie and Tom Colicchio on a bonus video episode of The Build, brought to you by TILIT and Square. Watch now.