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How This 30-Year Software Industry Veteran Scaled His Company to a Successful IPO Nine leadership lessons with Medallia president and CEO Leslie Stretch.

By Jason Nazar Edited by Jessica Thomas

Opinions expressed by Entrepreneur contributors are their own.


Growing a software company, let alone scaling globally, is no easy feat. For the latest episode of Comparably and Entrepreneur's Leadership Lessons series, I got the inside scoop from a true industry veteran with a storied 30-year career leading cloud software businesses: Medallia (NYSE: MDLA) President and CEO Leslie Stretch.

Related: Free On-Demand Webinar: How to Grow a Disruptive Software Company & Scale Globally

As the pioneer and market leader in customer and employee experience and engagement, Medallia collects and analyzes user data and transforms it into actionable insights for company leaders. With more than $477 million in annual revenue, and an enterprise value north of $4 billion, Stretch led the San Francisco-based SaaS platform to a successful IPO in July 2019. Prior to working at Medallia, he was president and CEO of CallidusCloud, leading the company to its $2.6 billion acquisition by SAP in 2018. Stretch shared his most valuable leadership lessons during our enlightening talk, from his executive positions at Sun Microsystems and Oracle to his CEO roles.

Considering himself "a conductor of his people," Stretch gallantly credited his team with his success more times than I can count. But there's no doubt that he's the real deal as a sales leader: His journey is one of a brilliant and driven individual who came from humble means in Scotland to lead Medallia to massive public, global success, and — as he told me — he hasn't even peaked yet. Here are nine remarkably prescient lessons from Leslie Stretch:

1. Companies that don't dialogue at scale get bad feedback

"There's actually a very close correlation between negative public, disgruntled, value compromising feedback and companies that don't dialogue at scale with customers and employees," Stretch says. The frustration employees and customers feel about the lack of clear, scaled communication can easily color any kind of more generalized survey response.

2. Treat your colleagues and all employees like customers

It might be largely unquantifiable, but there's an expectation when you're hired anywhere that you'll develop a genuine sense of loyalty. Stretch remembers an encounter with a manager early in his career. The manager, upon hearing that Stretch was potentially looking to leave the company, showed genuine emotion at the thought of the loss. (Stretch ended up staying with that manager another nine years.)

3. Early life is always a motivator

Our goals in life are often set by the experiences we have as we begin to get a sense of the world as a young person. Growing up financially strapped in Scotland lit a fire in Stretch to be free of money worries that still burns inside him today. "We didn't own a home as a family. We really wanted to taste life, have the best things we could and be able to enjoy our lives without the worry of making ends meet," he remembers.

Related: How Lynn Jurich Turned an Innate Passion for Saving the Environment into a Definitively Disruptive Energy Company

4. Good salesmanship is a learned behavior

Stretch says that sales does not come easily to introverts like him, and he admits to experiencing anxiety prior to social interactions. So how did he overcome this challenge? He studied experienced and successful people... and he practiced.

5. Despite tired stereotypes, sales is about integrity

"Anyone can be a great salesperson if they tell lies, mis-set expectations or try to fool people into a contract," Stretch says. Sales integrity means a belief in what you're selling and an understanding that software is never perfect or complete and can always be improved.

6. Don't be paranoid about competition

Paranoia just isn't worth the stress that goes hand-in-hand with constant negative anxiety. Worry less about what the competition is doing and focus on your customers, because the market keeps moving, and competitors don't always keep up. Instead of paranoia, Stretch says, be prepared: "Be ready for a fight and be ready for the public investor to confront you and challenge you on a daily basis."

7. Money is energy, so a CEO's job is to make sure the team energy is right

"You have to keep an eye on the corner cases," Stretch says, referring to the engineering term for situations that occur outside of normal operating parameters. Does the team gel? Do its members have the right energy level to take this to where it needs to go? "As CEO, you make sure that the integrity doesn't go out of shape, and that the energy levels don't drop."

Related: 20 Leadership Lessons with ZipRecruiter Co-Founder and CEO Ian Siegel

8. In a company filled with smart people, coaching trumps managing

"I don't really believe in performance management at all," Stretch admits. It's the 21st century, so when you've hired a team full of smart people who are capable, traditional line-of-sight management is much less valuable than the kind of coach who can roll up their sleeves and dive in to help when needed.

9. The future is hybrid

Stretch thinks the new normal of working will involve a physical and remote hybrid, with in-person gatherings saved for important meetings and celebrations. "When we do go back and have a company meeting, it's going to be shorter, it's going to be more intense, it's going to be rich, and we're going to love it."

To learn more about Stretch and his unique leadership methods, watch the full webinar here. For more extraordinary talks with other CEOs from high-profile brands like Zoom, ZipRecruiter, Dallas Mavericks, GoDaddy and Mailchimp, check out our series page.

Related: 13 Leadership Lessons from Zoom Founder and CEO Eric Yuan

Jason Nazar

Entrepreneur Leadership Network® VIP

Comparably Co-Founder & Serial Tech Entrepreneur

Jason Nazar is a serial tech entrepreneur, investor and advisor with two successful exits under his belt. Most recently he was co-founder/CEO of Comparably (acquired by ZoomInfo), a leading workplace culture and employee review site. Prior to that, he was founder/CEO of Docstoc (acquired by Intuit).

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