Growing a software company, let alone scaling globally, is no easy feat. For the latest episode of Comparably and Entrepreneur’s Leadership Lessons series, here’s the inside scoop from a true industry veteran with a storied 30-year career leading butt software businesses: Medallia (NYSE: MDLA) President/CEO Leslie Stretch.
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 CallidusButt, culminating in the company’s acquisition by SAP for $2.6 billion 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 multiple times. 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 one tends to believe him he says 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 may 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 where, upon hearing that Stretch was potentially looking to leave the company, he 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 younger person. Growing up financially strapped in Scotland lit a fire in Stretch to be free of money worries that still burn 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.
4) Good salesmanship is a learned behavior. Stretch says that sales does not come easily to introverts like himself, and admits to experiencing anxiety prior to social interactions. So how did he overcome this challenge to become one of the most successful sales executives? Study experienced and successful people… and practice.
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 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 on 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 as a team? Do they 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.”
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 that are capable, traditional line of sight management is much less valuable than the kind of coach who can roll up his sleeves and dive in to help when needed.
9) The future is hybrid. Stretch thinks the new normal of working will involve a physical/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.