Software Business Advice from 12 Leaders

March 27, 2019 Saas & Platforms
By Owen Linderholm, Senior Content Strategist
By Owen Linderholm, Senior Content Strategist

WePay asked some of our partners for their leadership advice and to share a nugget of business wisdom. These became part of our partnership with the popular SaaStr podcast and we’ve collected them here.

From SaaStr Podcast Episode 206: Kashoo CEO Jim Secord, “The most important thing we’ve learned is to really use your own software. I don’t think there’s any better way to develop product and customer insight than actually eating your own dog food. We are the biggest critics or fans of our own software and it drives us to constantly improve.”

From SaaStr Podcast Episode 207: BigCommerce CEO Brent Bellm, “My tip is to remember the definition of disruptive technology. By definition, it always starts at the underserved, low end of the market, builds scale and then migrates up to go after the mid-market and the mainstream of the market.”

From SaaStr Podcast Episode 208: Fusebill Co-founder and CEO Tyler Eyamie, “There are two key areas of advice that I have that other CEO/Founders could benefit from. #1 Be patiently impatient and #2 Establish KPIs early. For #1 – be patient enough to trust your plan and your team. Impatient enough to ensure your foot is always on the gas. #2 On the KPI side establish these early to hold your people quantifiably accountable for their efforts.”

From SaaStr Podcast Episode 209: AmeriCommerce VP of Operations Jack Cravy, “It took us several years to get to where we are today but it all started with customers telling us what they were looking for and us doing everything in our power to fit those needs. It wasn’t perfect on the first time around but with enough feedback and enough communication we were able to satisfy what they were looking for and that’s played a big factor in our success.”

From SaaStr Podcast Episode 210: Webconnex Co-founder John Russell, “We took a bit of a different approach when we decided to bootstrap our startup. And yeah there sure are  challenges but it was probably the best decision we ever made. Eric and I have been able to make better long term decisions for our customers and our team. It’s forced us to prioritize what really matters and it’s given us the freedom to risk and the freedom to be generous. It might have been a bit slower path but we’ve now processed almost $2 billion dollars for our customers and our team has doubled in the past 12 months.”

From SaaStr Podcast Episode 211: PayRent CEO and founder Ryan Abell, “In our culture today it is easy to get distracted and sidetrack your business. It is important to set realistic and clear expectations for you and your team that ultimately align with your goals. I ask myself if Warren Buffet were to watch over me would he be impressed with my actions?

From SaaStr Podcast Episode 212: FreshBooks CEO and co-founder Mike McDerment, “If you care about culture and you’re scaling you’ve gotta think about organizational breakpoints. With four or five people in the room, I think everyone knows what’s going on. But 15 people you might start getting into your first managers and that’ll freak some of your team out and then when you hit 40 people not everyone will know what’s going on anymore, that’ll spook some others. At 80 everything breaks down communication-wise. You need new tools. And 150 is kind of another place. So look out for these things when you are scaling your company.”

From SaaStr Podcast Episode 213: Printavo founder Bruce Ackerman, “The two most important things I would say are number one, really focus on niching your business into an area and then be able to expand from there. And then number two, not really worrying about competition. Truly focus on your product and your customers.”

From SaaStr Podcast Episode 214: JotForm Director of Communications Chad Reid, “So a big mistake that SaaS companies make is over-monetization. It’s so easy for any business to see a dollar number assigned to each user. But when you offer sizable discounts, sales, free features, and rewards, you get something that’s much more valuable than just immediate revenue, which is customer loyalty.

From SaaStr Podcast Episode 216: Agree founder David Jay, “When I was 16 years old, my Dad sat me down and gave me the best advice. He said, ‘Build your business around helping other people and you’ll always have plenty of work.’ So the more that we can listen to our customers and feel their pain the better we are able to understand them, empathize with them and then create solutions that meet their needs.”

From SaaStr Podcast Episode 218: GreekTrack founder and CEO Tony Schmidt, “Here at GreekTrack we focus on every single support ticket as a design opportunity. So we don’t just solve a support ticket and close it but we take it all the way down to the development team and try and find a solution that will completely eliminate that type of support ticket forever.

From SaaStr Podcast Episode 222: Trellis founder and CEO Justin Goodhew, “My one piece of advice is do less. I know that sounds crazy but the SaaS platforms that try to do everything end up failing every single time. The ones that can do one specific pain point the best in the world always win.”

About the author


Owen Linderholm, Senior Content Strategist

Owen Linderholm is Senior Content Strategist at WePay. He has previously held content and editorial roles at Yahoo, Microsoft, IDG and the BBC.

More blog posts by Owen Linderholm

Discover how you can generate more revenue while helping users get paid effortlessly, all without overhead or fraud.

Show me how