Software Sales Tips by Matt Wolach

Scale Your SaaS

From Side Project to Millions in Revenue – with Chase Summers


Every successful megacorporation that has ever existed was once small. We’ve all heard of the stories of a software startup founder that started their business in their parent’s garage, or created it while still in college. And so with the right process and mindset, know that your company can be just as successful.

Dataedo Director of Customer Operations Chase Summers shares his experience in helping Dataedo grow from a side project to the profitable company that it currently is. He also talks about his transition from sales rep to a director with Host and B2B SaaS Sales Coach Matt Wolach. Watch and get ready to welcome growth for both yourself and your company!


Podcast: Scale your SaaS with Matt Wolach

Episode: Episode No. 256, “From Side Project to Millions in Revenue – with Chase Summers”

Host: Matt Wolach, a B2B SaaS sales coach, Entrepreneur, and Investor

Guest: Chase Summers, Director of Customer Operations at Dataedo


Solicit and Implement Customer Feedback

Feedback matters a lot when it comes to increasing your sales, as it allows you to match your product better with your customer’s needs. This is why Summers advocates getting close to your customers. And more than collecting feedback, it’s crucial that your team actually applies them to the product

Summers adds that they regularly check in with customer success to feel the customers’ pulse. He explains, “We’re constantly, through customer success, really getting to meet with them and have an inside look at what they’re doing, what they’re willing to spend, (and) what they have problems with outside what we currently do.”

Identify the Market Gap

Whenever software businessmen think of the gaps in the market, the first thing that comes to mind is that it’s for the sake of product development. You identify something missing in the industry you want to penetrate and offer that as your unique value proposition. On the other hand, Dataedo decided their pricing through a market gap.

Summers and his teams compared the pricing of Dataedo with that of competitors. After going through the hoops of hidden prices or complex calculations, they quickly found that the pricing is either extremely low or extremely high for their market. Take advantage of an opportunity, Dataedo quickly set itself on the mid-market tier.

Don’t Take Yourself So Seriously

One of the mantras by Summers for his team is rule six, which states to not take yourself too seriously. He understands that the further you succeed, the higher the stakes are, which means more pressure. But that doesn’t necessitate mentally beating yourself up for every lost deal.

Passion is a strong force to have for any venture but it’s important to remain balanced. Always remember that making a mistake does not mean that the world will end or that your company’s bottom line will sink deeper than the Mariana Trench. Remember that it’s just as important to have fun in what you’re doing and that this actually leads to better performance.

Provide Autonomy But Do Not Neglect

One of Summers’ management mantras is “autonomy without neglect.” As a software sales leader, Summers values giving people autonomy in handling their tasks. He leans on the type of supervisor that empowers his teammates and puts his faith in them. While this can be noble, too much of anything leads to consequences.

Summers quickly realized that his approach during his early management days was basically the opposite of micromanagement. He realized that he was too hands-off with his employees. Given Summers’ personality, he attracted employees that are growth-oriented. This means that they actually wanted to be coached by him. Upon this realization, Summers set out to strike a balance and became more hands-on with his team.

Be Comfortable with Being Uncomfortable

When it comes to hiring talents, Summers looks for people who can put themselves out of their comfort zone. This is crucial because growth itself is uncomfortable. To be fine with discomfort means having a higher learning rate, and getting better in business means constantly upskilling.

Summers personally put himself in uncomfortable situations during his transition from being a sales rep to being the director of customer operations. Summers had to seek out mentors and even roleplay scenarios with them, making him uncomfortable. Regardless, he pushed through with it and gained valuable wisdom that translated to fostering an amazing team.

Be More Interested Than Interesting

Many business people and entrepreneurs out there are usually more concerned with beefing up their resumé. You peek at LinkedIn and find this person who’s the same age as you with twice or thrice as much work experience. While ambition is an inspiring value to have, Summers states that people are too concerned about being someone interesting.

Rather than being interesting, Summers believes in being someone who is interested. He believes that curiosity is much better as it pushes people to go out there and learn. Being someone who is always interested means inevitably and constantly developing yourself. Note that it’s also helpful when it comes to sales and customer service, as you would be a better listener to your clients.


Fewer Variables Equals Faster Customer Decision

On Dataedo’s pricing journey, they discovered that a customer is more likely to buy if they have lesser things to consider. Just like with writing, you want to keep your pricing short and sweet so that you will close more deals. This is why Dataedo has opted for a set price, simplifying the decision-making process for its customers.

More Failure Equals Clearer Vision

Another reason failure shouldn’t be feared is that it teaches you the things you must avoid. It paints a more vivid picture of what you should actually be doing in your business. Summers made many failures, be it as a sales rep, head of sales or customer operations director.

A Leader’s Response to Failure Matters

When it comes to your employees’ making mistakes, Summers believes that your reaction is crucial. You’d want to provide feedback to your customers but also empower them instead of just being critical or being dismissive of their mistakes. He believes that this way, your employees will be confident to tell you of any problems.


Chase Summers

[14:33] “My whole mantra with management is autonomy without neglect.”

[15:12] “You can be an empathetic person but still be a really good leader. And so that’s something that I’ve worked on is leading the people and giving them feedback at the same time, and being empathetic but also challenging.”

[21:55] “Just learn to be interested and stop thinking that you’re interesting because chances are you’re not.”

Matt Wolach

[16:54] “You just don’t do as well when you’re under stress. And so I love the idea of just, breathe, take a step back. Don’t take yourself seriously because it can really help you perform better.”


To learn more about Chase Summers and Dataedo, visit

You can also find Chase Summers on LinkedIn at:

For more about how host Matt Wolach helps software companies achieve maximum growth, visit