Q&A with Mark Tipton, CEO of Aspire Software

Aspire Software, a Mainsail Partners portfolio company, was recently named on the 2019 Inc. 5000 list, an annual guide to the 5,000 fastest-growing privately held companies in the U.S according to Inc Magazine

Aspire is a leading business management software for landscaping, snow & ice, and construction companies. We caught up with Aspire’s CEO, Mark Tipton, to congratulate him and learn some of the secrets that have helped his company grow.

Where did the idea to start Aspire initially come from? How did you get started?

My partner Kevin Kehoe and I both had a history in the landscaping industry—he is a longtime consultant which was a good match with my experience in the software industry. In our experience working with commercial landscaping businesses, we observed that the vast majority of landscaping professionals were using a hodge-podge of solutions to run their companies, but there was no central management system. We saw this as a huge opportunity to address an unmet need. Our goal was to develop a software solution to serve these needs and our mission was to “Change the industry through technology.” That remains our mission statement to this day.

We started formulating our business plan toward the end of 2013, then circulated it within the landscaping industry to raise the initial capital to launch the business. We spent a year building the software, putting the service model in place, and hiring the team to deliver. The first full version of the product rolled out to our initial clients in 2015.

What decisions did you make when scaling that made the difference between growth and failure?

Building a comprehensive and specific business plan was a critical step in the process.  This sounds obvious, but with the first business I started, I was not purposeful enough in writing the plan down and sharing it with others which created challenges down the road.  Having a foundational plan for Aspire was important not only for communicating with others, but also for ensuring alignment between Kevin and me and to have something to refer back to if we ever felt we were going off track.  We shared it with many of our industry connections to be sure our plan would serve their needs. The plan changed over time, but it served as a roadmap and a communication tool to keep us on track and aligned.

The second thing I would highlight is not so much a single decision, but an approach we took to building the business. We overcame some natural tendencies most entrepreneurs have to be too controlling and made a commitment to hiring talented teams and delegating responsibilities to those team members.  That freed us up to continue building the business.

What advice would you give other bootstrapped software founders going through the same growth phase you went through?

Don’t be afraid to ask for advice. There is a massive network of people out there who have walked the road you’re on and are happy to share the lessons they’ve learned. I connected with a local group of entrepreneurs and their advice has been immeasurably helpful. They didn’t necessarily give me the answer, but they provided a valuable sounding board as we were going through key decisions for the business. They also shared ideas and resources they’d used to be successful. I only wish I’d made those connections sooner.

There is a massive network of people out there who have walked the road you’re on and are happy to share the lessons they’ve learned.

You brought on Mainsail as your growth equity partner in March 2019. What led you to that decision?

It was a two-step decision process. First, we had to decide whether growth equity was the path for us. Firms found that we had become a successful company, which meant our phones started ringing with their calls. Why were they interested? What did they see in us? We started to realize there was a specific window of opportunity for growth in our industry and the faster we could get there, the farther we could go. Competitors catching up, missing partnership opportunities, slowing innovation – these were the things that kept us up at night and were still in our control under the right circumstances. That’s when we decided growth equity was the right strategy for us.

The second step was selecting a partner. We wanted a firm that would allow us to preserve our company culture and maintain a focus on delivering quality products and services to our customers. Mainsail made it clear that they were aligned with these goals. They were not trying to run our company, but they did have resources and expertise to help us run it better.

One of the things that stood out in the process was speaking with other founders and CEOs at Mainsail’s portfolio companies.  We saw a lot of value in becoming part of a network of companies that were so similar to Aspire.

What have been the biggest changes since partnering with Mainsail?

With their help, we’ve made a few key hires that we believe have put us in a strong position for growth. Even better, these hires have freed up my time to work on the business. Already we’ve launched some big initiatives including:

  • Sales: We’ve reorganized the sales team to better attack the market, hired additional leadership to support scaling the organization and improved reporting to have better predictability and visibility into the pipeline.
  • Product: We transformed from a waterfall methodology to an Agile one, with a focus on test-driven development. Our product management team is now focused on hitting the right targets for our customer. Instead of launching and then getting feedback, we’re testing ideas with our customers before sending them over to engineering, ensuring we’re building new features efficiently.
  • Service: We’ve implemented a tiered support system that allows us to effectively respond to issues as they escalate. We’ve also created a new role for Customer Success that proactively works with clients to understand how they’re using the system and how we can better serve them.

All of this, in just under six months. We have already accomplished a lot in under six months and we are only getting started.

We have already accomplished a lot in under six months and we are just getting started.

In a 12-month period, you’re on track to grow from 35 people to 65. How do you plan to preserve your culture as you scale and grow?

Culture is critically important to me and more significantly, it’s important to our people. We pay attention to it and that’s half the battle.

To translate that on a larger scale, we hired a Director of Talent and tasked her with hiring the right skillsets as well as the right fit. This role has helped us improve the clarity and consistency of internal communications. They also keep tabs on employee engagement, so we know how our people are feeling. A recent employee survey asked, “Am I proud of my job?” and “Am I proud of the team I work with?” Both scored 4.7 out of 5 points. To me, that says we’re nailing our culture, and we will continuously be focusing on this.

What gets you most excited about the future of the company?

Our team and the impact we are having on the industry. We are continuing to build our team of what we view as high caliber talent, and talent tends to attract talent. It is amazing to watch our team get better and better, not just with new talent, but people who have been here for a while continue to grow and take on new responsibilities.

We really do have great customers and seeing the impact we have on their businesses is rewarding. It’s incredibly motivating to see our mission become reality.

¹ “2019 Inc. 5000: The Most Successful Companies in America.” Inc., Mansueto Ventures, 14 August 2019.

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