Case Study

Aspire Software

Capturing the Market Opportunity for a Growing Landscape Software Business

“As a founder, bringing in your first investor is one of the hardest and most important decisions you’ll make. We were fortunate to get it right when we partnered with Mainsail. Their help in recruiting talent, optimizing our go-to-market motions, and executing M&A has been instrumental in scaling our organization and continuing our growth trajectory."
– Mark Tipton, Co-Founder and CEO of Aspire Software

At a Glance

  • Recruited management team (CTO, Head of Product, Sales, Marketing, and Talent)
  • Recruited two independent board members
  • Enhanced pricing model
  • Completed a strategic acquisition, resulting in product line extensions
  • Grew employee base by 3x (from 35 to 100)
  • Customer growth increased 184%
  • Scaled Sales & Marketing organizations

The Company

Aspire Software offers business management software for landscape, snow and ice, and construction companies. Aspire’s cloud-based SaaS platform helps landscapers manage, create, and execute against their business opportunities and challenges.

The Story

Aspire co-founders, Mark Tipton and Kevin Kehoe both had a history in the landscaping industry. In their experience working with commercial landscaping businesses, they observed that the majority of landscaping professionals were using a patchwork of solutions to run their companies, and there was no central management system. They recognized a huge opportunity to address an unmet need.

When they founded Aspire, the goal was to develop a software solution to serve these needs. Their mission was to, “Change the industry through technology.”

In 2013, Tipton and Kehoe formulated a business plan and circulated it within the landscaping industry to raise the initial capital required to launch the business. The first full version of the product rolled out to preliminary clients in 2015. In 2019, Tipton and Kehoe started to realize there was a specific window of opportunity for growth in their industry and believed that partnering with Mainsail could help them get there faster, and go farther, as compared to going it alone.

Mainsail’s Value

Talent Acquisition: At the time of investment, Aspire’s executive team was comprised of a CEO (Mark Tipton) and CFO (Mike Wylie). The pair leveraged Mainsail’s extensive network of executives and internal recruiting team to build out a complete management team including a CTO, Head of Product, Head of Sales, Head of Marketing and Head of Talent. In addition, Mark and Mainsail collaborated to recruit outside board members Cameron Darby and Tom Bogan.

Pricing Study: With guidance from Mainsail, Aspire ran and executed a pricing study that helped optimize revenue per client. The updated pricing model and product packaging aligned with key market segments and provided clear upgrade paths for customers.

Product Line expansion: Mainsail supported Aspire in the expansion of its product line-up, including integrating with several strategic partners. This work included:

    • – Launching payments and GPS tracking products
    • – Launching multiple new integration partnerships
    • – Launching payments for Crew Control product

Go-to-Market support: Collaborating with Sales and Marketing leaders, Mainsail helped Aspire scale its GTM organization through several initiatives, including:

    • – Optimizing lead-to-close process and CRM implementation
    • – Conducting a messaging and persona development
    • – Launching an outbound SDR team

Strategic Acquisition

Mainsail identified a number of potential acquisitions that could benefit the Aspire product suite, including a scheduling software solution for lawn care and landscaping companies called Crew Control. Mainsail worked with Aspire to acquire Crew Control in 2021 after which Mainsail helped launch a new payments product and accelerate the growth rate of the business by increasing and optimizing investments in sales and marketing.


In 2021, Aspire was acquired by Service Titan.  See more details here.

  • LOCATION: Chesterfield, MO
  • SECTOR: Software-as-a-Service (SaaS)
  • CEO: Mark Tipton
  • FOUNDED: 2015
  • INVESTED IN: 2019
  • STATUS: Acquired