Cascade

Tom Wright founded Cascade in 2013 after witnessing firsthand how badly most organizations execute on their strategic plans. Strategy documents would sit in PowerPoint presentations while teams struggled to measure progress or connect daily work to strategic goals. Tom saw an opportunity to build an affordable SaaS solution that could bridge the gap between strategy planning and reality.

The company initially launched in 2013, with a proper office established in 2014. Tom and his team built an online SaaS platform that helps companies measure strategy through planning, day-to-day management, and dashboarding/tracking solutions. The pricing evolved significantly—starting at just $20/month for solopreneurs and scaling up to $48/month for enterprise customers. By the time of this interview, the average customer across their entire base was paying roughly $5,000 per year, with new enterprise deals averaging $6,500 per year.

Cascade's growth strategy was uniquely organic. Rather than relying on paid advertising or traditional sales models, Tom and his small marketing team focused on ranking for generic strategy keywords. By creating blog posts and ebooks targeting searches like "how to write a vision statement" and "how to create a strategic plan," Cascade became the top-ranked result for nearly all these terms. This inbound marketing engine required minimal paid spend—just one full-time marketer, Tom's personal blogging efforts, and some remarketing on Google AdWords. The team had only recently added three salespeople to a new Portland office.

The land-and-expand strategy proved remarkably effective. Tom would target Fortune 500 companies but focus on individual teams or divisions rather than enterprise-wide rollouts. Once a general manager could demonstrate measurable results from using Cascade for one quarter, they became internal advocates—essentially an unpaid sales force. Tom would sometimes present alongside these champions to other divisions within the same organization. The retention metrics were exceptional: 90% annual retention for enterprise accounts (anyone paying $2,000+ per year) with 120% net revenue retention driven by 30% expansion revenue, offset by just 10% gross churn. However, Tom acknowledged that measured CAC was impossible at this stage since inbound marketing was so dominant and difficult to quantify beyond the salaries of his tiny team.

Cascade hit 1,076 customers and was generating $450,000 in monthly recurring revenue, up from $200,000 a month just a year prior—representing roughly 150-200% year-over-year growth. The company remained 100% bootstrapped and operating at breakeven, having invested only $50,000 in founder loans to reach profitability by the end of year one. With 30 people based primarily in Sydney, Australia, Tom believed the current inbound model could sustain 150-200% growth for another year or two before hitting a ceiling and requiring a more traditional sales and marketing infrastructure.