Convey

Steven Rine made a bold decision in 2009: he quit his sales job, taught himself to code, and launched his first SaaS product, WebPDI—a sales relationship manager—within a year. It was profitable from day one, generating $100,000 in profit that first year. The internal sale to his former employer meant quick validation and high demand. This early success gave him the confidence and capital to keep building.

For years, Rine and his co-founder experimented with different products—WebPDI, a voter relationship management platform, and others. The real breakthrough came when his co-founder started a talent agency for speakers and thought leaders in Bend, Oregon. He was building high-end e-learning experiences for corporate trainers and kept running into the same problem: traditional e-learning platforms (large WordPress sites, MOOCs) had terrible engagement. Not because the content was bad, but because the format was wrong. In 2016, they decided to build Convey—a micro-learning platform inspired by how marketing automation works: timely, relevant, personalized messaging spread over time instead of forcing users through massive course modules.

The co-founder's talent agency became the first beta customer. From there, something magical happened: satisfied corporate trainers started recommending Convey to their clients—the large corporations they worked with. One trainer who ran training for 4,500 companies loved Convey so much, he became a customer himself, and his recommendation opened doors to enterprise buyers. This word-of-mouth loop proved so effective that Rine decided to lean into it. Rather than chasing hundreds of small customers, he'd go upmarket.

The initial $100/month plan for individual corporate trainers and speakers was a good starting point, but scaling it required too much hand-holding. These busy professionals didn't have time to set up automations and build funnels. The real insight came when Rine realized he could acquire enterprise customers (1,000+ employees) for nearly the same CAC cost through LinkedIn outreach and automated webinars. He built a network of instructional designers to handle onboarding, taking on some of the cost upfront to ensure customers got quick wins. This flipped the unit economics: instead of struggling to retain 100 small customers, he now had 100 enterprise customers paying $700/month each. Revenue churn plummeted from 15% monthly (2017) to 7%, and the lifetime value climbed to 29 months (~$20K per customer). Payback was less than a month—nearly frictionless.

Convey is fully bootstrapped, generating ~$70K/month (~$845K ARR) with just five contractors spread across Ohio, Oregon, Ireland, and Portugal. Rine handles operations and the software team; his co-founder leads marketing and sales. The team deliberately avoids hiring traditional in-house sales staff, relying instead on LinkedIn, webinars, and word-of-mouth. By focusing on the right customer fit and investing in proactive onboarding, they've built a cash-flowing, profitable machine that makes corporate training less boring and actually works.