Better Agency
Will saw a massive gap in the market while doing custom implementations for insurance agencies. They were piecing together Infusionsoft, HubSpot, Salesforce, and 4-5 other platforms because no one had built software specifically for independent insurance agents. "Nobody's been really focused on the insurance industry," he explains. By end of 2019, he decided to go all-in on Better Agency as the first CRM purpose-built for this vertical.
The company bootstrapped from the beginning. They pre-sold to early customers while building, so they didn't actually bring in their first dollar until November 2019—about six months later than initially expected. But this foundation meant they had real customers validating the product from day one. By the time Nathan last spoke with Will in 2019, they had around 100 customers at roughly $300/month.
Word-of-mouth and organic channels became the dominant growth drivers. About 70% of new customers came through referrals or organic (primarily their blog), while 30% came from paid (Facebook and Google ads). They're conservative with paid spend—just $9-10K per month in June—which generated about 25 net new customers at a 70% trial-to-paid conversion rate. The affiliate program is small but concentrated: five affiliates driving $6-7K in monthly payouts, with one affiliate carrying the majority of volume.
Their biggest lever has been investment in onboarding. Rather than charging setup fees (like Infusionsoft did), they spend heavily on hands-on onboarding to increase lifetime value and customer retention. This paid off dramatically: they went from 36% annual churn in 2019 to just 2% monthly (24% annual) today. Net dollar retention sits at 105%+, driven by both seat expansion and feature upsells (now roughly 50-50). Their LTV sits between $12-14K, and they're willing to spend $1,500 CAC all-in because the math works—they're aiming to push that to $2,000 CAC.
They grew from ~$30K MRR a year ago to over $85K MRR today while maintaining an incredibly lean burn rate of just $10-12K/month. That bootstrap discipline meant fundraising was easy when they decided it was time.
Better Agency is announcing their first institutional raise: $2.1M at a $15M post-money valuation. The round was split 50% from a local angel lead investor (who set favorable terms) and 50% from insurance-specific angels and other vertical SaaS founders Will knows. The founders still own 75-80% of the company, new investors get ~15-20%, and employees have a 5-7% option pool. They're 16 people today (6 engineers, 1 sales rep with a $150-160K OTE crushing a $500K+ ARR quota) and plan to grow to 20-25 by year-end. The capital will fund bringing product and development in-house (previously outsourced) and scaling sales and marketing. Will is betting the insurance vertical will stay a focus—the space is ripe for disruption with many competitors still not cloud-based and some dating back to the 80s and 90s.
- •By solving a specific pain point he experienced firsthand in insurance agency operations, Will built a product with product-market fit strong enough to achieve 105%+ net dollar retention and reduce churn from 36% to 24% annually.
- •Pre-selling to customers before launch forced the team to validate demand early and build with real customer input, eliminating the risk of building something nobody wanted.
- •Heavy investment in hands-on onboarding rather than charging setup fees created a retention moat that generated 3-4x higher lifetime value ($12-14K LTV) compared to competitors, justifying aggressive customer acquisition spending.
- •Organic and word-of-mouth growth (70% of new customers) meant the unit economics were favorable enough to bootstrap profitably while maintaining a lean $10-12K monthly burn, making eventual fundraising a choice rather than a necessity.
- •Vertical specialization in insurance allowed the founder to build deep credibility, concentrate sales through high-performing affiliates, and differentiate against horizontal CRM platforms trying to serve every industry.
- 1.Identify a specific industry or use case where you have direct operational experience and where existing solutions force users to cobble together 5+ different tools.
- 2.Pre-sell your solution to 5-10 early customers before you fully build the product, using their feedback to shape your roadmap and ensure you're solving a real problem they'll pay for.
- 3.Allocate 30-40% of your customer acquisition budget to hands-on onboarding and direct engagement with trial users rather than generic product support, measuring success by trial-to-paid conversion and monthly churn reduction.
- 4.Build a content strategy (e.g., blog, case studies) and affiliate program targeting 3-5 trusted figures or partners in your vertical who can generate word-of-mouth referrals, rather than spreading marketing spend across broad channels.
- 5.Run unit economics calculations (LTV vs CAC) to determine your true customer acquisition capacity, then set a lean monthly burn rate (target: 10-15% of MRR) to bootstrap profitably while maintaining founder control until fundraising becomes a strategic choice.
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