Add-on strategy - $0 to $100 million ARR

Going multi-product is the fastest way for vertical SaaS companies to grow ACV and retention — if done correctly. A single platform can evolve into a portfolio of revenue drivers, including embedded payments, marketing automation, product catalog, and early AI assistants, scaling add-ons from $0 to $100M+ ARR in under five years.

But multi-product only works when add-ons deepen the core workflow, not distract from it. The goal is to systematically increase share of wallet by embedding into where customers already spend time and money — while preserving focus on the system of record.

Success requires identifying the right “share of wallet” opportunities, timing the first add-on carefully, and standing up a focused tiger team to ship an MVP without derailing the core product. It also demands a clear framework around build vs. partner vs. buy, product packaging, and an understanding of why CSM-led upsells often stall.

The right KPIs are critical so the motion compounds rather than distracts.

Key Takeaways

• Start with share of wallet. Pull customer P&Ls, run surveys or webinars, and map where your users already spend (payments, financing, marketing, telecom, fleet, insurance). The best add-ons replace existing spend, not create new line items.
• Anchor add-ons in workflow gravity. The strongest add-ons live inside daily workflows, increase switching costs, and are hard to rip out once adopted.
• Stand up a tiger team. One PM, 1–2 engineers, and a part-time GTM owner can ship an MVP, validate demand, and de-risk execution without pulling the core team off roadmap.
• Partner first on complex offerings. For payments, financing, payroll, or compliance-heavy products, the right partner often beats building from scratch in speed, risk, and economics.
• Sequence add-ons deliberately. Lead with products that touch money flow or customer flow (e.g., payments, invoicing, scheduling). Optimization tools come later.
• Package for fast ROI. If an add-on doesn’t pay for itself within ~90 days, adoption and expansion stall.
• Sell at the right moment. Activate payments during implementation to lock in workflows; sell marketing automation once customers are live and seeing value.
• Don’t let CSMs carry upsells. Use commercially oriented AEs or SDRs for expansion, with clear ownership and incentives. Keep CSMs focused on value delivery.
• Measure what matters. The goal isn’t more features — it’s higher net revenue retention without increasing GTM complexity or churn risk.

The winners in vertical SaaS won’t be the companies with the most features — they’ll be the ones that become the financial and operational backbone of their customers.