Enterprise Sales: $2K MRR to 7 Figures With Cold Email

Santi Bibiloni was stuck at $2K MRR selling to small agencies. Then he shifted his enterprise sales strategy upmarket and started closing multi-year contracts with some of the largest agencies in the world.

In this episode, Santi reveals how COR went from offering free trials and monthly plans to eliminating free trials entirely, selling annual and multi-year contracts to CFOs, and growing to between $1M and $2M ARR with 9% month-over-month growth. His enterprise sales playbook targets CFOs at agencies with 50-200 employees through B2B SaaS sales cold email with an 86-day average cycle.

COR's shift from SMB to enterprise SaaS transformed their metrics: 114% net revenue retention and just 4.5% annual dollar churn. Santi's B2B sales process proves that customizing the demo - not the product - closes enterprise sales deals faster.

Key Lessons

• 🏢 Move enterprise sales upmarket when SMB growth stalls: COR was stuck at $2K MRR selling to small agencies. Shifting to mid-market and enterprise with 50-200 employees unlocked 7-figure ARR and 9% monthly growth.
• 🎯 Define your ICP down to buyer persona and company size: Santi targeted CFOs at creative agencies with 50-200 employees. This specificity made cold email outreach and enterprise sales messaging dramatically more effective.
• 💰 Eliminate free trials and sell multi-year contracts instead: COR dropped free trials entirely and moved to annual and multi-year contracts, increasing prospect commitment and reducing churn from 15%+ to 4.5% annually.
• 📧 Cold email to CFOs outperforms paid ads for enterprise sales: COR spent their angel round on Google and Facebook ads with poor results. Almost all enterprise SaaS revenue came from cold email outreach and email lead nurturing.
• 🤝 Customize the demo, not the product in enterprise sales: COR shows each prospect how their specific pain points are solved rather than doing generic feature walkthroughs, making every demo feel personal without building custom features.

Chapters

• Introduction
• Santi's favorite quote: think big, take risks, be resilient
• What COR does: project profitability platform
• Business size: $1-2M ARR with 9% monthly growth
• Origin story: running an e-commerce agency in Argentina
• Building the MVP and getting two agencies to try it
• Early users hated the product but kept using it
• Raising an angel round and wasting money on paid ads
• Why paid advertising failed without a clear ICP
• Moving upmarket from SMB to enterprise sales
• Cold email vs. paid ads: what actually worked
• Lead nurturing and email marketing strategy
• Defining ICP: CFOs at agencies with 50-200 employees
• Personalizing cold email for enterprise sales
• Eliminating free trials and selling multi-year contracts
• Multi-stakeholder enterprise sales process
• Average 86-day enterprise sales cycle
• Lightning Round
• Where to find COR and Santi

Resources

• Full show notes: https://saasclub.io/297
• Join 5,000+ SaaS founders: https://saasclub.io/email