SaasRise Mastermind Recap - Jan 21, 2026

Come join us next Wednesday at 8am PT and 12pm PT on Zoom for the type of peer advice you can only get from other SaaS CEOs who are in the trenches.

🎯 AI-Driven Cold Outreach Personalization

Challenges: AI personalization can backfire when details are slightly wrong (city, metrics, role). It takes high effort to scrape/enrich leads and write strong prompts, and returns have diminished as inboxes saturate. Over-personalization can hurt credibility (especially with C-level), and it often distracts from the core value proposition. chat text (31)

Advice: Stop over-personalizing large cold lists—lead with clear, targeted offers instead. Use personalization selectively for smaller engaged subsequences or warm leads, and prioritize a strong value proposition over gimmicks. Invest in higher-quality prompts rather than more scraping, and use AI enrichment after initial engagement to control costs.

🧑‍💻 CTO Hiring for Growth-Stage SaaS

Challenges: It’s hard to find senior technical leaders with scaling experience. Some CTOs prefer coding over people management, and teams struggle to balance development velocity with leadership—especially when planning for a potential exit in the next 12–24 months.

Advice: If the exit timeline is short, prioritize revenue and growth over perfect technology. Avoid major technical overhauls that slow momentum, expect temporary slowdown when introducing new leadership, and use referrals (not job boards) for senior technical roles. Confirm whether the current team can support exit goals before making major hires.

🧭 EOS Implementation Approaches

Challenges: Founder fatigue from self-implementation, uncertainty about hiring external help, and weighing cost vs. value of facilitation.

Advice: Choose one of three paths: (1) self-implement if disciplined, (2) hire a facilitator (~$7,000/quarter for 1–2 years), or (3) hybrid—6–12 months facilitated, then transition to self-management. Interview multiple facilitators for cultural fit.

🗓️ L10 Meeting Structure

Challenges: Keeping meetings efficient as teams grow, deciding between company-wide vs. departmental meetings, and maintaining a 90-minute cap. chat text (31)

Advice: Limit L10s to 5–8 participants. For larger orgs, run multiple L10s (exec + departmental). Keep a consistent weekly schedule and anchor execution around quarterly rocks and IDS.

📊 Technology and Data Management

Challenges: Picking EOS tooling (Ninety vs. alternatives), tracking 200+ KPIs, and maintaining data accuracy and accountability.

Advice: Google Sheets and ClickUp can work well as alternatives. Assign one person to gather data centrally, create department-specific views, automate data pulls where possible, and prioritize consistency over sophistication.

🤝 Finding and Working with Facilitators

Challenges: Locating qualified EOS implementers, understanding the right investment level, and knowing when facilitation is truly necessary.

Advice: Contact EOS directly for vetted implementers in your region, and expect a ~$7,000/quarter commitment. Treat facilitation like COO coaching—most valuable for teams new to EOS or needing accountability.

Recommended Tools

LinkedIn Outreach & Automation

• Kakiyo AR
• HeyReach

Data Enrichment & List Building

• Clay

Cold Email Outreach

• Instantly

AI Coding & Development

• Claude Code (Opus 4.5)
• Cursor
• Google AI Studio
• Figma AI
• Locify
• Anima App
• Tailwind CSS
• Reloom.io
• N8N
• GitHub Copilot
• Lovable
• Replit
• Bolt
• Supabase
• Vercel

Sales & Communication

• Dialpad
• Sales Navigator (LinkedIn)
• Yet Another Mail Merge
• Wise

EOS Implementation

• Google Sheets
• ClickUp

Other

• K-Stitch

Best Advice

The most valuable takeaway was to rethink AI personalization entirely. AI-driven personalization that worked a year or two ago now often damages credibility when details are even slightly wrong. Instead of chasing hyper-personalized cold outreach at scale, founders should focus on clear, targeted value propositions, quality messaging to the right audience, selective personalization only after engagement, and prioritizing revenue and growth over technical perfection when approaching an exit.