SaasRise Enterprise Mastermind Call Recap May 19, 2026

Topic 1: Unusually High Churn

Challenge:

• Revenue down ~8% since December, with a slow multi-year decline
• ~60 customers total; retention normally above 80% (3-year ~50% revenue retention)
• Cancellation reasons are varied and often unclear from exit interviews
Customers no longer displaying coupons
Customers building DIY solutions
Entire affiliate departments shut down
Budget/belt-tightening pressures
Stack decisions made above the contact's level
One customer cited a cheaper competitor (identity unknown)

Advice:

• Conduct honest exit interviews; make yourself vulnerable and ask for help rather than using formal outreach
• Speak directly with ongoing customers to gauge health, not just rely on the account team
• Consider selling best data on-demand via API rather than in bulk to protect IP

Topic 2: Enterprise Unlimited License Pricing (300 → 30,000 Users)

Challenge:

• At ~300 licenses, an "unlimited" enterprise tier is priced at ~$150K
• A customer with 90,000 employees plans to 10x active users, making flat "unlimited" pricing untenable

Advice:

• Use tiered/packaged pricing (e.g., plant vs. enterprise tiers) rather than per-user or pure unlimited
• Anchor tiers to metrics customers already know (locations, SKUs, business units)
• Never offer truly unlimited — use fair use policies or overage conversations instead

Topic 3: Outbound Messaging & AI Positioning

Challenge:

• Outbound is new (~2 months old); prior growth came from SEO and podcast
• Cost-savings messaging feels less effective; buyers seem to expect an AI angle
• Unclear how to authentically incorporate AI without overstating capabilities

Advice:

• Test messaging with ~1,000 sends before concluding it isn't working; benchmark ~1–2% reply/click rates
• Use alternate domains for outbound to protect main domain reputation
• Lead with safe, usable AI framing — not hype — addressing both fear of missing out and data security concerns
• Consider building connectors so enterprise customers can plug in their own AI agents rather than building AI natively

The following tools and resources were mentioned or recommended during the call:

For Churn / Customer Retention

• NPS and customer health scoring — suggested as tactics to measure ongoing customer satisfaction
• Exit interview frameworks — a cheat sheet for exit interview questions was requested; no specific tool named, but a pricing podcast was referenced as a resource with good ideas around pricing and usage metrics

For Outbound & Sales Messaging

• LinkedIn, email, and phone — recommended channels for personalized outbound outreach
• Alternate/subdomain email domains — recommended to protect the main domain's reputation when sending high-volume outbound
• AI agents for outreach automation — described as a pilot approach for automating personalized LinkedIn/email outreach and replies, though manual outreach outperformed it in early results

For Pricing

• Custom price calculator — described as a tool salespeople use to build any custom package, where higher volume yields a lower unit price

For Ad Spend Analysis

• SaasRise metrics model — mentioned as a framework being used to track CPM, CPL, and CPC for evaluating ad spend effectiveness

General AI Tools Referenced

• ChatGPT — noted as readily suggesting API call-based pricing models
• Codex — mentioned as an example of a credits-based usage pricing model