ABOUT MICHAEL CUMMINS

Enterprise sales experience without the enterprise-sized overhead.

I have spent 15 years closing complex SaaS deals, building sales teams, and helping companies turn individual seller performance into repeatable commercial capability.

From a restaurant floor to building enterprise sales teams.

I spent a decade managing restaurants before I sold nearly everything, drove across the United States with $1,300, and started over. There was no polished career plan—just a willingness to learn, work, and sell.

That path led to Google, where I helped take Apps for Work to market. From there I joined AlienVault as employee #44, helped it grow through its acquisition by AT&T, led enterprise sellers at WP Engine, and helped build Cloudflare’s Austin operation through its IPO.

At Cloudflare, I worked on the training team and helped cut ramp time from roughly nine months to three. I have now trained more than 10,000 salespeople. Across my IC career I closed $20M+ in ARR, then directly contributed to more than $200M in ARR while leading teams through three exits: two acquisitions and one IPO.

Across all of it, the pattern stayed the same: the strongest systems begin with someone learning how the product actually gets bought. That is why SaaS Scalers starts with the founder.

Now I work directly with founder-led B2B SaaS companies that have customer proof but need the positioning, process, people, and management system required to reach the next stage.

WHAT MICHAEL HELPS BUILD

Turn founder-led wins into a company sales system.

Michael helps founder-led SaaS companies identify what is constraining growth and install the commercial system needed to reach the next stage.

01

Positioning

Clarify who you should target, which problem is valuable enough to solve, and why the right companies should act now.

02

Qualification

Create a consistent framework for separating real enterprise opportunities from interest, enthusiasm, and polite demos.

03

Deal process

Build clear discovery, stakeholder, proof, objection, and next-step standards so deals progress for identifiable reasons.

04

Pipeline & forecasting

Replace seller activity and gut feel with buyer evidence, visible deal risk, and clear stage criteria.

05

First sales team

Hire the right people, set clear expectations, and lead a focused rhythm of coaching, accountability, and deal inspection.

06

AI enablement

Use AI for research, preparation, call analysis, follow-up, coaching, and knowledge capture without asking software to replace commercial judgment.

BUILD THE ENTERPRISE ENGINE

Ready to find the constraint holding growth back?

Book a Call With Michael →