Moving Up Market in The SaaS World: The Transition from SMBs to Mid-Market & Enterprise

Moving Up Market in The SaaS World: The Transition from SMBs to Mid-Market & Enterprise

“10x more money per customer?”


Moving your business upmarket can mean massive revenue boosts.

It’s where the big-bucks get made.

Upmarket customers are the affluent, enterprise-level businesses that demand more from your SaaS… but also write bigger checks without even blinking.

By moving upmarket, your company’s growth can scale quicker from fewer customers.

I bet you’re already thinking: “SIGN ME UP!”

Like a cartoon character, your eyeballs become dollar signs, tongue hanging out, dreaming “money-money-money”!


It’s a trap.

I’ve had the privilege of working closely with SaaS founders, seeing the numbers behind the scenes and I can tell you this:

Moving upmarket can destroy your business.

I’ve seen businesses commit to aggressively pursuing these upmarket customers by hiring new teams and launching new campaigns…

…only to fall flat on their face.

What happens then? You retreat. Tail between your legs, you let go of your new teams and crawl back to the market of low-ROI customers in the hopes of recouping some costs.

You simply can’t make that transition without a strategy.

This is Mark Roberge’s specialty.

Mark was HubSpots Chief Revenue Officer, a lecturer at Harvard Business School, ranked in Forbes top 30 Social Sellers in the world and the writer of The Sales Acceleration Formula.

A while ago I had a conversation with Mark about the process he uses to build a strategy for moving upmarket successfully.

That conversation inspired this week’s video.



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If you want to transition to upmarket customers, then these are the 5 points I consider necessary to pull it off.

  1. GTM metrics (it’ll make sense in the video)
  2. Segment Map
  3. Triple Review
  4. Capture Fix
  5. Lock-In Playbook

It should be no surprise to you that everything in business requires good strategies.

Some entrepreneurs just ride the right wave at the right time unaware that a portion of their success was luck.

But repeatable success is a different story.

In the last 20 years, I’ve started multiple 7-figure businesses in different industries, and successfully exited 3. Each company has challenged me in new ways I could never have imagined.

The only thing I can attribute to my success was remaining extremely realistic, grounded and developing proven strategies.

That’s why I make these videos for you every week.

Drop by the video here and leave me a comment. I love hearing from you and challenging my own thoughts.

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