Cirrus Insight Origin Story — Part 1

Ryan Huff
3 min readMar 31, 2023

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Brandon Bruce and I started Cirrus Insight over ten years ago. I was the CEO and managed Product and Technology on a day-to-day basis from Irvine, CA. Brandon was the COO, handling Sales, Marketing, and Customer Support from Knoxville, TN. We helped companies make the most of their Salesforce.com investment by bringing their CRM into the Inbox — and we were doing it before it was cool.

A few milestones:

  • We bootstrapped the company to over $12M ARR,
  • We were on the Inc 5000 List 3 times (#41 in 2016!),
  • We were the highest-rated app on the AppExchange for several years,
  • We topped out at over 70 employees while I led the company,
  • We acquired four companies,
  • We exited to a private equity firm

When we started, we knew nothing about building and running a company. We certainly didn’t know how to support an application that would get millions of requests daily.

This will be the start of a series of posts about how we figured out a solution to problems, one by one, day after day, every day. And the mistakes we made along the way.

The Idea 💡

Back around 2010, a company called Rapportive was started. It had the clever idea of bringing LinkedIn into Gmail, giving it a home on the right side of the inbox. They had one of those mythological startup stories where someone “accidentally” and unknowingly launched before they meant to… By morning, they had over 10,000 new users.

I found Rapportive a few months after its launch, and I noticed that I was using LinkedIn a lot more as a result. I was running a Salesforce.com consulting practice at the time, and I just thought, “Wouldn’t it be great if that was Salesforce?” ⚡️

I did some research and couldn’t find anything like this (it might be hard to believe that given the number of solutions like this today but in 2011, it was true). And so I just jumped right in and started coding!

Just kidding. I sat on the idea for months.

It seemed like such an obvious idea that if it wasn’t already around, someone had to be working on it. I would do another search a month or two later, and then a month or two after that — each time, I was surprised that this new app hadn’t launched yet (what was taking so long?!).

At some point, it occurred to me that there might not be anyone building this, and I started pursuing the idea seriously.

What problem did this solve?

An idea is great, but what actual problem did it solve? People/Companies will pay for solutions to their problems. The more painful that problem, the more you can charge, and the faster deals will close.

My problem thesis:

Companies are spending a lot of money on Salesforce.com and getting little value from it because their teams don’t use it.

Why did I think that? Because I was a Salesforce consultant and I saw it every day.

Why weren’t teams using it? Companies would buy Salesforce and hire consultants to customize it just to find that it was underutilized six months later. Managers would even threaten to take away commissions if Opportunities and sales activities weren’t tracked in Salesforce, so why wasn’t even that working? There were a lot of reasons:

  1. Salespeople hate data entry.
    Solution: This could make it easy to get emails and data into Salesforce.
  2. Salesforce was for managers, not reps.
    Solution: By bringing Salesforce data into every email conversation, salespeople have immediate context.
  3. Salesforce was hard to use.
    Solution: This could simplify the interface by only showing them what was most important to see.

It seemed like this could solve a problem for not just sales managers but also salespeople. And we learned later that while sales managers paid for solutions, productive sales reps would make those solutions an imperative purchase for sales teams.

Next, Part 2: Validating the idea and deciding on the MVP

Originally published at https://www.fractionalfounders.tech on March 31, 2023.

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Ryan Huff

Entrepreneur, Start-up guy, Husband, and Father of two. SoCal Native. Writing for first-time founders and people crazy enough to create new things.