Startup Feature: Sidekick

Sidekick CEO, Doug MacKay.

Sidekick was a participating startup in Batch#4 of The Accelerator; connecting users to all the business information they need.

Interview with Founder and CEO, Doug Mackay.

Sidekick allows users to conveniently simplify the cloud procurement experience. It helps solve how and where people find and select business solutions within an industry.

1.     Tell us about yourself.

I’m Sidekick. It’s a company of one person. It started two years ago in my basement, along with a few cases of coffee.  

2.     What problem have you solved? / How do you solve such a problem?

I created Sidekick to solve two problems: finding software in an increasingly cluttered world and which local expertise is available that can help me make the software work for my business.  Sidekick solves these problems through big data web scraping and sorting algorithms to provide business people with a single pane of glass to source software solutions and expertise around the world. Each solution or company has their individualized detail pages and are geo-located for easy access. This enables businesses to discover new solutions and engage with those experts directly, through our platform.

3.     When did you notice this gap in the market?

I found as an IT leader that I could never keep up with the vast array of solutions available and had little awareness into local expertise. Previously I relied on Google or secondary research like Gartner, but it was all marketing and advertising. I experienced this inconvenience for years before I dreamt up Sidekick.

4.     What is your company culture?

Well, there’s a dog on the couch, the music playing and we’re enjoying the view from the basement. I like to think that we take chances and learn new things every day. We’re courageous, nimble and willing to take a chance.

5.     What has your experience been like with The Accelerator program?

My Accelerator experience has been great. I’ve learned how to pitch better, made close friends and met a fantastic mentor who’s helping me pivot my company.

6.     What was the biggest lesson you learned throughout your experience with The Accelerator?

The biggest lesson is TALK LOUDER! That was Pat Lor, from the last session. It was possibly the best, most riveting session so far.

7.     What has been a major accomplishment for you in 2018?

My most major accomplishment was realizing that I didn’t really have a product yet. My mentor, Dave Nagy, helped identify that tiny little problem.

8.     What is next for you?

I’m actively working with a major Oil & Gas services company to help make my business pivot a success. This is my next thing. A pivot isn’t a tiny thing. It’s like remaking a car after you bought it. My hope is to have that agreement finalized before demo night. Otherwise, you’ll see me at Starbucks. Grande Latte? Just kidding. I have another product (a real product) up my sleeve, just cooking away.

Want to learn more? Go to or call 403-8603741.