Always Be Iterating: A Key Mantra for Successful YEG Businesses

A friendly 2D cartoon avatar wearing a burgundy t-shirt with a white stylized 'A' portion of the Elevate Your Tech logo. He is pointing at a blackboard with the words 'Always Be Iterating' written on it with white chalk.
Johnathan Klimo

Johnathan Klimo, BCom, CFA

June 9, 2026

A previous colleague of mine once introduced me to the famous “ABC” (Always Be Closing) line from Glengarry Glen Ross. If you haven’t seen the movie, it features a “motivational speech” that is a textbook example of hyper-aggressive, high-pressure sales tactics.

While sales clearly matter for every business, I would also argue that there is another acronym that is even more crucial for long-term business success: “ABI” (Always Be Iterating).

Throughout my career, I’ve worked with a wide variety of organizations, including scrappy startups, small family businesses, a private lender, a boutique private equity firm, and a financial institution that now has Assets Under Management (AUM) of over $100 billion. I also advised a number of additional companies while running my previous IT consulting firm.

What was notable for me about these experiences was that the most successful organizations were never stagnant. In fact, they were exactly the opposite. The best companies were consistently doing three things:

  • Constantly seeking to improve the overall customer experience
  • Being thoughtful about the customer’s journey, from the initial phone call or e-mail to the final purchase
  • Investing in technology to incrementally improve their operations over time

This philosophy is a big part of what inspired me to choose the name Elevate Your Tech for my new business. “Elevating” isn't a one-time thing. It’s a process of deliberate, ongoing iteration.

The Real-World Cost of Failing to Iterate

To see what happens when a business doesn’t iterate, you only have to look as far as your local aspiring restaurateur.

My wife and I are both foodies, and we love checking out new places to eat around Edmonton. Like most people, we always look at a restaurant’s website in advance. We want to know super basic things, such as:

  • What does their menu look like?
  • What does the restaurant look like inside?
  • Where are they located?
  • When are they open?
  • Can we reserve a table online if we’re planning to go there during peak hours?

The unfortunate reality is that we constantly encounter local restaurants that either have no online presence at all, or that have a website so bad that it harms the business, rather than helping it. Does this make us more likely or less likely to check the place out?

As you can guess, it’s the latter. A poor digital presence actively turns away potential paying customers. Implementing one of our high-quality, mobile-friendly, cost-effective web solutions would instantly elevate their online presence, which in turn would help to drive increased sales from new customers.

De-Risking Technology Changes with Smaller Steps

Improving your organization’s technology doesn’t necessarily have to mean investing millions of dollars into huge, expensive projects. Even small, incremental technology projects can iteratively improve your organization’s technology, with each project making your technology better than it was the day before.

It’s also worth mentioning that large projects also tend to be substantially riskier than smaller, multi-stage, incremental projects. These risks include things like:

  • Scope creep and moving goalposts
  • Unanticipated budget overruns
  • Significant project delays
  • Spending a fortune on technology that fails to meet expectations

Trust me, nobody wants to have their name associated with approving an expensive project that fails to deliver, or worse, doesn’t even get across the finish line!

By contrast, smaller, incremental technology projects are substantially safer, more likely to succeed, and more effective. By breaking your digital evolution into multi-stage, manageable pieces, you iteratively improve your business without betting the farm. Each small project leaves your technology stack better today than it was yesterday.

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About the Author

John is a multi-disciplinary professional who has spent twenty years mastering the intersection of business, finance, and information technology. His technical journey began with building and repairing computers, a foundation that led to him being recruited by a pioneering video alarm monitoring startup as a network administrator and web developer. He subsequently attended the University of Alberta, discovering a passion for finance while completing his Bachelor of Commerce degree, and he later became a CFA charterholder.

He has over a decade of experience in the finance industry, including roles with Canada’s largest independent mortgage finance company, a highly successful private lender, and a boutique private equity firm. John also previously owned and operated a dedicated IT consulting practice, and he was the sole web developer for an online media company that he co-founded.