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The ‘Mad Men’ Approach to Pitching DevOps

(This blog post originally appeared on

It’s been said that the mark of a good salesman is having the ability to sell ice to an Eskimo. And, if you’re familiar with the 1960s-era T.V. hit “Mad Men,” you know that ad exec Don Draper could do just that. His character was debonair, brash and unapologetic—but one hell of a businessman.

So, what does a smoke-filled, Madison Avenue ad agency have to do with DevOps? Well, if you’re in the market of adopting (and selling) the methodology to the powers that be, the parallels are abundant.

Before we dive into those similarities, let’s tackle some fundamentals of the DevOps movement, as well as the benefits and value of the agile-inspired approach. DevOps focuses on rapid IT service delivery through the adoption of agile, lean practices with an emphasis on people and company culture. The collaborative practice utilizes automation tools to bridge Dev and Ops teams together throughout the entire service lifecycle, from design to the development process to production support.

While that’s a broad definition of DevOps, the specific benefits are vast: Faster software releases with fewer defects; increased operational efficiency; and improved scalability, security and compliance (not to mention a substantial savings in time, money and resources). By practicing DevOps, you also attract a top-notch, hungry talent pool, as well as a different generation and brand of customer.

For instance, let’s compare TransUnion, a 50-year-old company, versus Credit Karma, a 10-year-old company. In this day and age, folks in their 20s and 30s manage their finances differently than baby boomers—and need an agile, modern and DevOps-forward company that can operate like a startup on an enterprise level (granted, Credit Karma consumes data from TransUnion and other reporting bureaus). For years, we only saw our credit report when we applied for a loan or mortgage. Enter a smartphone app that enables consumers to view their credit report on-demand and the game changes. The TransUnions of the world see this and realize they, too, need to pivot and adjust to their market. Catch my drift?

With that said, let’s get back to our “Mad Men” DevOps scenario. One of Don Draper’s more notable quotes was, “Change is neither bad or good; it simply is.” You often hear a similar phrase of “adapt or die” in the tech world, and this is particularly true for DevOps adoption.

So, how do you sell this critical undertaking to the suits in the boardroom? To start, let’s look at three key components of any effective ad campaign pitch: the support of your team, a ton of preparation and a killer presentation.

Don’t Go It Alone

There are mixed opinions on whether DevOps adoption is a top-down or a bottom-up initiative, but I’m from the school of thought that it’s both. The key to an effective DevOps approach is not only getting buy-in from leadership, but also getting your Dev and Ops teams to collaborate on a common goal (such as agility or security) and to be willing to adapt to change.

Think of your colleagues as your creative department in an agency setting: Without their feedback and support, your pitch is likely to fail (and you’ll become the heavily ostracized, needle-nosed “Pete Campbell” of the office).

Some advice? Become a DevOps evangelist and seek out department innovators to help spread your message. Start small and organize a lunch-and-learn. But, most of all, get people excited and ask for constructive criticism.

Start with the ‘Why’

When formulating a business case for DevOps, the most important question to ask is, “Why?” Put yourself in the c-suite’s shoes, understand their management and company goals and find ways to align your strategy with those.

For example, maybe your CIO is concerned by the cost of application delivery. Work to calculate the cost of an application by estimating staffing costs, labor hours, number of deployments/releases and the potential cost of a production failure—and how practicing DevOps would reduce that costly downtime.

You’re the ad executive making the pitch—the Don Draper of DevOps, if you will. If you can’t prove its value and make the room as excited about DevOps as you are, you’ll be leaving the boardroom with your tail between your legs.

Speak Their Language

Most management doesn’t care about speeds and feeds, so tailor your message according to your audience. While tech folks care about features, non-technical people are excited about benefits, particularly how they outweigh the costs. Consider advantages like faster release times, attracting new customers and creating fewer unplanned outages.

It’s important to think of these business executives as the ad agency’s client. And, while the concept of DevOps won’t fit into an “elevator pitch” format, try to keep the meeting as brief as possible (providing lunch doesn’t hurt either!). Don’t gloss over fundamentals, but ask questions to gauge your audience’s knowledge and adapt your content to further their understanding.

And, most importantly, keep the jargon to a minimum.

Finally, I’d be remiss if I didn’t mention one final piece of pitch advice from our resident ad man: “Make it simple, but significant.”

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