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Outsider Insights | You Can't Measure AI ROI If You Can't Measure Marketing ROI
Outsider Insights
Across Chief Outsiders, we talk to hundreds of CEOs every month. In this series, we explore the trends and challenges we’re hearing from these discussions – and what you can do if you’re facing the same issues in your business.
From Concept to Execution: A Step-by-Step CEO Playbook for Go-to-Market Success, Part One
Mon, Jun 23, 2025 — Every CEO knows this nightmare scenario: Your team spent months crafting the "perfect" go-to-market strategy, only to watch it crumble during execution. Resources hemorrhage, timelines slip, and while you're still troubleshooting internal alignment issues, competitors are capturing the market opportunity you identified first.
Winning the Fraud and Cybersecurity Race: A Go-to-Market Blueprint for Competitive Edge
Thu, Jun 5, 2025 — Fraud and cybercrime have become a systemic, trillion-dollar drag on the global economy—but the fight to turn the curve is more than a market opportunity. Over the past few years, I have worked alongside cybersecurity and fraud-management teams in government, banking, and payments, and nothing is more satisfying than seeing a new solution stop a romance scam or prevent a pensioner from losing their life savings.
Top 10 Digital Marketing Missteps
Thu, Aug 1, 2024 — Today digital often seems like the easy way to expand a company’s prospect and lead pool. After all, it takes just minutes to set up an ad account on Google or Facebook. Then you’re good to go, right? Not necessarily. In reality, it’s not as easy as many people think. Marketers are often under intense pressure to get campaigns to work without adequate leadership support or understanding as to how to successfully test digital channels. Others hire agencies without clear knowledge of the strategies and tactics required to drive success and therefore have difficulty holding their agencies accountable.
CEO Go-To-Market Warning: Avoid the Blind Spots That Cause Products to Miss the Mark | Part 5
Thu, Feb 2, 2023 — Part 5: Only Teamwork Can Make the Dream Work We have become a nation of isolation. COVID-19 taught everyone how to use technology to carry on safely. Though Zoom, Teams, and other tools have made communication more efficient, we’ve never felt more distant from our colleagues. Through this “together, but apart” mindset, many businesses feel pressured to enable remote work and grant greater autonomy. As a CEO trying to manage in this environment, it’s tempting -- in the spirit of efficiency – to let everyone stay focused on their “swim lane” and not encourage complex collaboration between divisions.
Consider These Six Focus Areas Now to Secure Market Success in 2023
Thu, Jan 12, 2023 — By: Rich DePencier and Scott Wright After the bubbly has lost its fizz, and the first quarter is – ready or not – swinging into motion, thousands of SMB owners, founders, and CEOs are looking to encourage and cajole their senior leadership to finalize their 2023 plans. But, framed against the backdrop of economic headwinds, hiring challenges, and political headlines, this year’s planning process is taking on a whole new sense of urgency. Rather than mapping out a strategy for maintaining the status quo or eking out incremental growth, it is clear that 2023 requires a dig-deep mentality. The question you may be asking as you face what’s to come is: What is my company’s next “big idea” -- and how will I get the team to achieve a loftier set of goals?
CEO Go-To-Market Warning: Avoid the Blind Spots That Cause Products to Miss the Mark | Part 2
Mon, Oct 31, 2022 — Part 2: Beware of Market Forces that Impact Company and Category Survival In 2022, the market has been turned upside down. Remote work, the supply chain squeeze, and the rollercoaster economic environment all have roiled even the best of intentions for businesses of all sizes. And though your company’s go-to-market approach will still help you gain or maintain your share of the market, winning the “checkboxes” isn’t enough to stave off the macro forces that are constantly reshaping and disfiguring the landscape you’re selling into.
CEO Go-To-Market Warning: Avoid the Blind Spots That Cause Products to Miss the Mark
Tue, Oct 4, 2022 — Part 1: Avoiding the Dust Bin Requires an Insights-Driven Approach Have you ever heard of the Apple Pippin or the Twitter Peek? Played a game of TowerFall on the Ouya Console? Taken an important call on your Amazon Fire Phone? If so, you are among the rarest of the rare – the chosen few who took the calculated risk of trying a new product during its brief run on earth. The world is littered with also-rans, whoopsies, and well-intentions gone awry. There are so many consumer product failures each year – some that miss with a whimper, and some that make a giant megaton splash into the depths of nowhere – that several “Museums of Failure” warehouse the worst and dimmest of the bunch. In fact, up to 95 percent of new product launches fail to hit a target, according to one market analyst.
Stirring Up Success: How to Win at Commercialization
Fri, Sep 23, 2022 — Blog 1: Breaking Down the Wall Between Success and Failure It starts with a dream – perhaps hatched in a home kitchen, or concocted in a plastic Gatorade bucket. The ideas of countless aspirants – hoping to bring a food or beverage product to the masses – start with a “pinch of this,” a “touch of that,” and a truckload of sweat, muscle – and prayers. Despite these dreams, struggles, and countless hours at tastings, state fairs, and in the boardrooms of grocers, only about 5 percent of aspiring food and beverage products ever find mass-market success.
The Innovator’s Dilemma – Fast, Correct, or Both?
Mon, Aug 15, 2022 — Most people would say Tesla is an innovative company. Others would say maybe they push the envelope a bit, for example, with “self-driving” software that is truly amazing but is not yet fully “self-driving.” The other side of the coin is other companies who wait until an idea is thoroughly tested, I’s dotted, and T’s crossed, fully qualified but maybe at the cost of missing the market. Innovation is the lifeblood of growth in any industry or channel. Companies with high levels of innovation do better over time than companies that do not have it. So how to address the Innovator's Dilemma? Is it one or the other? Here are four ways to think about it: