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Karen Hayward
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Recent Posts
Outsider Insights | The Backup Plan You Don't Have Is Already Costing You
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.
Vistage Chairs: There's One Buyer Conversation Your CEOs Aren't Having
Wed, Jun 10, 2026 — Executive Takeaways Most CEOs misdiagnose why they lose deals — and it's costing them. Buyers won't tell your salespeople the real reason. They'll tell a neutral third party. The most common loss reasons are fixable — if you know what they actually are. Insight without action is just a good conversation. Win/loss analysis turns it into revenue.
Growth Without Guesswork: The Questions Great Vistage Chairs Ask
Fri, May 15, 2026 — Executive Takeaways Most CEOs are managing growth on assumptions that no longer reflect how buyers actually buy. The best Chair question isn't "how is sales going?" It's "where are the growth leaks?" AI search is already a revenue issue, not a future one. Insight without commitment is just a good conversation.
The New Sales Funnel: How to Revitalize Your Messaging to “Wow” Today’s Consumer
Mon, Dec 11, 2017 — For sales-driven organizations, 2017 marked the year that the baton was finally – and permanently – passed to the consumer. This was the year, it was declared, that all of the growing technology megatrends finally gave the consuming public the upper hand in the relationship with marketers. This means that, despite all of the efforts and resources we’ve invested into outbound sales and marketing efforts, heretofore, we’re simply going to find ourselves several paces behind an educated and savvy buying public.
The 1 Percent Secret: How to Price Your Product for Mid-Market Revenue Success
Fri, Aug 18, 2017 — Psst. I have a secret for you, CEO. How would you like to learn one easy, surefire way to immediately add more than 10 percent in operating profits to your bottom line? Before you declare this another attempt at “fake news,”– let me assure you, this is a legitimate, real, and practical offer. Though it requires very little in terms of effort to achieve – it does require a leap of faith, and resolve of focus, that many CEOs have either been reticent, or reluctant, to make.
Take the “Path to Closure” to Ensure Forecast Accuracy Success
Tue, Jan 17, 2017 — Only a half a generation ago, we thought we had it made, technology-wise. Getting onto the World Wide Web was as easy as loading up the latest CD mailer from America Online; and we were able to send important messages to beeping little black boxes that resided on our belt clip or purse strap. We truly had it made – or so we thought.
Enabling the Sale: How to Handle Requests for Customer References Without Losing Momentum
Thu, Sep 8, 2016 — Sales and marketing in the B2B space is ever-evolving, often disrupted with new technologies or strategies that revolutionize traditional processes. Sales enablement is a relatively new concept in the B2B sales industry, one that refers to the utilization of training, tools, metrics and marketing alignment to maximize a deal’s potential and close it faster, no matter the product or service.
The Art of the Sale: How to Conquer Your Prospect’s Objections and Close the Deal
Wed, Jul 20, 2016 — The face of sales has certainly changed, hasn’t it? When I started my career, the best sales reps were traditionally hired by large companies, and trained to execute a strategic sales process, using a specific methodology. Like soldiers in a battalion, each sales rep knew their role, was aware of the various possible strategies, and was armed for each deal with the scripts and insights necessary to succeed.
Rebooting Your Marketing Strategy to Meet B2B Buyer Expectations
Wed, Oct 21, 2015 — Before the digital marketing boom, sales teams were the hunter-gatherers – the ones that had to go into the forest and slay or harvest what our company would subsist upon. In those days, the typical B2B marketer was asked to sharpen the arrows, restring the bows – and hope that our prep work was good enough to ensure an acceptable bounty. When the sales team shouldered 100 percent of the prospective buyer’s journey, it was up to us to ensure the prospect knew about your company, could call or visit the office for more information, and were loaded down with a highly polished set of sales materials (and telephone script) that hooked them on the notion that yes, we are the definitive answer to their problem.
Learn from the Lost Bid, and Win the Next One
Mon, Oct 6, 2014 — Winning is wonderful; losing is lousy and finding out why you have won or lost is serious business. It is also insightful and critical input to your marketing and sales execution effort. The main goal for most organizations selling services or products is to win more business faster and more cost efficiently. And this often involves a bidding process. We can all relate to the stifling anxiety that comes from waiting for a response—and when unsuccessful at garnering the bid—those moments of depression. It can be an expensive and time-consuming effort to prepare a bid for a major opportunity. With that said, companies often move on to the next prospect without considering the data that may be indispensable for future pursuits. Why a company won or lost a client’s business is just as important as the business itself, since it predicts future business.