Business Growth Strategies For CEOs: Top CMOs On Marketing Strategy Implementations

John Blessing

As the Chief Outsiders Chief Sales Program Manager and CSO, John is an accomplished leader who consistently builds success in growth and turnaround situations in a variety of industries, including professional and financial services, retail, and SaaS. He turns around poor performance and accelerates growth by building and executing strategic sales programs. He also drives sales and operations alignment to deliver breakthrough revenue. With experience in several industries, John offers perspectives not hindered by industry-specific paradigms.

Outsider Insights | The Comp Plan Is Quietly Telling Your Sales Team Not to Hunt

Fri, Jul 24, 2026 | Posted by Dawn Werry

Executive Takeaways

Sales reps focus on what they're paid and measured on, even if that strays from business strategy and goals.
Many compensation plans and account structures quietly reward protecting revenue, not creating it.
Adding a quota target without changing the underlying structure just adds pressure, not pipeline.
Fixing this starts with the comp plan and account map, not a pep talk about hustle.

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.

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The Art of Value-Based Selling: Boosting Your Bottom Line

Tue, Oct 24, 2023 — Attention, bargain shoppers! In the realm of business-to-business (B2B) sales, blue lights, doorbusters, Black Friday sales, or penny pinchers don’t apply. That said, in our ever-evolving battleground, the age-old theory that "everyone buys a bargain" still holds.

Reap Big Rewards with Sales & Marketing Alignment in 2023

Tue, Jan 17, 2023 — When it comes to corporate synergy, there’s perhaps no greater return on your investment than to align your sales and marketing efforts. Though it’s simply common sense to have the two revenue-responsible departments working in sync, it can also mean dollars and cents. One study found that sales and marketing teams, when well-aligned, can wring out 200 percent more revenue as a result of their collaboration. You may already feel like this cross-pollination is happening at your company: Key personnel are collaborating on projects, keeping each other informed, using a common language, and possibly even delivering cross-functional reports from Salesforce, Tableau, and other analytical tools.

Chief Outsiders’ Commitment to Go-to-Market Success Expands With New Chief Sales Officer Role

Tue, Jan 10, 2023 — Today’s CEO has to work harder than ever. With a tightening economy, fears of a recession, and a post-COVID marketplace that remains hard to read, the CEO truly is in the hot seat. With an average tenure of fewer than seven years, according to some estimates, the CEO has little runway with which to work in creating market and revenue success. It’s an unfamiliar place for many CEOs – particularly those in the SMB and mid-market space. They’ve built their business on a foundation of great industry knowledge, hard work, dedication, and a healthy dose of sweat equity. But in changing times, and with little understanding of market forces outside their particular industry, it can be difficult to get an infusion of the right market insights needed to build next-generation strategies for success.

Growth Insights for CEOs