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The Chief Outsider
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Recent Posts
How to Develop Future C-suite Leaders: A Guide for Mentoring and Succession Planning
Ambition is the easy part. The real question is whether your company’s future CEO’s, CFOs, COOs, CMO’s and CROs are already growing inside the business long before you need them.
The Revenue-Ready Marketing Playbook: Why Your Brand Is Your Most Powerful Compounding Asset
Tue, Apr 22, 2025 — This is Part 1 of the Revenue-Ready Marketing Playbook, a 4-part series for mid-market CEOs who want marketing to move the needle. Each chapter explores how to turn brand, positioning, operations, and customer experience into engines for measurable growth.
Respected Boss? Trusted Coach? Why Sales Managers Need to Be Both
Mon, Apr 7, 2025 — As a front-line sales manager, distinguishing leadership from management responsibilities is critical to a sales team’s culture and success. Distinguishing between the two helps managers be more intentional about developing these very different skill sets. Sales leadership focuses on inspiring and developing people, while sales management concentrates on processes and immediate results. Effective sales professionals must balance both roles.
Sales Terraformance: A Scientific Approach to Sales Growth
Fri, Mar 28, 2025 — Most companies deploy a sales “force.” Too often, this means a bunch of people do things with good intentions, but their combined efforts do not meet company growth expectations. Most CEOs and Founders would like a better salesforce but struggle with how to impact the “art and science” of sales improvement. At Chief Outsiders, we believe more science can help uncover and develop the insights, strategies, and execution required to achieve breakthrough performance.
Drive Revenue With B2B Sales Consulting
Mon, Mar 3, 2025 — Growth doesn't happen simply by chance. It's engineered by insight, strategy, and execution, especially in complex B2B environments where longer sales cycles, shifting buyer expectations, and pressure to prove return on investment (ROI) dominate the landscape. That's where B2B sales consulting becomes a revenue accelerator, not a luxury.
How to Use Positioning to Own Your Market
Wed, Feb 26, 2025 — Become a big fish in your pond Of all the marketing strategy lessons we at Chief Outsiders share with founders and business leaders, positioning ranks among the most critical. It truly is a difference-maker for businesses that wish to become the leader of the pack—to become, in fishing parlance, the big fish in your pond.
Digital Marketing Mastery: A CEO's Roadmap to Competitive Advantage
Thu, Oct 17, 2024 — In today's digital-driven business landscape, CEOs can no longer afford to take a hands-off approach to their company's marketing efforts. With over 80% of the modern buyer's journey happening online, a solid digital marketing strategy has become critical for driving growth and staying competitive.
Maximizing Returns with AI-Enabled Selling – A Strategic Blueprint
Mon, Oct 14, 2024 — In the first two blogs of this three-part series, we introduced the concept of AI-enabled selling, the need for an integrated strategy, and a framework for mapping the myriad technologies available to the needs of the sales organization. We learned that the adoption of AI-enabled selling—the sophisticated merger of AI technologies with traditional sales processes—has become instrumental in transforming organizational sales approaches. With this foundation in place, we are in a better position to discuss the payback and chart a path forward that aligns with a company’s highest priorities.
Mastering Digital Marketing: Key Strategies for SMB Growth
Fri, Oct 4, 2024 — In today's digital-first business landscape, CEOs and business owners of small and medium-sized businesses (SMBs) often find themselves grappling with the complexities of digital marketing. How can you ensure your marketing efforts drive real growth and provide a solid return on investment? In the first of our new Mastering SMB Digital Marketing webinar series, we explore essential digital marketing strategies to drive leads and sustain business growth. Moderated by Sajal Sahay, with marketing experts Carol Eversen and Angela Hill, read about key strategies and insights shared.
Navigating the AI-Enabled Selling Software Landscape
Thu, Oct 3, 2024 — There was a time not so long ago when the tools-of-the-trade for a salesperson were a Rolodex, a landline phone, and a pair of comfortable shoes. Not anymore. Rolodexes of relationships have been replaced by LinkedIn connections, landline phones by synchronized communication streams, and comfortable shoes by online meetings and note takers, all powered by artificial intelligence.