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Outsider Insights | From Hustle to System: Why More CEOs Are Rebuilding Their Sales Function
Outsider Insights
Across Chief Outsiders, we talk to hundreds of CEOs every month. In this new 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.
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.
Is Your Sales Strategy Built to Adapt?
Tue, Jan 7, 2025 — In today's changing business environment, agility isn't just an advantage—it's essential for survival. According to McKinsey's 2023 B2B Sales Pulse Survey, 71% of sales leaders say market unpredictability is their biggest challenge, and 65% report struggling to adapt their plans quickly enough to keep pace with change. Yet 65% of sales leaders report they can't adapt their plans fast enough to keep pace with rapid change.
Tech Stacks: Transforming Your Business in the Digital Age
Mon, Jan 6, 2025 — In today's hyper-connected business world, technology isn't just a tool—it's the difference between thriving and merely surviving. The digital landscape has transformed how companies approach sales and marketing, making a strategic technology stack more critical than ever.
Top 10 Ways CEOs Can Improve Sales & Marketing Alignment
Mon, Nov 25, 2024 — Close Collaboration Ensures Go-to-Market Success A survey conducted by Chief Outsiders among mid-market companies found that nearly one-third of C-suite executives noted a misalignment between their Sales and Marketing teams. Further, only one-third of that group reported that their Sales and Marketing teams were working toward a common set of goals.
Financial Resilience: ITR Economics’ 15-Year Forecast to Help You Through the 2030s
Thu, Nov 14, 2024 — The below article from ITR Economics, a valuable and trusted resource for Chief Outsiders, details steps you can take to prepare for the economic depression coming in the 2030s. If you aren't confident that your business can weather the downturn, it may be a good time to reach out to one of our Fractional Chief Marketing Officers and Chief Sales Officers. They can provide the agile, adaptable support required to quickly pivot marketing and sales strategies as economic conditions evolve.
Shifting from a Founder-Led Business
Wed, Oct 30, 2024 — I recently sat down with Scott Alexander from Jairus Marketing for another insightful discussion about a topic that resonates deeply with both of us: shifting from a founder-led business to more sustainable business models. This is especially relevant for early-stage companies, particularly those in the healthcare sector where the CEO is vital as both the visionary and primary salesperson.
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.
The Untapped Powerhouse: Why CEO Social Media Presence Matters
Fri, Jun 7, 2024 — In today's digital age, consumers and potential employees are increasingly turning to social media to understand the companies they interact with. This extends beyond just a catchy company bio and curated product photos. For private CEOs, social media offers a powerful, yet often underutilized platform to build brand awareness, establish thought leadership, and connect with your target audience on a deeper level.