Growth Insights for CEOs
The Chief Outsider
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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.
Recent Posts

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 Rolodexes of relationships have been replaced by LinkedIn connections, landline phones by synchronized communication streams, and comfortable shoes by online meetings and note takers, all powered by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.

20 AI-Powered Strategies to Supercharge Your SaaS Sales
Wed, Oct 2, 2024 — AI (artificial intelligence) is taking the entire technology sector by storm. And all SaaS vendors are adding AI functionality to their product offerings to stay competitive, as FOMO (Fear of Missing Out) syndrome takes hold. The same is happening in the SaaS industry; smart tools can help your sales and marketing team make better and faster decisions, plan, and craft a better customer service approach. As a SaaS CEO, CSO, or CMO, these solutions will open a whole new set of opportunities for growth, oversight, and measurement that can help you be a more prepared and better-informed leader.

What is AI-Enabled Selling and Why is it Important?
Tue, Sep 24, 2024 — Salesforce’s “State of Sales” report surveyed 5,500 sales professionals earlier this year. Two findings caught my attention. First, sales reps spend only 30% of their time selling during an average week. Second, 81% of sales teams said they are investing in AI. Of those using AI, 41% believe that they have “fully implemented AI.” The remaining 59% range from having no strategy at all, to tinkering with tools.
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Harnessing AI and Digital Marketing: A Competitive Edge for Healthcare and Life Sciences – Part Two
Thu, Sep 19, 2024 — Our last blog discussed how artificial intelligence can be a competitive difference-maker for companies in the healthcare and life sciences industries. As we continue the conversation, we will highlight the importance of AI in the social media marketing landscape, especially how AI is re-imagining traditional content creation and audience targeting strategies.

Harnessing AI and Digital Marketing: A Competitive Edge for Healthcare and Life Sciences – Part One
Wed, Sep 11, 2024 — In today’s dynamic business landscape, the healthcare, life sciences, and health tech sectors are undergoing rapid transformation driven by digital innovation. Social media and digital marketing have emerged as indispensable tools, enabling organizations to enhance efficiency, drive competitiveness, and engage with stakeholders in unprecedented ways. However, balancing innovation with strict adherence to regulatory compliance is crucial. As an industry expert with deep experience guiding companies through digital evolution, I see tremendous opportunities for leveraging these tools to gain a strategic edge.

Rediscover Your Business Strategy: A Guide for Frustrated CEOs
Mon, Jun 3, 2024 — Are you a small or mid-sized business CEO grappling with stagnant growth? Resetting your business strategy could be the key to regaining momentum. This step is essential in my five essentials for frustrated CEOs.

Quarterly Business Reviews: A CXO guide to Best Practices
Thu, May 16, 2024 — Most companies run regular QBRs (Quarterly Business Reviews). Getting into QBR practice its benefits, like getting your broader team buy-in on your sales and marketing team issues, creating a sense of urgency on important cross-team action items, building a learning culture within your team, sharing new product initiatives in advance, collect and measure customer feedback (or NPS) regularly. Not to mention you get valuable team face time, undistracted by daily sales activities.

The Power of a Positioning Statement for Growth in Small and Mid-Sized Businesses
Tue, May 7, 2024 — Many small and mid-market businesses find themselves at a growth impasse, not due to a lack of opportunity but because of misalignment across various functional areas. As a fractional Chief Marketing Officer (CMO), my role often involves diagnosing these misalignments and charting a course for renewed growth. One of the most effective tools I recommend is creating and utilizing a clear positioning statement.

5 Essential Tools for Frustrated C-Level Executives
Wed, May 1, 2024 — Are you a C-level executive grappling with stagnant growth despite your best efforts and a talented marketing team? If so, you're not alone. Many businesses face this challenge, but the good news is that there are solutions. After over twenty years in the marketing industry, with the last two years as a fractional CMO, I’ve identified five essential elements that can reignite your growth engine.