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AI Strategy for Financial Services CEOs: Why “Good Enough” is no Longer Enough
AI in financial services has moved from lofty claims about AI's use to being at the center of the growth conversation, shaping how you compete, run, and stay trusted. Margins are under pressure as customers benchmark you against their best digital experiences, whether they are opening a checking account, redeeming loyalty points, disputing a card charge, or seeking hardship help.
Outsider Insights | Beyond the Sale—Why CEOs Are Turning Attention to Retention and Expansion
Wed, Jan 14, 2026 — 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.
Outsider Insights | What We Learned Helping CEOs Grow in 2025
Mon, Jan 5, 2026 — 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.
Outsider Insights | From Hustle to System: Why More CEOs Are Rebuilding Their Sales Function
Mon, Nov 3, 2025 — 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.
Sales Velocity Model: A Tool for Growth Engine Mechanics
Wed, May 14, 2025 — Most companies deploy a sales “force”. Too often, their combined efforts are not meeting company growth expectations. Most CEOs would like a better growth engine, a larger sales pipeline, and more sales, but they struggle with exactly how to help their sales teams. Busy CEOs combined with people and process related complexities of Sales, often results in companies not being clear on the root cause of their growth engine problems.
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.
The Power of the SKO (Sales Kickoff Meeting)
Thu, Feb 20, 2025 — It's that time of year again! A Sales Kickoff (SKO) meeting is a cornerstone for energizing your sales team and aligning them with your company's goals. It sets the tone for the year, fosters collaboration, and provides valuable insights to empower your team to succeed.
The Hidden Costs of Overwhelmed Sales Teams
Fri, Feb 7, 2025 — An alarming insight from Gartner: Overwhelmed sellers are 45% less likely to hit their quota. The culprit? Too many required skills and tech tools meant to "help." Overwhelming sales teams with non-sales tasks and excessive technology can significantly impact performance and profitability. Salespeople burdened with administrative duties and complex tools have less time for core selling activities, leading to decreased sales performance and lower conversion rates.
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.