This episode originally aired live on 5/9/25

In this episode, Joseph Lewin is joined by Chelsea Olson, who helps agencies and B2B service-based companies scale by building the right sales strategies. Together, they dive deep into the real challenges businesses face when trying to grow beyond word-of-mouth referrals and founder-led sales.

Chelsea shares why CEOs often become the bottleneck for growth, how over-reliance on referrals limits scalability, and why building a repeatable sales process is non-negotiable if you want your company to thrive past $5M, $20M, or even $50M in revenue.

They also explore the emotional side of sales—why cold outreach feels so different from warm referrals, how leadership teams often set new hires up for failure, and why developing patience, resilience, and the right expectations are crucial for scaling.

If you’re a founder or CEO tired of being the only one closing deals—or frustrated that your sales team isn’t hitting targets—this conversation will give you clarity on what’s missing and how to fix it.

What You’ll Learn in This Episode:

• The biggest hurdles companies face at different revenue stages.
• Why CEOs often sabotage their own sales teams (without realizing it).
• The emotional challenges of moving from referrals to outbound sales.
• How to build a sales strategy that actually scales.
• Why outsourcing sales too early can hurt your long-term growth.
• The role of fractional sales leaders in setting companies up for success.
• Why empowering employees to build personal brands on LinkedIn is a growth multiplier—not a threat.

About Our Guest:

Chelsea Olson works with agencies and B2B service companies to create scalable sales systems. With nearly 20 years of experience in sales and leadership, she specializes in helping CEOs transition from founder-led selling to building sustainable growth strategies that free up leadership and fuel long-term success.