In this episode of Sell Through Social Live, Joseph Lewin sits down with Chelsea Olson, who helps agencies and B2B service-based companies scale and grow with sustainable sales strategies. Together, they dig into why so many companies plateau and what leaders can do to break through those barriers.
Sell Through Social produced this podcast.
Key Topics Covered
Chelsea explains that growth challenges vary depending on company size. For businesses under $5 million in revenue, CEOs are stretched too thin, juggling sales, marketing, and operations, which leaves no room to create a repeatable sales strategy. For larger companies, the absence of a clear and scalable sales plan often stalls momentum, especially when they continue to rely only on referrals and word-of-mouth.
Referrals alone, while valuable, are not a long-term strategy. Warm leads behave very differently from cold outreach, yet many leadership teams fail to account for that. Cold prospecting requires resilience, grit, and a willingness to face rejection—something many CEOs struggle to accept after years of relying on warm introductions.
Another issue is the CEO bottleneck in sales. Too often, founders and leaders hold all the client success stories and sales knowledge in their heads. Without documentation, case studies, and accessible materials, new hires are set up to fail. When CEOs expect new salespeople to deliver results at their level without sharing the tools, knowledge, and industry context, frustration builds quickly on both sides.
The conversation also highlights the dangers of outsourcing too early. Handing off the entire sales function might feel like a quick solution, but it stunts long-term growth. Instead, companies must own their business development and go-to-market strategy before outsourcing pieces of execution. A fractional sales leader can accelerate this process, bringing in expertise while training internal talent to take over sustainably.
Joseph and Chelsea explore the myth of the “unicorn hire”—the belief that one superstar salesperson can put the company on their back. This approach is risky and unsustainable. When that individual eventually leaves, the pipeline collapses. Instead, leaders should invest in systems that allow junior reps and subject matter experts to succeed. CEOs also need to decide whether they require an individual contributor to drive deals or a sales leader capable of building a scalable organization.
Finally, the discussion turns to empowering employees on LinkedIn. Many CEOs resist allowing their teams to build personal brands online, fearing they will be poached. Chelsea and Joseph argue that this mindset holds companies back. A strong LinkedIn presence creates awareness, generates inbound opportunities, attracts talent, and strengthens employer branding. If leaders fear losing employees, the real solution lies in creating a culture that people want to stay in, not limiting their professional growth.
Chelsea Olson’s Approach
Chelsea specializes in guiding companies through the transition from referral-based selling to scalable growth systems. She helps define the ideal customer profile, sharpen go-to-market strategies, and create documented sales plans that can be executed by the whole team. Her role as a fractional sales leader allows her to mentor internal staff, set up repeatable processes, and gradually transfer ownership back to the company once a foundation is in place.
Episode Takeaways
Growth requires more than enthusiasm—it requires a plan. CEOs must document their knowledge, set realistic expectations, and accept that referrals alone cannot fuel sustained success. Building a scalable sales system means creating a strategy, empowering a team, and embracing tools like LinkedIn to expand visibility. Companies that fail to do this risk staying stuck, no matter their size, while those who invest in building the right system unlock real growth.