How Booyah Advertising Turned its Founder's Charisma into a Scalable Sales System

Here’s how a $100M digital agency turned their sales superstar problem into a scalable success story. Discover how Booyah Advertising freed up 8 hours a week for their VP of Sales and built a repeatable process that didn't sacrifice their secret sauce.

When Jay met Troy

I've always admired Troy Lerner, CEO of Booyah Advertising. His charisma, authenticity, and genuine approach to clients are truly something special. When you talk to Troy, you can't help but be drawn in by his straightforward, no-ego style that's refreshingly rare in the agency world.

It's no wonder Booyah, under Troy's leadership, has grown to manage over $100M in media annually for major brands across multiple industries. But as I learned during our collaboration, even natural-born salespeople like Troy and his VP of Sales, Crystal Stewart, can face unexpected challenges when scaling their success.

CEO Troy Lerner and VP of Sales Crystal Stewart were naturally gifted salespeople: 

• Troy's charisma, authenticity, and genuine approach won clients over

• Crystal's background in digital marketing execution gave her valuable insights that clients trusted

• Both had an intuitive understanding of how to take care of prospects and drive them to closed won 

However, their success created a new challenge. Booyah lacked the necessary sales frameworks to quickly ramp up additional resources. This made it difficult to delegate lower priority sales tasks, keeping Crystal involved in every aspect of the sales process instead of focusing on high-value activities.

They needed a more repeatable and scalable sales process that would allow junior team members to handle lower-level tasks. This would free up both Troy and Crystal to focus on the most important deals and be present at crucial stages of the sales process, particularly during pitches.

The Solution: Building a Scalable Sales Engine 

Pitch Lab Sales Consulting was brought in to address several key objectives: 

• Improve Crystal's productivity by freeing her up to focus on qualified leads and larger opportunities

• Implement a new CRM system for better visibility into the sales process

• Create a "minor league" system to train new salespeople, recruiting talent from elsewhere in the company

• Test strategies to increase conversion rates throughout the sales funnel and improve overall win rates

To achieve these goals, Pitch Lab implemented the following tactics:

• Recruited and trained 3 team members as "inbound qualifiers"

• Documented processes for scheduling and holding initial discovery meetings with inbound leads

• Created a customized discovery framework including both technical and business questions to qualify opportunities

• Provided education, coaching, and management on sales best practices during discovery

• Conducted ride-alongs and listen-ins during various sales discovery and pitch meetings

• Advised on CRM best practices and essential sales funnel reporting

• Modified pitch decks to improve storytelling and engagement

• Provided fractional sales management, including facilitating internal sales meetings, one-on-one coaching, and team training

The Results: 25% Productivity Boost for the VP of Sales

After a 12-month engagement, Booyah achieved significant improvements in their sales process: 

• 3 fully-trained sales resources (with a 6-month ramp-up period for part-time resources)

• Documented sales process from lead to proposal

• Implemented a lead scoring system

• Created and documented strategic sales messaging

• Increased prospect engagement during the pitch/proposal stage

• 25% productivity boost for Crystal, giving her back roughly 8 hours per week

These improvements allowed Crystal to focus solely on qualified leads and larger opportunities. Additionally, it removed the burden of training, documentation, coaching, feedback, and one-on-one meetings from her plate.

Troy's hilarious take on the engagement:

"This engagement with Pitch Lab was short and valuable, just like Jay."

Key Takeaways for CEOs: The Truth About Sales Role Specialization

While Pitch Lab’s engagement with Booyah delivered significant improvements in sales efficiency—notably freeing up 8 hours per week for their VP of Sales—it also revealed a crucial insight about scaling agency sales teams. The initial strategy of having digital marketing specialists double as part-time salespeople seemed logical. After all, these team members possessed deep technical knowledge and existing client relationships. However, this approach ultimately proved unsustainable for a high-growth agency.

✅ The Reality of Hybrid Roles

Despite best intentions, client deliverables inevitably trumped sales activities when team members wore both hats. What began as an efficient use of resources became a constant tug-of-war between serving existing clients and developing new business. Even the most organized team members struggled to maintain consistent pipeline development while meeting urgent client needs.

✅ The Skills Gap Challenge

While marketing expertise provided a strong foundation for understanding client needs, we discovered that consultative selling required a distinct skill set. Discovery conversations, objection handling, and deal closure demanded focused training and daily practice—something part-time sales resources simply couldn't continually maintain while juggling client responsibilities.

✅ The Infrastructure Investment

For agencies generating $10M+ in annual revenue, scaling sales requires more than just talented people—it demands dedicated resources to build and maintain sales infrastructure. This includes developing standardized processes, implementing proper qualification frameworks, and maintaining consistent training programs. Our experience at Booyah showed that these critical elements only flourish with full-time sales professionals who can give them the attention they deserve.

The key message for agency CEOs? While using existing team members for sales roles might seem cost-effective initially, sustainable growth requires dedicated sales professionals. This investment not only leads to better sales outcomes but also allows your technical experts to focus on what they do best—delivering exceptional client work.

Ready to Grow Your Agency Sales Team?

Is your agency struggling with similar challenges? Are you looking to scale your sales efforts without compromising on quality or burning out your top performers?

Let us help you leverage the power of combining innate sales talent with strategic processes.