A frequent mistake service businesses make is hiring a dedicated marketing employee and then gradually shifting their responsibilities to customer service or dispatching. This negates the role's strategic value and turns a key growth driver into an overpaid administrative position, ultimately stifling marketing efforts.

Promoting top individual contributors into management often backfires. Their competitive nature, which drove individual success, makes it hard to share tips, empathize with struggling team members, or handle interpersonal issues, turning a perceived win-win into a lose-lose situation.

A cultural shift towards top-down management, where engineers were no longer part of key decisions like moving to the cloud, led to a mass exodus of senior talent. When senior ICs cannot stand behind leadership's decisions, they lose the motivation to stay, even if the pay is good.

When a useful metric like "average handling time" becomes a performance target, employees game the system. Reps may hang up on customers to meet quotas, destroying the metric's ability to reflect actual customer satisfaction.

Customers interact with a company as a single entity, but internally, separate departments like sales and support optimize for their own conflicting metrics. This creates a confusing and inefficient experience, a direct result of Conway's Law in action.

Tying SDR promotions to time-in-seat fosters stagnation. Instead, create a clear, multi-level roadmap where advancement is based solely on hitting performance thresholds. This model rewards high-achievers, provides constant motivation, and gives reps control over their career trajectory.

Where the SDR/BDR team reports has significant cultural and career-pathing consequences. When Snowflake moved SDRs under marketing, they began aspiring to be marketers, not salespeople. This created a hiring bottleneck for the sales organization, which needed that talent pipeline to fuel its growth.

A large customer support organization signals that a product is too complex, hard to onboard, or buggy. Instead of optimizing the support function, companies should focus on improving the product to the point where extensive human support becomes unnecessary.

Chris Degnan got rid of the Customer Success function at Snowflake because he wasn't willing to give the "B team" access to his "A accounts." He made the sales team responsible for the entire customer lifecycle, including upsells and renewals, to ensure top talent handled high-stakes competitive situations.