Assigning expansion quotas to Customer Success (CS) is a critical mistake. CS should focus on implementation, adoption, and value realization, creating the conditions for growth. However, the act of selling the expansion is a core sales responsibility that requires a sales skillset and incentive structure.

Many companies mistakenly hire salespeople and then define their job and compensation. The correct sequence is to first determine the business need, then construct the specific job role to address it, and finally design a compensation plan that incentivizes the required activities before ever posting the job.

Expecting salespeople to build their own target lists creates a major barrier to action. To get reps to prospect consistently, leaders must take responsibility for organizing the lists, defining the targets, and pointing the team in the right direction so they can focus purely on outreach.

A common scaling mistake is continuing to hire for broad, 'multi-hyphen' roles (e.g., 'sales and retail manager'). As the business grows, these generalist positions dilute focus. Instead, create tighter, more specialized job descriptions to bring clarity and attract hyper-focused candidates.

A one-size-fits-all sales role fails in consumption models. Success requires segmenting the team into specialized roles—new business acquisition, customer onboarding, and account management—each with distinct incentives aligned to their specific function, from initial sign-up to value realization and expansion.

When tenured salespeople stop seeking new business, the root cause is a leadership gap, not individual laziness. Leaders must actively set the conditions, message the importance, and model the behavior of prospecting, as reps naturally gravitate towards easier, relationship-focused tasks.

Salespeople follow the money. If your compensation plan makes it easier or more lucrative to manage existing accounts than to land new ones, you are financially incentivizing them to stop prospecting. The reward for the difficult work of hunting must be significantly higher.

Small companies often overload their first salesperson with both new logo acquisition and existing account management. This is a trap. Prospecting will always lose out to servicing known customers. Plan for account continuity early to protect your growth engine, even before you can afford a second hire.

AE prospecting fails when given a watered-down SDR activity quota. Instead, have AEs build a strategic plan to land three deals at 2x average contract value from a target list of just 10 accounts per quarter. This focuses their limited prospecting time on high-impact activities.