AI Coach: find and fix deal issues before they result in closed-lost using AI

Sales Process

Who Owns Upsells: Sales or Customer Success?

8 min
Average Score


Technology, Information and Internet

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In this episode of the Closing Intelligence Show, we delve into the world of sales reps, their evolving roles, and the strategies that have transformed our sales cycles and boosted deal values. In a constantly changing landscape, the role of a sales representative has evolved dramatically. In this session, we'll explore how to be more productive as a sales rep in today's competitive market.

Aligning Compensation Models for Success

When the narrator first joined the team at Proposify, they encountered a unique challenge - misaligned compensation models. The sales team was responsible for both closing new deals and renewing existing ones. This approach led to conflicts of interest and did not prioritize the best interests of the customers or the business.

As a result, renewals were often delayed, expansion revenue was elusive, and the customer success team found themselves without the authority to influence outcomes. The solution? Realignment of compensation models to ensure they truly benefited the business and individual representatives.

Evolving with Customer Success

At Proposify, the journey toward optimizing sales reps' productivity started by building a robust Customer Success Management (CSM) team. This shift allowed them to focus on proactive rather than reactive customer interactions. Furthermore, they aimed to predict customer behavior accurately.

This strategy paid off significantly when they encountered a financial services company opportunity, which initially appeared modest. However, with the guidance of a strong CSM, the deal expanded into a lucrative partnership, highlighting the critical role of customer success in identifying growth opportunities.

Land and Expand: A Winning Strategy

The concept of "land and expand" emerged as a winning strategy for Proposify. Instead of closing the largest possible deals, they opted for a more sustainable approach. This meant beginning with a small number of seats and allowing the CSMs to gradually expand the account over time.

While this required some effort to convince account executives to adopt this model, it ultimately resulted in an impressive average annual net expansion of 120% for customers. The focus shifted from immediate commissions to long-term customer success.

Two Key Factors: Desired Outcomes and Customer Experience

In the realm of customer success, two critical factors determine if a customer is primed for further purchases. First, have they achieved their desired outcomes? Second, what has been their overall experience? These considerations are essential when deciding whether to upsell or renew a customer.

Sales reps need to understand that it's not just about achieving outcomes but ensuring a positive customer experience. A seamless partnership can make all the difference when it comes to expanding a customer's commitment.

Transitioning Responsibilities to CSMs

If you're considering shifting renewal and upsell responsibilities to your CSM team, it's crucial to start with what already works. Identify best practices from your sales team's interactions and build upon them.

Select one CSM to act as a "guinea pig" to test the new process, allowing for a quick feedback loop before implementing it across the entire team. Emphasize to your CSMs that customers expect them to ask for more business, and even a "no" can be an opportunity for deeper understanding and research.

Adapting to Business Growth

Finally, it's essential to recognize that as businesses grow, their sales models may need to evolve. There may come a point when the complexity of deals, deal sizes, and relationship management necessitate the inclusion of specialized roles such as renewal-focused sales representatives.

The role of a sales representative is constantly evolving. To be more productive in today's market, it's vital to align compensation models, prioritize customer success, and adopt a sustainable "land and expand" strategy. By focusing on desired outcomes and customer experience, sales reps can effectively transition responsibilities to CSMs and adapt to the changing needs of the business.

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