This article is based on a presentation given by Rob at our Customer Success Festival in Boston 2023.

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Embarking on the journey of refining sales and customer success handoffs has been a pivotal aspect of my career. It's not just about transferring information, it's about creating a seamless, collaborative process that sets the stage for long-term customer relationships. 

I've navigated through various challenges and learned valuable lessons along the way. In this industry, where dynamics between sales and customer success can make or break customer experiences, developing a cohesive strategy is crucial. 

In this article, I'll share insights from my playbook – a collection of 11 best practices and strategies – to enhance the synergy between sales and customer success, ensuring we deliver exceptional value right from the first interaction.

Early challenges in customer success

Let me take you back to my early days in customer success, specifically to 2016. I was new to the field, unfamiliar with the industry and our product, and grappling with intense imposter syndrome. The CTO tasked me with onboarding the company's most crucial customer, stating that the company's success hinged on this customer's success. No pressure, right?

During my first call with this customer, they immediately inquired about "reverse positive pay" – a feature I soon realized we didn't offer, despite the sales team's promises. As you can imagine, this put me in a very uncomfortable position. 

Faced with this dilemma, I considered several options. The first was to “sell through it” – acknowledging the oversell but emphasizing the overall quality of our product. The second option was to deny the customer's claim outright. Third, I could apologize and commit to rectifying the situation. Fourth, I could buy time by promising to consult with the product team.

In practice, I often employed a combination of these strategies. I would start by apologizing, then assure the customer of our robust quality control measures (which were non-existent at the time), before reaffirming the superior quality of our product. Finally, I'd promise to advocate for their needs with the product team.

This constant mental gymnastics, fulfilling promises I never made, was exhausting and unsustainable. It even drove me to contemplate quitting. However, thanks to the support of my then-colleague, now wife, I didn't. She helped me see a sixth option: creating a playbook of best practices to prevent such situations in the future.

I'm excited to share with you this playbook, consisting of 11 steps, designed to prevent these misalignments and enhance the synergy between sales and customer success.

Understanding the bigger picture of customer success

Before diving into the steps, I'd like to share a bit more about my background. As a three-time customer success leader and now a full-time consultant, my journey has been both enriching and challenging. I've held full-time positions at Qualia and Rigorous Tradewing, among others, and have worked with several companies in a consulting capacity. 

When I first started my current role, I was swamped. Different customers had different issues – low NPS, low usage, onboarding challenges, threats of churning. Meanwhile, the CEO wanted upsells and referrals. It felt impossible to manage. That's when I created a diagram that helped me prioritize: focus on retention, followed by upsell/cross-sell, and then customer advocacy. 

All other metrics like NPS, time to value, and usage, are steps towards these primary goals. This approach redefines customer success as a proactive, revenue-generating function rather than a reactive cost center.

Poor handoffs between sales and customer success can lead to various negative outcomes - retention risks, low NPS, reduced upsell opportunities, and a broken trust that's hard to rebuild. Trust me, you won't be getting referrals or case studies from customers who feel betrayed.

More importantly, I realized the profound impact bad handoffs have on our own well-being. In customer success roles, poor handoffs lead to low morale, reduced employee retention, and high turnover costs. I've seen colleagues leave jobs over this, which is both a significant and unfortunate outcome.

So, understanding and addressing these issues is not just about improving customer metrics; it's about enhancing our work environment and ensuring the well-being of our teams.

The changing landscape of customer success and sales

It's crucial to recognize the current trends impacting customer success and sales. Lately, a common saying resonating in our industry is "do more with less." This phrase has become a familiar echo across many professional networks, including mine. It seems like everyone, everywhere, is hearing it.

We're experiencing a monumental shift in focus from growth to margins, and this has put immense pressure on customer success teams. Sales teams are now expected to deliver higher top-line revenue growth. 

Consequently, CEOs are increasingly allowing their sales teams more leeway to sell "stretch fit" deals. However, this often happens without adequate communication or alignment with customer success teams.

Another significant change in recent years is the widespread adoption of remote work. This has made building effective interdepartmental relationships between customer success and sales more challenging. 

In a large company, say with 500 employees, the likelihood of a Customer Success Manager (CSM) forming a personal relationship with a remote salesperson is quite low. This lack of personal connection can lead to a breakdown in communication and collaboration, further complicating the handoff process.

Understanding and adapting to these changes is essential. As customer success professionals, we need to be proactive in bridging these gaps. The strategies in the upcoming sections of my playbook are designed to address these very challenges, ensuring seamless collaboration between sales and customer success teams, even in a remote work environment.

Empathy and understanding: A deeper dive into sales-CS handoffs

As I delved deeper into the study of handoffs between sales and customer success, I realized the importance of empathy for my colleagues in sales. This was a crucial moment of self-reflection, where I had to challenge my own narratives and biases.

Initially, I believed that handoffs failed predominantly due to overselling. However, upon closer inspection, I discovered that the reasons were often more complex. In many cases, it wasn't a people problem but rather a process issue. Information about the customer was lost, leading to miscommunications and misunderstandings.

Causes of handoff challenges:

  • Sales miscommunications: Sometimes, it was simply a matter of sales representatives misspeaking, not out of malice, but due to a lack of knowledge or resources. Especially for new account executives unfamiliar with the product, accessing the right information at the right time can be challenging.
  • Customer misunderstandings: On the customer side, things get even more nuanced. Customers can misunderstand, forget, or even be unclear about their own expectations.
  • Internal overselling by customer champions: Another intriguing scenario is when a champion within the customer's organization oversells the capabilities of our product to their superiors. In such cases, sales teams aren't necessarily equipped or inclined to correct these misconceptions, especially when a sale is imminent.

This exploration into the dynamics of sales and customer success interactions revealed a complex landscape. It's not just about assigning blame but understanding the multifaceted nature of these interactions. 

Recognizing these nuances was a turning point for me and led to the development of the playbook I'll be sharing. It's designed to navigate these complexities effectively, ensuring a smoother and more successful handoff process.

Now, let’s get to those 11 steps for a seamless sales handoff.

Step 1: Get managerial alignment

In my journey to streamline the sales to CS handoff, the first and most crucial step I identified was achieving managerial alignment. This foundational element dictates the effectiveness of the entire handoff process.

The involvement and support of C-level executives are indispensable. Without their backing, establishing a healthy relationship between sales and CS is almost impossible. It's essential to have their commitment to enforce and nurture this relationship.

In my experience, some CROs and CEOs were either indifferent or too preoccupied to actively engage in fostering this relationship. However, this indifference wasn't due to a lack of inherent care but rather a lack of awareness about its importance. Therefore, part of my role involved educating them on why this relationship matters.

It's also crucial to understand that the needs and priorities of these executives can evolve. For instance, at one company, the CEO initially prioritized defending customer success.

However, as pressure from the board to increase sales mounted, I noticed a shift towards accepting more "stretch-fit" deals. This change was unexpected, and initially, I felt unheard and confused. It highlighted the importance of staying informed about the changing needs and priorities at the executive level.

Ultimately, building and maintaining a strong relationship with C-level executives is vital. It ensures that the sales-CS handoff aligns with the broader goals and changing dynamics of the business. This alignment is the cornerstone upon which successful handoffs are built.