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.

Step 2: Customer success scripts the close

After securing managerial alignment, I discovered another pivotal strategy: having customer success script the closing remarks of sales. This approach may seem unconventional, but it stemmed from my unique position as a former salesperson who transitioned into customer success.

My transition from sales to customer success, coupled with frequent complaints about sales-CS misalignments, prompted my VP of Sales to ask for my input. He wanted to know exactly what his sales team should say during the closing stage to set up customer success for success.

The closing script we developed became a strategic tool for ensuring smooth handoffs. It involved several key components:

  • Confirming reasons for purchase: Sales would reiterate the customer's reasons for purchasing the product. This ensured that the core objectives and expectations of the customer were clearly understood and agreed upon.
  • Introducing customer success: The script included a proper introduction of the customer success team. This introduction framed CS as the strategic advisor and primary point of contact for the account. This positioning was crucial for setting the right tone for the ongoing relationship.
  • Recording and reviewing: The closing conversation was recorded, allowing my team to review it before the kickoff call. This ensured that we were fully informed and prepared to meet the customer's expectations.

An essential aspect of this approach was to echo the customer's purchase reasons during the kickoff call. This reflection not only validated the customer's decision to choose our product but also reinforced the continuity and consistency of the relationship from sales to customer success.

Step 3: Create a "10 commandments" document

The third step in refining the sales to CS handoff involved creating what I termed the "10 commandments" document. This initiative was proposed by my VP of Sales and required close collaboration with the sales team.

This document served as a clear guideline of what sales representatives were prohibited from promising or stating during the sales process. Its creation was a collaborative effort, where both sales and customer success teams worked together to identify key areas prone to miscommunication or over-promising.

During our workshops with the sales team, we focused on addressing habitual over-promising issues. Two recurring promises that often led to complications were:

  • Mobile app promises: Sales teams frequently promised mobile app capabilities, regardless of whether our product supported them or not.
  • Data migration assurances: Another common over-promise involves data migration. Sales teams would assure customers of our ability to support data migration, even when it wasn't feasible.

By establishing clear boundaries and guidelines through our "10 Commandments," we were able to significantly reduce misunderstandings and unrealistic customer expectations. This document was not just a set of rules but a tool for fostering trust and transparency between sales, customer success, and our customers.

Step 4: Align incentives within a clear graduation checklist

In my journey through customer success, I realized the importance of having a clear and structured approach to onboarding. This led me to develop the concept of a "graduation checklist" for customers, a concept I felt was my unique addition to the field.

The idea behind the graduation checklist was to provide customers with a tangible endpoint to their onboarding journey. This graduation marked the moment when they were fully equipped and ready to make the most out of our product.

To reinforce this concept and align incentives effectively, I worked with my sales colleagues to create a rebate model:

  • Onboarding fee: Sales would incorporate an onboarding fee into the initial customer agreement.
  • Rebate upon graduation: I communicated to customers during the kickoff call that this onboarding fee would be rebated back to them upon the successful completion of their onboarding process.

This model proved to be an excellent way to align incentives. It motivated customers to actively participate and complete the onboarding process, especially in situations where there might have been some misalignment or misunderstanding between sales and customer success.

Step 5: Require sales handoff forms or no one gets paid

In the fifth step, we focus on the creation and mandatory use of sales handoff forms. This practice is essential for structuring the transition from sales to customer success.

Many teams rely on ad-hoc methods for handoffs, often just "winging it" on calls. While calls are important, they aren't always sufficient or appropriate for every deal type. To address this, I recommend using structured handoff forms, especially if your current process lacks clarity or consistency.

It's crucial to understand that the handoff process should vary depending on the type of deal:

  • Transactional deals: In such cases, customer success rarely joins sales calls, and internal handoff calls or sales participation in kickoff calls are uncommon.
  • Enterprise-level deals: Here, the process is quite different. I advise having CS join sales calls in a sales engineering capacity. One of the best moves I made was transitioning a member of my support team into sales enablement, which benefited his career, sales, and my team. Regular internal handoff calls become more prevalent at this level.
  • Mid-market deals: This is where things often get tricky, as the lines can blur. It's important to critically assess whether your current handoff protocols are effective and make adjustments as needed.

Ask yourself: Are our handoff protocols serving our needs effectively? Do they cater to different deal types appropriately? By implementing structured handoff forms and tailoring the process to the deal type, we can ensure a smoother, more effective transition from sales to customer success.

Step 6: Be clear and consistent with clawback

Step six delves into a more contentious aspect of the sales-CS handoff: the clawback policy. Clawback refers to the practice of revoking a salesperson's commission for deals that are improperly sold. This concept often stirs controversy and can be a source of tension between sales and customer success teams.

To implement clawback effectively, it's essential to have clear protocols backed by C-level management. These protocols define the circumstances under which a salesperson's commission can be clawed back. It's a delicate balance to maintain, as it directly impacts the relationships between teams.

Salespeople often worry that CS teams will eagerly claw back commissions. However, in my experience, the reality is quite different.

CS teams, accustomed to playing a more accommodating role, are generally hesitant to enforce clawback. They typically avoid causing conflict or harming relationships with the sales team.

As leaders, it's crucial to foster a safe environment where team members feel comfortable discussing potential issues related to improperly sold deals. This includes:

  • Structured feedback process: Developing a formal process for feedback can help manage these sensitive situations. This process should be controlled and not involve direct confrontations between individual contributors from different departments.
  • Managerial-level forms: Implementing forms that are directed to managers, rather than individual contributors, can facilitate a more measured and constructive approach to addressing issues. This prevents disrupting the sales team's deal flow, confidence, and self-assessment.

Ultimately, the objective is not to penalize salespeople indiscriminately but to ensure accountability and integrity in the sales process. It's about maintaining a balance where feedback and corrective actions are handled professionally and respectfully, safeguarding the interests of both teams and the overall health of the company.

Step 7: Track churn reasons and escalations by Account Executive

The seventh step involves a data-driven approach to understanding churn and customer dissatisfaction. This step was particularly impactful in my journey, as it involved creating reports and dashboards in Salesforce - my first foray into such analytics.

On the x-axis of these reports, I listed the salesperson responsible for each deal. On the y-axis, I tracked various customer metrics such as churn rates, Net Promoter Score (NPS) drops, and usage declines.

The goal was not to single out salespeople but to identify coaching opportunities. By correlating churn or dissatisfaction with the salesperson who closed the deal, we could determine if there were patterns that required attention.

These insights were invaluable for both myself and sales leaders. They allowed us to trace back to the beginning of the customer journey and understand the potential impact of the initial sale on the customer's long-term success.

To balance this analysis, we also recognized and celebrated top-performing salespeople:

  • Sales excellence award: We established an award for salespeople whose deals consistently resulted in satisfied, successful customers. This positive reinforcement encouraged best practices in sales.
  • Building a positive feedback loop: Acknowledging these top performers not only boosted morale but also created a positive feedback loop. It highlighted the importance of selling to the right customers and setting them up for success.

Step 8: Reassess your sales training strategy

In the eighth step, I realized the importance of reassessing and improving our sales training strategy. This realization stemmed from the understanding that some of the issues with incorrectly sold deals were partly due to a lack of proper sales training, for which I felt responsible.

One of the most effective strategies I implemented was the use of an internal learning management system (LMS) for training sales teams. I'm curious, how many of you utilize an LMS for your sales teams?

Initially, I questioned whether I had the time or responsibility to train sales teams, given that they were not directly under my department. However, I soon realized that the more pertinent question was whether I could afford not to invest time in this.

The shift in mindset from "I don’t have time to do this" to "I don’t have time not to do this" was crucial. It highlighted the importance of investing in sales enablement, not just for the benefit of sales but for the overall health of customer relationships and the company's success.

Investing in sales enablement through comprehensive training and development became a key focus. This was not just about equipping sales teams with product knowledge but also about fostering an understanding of the impact of their sales on customer success and the long-term relationship with the customer.

Step 9: Record and review sales calls on a routine basis

The ninth step in enhancing the sales-to-customer success handoff process involves a fundamental practice: routinely recording and reviewing sales calls.

There are numerous conversational intelligence tools available that can significantly aid in understanding and improving sales interactions. These tools can provide valuable insights into sales conversations, customer reactions, and areas for improvement.

It's crucial to deliberately set aside time in our calendars for this activity. This isn't just a task to be done in response to issues or red flags but should be a regular, proactive part of our process.

The goal here is to shift from a reactive to a proactive stance. Regular reviews of sales calls allow us to preemptively identify and address potential issues before they escalate. This approach helps fine-tune sales strategies and ensure that the sales team is aligned with customer success goals and expectations.

It's important to note that the intent of these reviews is not to create a "Big Brother" atmosphere of surveillance. Instead, they are meant to be constructive and educational, providing opportunities for coaching, learning, and continuous improvement in sales practices.

Step 10: Have CS join weekly sales pipeline meetings

In the tenth step, I discovered the significant benefits of having customer success join the weekly sales pipeline meetings. This integration wasn't always easy to establish, as there was initial resistance from sales teams who were hesitant to include 'the nerd' in their discussions. However, the advantages quickly became apparent.

With my product expertise, I could contribute to closing more deals, offering insights that could make a critical difference. Attending these meetings provided visibility into the sales pipeline, allowing for more accurate resource planning. This was crucial for anticipating the needs of the customer success team in the short and medium term.

By understanding the potential deals in the pipeline, I could identify and flag deals that might not be a good fit for our product or service. This helped in reducing future churn and maintaining customer satisfaction.

While in these meetings, I generally maintained a quiet presence, focusing on listening and gathering information. Post-meeting, I would follow up with managers to discuss any concerns or insights gathered from the meeting.

For those unable to join sales meetings directly, there's an alternative. Working with revenue operations (RevOps) to build a report that automatically provides updates on the sales pipeline can be equally effective. This allows the CS team to stay informed and plan accordingly, even without direct meeting participation.

This step emphasizes the importance of cross-departmental collaboration. By having CS participate in sales meetings, we foster a more cohesive approach to customer acquisition and success, ensuring that both teams are aligned in their objectives and strategies.

Step 11: Train your team on effective feedback

The eleventh and final step I learned in enhancing the sales-CS handoff process is about the importance of providing effective interdepartmental feedback. My initial experiences in giving feedback were shaped by my time in the restaurant industry, which, as you can imagine, wasn't the ideal learning environment for constructive feedback.

Giving feedback across departments is a delicate task. It requires a careful balance between honesty and tact, especially when addressing issues that might cause friction or defensiveness.

I came across a transformative method for giving feedback, which I discovered in "The Leader Lab" by LifeLabs Learning. It's called the QBIQ method, an acronym for Question, Behavior, Impact, Question.

  • Initial question: Start with a simple, respectful question like, "Can I provide some feedback?" or "Is now a good time for feedback?" This sets the stage and checks if the person is receptive.
  • Behavior: Clearly and objectively describe the behavior you observed. For instance, "You mentioned we support reverse positive pay, but we do not."
  • Impact: Explain the impact of this behavior. For example, "This causes customer escalation, increases churn risk, and negatively affects our company's margins and revenues."
  • Closing question: End with a collaborative question like, "What can we do to prevent this in the future?" This invites dialogue and joint problem-solving.

Initially, this method may feel unnatural or forced. However, like any skill, it becomes more fluid and instinctive with practice. The goal is to make feedback a constructive, collaborative process that contributes positively to interdepartmental relations and overall organizational health.

Additional tips for enhancing sales-CS relationships

In addition to the 11 steps, another useful practice is tracking the reasons for closed deals, both won and lost, over time. This can provide valuable insights into the sales process, customer preferences, and areas where the product or service could be improved.

Understanding why deals are won can help replicate successful strategies and identify what resonates with customers. Analyzing why deals are lost is crucial for identifying areas of improvement, whether it's in the product, pricing, sales approach, or customer expectations.

Another critical aspect is establishing clear rules of engagement regarding when and how sales teams can re-engage with existing customers, especially around renewals.

Having well-documented guidelines helps prevent conflicts and ensures that both sales and customer success teams are aligned in their approach to customer management. This is particularly important to avoid situations where sales efforts overlap or conflict with ongoing customer success initiatives, such as renewals or upsells.

Final thoughts

I hope these practices and tips provide you with a valuable playbook that you can bring to your sales leaders and C-level executives. The goal is to foster better sales-CS relationships and improve the overall customer experience. By implementing these strategies, you're not only enhancing interdepartmental collaboration but also driving greater success for your organization and your customers.