For CS Leaders

Fixing sales to CS handoff

If you are in SaaS, you already know that the cost of acquiring a new customer is much higher than retaining an existing customer. If you want customers to stay longer with you and increase the revenue per customer, you have to set the right expectations with your customers from day one and have smooth sales-to-customer success account handoffs.

Often the culprit contributing to a bad customer experience and thereby churn is the lack of visibility and a clearly defined account transition process between sales and customer success.

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Why is account handoff from sales to customer success so critical?

In absence of a proper transition from sales to customer success, customers can often feel like they are ignored or neglected. And when customers are not fully engaged with your brand, they don’t stick around for too long—hurting your customer lifetime value (CLV) and other key retention metrics.

Here are a few reasons why sales-to-customer success handoff is important.

1. It sets the tone

A seamless handoff between sales and customer success often results in improved customer retention. The opposite  is true too.  One of the top reasons for high customer churn is the disjointed onboarding process between sales and customer success. For instance, it feels like customers go through a contrasting onboarding experience that is not in sync with the expectations set during the deal closure.

On the other hand, a tight collaboration between both teams can help you manage customer expectations from the get-go. Therefore, a seamless handoff to customer success and setting the right expectations set the tone for customer retention.

2. It speeds up the time to ROI

For most subscription businesses, the real ROI of customer acquisition is dependent on the customer renewing their subscription regularly. Good communication and seamless transition go a long way in accelerating the time to ROI for your customer accounts.

3. It helps you build trust

New customers are often excited to see your product in action to solve their current pain points. They come in with a feeling that they’re onto something. But —the excitement is fragile and highly subject to change based on their experience with your organization in the first few weeks.

A smooth handoff between the two teams creates  an opportunity for you to build rapport and trust with your customers. And that’s exactly where a seamless handoff to customer success with enough intelligence on the customer’s objectives and pain points can be of great help.

Reasons for broken customer success experience

A Customer Success Manager (CSM) is always trying to ensure that their customers are getting the most value out of their product and identifying opportunities for upselling and cross-selling. But it all starts with a fundamental understanding of the goals of the customer, what their key pain points are, their use case for your product, etc.

Sadly in most cases, not enough context about the customer is shared with customer success when an account handover happens from sales to the customer success team. And it’s not just about information sharing, but a whole lot of factors that contribute to a broken customer experience.

1. Not setting the right expectations

Your brand is as good as your worst customer testimonial. B2B customers jump through several hoops to buy your product. Then, they discard an equally potent suite of alternatives to do business with you.

Sales is often the first point of contact for your customers. They do a pretty good job of building excitement in customers during the deal negotiation stage, giving them a high of your brand’s promises and product capabilities.

But when your customer success team doesn’t give them the experience they perceived during the sales stage (often because of lack of context)—they will soon fall back to their earlier options. And rest assured, they will leave scathing reviews about your brand on all public forums, which can dampen your reputation.

Besides customers, the broken process between sales and customer success also increases friction, leads to accountability issues, and instigates a vicious cycle of blame culture between the two teams.

2. Lack of documentation

Sales teams are primarily focused on closing deals. Based on our analysis at Avoma, the average number of meetings to close a deal is between 4 and 6. And each of these meetings tends to average between 30 minutes and 1 hour. Despite several conversations, very little information is captured as notes and updated into a central system such as a CRM.


And because there are no centralized notes or access to the history of conversations over the 4-6 meetings before the deal was closed, the customer success teams don’t have enough context about the customer.

3. Misalignment between sales and customer success KPIs

Sales is responsible for prospecting the leads, demoing the product features, and converting prospects into paying customers. Sales teams are often measured on KPIs (key performance indicators) such as sales revenue, achieving quota, potential revenue pipeline, average order value, and so on.

The core metrics on which a customer success team is measured typically include customer lifetime value (CLV), churn rate, number of upsell/cross-sell, etc.

Since sales and customer success goals are in opposite directions, there is often misalignment between the customer expectations set by sales teams and how customer success teams handle the account, starting with onboarding. And that broken experience ultimately results in customer churn.

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To give you an insight into how it impacts revenue—if you lose 5% of your paying subscription customers each month, you are looking at a close to 50% annual customer churn rate. And after just one year, you are looking at a ~30% divergence in customers and revenue!

The blueprint to fix the sales and customer success gap

Sales is like the ground staff at the airport that ushers us inside the plane. Once onboard, a different set of professionals from the same airline brand greet us, help us settle in, offer us drinks (usually through an upselling tactic), and help us make the most out of our in-flight experience.

The job of customer success begins where sales end—and customers expect nothing short of a royal treatment once they are on board with your brand. A good sales-to-customer success handoff process doesn’t happen by accident. It takes both teams working together—and developing a well thought out process.

Here’s a blueprint to set up the sales-customer success handoff process and offer a seamless experience. It falls into five stages namely:

  1. Build visibility before closing a deal
  2. Create an internal handover process
  3. Create an external customer success handover journey
  4. Customer success onboarding
  5. Frequently check in and ensure the ongoing success

1. Build visibility before closing a deal

In highly process-oriented organizations, the sales reps and AEs start building their account handoff document when they believe they are likely to close a deal. The document gets shared with the CSMs after the deal is closed.

But it makes more sense to bring the CSMs proactively into context much before the deal closure happens. Since we are in an era of instant gratification, most customers want to use your product as soon as they sign up or make a purchase. And if a CSM comes in only after the deal is closed, you’re already on the back foot.

Also, mapping accounts to CSMs during the negotiation stages helps increase the transition speed between sales and customer success. It ensures there’s no confusion about who in customer success will be taking up an account.

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Deal stage visibility in Avoma

From a customer perspective, it clarifies who is their point of contact for setting up the product.

And from the CSM’s perspective—they know what’s happening with an account assigned to them, much before the onboarding stages.

2. Create an internal handover process

There are two primary steps to fine tune the alignment between sales and customer success. One is internal handoff—conducting internal meetings to share account information, knowledge transfers, answering questionnaires, etc.

Another is external handoff—introducing the CSM and setting expectations with the customer on the further processes.

As part of the internal handover the common practice is to have the AE or sales rep fill up a questionnaire that covers key information such as:

  • Annual contract value
  • Potential contract value (in case of monthly renewals)
  • Number of licences/seats
  • Negotiated price if applicable
  • Use case/objectives
  • Pain points
  • Key stakeholders
  • Internal champion at the customer account
  • Blockers and decision-makers, etc.

That said, a much easier way to handle this is using conversation intelligence software to give your CSM access to the entire notes and conversation history, starting from the SDR reach out upto the deal closing conversations between the AE and the customer.

That way, the CSM gets to know every minute detail of how the sale went down. So, for example, if the customer was originally planning to buy ten licenses of your product —but then discovered some internal issues and then finally decided to start with five licenses, the CSMs will be able to weave those points into their post-handoff upsell conversations at a later period.

Also, using a tool like Avoma, CSMs can choose to listen to specific parts of the conversation based on topics of interest such as objections raised, customer pain points, etc.


And when the CSMs are handling multiple customer accounts, they can save time by quickly skimming through the AI-generated notes (call summary as seen in the left, in the screenshot below) without having to listen to conversations.

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In short, one of the simplest dipsticks to a seamless handoff process is that the customer doesn’t have to repeat themselves to customer success if they have already discussed a given topic with your AE.

3. Create an external customer success handover journey

As discussed under ‘building visibility’, the mapping of CSM to a customer account needs to happen much before a prospect turns into a customer. Therefore, at this stage, the introduction of the CSM to the customer is more of a formality and yet an important step to show that you are committed to the continued success of your customer.

The introduction typically happens over a Zoom meeting or via email—ideally within 24-48 hours of the deal sign off.

A key aspect to remember during the external handoff is—customers don’t necessarily know or care much about it. For them, the experience is always between them and your brand.

So regardless of whether they are being handed off from marketing to sales or from sales to customer success—they expect a uniform experience across all stages of their buyer journey.

Once the external handover is properly done, the AE can also get out of the way to focus on closing the next deal, ensuring that they didn’t leave their customers in a lurch.

4. Customer success onboarding

At this stage, the account is officially handed over to the CSM, and they begin helping the customer set up the product based on their use case. This step is of utmost importance to your customer and is their moment of truth towards solving their pain points.

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In cases where it’s mostly self-serve, the CSMs need to do the following:

  • Initiate the onboarding email sequence and in-product sequences using chat tools such as Intercom along with FAQs
  • Share collaterals and videos related to product set-up and specific use cases
  • Provide them with contacts and resources for any further questions

And in cases where products need initial set up based on customer’s use case:

  • The CSMs need to schedule onboarding sessions where they invite key stakeholders from the accounts and help them set up the product based on their specific needs, objectives, and pain points

5. Frequently check-in and ensure ongoing success

The final stage is to confirm that the handover is complete. Depending on the history gathered about the customer using conversation intelligence tools, the CSMs need to do periodic check-ins to ensure that the customers can achieve their objectives using the product.

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Both the AE and the CSM need to analyze what went well and what could have been improved during the handoff. From time to time, the CSMs also need to analyze trends of product issues, adoption friction, or feature requests mentioned across several conversations and share it with the product teams to ensure the issues are solved holistically and not just offering workarounds for the time being.

The intelligence from these conversations can also be used to train the new CSMs and ramp them up quickly to deliver the same level of frictionless customer experience.

Finally, the CSMs can curate playlists of their conversations that feature objections or specific customer requests to feed in as inputs to the marketing and product teams.

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Finally, ensure sales – customer success process adherence!

Wrapping up—it’s not just about setting up a process for account handoff but ensuring that the process setup is being adhered to. While the above process is a decent ballpark, you can structure your handoff in a thousand different ways depending on your industry and the kind of product.

The key is transparency and communication across functions. Cross-functional collaboration is one of the keys to a successful customer experience and reduced churn. So get together, create a plan, and democratize customer intelligence. Pretty soon, you’ll begin to see the improvements and impact compounding.


Should you charge for CS?

An overwhelming majority of people—including founders and CS leaders—feel that it’s wrong to ask buyers to pay extra for customer success.

I know this because I have been around in the customer success industry for far too long and I interact with dozens of company founders, CS experts, and customers every week. Most people I talk to are vehemently against the idea of charging customers for customer success.

We at Avoma are totally in the same camp. We currently don’t charge for customer success, but do have strong views on what kind of CS services should be free and what you can charge for.

However, there are plenty of examples—although in the minority—of companies that charge for customer service and their buyers don’t hold them against it. And I bet that lots of companies that aren’t asking any money for customer success today will have no problem making it a paid-for service in the future.

So what gives? Why is paid customer success such a contentious issue for so many companies (and customers) while some companies get away with it without any repercussions?

Should you hand out customer success as a free lunch or price it as a fancy dessert?

Like a lot of other things in business, there is no quick and dry answer to this topic. Look at it from the customers’ point of view and you will understand why most of them will have a knee-jerk reaction to it. Making customer success a paid service is like asking your customers to pay for customer support—not completely unheard of, but it can be very tricky to do so.

But if you get into the weeds of things—especially from the business perspective—you will discover that there’s a time and place for making customer success a paid line item, which is acceptable for most customers too.

In this blog, we’ll unpack some of the nuances around if and when you should charge for customer success.

Customer success is a very nuanced business offering

Whether to charge for customer success depends on a lot of things, like asking yourself these three important questions:

  1. What does customer success mean for your business?
  2. How mature are your product and the CS org within your company?
  3. What segment of the market does your product serve?

Let’s slice and dice these questions from all possible angles so that you can get to the answer that’s right for your business.

What does customer success mean for your business?

It sounds like an awfully simple question, but you would be surprised to know the number of businesses that don’t have a clear answer. And it’s a question you should have a concrete answer to—without or without the dilemma of charging for customer success.

In many small startups, customer success usually borrows many aspects of customer support. The role of customer success managers (CSMs) in such organizations is very mixed: they onboard customers, offer customer support, handle account management, work on renewals, and manage upsells.

In other growing companies, it’s a combination of onboarding, configuration assistance, and periodic strategic conversations such as quarterly business reviews (QBRs) with customers to help them hit their goals.

Bigger companies might have a very mature CS function that goes beyond the usual onboarding and configuration assistance, where each CSM is specifically assigned to a few accounts whose goals are more than improving retention and maximizing net revenue retention. It is about adding strategic value at a business level as their partner.

So if you were to ask what kind of CS orgs, out of the above three types, were likely to charge for customer success—it’s obviously the third one.

That’s because the customer success they offer is an add-on on top of their main offering. CS in the previous two companies is pretty basic and doesn’t merit additional fees. More on that later.

You first need to identify what customer success means for your business and the value that they provide to the customers to figure out if customers are willing to pay for customer success as an extra value-added service.

How mature are your product and CS org?

It’s critical to gauge the maturity of both—your product and your CS org—to understand if you are ready to ask customers to pay for customer success. Here’s why.

If you are just starting up or have secured a couple of rounds of funding for your company, you are likely growing your product rapidly. You might have hired your first few CSMs, and you likely have achieved the product-market fit—but it’s not quite there yet. Ideally, you should have lower ratios than the typical industry standards and build a tight-knit product and CS collaboration.

At such a crucial juncture of your company’s growth, you might want to overinvest in CS as a business function—not charge for it! That’s because the CS team at that stage of any company’s growth is getting a lot of good data, which helps you drive useful insights into the product and make it even better.

On the other hand, if your product is mature to the point that customers don’t need a lot of handholding in terms of usage, CS becomes an optional variable. You can make a judgment call to make it a paid-for line item, depending on your customer’s response to that decision.

What segment of the market does your product serve?

Just to be clear—we are not referring to a niche, domain, or industry when we say “segment.” By segment, we mean the maturity stage of your customers to which you are catering, such as small and medium businesses (SMBs), scaleups, or enterprises. It’s important to understand which segment of the market—regardless of the industry you serve—buys from you the most to align your CS operations and map them to their requirements.

And while you’re at it, it’s also worth considering what their expectations are from your product. As you can imagine, the expectations of a large-scale enterprise are going to be vastly different from an average SMB.

An up-and-coming startup might be narrowly focused on fighting churn, while a large enterprise might have wide-ranging expectations to build customer loyalty, maximize customer lifetime value, or identify revenue expansion opportunities. Therefore, the resources you need to pour into hitting or exceeding those different levels of expectations will be very different.

When does it make sense to charge for customer success?

A few years ago, we Avoma bought HubSpot’s all-in-one solution after doing extensive homework on the best software to help us streamline our go-to-market (GTM) operations. As a small startup, we obviously needed help to implement some of the workflows that HubSpot offered in its wide range of offers.

To our shock, the HubSpot team wanted us to pay extra for the onboarding help we needed to set up the software for our use cases. We felt betrayed because we had bought HubSpot’s annual subscription after discarding all other software options while they were demanding we pay more money instead of offering us a smooth onboarding experience.

As a business institution, we believe that onboarding is an integral part of the customer buying experience. But our beliefs and expectations around paid-for onboarding, customer success, or any other value-added services have changed since then, owing to a few first-hand experiences like that.

As we continue to grow, we understand that for many companies that are serious about helping their customers grow, offering customer success is less like a token org function and more like a consultative function.

I believe that there’s 100% value in charging for add-on services like customer success, onboarding, initial setup, and implementation, or any other forms of technical help—if these services add a ton of business value to your customers.

There’s a lot of consultative work that businesses have to invest in for that kind of business value. That kind of consultative work is more than just helping the customers set up the software or showing them how to use it.

Instead, it’s about giving them critical insights on how they can leverage the software to get ahead in their business and helping them see and avoid the usual pitfalls. Many customers expect you to not just sell a software solution but give them the industry best practices that can elevate their business to the next level. With an extra service component, you can help them with the change management and all the other “soft things” that aren’t limited to just setting up the actual application.

Think of it as hiring experts from one of the big five consulting companies like McKinsey or BCG to help you unearth the best practices and data points that could take you years to discover if you were to figure them out on your own.

Was HubSpot wrong in charging us for onboarding?

I think that HubSpot has its reasons to ask customers for onboarding as an additional service—but the way they do it could have been better. For instance, we came to know about the extra onboarding cost only after we went through with the annual subscription plan which, in retrospect, feels like a “hidden fee” that we weren’t informed about.

There was/is no mention of it on HubSpot’s pricing page and the salespeople we spoke to didn’t inform us about it through the entity of our buying process. So it was natural for us to feel surprised when they dropped that extra price bomb on us.

If you are evaluating HubSpot’s CRM or any of its other software solutions, here’s what Vanguard 86 has to say about its different onboarding costs:

“​​The costs vary in line with the tools available. With HubSpot Marketing Hub onboarding, for example, the costs for guided onboarding range from $250USD for Starter to $6,000USD for Enterprise onboarding support. HubSpot’s Sales Hub onboarding, however, ranges from $250USD for Starter to $3,000USD for Enterprise.”

Had the HubSpot salespeople who closed our deal given us a heads up about the onboarding fee, it would have been a much better customer experience on our part.

That incident raises an important question:

If you were to charge a fee for customer success, how should you break it to the customers?

It’s always the sales team’s responsibility to give customers the full context of what they are signing up for—including the additional services that would incur extra fees. As a norm across all industries, the sales team is commissioned for any services they sell.

So it’s in their best interest to really understand the value of these add-on services and articulate its extra benefits to the customers ahead of time.

When you shouldn’t charge for customer success

We have already established that it’s premature to charge for customer success (and perhaps other add-on services) when you are a young startup that can use CS to create a feedback loop with your customers.

That’s because an add-on customer success shouldn’t be an excuse for a poor product that’s not fully mature yet. Here’s what I mean.

Many companies use a customer success or setup fee as a crutch for their bad products. They roll out half-baked product experiences that aren’t fully capable of solving the customers’ problems. It’s hard for customers to set up and start using the product on their own because of how buggy the tool is.

In such a scenario, it’s best not to charge for customer success because—why should customers pay for something lacking on your part? It’s foolish and lazy to build products that require you to have experts who can fix gaps in your products—and charge customers for it.

Instead, it would help if you aimed to provide an out-of-the-box solution that can help customers be up and running quickly in no time. This is true even for relatively sophisticated tools requiring manual configuration or basic integrations.

As a rule of thumb, it’s better to hire more product experts who can build a seamless self-service product experience than to have more implementation managers. That’s because the former can compensate for the manual hiccups in your product and fix the gaps in the onboarding flow—making your product more customer-centric in the long run.

Having several implementation experts assisting your customers on a 1:1 basis, on the other hand, will continue to be a manual process that creates friction and doesn’t solve the problem at scale.

As a brand, it’s your responsibility to iterate on your product so that it offers seamless and product-led onboarding thus accelerating your product’s time-to-value for the customers.

Don’t use the extra service component as a negotiation tool

Many sales teams keep extra line item services as a trick up their sleeve to get the upper hand in sales negotiation and to close deals faster. They might introduce the price of all line items during the initial sales conversations and discount it heavily when negotiating the price.

You have to be careful about using paid-for customer success as a sales tactic because it devalues the service’s offering. When you aren’t intentional about making your product implementation-ready, the extra services and fees look like a cheap trick to inflate the price and slash it later as a discount.

Here’s a hypothetical example that we keep seeing in and around SaaS circles. Let’s suppose you have a one-time customer success fee of $5000. As a CS leader, you might have spent a lot of time packaging together a set of high-value consultative items that make a difference in the customers’ business. You might even have carved out a good compensation model for the sales reps who can upsell the services to interested customers.

But if your salespeople aren’t aware of the business value that this service offers, they sometimes discount it to zero—sometimes to get a deal across the table and other times to meet their annual quotas. The customers might see through the sales tactic and perceive the extra service to be “garbage”—since discounting it to zero means it had no value to begin with.

A better alternative is to sell the value of the service component internally to the sales team first and help them align on the same page. Roll out the CS service component first with the sales leadership before launching it to the customers. Help the sales team see the value in the service offering and have meaningful conversations with them on:

  • How are you going to price it?
  • What does the flow for discounting look like?
  • The maximum possible discounts

If you face backlash from customers or find that customers aren’t willing to spend money on your service, you need to change gear, re-enable the team, and package the service better to communicate its business value. Perhaps you can include case studies of previous customers who saw tremendous value through the CS package.

If you package the service component nicely, you should be able to sell it without any hiccups. But don’t use heavy discounts as an afterthought to make your sales negotiation easy.

How to package an add-on service component

Although we don’t charge for customer success at Avoma, we do a lot of debates around several modern SaaS topics, including how businesses should package their paid-for customer success.

  • Should you have it as an additional line item on top of your core SaaS product?
  • Should you bake it with your core SaaS pricing?

There are arguments for and against both options. If you charge the service as an extra line item, it might look like you are charging customers twice—once for the core product and again for the add-on service. But doing so makes the pricing information transparent and upfront so that there aren’t any last-minute surprises.

On the other hand, factoring in the extra service as part of your core SaaS offering is a psychological manipulation tactic that might or might not serve you well. Granted, customers might like your pricing with the fringe benefits—even if the price looks steep at a glance. But it can end up creating more problems at a later stage.

For example, let’s say you have designed your SaaS pricing to factor some level of customer success pricing baked into it. Perhaps your starter plan doesn’t offer customer success, the middle tier plan offers a CSM on an as-needed basis, and your enterprise plan offers a white glove service with dedicated CSM plus a QBR thrown in the mix.

But what happens when a huge client—who pays you in seven figures subscription fees—chooses to buy the starter or the middle tier plan? Will you not offer them the privileges of the enterprise plan because they are paying for the low-tier subscription? They might be contributing to 1 million in ARR (annual recurring revenue), but a concierge service can raise the revenue potential to 6 million in ARR three years down the road.

In such situations, it can be tricky explaining why you are offering them all the bells and whistles when they deliberately went with a plan that didn’t offer the extra toppings.

In contrast, having it as an upfront line item has many benefits. It shows confidence in your service quality, makes your conversation with customers more transparent, and keeps your core product’s value metrics separate from the add-on service.

This allows you a lot of room for flexibility to offer a customer experience that aligns with their expectations. For instance, you can automate the experience of customers who expect to be left alone and invest your resources in high-ticket customers who need your expertise every step of the way.

Customers who opt for a dedicated CSM as an extra service can get a high-touch KAM (key account management) at their behest, faster response time, and additional benefits related to SLAs (service level agreements).

Is customer success a cost center or a growth lever?

The entire discussion around “should customer success be free or paid-for service” circles around a fundamental question: how do you perceive customer success as a business function? Is it a cost center or a growth lever?

If you think of it as a cost center, you will always look at it from the angle of covering your costs. That’s why businesses have compensation structures for CSMs based on accounts, retention, upsells, cross-sells, etc.—just like in sales. They look at the short-term and want to recover the time and resources they are pouring into the CS function to justify the unit economics.

Objectively speaking, CS is a powerful engine for growth because it helps you:

  • Keep the gross churn low
  • Improve your product because of the healthy feedback loop with the customers
  • Maintain a high net retention rate and drive additional adoption

When you see CS as an enabler of growth, you can truly enable your CSMs to help customers achieve their goals so that you can help them grow and retain them in the long run. You can get your return on investment from the CS function when the CSMs help you maximize the customer lifetime value, identify expansion opportunities, and build brand loyalty. In that sense, customer success is a growth lever for your business in the truest sense.

Parting advice

If you have the opportunity to charge for customer success as an add-on service component, keep it as simple as you can. Adding a paid-for service is tricky to play around with, and it can get complicated if you don’t pay attention to the small details.

You might want to think through how to charge: should you charge for the service by the hour or buckets of hours? Should you have a flat fee structure for CSM? Should you offer a certification program—if you are rolling out technical implementations?

Make sure you offer the service component at the right time of your company’s growth—combined with the right packages priced at the right price points—so that you have all the resources you need to manage it well. And finally, don’t attach yourself too strongly to one strategy. The answer to whether to charge for customer success or not isn’t written in stone—do what’s mutually beneficial for your customers and your business in the long run.

Perhaps you don’t have it as a paid-for service right now—be open to positioning CS as an additional line item in your pricing strategy as you evolve to become a more mature brand. If you are already doing it and there’s less traction for it, plug it out and bake it in as a free offering as part of your subscription plans. Revise the service offering as your company evolves, moves up to a different market segment, or the product advances to offer a self-service customer experience.


How to hire your CS leader

Customer success (CS) is an important profit center for any SaaS business because it is a function that’s at the epicenter of customer relationships. In fact, CS is at the intersection of people, processes, and data—three core pillars of any organization. When done well, customer success builds loyalty, improves retention, and ensures recurring revenue.

According to Jason Lemkin—one of the most renowned voices in the SaaS industry—customer success is where 90% of the revenue is. The CS leader is someone who comes in, sets up the customer success process, necessary technology to support the process, builds momentum and unlocks growth opportunities.

For such a critical role, as you would expect, finding and hiring the right CS leader for an organization is a huge responsibility. You need a lot of clarity in terms of—the expectations from the Head of Customer Success, in terms of specific experience and expertise.

Going by some of the lessons we have learnt over the years, here are nine key questions you might want to ask potential candidates applying to your organization to be your first Head of Customer Success.

9 questions to ask your potential Head of Customer Success

We are not prescribing that you should only stick to these questions as qualifying criteria to recruit your first Head of Customer Success. That would be too myopic without doing background checks, asking them about their past experience, and keeping room for contextual questions that you might want to ask on the fly.

However, use the following questions as a checklist—sort of like an agenda template—to open conversion loops with each candidate you interview for the role. These questions come from the perspective of getting to know the depth of their understanding, and are designed to understand a person’s leadership quality, management style, and expertise about the customer success function.

Feel free to tweak the questions in your own words or ask relevant follow-up questions to dive deeper into a topic.

1. “What do you think should be the key customer success KPIs for a company of our size?” 

This question will give you a quick insight into the candidate’s understanding of how things work for companies of different levels of market maturity, and bring forth their ability to adapt their approach.

Though the answer can range across metrics such as customer churn, monthly recurring revenue (MRR), number of customer support tickets, expansion revenue, etc.—the KPIs they prioritize gives you a perspective into whether or not they’re a good fit for the stage your company is in.

Also, the answer to this question gives you some insights into their school of thought. For instance, depending on the kind of background each candidate comes from—some tend to lean heavily on the customer support side, some others on retention and metrics like Net Promoter Score (NPS), and some on account growth.

It helps you identify the right person based on what your vision and goals for customer success are. For example—one of your key goals might be improving your profit margins or average revenue per customer. With that in the backdrop, you might want to look for CS leaders who prioritize account expansion and enjoy building levers that can accelerate your overall payback period, i.e., shortening the time taken to recover your customer acquisition cost.

Lastly, if the answers are not specific—give them a pass. It shows a lack of clarity.

2. “What would be your #1 priority your first month?”

This is a question that’s not supposed to have one right answer. The answer can vary—again, depending on the GTM motion of your SaaS (product-led, sales-led, etc.), your competitive landscape and a lot of other factors.

Honestly speaking, the answer to this question should already be available with the CEO—or, whoever the new Head of Customer Success reports to in your company. But, similar to the previous question, this one too tends to bring out the thought process and priorities of the candidate. It’s one of the best questions to check whether the candidate and your organization are aligned in terms of the organizational DNA.

Alignment is super important, especially in the early stages. Your first 50 employees are very critical to how your organization will shape up to be.

The interesting part about this question is—some candidates give their perspective of what they would like to do in the first 30 days. For example—’I would like to talk to as many customers as possible.’

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While some others will come back with a counter-question—and that’s great as well. For instance, they might ask “what’s the biggest problem you want customer success to solve in the first month?” To keep the conversation meaningful, you can give them your vision and follow up by asking how they will solve the said problem.

We often see that great candidates tend to say something to the tune of “talking to as many customers as I can.” That, right there, in my personal opinion, is a huge check. Others might answer with topics like improving the metrics, hiring more CSMs, streamlining the existing processes, or recruiting new tools to match your company’s fast-paced growth. All of them are good answers to the question—but the best candidates always substantiate why they think it’s a priority and how they will help the company get there.

3. “What teams outside of CS do you usually collaborate with?”

In the modern collaborative workplace, no team can function as a standalone department—and the customer success team is certainly not an isolated island. If anything, the customer success team depends on other teams such as sales, product and customer support to function well.

For instance, sales precedes customer success in knowing a customer account. Sales reps and Account Executives have rich insights about the customer pain points, the ultimate goals they are trying to solve, why they decided to buy from your brand, and so on. It’s ideal that the success team gets the knowledge transfer during the sales to customer success account handoff.

Similarly, customer success needs to contribute a lot in driving product changes, feature requests and the product roadmap. Based on their regular customer success check-ins, and their relationship with the customers, they can bring in vital information about the most requested product features, the criticality of these features for customers, their use cases and a lot more.

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Customer support is another key function that can feed into customer success. The support team can share important data about the common problems that existing customers experience in using your product so that the CSMs can proactively help their respective accounts resolve the issues before it’s too late.

Therefore, asking a candidate the above question will help you understand their take on cross-functional team collaboration. The right candidate will probably mention marketing, product, sales, and support because all of these teams have a direct role to play in improving the customer experience.

4. “Can you talk about your experience in bridging gaps and bringing alignment across teams to improve collaboration?”

It’s a question to gauge the leadership quality of a candidate. For instance, if they answer that they would escalate the problem to the higher management—most likely, the company CEO—it often (not always) signals lack of ownership.

Most candidates interviewing for this position have been in senior management. Therefore, the ideal candidate will likely take ownership of the situation and propose solutions displaying their creative-problem solving ability.

For instance, promising candidates talk about their experience in finding out what’s causing the misalignment or break in collaboration. If it’s miscommunication, it’s a fairly simple problem to solve by making the teams aware or by introducing a suitable tool or process to facilitate smooth communication.

If it’s an attitudinal problem—like people not getting along with each other—that’s a more serious problem, where the Head of Customer Success might collaborate with the leaders of cross functional teams to come up with a solution.

To be fair, there are often a myriad of reasons that break down collaboration between teams. Hence, the question comes from the standpoint of assessing leadership skills rather than looking for perfect answers.

5. “How often should we have check-in meetings with the customers?”

While there is no right or wrong answer to this question, a seasoned expert will have a response that reinforces the importance of having frequent meetings with customers.

Running a SaaS business is surprisingly similar to keeping your car running healthy. If you have a customer success team that regularly checks in with your customers, you will build a revenue engine that gives you great mileage and runs smoothly. But if you don’t have a system to regularly check in with your customers, your relationship with them suffers and you will soon run into problems that can lead to a high degree of churn.

Regular check-ins with your customers are critical in helping your business deepen your customer relationships, align better to the workflow and goals of your customer, and identify potential growth opportunities.

The answer to the question can be varied—ranging from every month to every quarter. It also largely depends on the goal that is given to the customer success team. What matters most is maintaining a regular cadence of customer interactions instead of doing it on a one-off, as-needed basis.

This is also a process-related question. While you’re asking “how often”—the question is actually aimed to find out how the person plans to carry it out. Do they have a framework for the kind of things they touch-up on in a check-in call?

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You can further understand their approach by asking:

Do you usually assign a dedicated customer success manager to check in with a respective account? Or do you randomize the meeting in a round-robin style to give each CSM a chance to know all the customer accounts? Should you do it exclusively over phone calls? Or is a combination of email+phone+video conferencing a better way to engage with a customer?

Look for the smaller details in the candidate’s answer to understand how process-oriented they are in their thought process.

6. “What’s your typical approach when it comes to upselling and cross-selling?”

As two of the key components under the broader context of account management activity, upselling and cross-selling are great opportunities to improve a company’s revenue potential. Ignoring these opportunities isn’t just costly but also counterproductive to your growth.

However, most SaaS companies either don’t realize these opportunities presented to them or don’t execute them effectively enough. On the latter—the CSMs at times, may not personalize an upsell or cross-sell, fail to communicate the value of an offer, or push the upselling and cross-selling campaigns separately from their recurring customer conversations.

Asking the above question to a potential hire will give you an idea of what they think about upselling and cross-selling in general and specific tactics to improve them.

You can look for—their thoughts around improving the CSMs’ understanding of the customers, carrying out more frequent check-in meetings, and incentivizing upsell/cross-sell as part of the CSMs’ variable pay.

Any account expansion or upsell approach that comes without any context or deprived of account-specific intelligence—is a red flag.

7. “How will you coach your CSMs?”

One of the pillars of growth in any organization is continuously improving the products, services, or processes—which also includes efforts to upskill the personnel. Training and development is a crucial part of a CS team because it helps the CSMs stay on top of their game, adapt to the remote work environment, learn about the latest industry trends, and hone their soft skills.

A good Head of Customer Success knows this—and they will formalize regular coaching programs for the CS reps over other activities. But how they plan to do it is totally up to an individual candidate.

Your intention behind the coaching question is to basically understand their management style and to see how seriously they take their team. If they make passing comments about conducting workshops, it’s a tip-off that they might not be the right fit for the role. But if they go on to elaborate their plans about how they remotely onboarded their new CSMs, how they prioritize training and development as a must-have for the CS team, you might be looking at the right person for the job.

Good managers often draw their experience from the past jobs and will express a strong interest in personally coaching the CS reps. There’s nothing better for a team than having a direct feedback loop with the reporting manager.

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8. “Can you walk me through how you run your QBRs?”

Sometimes, customer success is about offering a high-touch engagement to selected accounts. Many SaaS companies offer an executive sponsorship program or quarterly business reviews (QBRs) to key accounts in order to demonstrate the value they are getting out of using your product.

And how well a CS team runs its QBRs says a lot about your commitment to the customers. A lot of young startups, for instance, might not even have a QBR process to begin with. But it becomes important once your company earns a few big-ticket clients who you want to retain for a lifetime.

The first Head of Customer Success should have QBRs as part of their account enrichment strategy—especially if you are planning to move upmarket. A lot of mid-market and enterprise customers expect a white-glove service that can act as differentiation between you and your closest competitor.

This question is, therefore, important to understand if the candidate has experience handling mid-market and enterprise level accounts. An experienced Head of Customer Success will be able to walk you through their current process and give you the logic behind it. You’ll often clearly see the difference between the ones that have run QBRs and the ones that talk about it as a to-do.

All said, if they have a contradictory take about QBRs, that’s an interesting proposition too. Hear them out and form your opinion based on the arguments they make against it.

9. “Suppose the churn is through the roof. What are a few things you would do to remediate the problem?”

This better be a hypothetical question because no SaaS company wants churn to be the only reason for their hiring. But it’s an important question nonetheless—especially for the role of a customer success leader.

Churn is what gives your customer success team fever chills, hurts your recurring revenue numbers, and anything beyond 5% will rock your company’s foundation. As a Head of Customer Success, addressing churn should be one of the biggest priorities. Inevitably, it will also be a key KPI for this role as well as for the entire CS team.

Therefore, asking this question will give you a lot of insights about a candidate’s experience—possibly in a high-churn environment—and qualifications for the role.

The interesting thing about churn is that it’s not always in the CS team’s control. Sure, they can do a dozen things in their capacity to improve customer retention. But that can never compensate for the poor customer experience that takes place in other areas of a customer journey—such as bad customer service or fierce market competition.

The answer to this question usually transcends beyond what customer success can do. The potential candidate can point to a host of reasons, such as:

  • Poor customer fit
  • Bad sales-to-customer success handoff
  • Unmet customer expectations
  • Bad product experience

As to the answer pertaining to how to remedy churn, they should ideally suggest analyzing existing customer data to identify what’s causing the problem. Additionally, they should talk about closing the gap between other teams to offer a cohesive customer experience and also to work together to devise an anti-churn strategy.

Final thoughts…

We hope that the above questions will be helpful next time you are preparing to interview candidates for the role of Head of Customer Success. Our parting message to you is that don’t just limit yourself to the above list. Feel free to come up with your own set of questions that go deeper than just scratching the surface of the candidate’s background and experiences.

Leveraging an interview intelligence is often a good way to not just prepare good interview questions but improve the candidate experience in general.

And remember to have a good mix of questions that can probe the potential candidate about their thinking around setting up processes, managing people, and organizing the right tools for the CS function.

Finally, watch out for quality questions in return and not just smart-sounding answers because the kind of questions someone asks in a conversation says a lot about their ingenuity.