Key questions to ask when hiring your first Head of Customer Success

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.’

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.

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?

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.

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.