The key responsibilities of a VP Customer Success are typically: 

1. Defining the customer journey, designing a strategy to identify improvement areas, and implementing an execution plan to realize that strategy
2. Managing ongoing customer relationships and implementing systems to proactively identify churn risks and upsell opportunities  
3. Building relationships and feedback loops to understand customer usage patterns, priority areas of development, and drive customer value
4. Acting as the primary customer advocate and inspiring a “Customer First” culture
5. Hiring and motivating a team of individual contributors and managers to accomplish objectives on time
6. Collaborating with management team to achieve company objectives

Hiring and Management: 

How do they create a strong pipeline of candidates and maximize close rates? Do they have people that would follow them to a new company?‍

• Ownership of the hiring pipeline from end to end, especially closing.
• Should articulate the specific techniques for closing (e.g. team lunches, building empathy, connection with candidate, etc.).
• Should dedicate a substantial amount of time to hiring.

What do they look for in their post-sales hires? 

• Intellectual horsepower, competitiveness, technical acumen, coachability, teamwork, grit etc. Can be a variety of answers but should know exactly what they look for.
• How do they evaluate candidates on those dimensions?

How have they structured their teams, and how many people were in those orgs?

• Customer success can be structured in a variety of ways, but should be able to clearly articulate how and why they structured the way they did. 

Can they manage across geographies? Have you done so in the past? 

• If this is or will be applicable for your role, ask for examples of managing remote teams or individuals. Candid description of challenges and what they learned.

Can they give you an example of a time they had a difficult conversation/issue with an employee and how they handled it?

• Clear communication and concrete milestones. 
• Holding the person accountable for meeting those milestones and making the hard call in the case the employee doesn’t succeed.

How do they motivate a team, retain top performers, and foster a strong culture?

• Looking for empathy and the deliberate creation of an environment where the team feels supported, invested in, and safe to learn from their failures.

How do they manage up, and how does it compare to how they manage down?

• Looking for a balance between the two. Responsibility for the team they manage, but not friends first. Understand the same relationship for their managers.

Have they successfully mentored people? Can they share specific stories or outcomes?

Customer Success: 

What were they hired to do in their roles and did they succeed?

• This is an important distinction - did they successfully deliver on the specifics of what they were hired for, or did they ride the wave of a successful company?
• Were they hired on as a Renewals Director and then promoted to VP Customer Success 6 months before they left? Understand the arc of their career and tenure.

What was the state of the post-sales organization and company when they joined? How did they prioritize assessing the company’s challenges and how successfully did they do so?

• It should be extremely easy for them to provide a detailed answer, including specific data around team size/makeup, revenue, ACV, etc. and a holistic explanation of the customer journey and their primary problem areas.
• Should be able to give a complete perspective of what was working and what wasn’t, and why their changes made valuable improvements. Answers should be tied to metrics. 
• Bad answers will blame the people around them.

Where does the customer journey start and end in your mind? Which parts of that journey did you own?

• Again, this should be an easy one for them to answer.
• When did they hand customers off to other departments?
• Is there a sense that they had tension with other departments? This can be valid, but try to understand why that tension was there.
• Have they owned presales? Implementation? Adoption? Support? Renewals/Upsell/Cross-sell? 
• Because there are various post sales models, they should be able to give a detailed answer around WHY they structured the way they did. 

Are you more of a tactical operator, or more of a strategic visionary?

• Have they focused on executing against someone else’s vision, or setting it themselves with others to support them, or some combination? Does their point on that spectrum fit with what you need done? 
• Are they sophisticated enough in the way they think about these problems to grow into a broader role?

What did customers look like in your previous companies (department, buyer, size etc) and what did the sales motion look like? 

• Has their focus been on fostering relationships with IT, Engineering, Marketing etc. and at what level of seniority?
• Post-sales in a “bottoms-up” model might focus more on upselling, self-service, and eliminating complexity. Direct enterprise sales will focus more on relationship building, churn mitigation, and gathering customer feedback.
• Did they have a significant channel strategy in place? How did they work with or enable their channel partners?
• Did their company sell one product, a suite of products, or a platform? Did that change over time?

How much of their time was spent in front of customers in their last few roles?

• All customer success leaders should be spending some time with customers, regardless of their target customer segment.
• In an enterprise or mid-market motion, this % should be significant.

What is their strong suit within post-sales?

• Do you need a professional services leader to help with implementations? Or do you need a support expert who can quickly scale up worldwide 24/7 help centers? More on this below.
• Because Customer Success is a relatively new function, many current post-sales leaders will come up in Sales, Product, Support, etc. How does their background color their perspective and strengths?

How have they typically been evaluated?

• What metrics were attached to their role? Why?
• Should have quantitative data available to point to churn rates, NPS, Net Dollar Retention, ticket resolution time, professional services efficiency, etc. 

Customer Success Subcategories

Account Management:

• What post-sales revenue did they own? Renewals, upsell, cross-sell
• Did they own a quota?
• How did they segment customers? Size, geography, other
• When/how were new customers handed off to their team? 
• Did all customers go through the same motion?
• What systems did they put in place to monitor customer health and expansion opportunities?
• What changes that they made had the biggest impact?
  

Implementation and Services:

• Did the product require a dedicated training team?
• What did their self-service resources look like? What aspects of the onboarding process were scalable vs. linear?
• Was the product technically complex and how did they implement it with new customers?
• Did they charge for services? Why or why not?
• What was the goal of services - revenue generation, product adoption, or solely implementation?
• How did they price and package services?
• Did they have geographically distributed customers and how did that affect implementation?
• Were they strategic consultants with their customers, beyond solely their own products?
  

Support:

• How technical of a product were they supporting?
• Did they have support tiers in place and how were those defined?
• Were their customers geographically distributed?
• Were their support teams geographically distributed? Why did they choose the locations they did?
• Did geography affect the level of support customers received?
• What was the overarching goal of the support team?
• What did resolution times look like and what did they do to improve them?
• Did they implement self-service support resources? Why? How effective were they?
  

Pre-sales (less common):

• Did they own sales engineering or any other aspects of the pre-sales motion?
• How did they measure success in those functions?
• How technical was the sales motion?
• What was the ratio of pre-sales/technical resources to account executives?

Management Team Success

What were the keys to success in working with the management team at their last company?

• Building relationships with each of the key executives, especially the ones that they’re working with frequently (Sales & Product likely most important)
• Communicating clear expectations and forecasting for what the post-sales team can and cannot deliver
• Standing firm on things that don’t make sense for their team but working to collaborate whenever possible

How do they assess their peers and the company landscape when joining something new? How would they do that in this role?

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