The CS Leaders Interview Guide

Dear up-and-coming Vice Presidents of Customer Success (and CS Job hunters in general),

I have had many of you reach out to me to ask me what you should be doing differently during your interview process to make it to the offer stage.

You're eager to move from the Director to the VP level but keep hitting roadblocks along the way.?

I want you to know that you're not alone.?

Over the past 7-8 years, I have interviewed and participated in hiring multiple execs, held the exec position at numerous companies, and mentored many leaders making this pivot.?

I don't have a magical tidbit to share that'll suddenly make offers rain down, and each situation will highly depend, but I wanted to share a few things that could help you with your prep.?

Paint the picture of how you will drive a positive impact:

• Tie everything you share to the reality of what the company is trying to solve. Understand their pain points, goals, what they want to achieve and how they hope this position will help move the needle.?
• Understand the business. Your potential employers want to see what you'll bring to the table—the scope of responsibility from a Director to a VP changes...a lot. While you are still the head of a department, you are now responsible for helping move the entire company forward in partnership with the other execs. It's crucial to show the hiring committee that you understand how it all plays together and demonstrate how you can help drive an impact.
• Culture. Let them see who you are. At the VP level, you will greatly impact the culture. It'll be an immediate no if the interviewing team cannot see how you'd positively impact and add to the culture.?
• Results. Spotlight the work your team has delivered at previous companies. Being a VP is not all about what you can personally accomplish; it's what you can help others achieve as a team.?
• But... also show what you can do. I have a portfolio that shows things I've done throughout my career. I highly recommend it.
• Critical thinking, decision making, change management... be prepared to show off your skills in these three areas. Have stories, examples, and data that help paint the picture.?
• Know your numbers. Have examples of your KPIs from previous organizations, the levers you used to drive success, and how you have executed with your team against goals. Instead of talking in generalities, talk in reality, and tie it back to show them how this experience will solve the problems they are looking to solve.
• Know your failures. We all have lessons we've learned along the way. They give us insight and help us see around corners. Come prepared to share a few of those lessons.
• Know your audience and what they care about—interviewing with a CFO? A CRO? A CMO? A CSM? They will all care about very different things. Know what they care about, who they are, and their background. Do your homework.?

And along those lines, while you are interviewing, make sure you are doing your research. It's important that you have a good understanding of the organization that you may be joining. This position will be a major part of your day-to-day, and as a leader, it's important that you are somewhere that excites you as it'll increase the impact you can have.?

Here are a few areas to dig in on:?

Business-related questions/stats

• ARR/MRR/ACV/LTV (all the acronyms) -- get the stats, know the revenue model and why it matters.
• Gross Renewal and Net Retention
• Top reasons for churn
• Growth over the past couple of years (revenue and team)
• Runway
• TAM (total addressable market)
• Employee attrition (you may be able to get this from LI)
• What are the key strengths of the business??
• What are the biggest challenges the business will need to overcome in the next 1-3 years?
• Who are your biggest competitors??

CS-Related questions

• What functions live in CS? Renewals? Upsells? Support?
• What are the KPIs that CS is held accountable for? The company?
• Is this a new role or a backfill?
• If you are a backfill, what happened to the previous leader?
• If new, why now?
• Describe the CS orgs relationship with the Sales organization. What's working well? What could be improved?
• What are some of the biggest problems this team is currently facing??
• What problems are you hoping to see this role solve?
• Where does CS report to in the org? CEO? CRO? CCO? This matters more than you think (but I'll save that for a later article).
• Talk to me about the makeup of my potential team. Any skills gaps that are obvious?
• What does success look like in this position??
• Have you had any attrition on the team? If so, why?
• What does the tool stack look like?
• How is tech debt addressed?

Team-related questions

• How do you measure and invest in team engagement?
• How have you kept the team unified with the new remote/hybrid environment?
• How do you plan what the company and teams will work on?
• How is the product roadmap created?
• What does accountability look like here if goals are missed?
• Tell me about the dynamics of the exec team. What happens if folks disagree on a direction?
• How does budgeting work for hiring and investments in the team??

Board-related questions

• Will this position participate in board meetings? If no, how is CS represented to the board?
• What's the makeup of the board??
• What do board meetings look like? What topics are generally covered??
• What are the expectations of the board for this position??

Lastly, do your research on the company.?

Things that you should check on or do:

• Become a customer! Sign up for an account (if possible) on the platform. What's your experience like? Keep this in mind, as this is what you will support.
• Click through everything on the company website. Read through the Help Center. Get a good understanding of the product.?
• Read both customer and employee reviews. Google the company and see what's out there!
• Look at their social media accounts and read comments.?
• Read through job descriptions for current openings, especially those in your organization.?
• (If the role is not a confidential hire) Reach out to previous employees and ask them about their experience. Remember to take your findings in as a data point and not gospel.?
• Check out funding and investors on Crunchbase. Get an understanding of the investors, who they typically invest in, and their reputation.?

While this is not the end-all-be-all guide, the key to success in any interview situation, regardless of level, is that you prepare. No one expects that you will know all the answers all the time, but good preparation shows every single time.?

Side Note: Thank you to anyone that shared any of these questions with me at some point in time. I'd like to claim to be the genius that created all of these questions, but I am sure that someone at some point either asked me these questions in an interview or shared the questions with me, and they just stuck with me along the way. If you are one of those folks, thank you.