How to Get Hired as a Customer Success Director Image

How to Get Hired as a Customer Success Director

In January, as a result of a merger, I started to search for a customer success leadership position.

Over the course of a few months, I met with many CS leaders and got to hear about their challenges and also learned many lessons about the search process. The easiest way to move into leadership is by being promoted at your current company. However, that may not be an option, and this post focuses on how to be hired into a new company.

Title confusion

There seems to be some grade inflation going on. Some companies are calling their CSMs Customer Success Directors (CSD) instead. A closer look indicates that they are looking for an individual contributor. To me, a CSM manages accounts and a CSD manages people. Just to add to the confusion, you will sometimes see “Manager, Customer Success,” which is a people manager. As you move up a level, there are VPs of Customer Success. This can either be someone who manages CSMs or all post-sales tasks (support, onboarding, etc.). It’s important to read the job description to determine what the employer is looking for.

It’s difficult for a CSM to make the leap to managing people and it’s just as hard for a CSD to become a VP. Companies are looking for someone who has been there, done that—they’re often risk-averse. That said, last season, the Red Sox took a risk and hired the Astros’ bench coach, Alex Cora to be their manager. In his first season he won a World Series ring. If you are looking to become a director, consider a smaller company with fewer people or functions to manage.

Be careful what you wish for

Middle management is difficult. You have more information but not enough juice to make business decisions. Middle managers not only need to learn how to manage up and down they also need to manage across and develop relations with the other managers. If you aspire to become a director, read this article, Middle Managers Deserve More Respect:

Middle managers are our leaders. […] Not only do they know how things get done, they ensure that things get done. […] They know far more about what employees need and what customers want than senior leaders do. […] In spite of all of this, middle managers are seen and treated as expendable. When times get tough, their numbers get cut as if they were deadweight. […] Instead of releasing managers, perhaps senior leaders should be thinking about releasing their potential.

Positioning yourself

There are literally hundreds of CSM openings. Customer success is one of the top 10 fields for employment in the tech sector and the CS community is starting to grapple with the shortage.

Now that you’ve decided to start your search, you need to think about how to best position yourself. Are you tactical or strategic? Do you have multiple skills or specific domain expertise (especially important for health and cyber security)? You may need a few versions of your resume based on the openings. This is not dishonest. Think about companies that market their product to different verticals.

A fantastic way to position yourself and expand your network is to do some blogging or public speaking. These activities will also enhance your LinkedIn profile and resume. Imagine the impact of this follow-up email after interviews I’ve been sending…

Thanks so much for your time. During our conversation, I mentioned my blog post, 4 Ways Product Can Help Make Customers Successful, that Gainsight published. Most of the ideas relate to connecting the dots with customers and it provides a window into my approach to customer success…

Finding opportunities

The best places to look for customer success jobs are LinkedIn, Indeed, and Gainsight’s Customer Success Career Hub. My experience says that for every 20 CSM openings there is one in leadership. Recruiters are generally placing VP level candidates so they are not that helpful for a CSD. If you are ready to start a public search, make sure to check this box in your LinkedIn privacy settings.


It’s also time to activate your network as they can refer you and may know about hidden opportunities. A fantastic group to connect with are your vendors. My contacts at Influitive and Gainsight were able to make some great intros for me. Think about it: their CS teams should know who is coming and going at their accounts. Also, do not limit yourself to companies in your city. I looked at west coast and EMEA companies looking for a CS leader in New York. A few were open to Boston, especially if they needed someone to build a team or their CSMs were remote.

Think like a salesperson by keeping the funnel full with prospects in all stages. The quicker you can either move the opportunity out of the funnel or deeper into the funnel the quicker you’ll find a job. Remember, internal recruiters are doing the same thing with their prospect funnels. I had a few opportunities where I had a great call and was told to expect an interview with the hiring manager. In the end, the hiring manager did not want to speak with me as they were too far into their process.      

Once you find the opening

If you know somebody at the company, have them refer you. The advantage of a referral is their internal recruiters want to encourage references and should pay more attention to your resume. If your referrer has direct access to the recruiter, they will most likely get you the phone screen, even if it is a courtesy. Then it’s up to you to shine.

If you are in full search mode you’ll recognize the newly posted positions. Apply as soon as you see them. There is an argument to wait a few weeks and hope the employer is getting discouraged and that you can become the “knight in shining armor.” You run the risk of being too late.

Lessons learned

  1. Most of the internal recruiters are okay, and occasionally you will find a great one who knows the business and will coach you as you move through the process. Remember, they’re trying to add value to the business by presenting the best candidates as quickly as possible. With that in mind, you have a mutual goal.
  2. Do your research on the company and come up with your two or three key differentiators. Try to weave them into your cover letter, interview, and follow-up communications.
  3. Apply for as many relevant jobs as possible and take every meeting. The more you interview, the better you will get at it. Two-to-three months after I was told no by a few companies, a good percentage of the positions were still open. Could it be they are waiting for the perfect person? Or is everybody saying no to them? My theory is that some companies use the hiring process to figure out what they are looking for. Here are examples at both ends of the spectrum:
    1. A cyber security company advertised they were looking to back-fill with an out-of-the-box thinker or change agent, and throughout the process, that’s how I positioned myself. When they finally said no, they wrote that they were looking for someone more tactical.
    2. A company was looking for a CS leader. As this was a new position, they were up front, not being sure about their timing. In the end, they decided to delay for six months.
    3. Neither of these scenarios is unethical, but it helps to understand the employer’s thinking. You should ask if this is a replacement or a new position. In either case, the company will be making mid-course corrections as they meet candidates. If it is a new role, you can probe in order to determine how much soul searching they are doing. If it’s a replacement, you may want to ask why the person is leaving. A good question to ask is how will the position evolve over the next few months? If they don’t know, it may mean they are using the search to help define the role.
  4. During the interview, steer the conversation to your strengths. Talk about segmentation models, use case studies, data integrity, or anything else you have expertise in. Having a print-out or a PowerPoint slide on a relevant topic gives you an opening to talk about it, explain it visually, and it’s a nice leave-behind at an in-person interview.
  5. Think about what you will do when the interviewer admits they did not review your resume. It really happened! I froze and should have said, “Here’s my resume, why don’t I get a drink of water and we can talk in two minutes?”

In the End

The good news: I will be joining Luminoso as their Director of Customer Success reporting to the CEO. I got the furthest in the process when an internal person referred me. However, at Luminoso, I just submitted a resume and the timing and fit were just right.

It took three months and 30 applications for both Customer Success and Customer Marketing/Advocacy roles:

  • 40%: Never heard back from the employer.
  • 20%: Did not get a phone screen, but did get a note.
  • 15%: Did not get past the phone screen.
  • 25%: Went on-site for either a multi-hour or executive interview.
  • One formal presentation, one aptitude, and two personality tests taken.

What’s on the mind of CS Leaders

The two things I heard over and over again were:

  1. How do you have CSMs become more consultative and strategic? My response was to bring on some CSMs with domain expertise. In an ideal world, having a balance of CSMs with customer success backgrounds, internal hires, and domain expertise should create an environment where CSMs learn from each other. It’s a major bonus if you can identify someone with two out of the three.
  2. How do you develop career paths for CSMs? My response was progression through account segmentation. However, it may be that a CSM can only progress in their career by going to a new company and leaders should be willing and able to coach their CSMs.