My Biggest Mistakes & Biggest Wins Hiring in Customer Success

…to you, it the best rarely will. Hiring managers should be sourcing talent in tandem with recruiters. This is time well spent as it helps the recruiting team align on…

Luke Ferrel | February 22, 2022 | 7 min read time

Article Last Updated: December 21, 2023

My Biggest Mistakes & Biggest Wins Hiring in Customer Success

There are no easy tricks to hiring a great customer success team. It’s a process that requires thought and understanding before you even begin. The good news is; as a customer success leader, this is the type of design thinking you’re accustomed to.

I’ve built multiple customer success teams. I’ve had some great successes and made a lot of mistakes. My goal is to be transparent about both my mistakes and wins – so the reader can adapt these hiring tips to their organization by understanding the ‘why’ behind these recommendations. 

Why hiring the right people matters

it’s important to hire the right people. Why is this particularly important in customer success? Because customer success is a new discipline, and you’re going to have a long road ahead of you defining what you want customer success to be. It’s very easy for customer success managers to turn into support reps or account managers.

If you have pre-defined what you want customer success to be (CS should be an advisory function – NOT technical support, and NOT account management), then you know you must hire for different skills than those departments. Although you may define your department as an advisory function rather than support or account management – there will be internal pressure to do those things. To be successful you need hires who:

  • Have a clear understanding of their role and responsibilities
  • Possess backbone to hold firm, both with customers and internally
  • Can proactively provide value outside of account escalations
  • Improve processes on their own

Who is “the right person”? 

Now that we agree hiring the right person is incredibly important, let’s define who that person is. This is a 4-step process. If you skip this 4-step process you will be shooting in the dark and make building your customer success organization more difficult than it needs to be.

1. Gather Stakeholders

Depending on the size of your organization, there are different stakeholders who should be involved. For the sake of this exercise, we’ll assume a mid-size organization. If these positions don’t exist in your organization, there are people likely fulfilling these roles as part of their job.

–   VP (or top-level leader) of CS. This person’s role in the process is primarily to listen, and provide direction about where the organization is going. Often, we see this play out in organizations as: “We are currently primarily reactive and support based, we need to be proactive and advisory in the future”.

–   Recruiting sourcer/coordinator. This person’s role is to listen to what is desired and be able to translate the discussion from theoretical to tactical. Their goal is to understand HOW to find the profile the team decides on – in the open market.

–   Recruiting manager (or the person who is responsible for filling seats in customer success). Does this talent exist in the marketplace? Can it be had at a reasonable price point. The recruiting manager isn’t going to set pay bands (that’s best left to your compensation team), but they should

–   Trusted front line leader or two of customer success reps. Pick these reps based on who can differentiate high performers and what makes a low and high performer. As principles for hiring are laid out by the team, this person (or people) should be able to define which high performers possess which principles. They should also advise the VP or top-level leader of CS on which skills the team needs improvement – especially in the context of the VP’s future vision

2. Understand Principles

 This is the easiest part of your process to miss. It’s also where you can REALLY differentiate your talent pipeline. When I have made mistakes in the past it has been because we skip this step and go directly to step #4 (Solidify your hiring profile). Every CS organization is different, but there are core principles that make a strong customer success manager. Feel free to define yours with your team, but these 4 make a great start for almost any CS org.

–   Ability to influence executives

–   Advisory ability (can you push back on a senior leader about their strategy, not just their tactics?)

–   Passion for, and ability to explain tech

–   Interest (hopefully demonstrated) in your domain

By defining your principles before you define your hiring profile, you open the aperture on your hiring search. You’re able to hire talented individuals that may not fit your expected background. Not only do you make more talent available to you, you also increase the diversity of thought on your team. 

3. Define your risk appetite

Step 3 is a counterbalance to step 2. Understanding the principles of a strong hire opens the world to your team. Defining risk helps keep us safe. Do you want a team full of experienced CS practitioners? Maybe – but your upside is limited. Do you want a team of high performers who fit your profile, but have no CS experience? Maybe, but you’re taking quite the risk. The answer is probably somewhere in the middle

4. Solidify your hiring profile

Time to get tactical. Define which backgrounds you think are likely to fit your principles as well as your risk tolerance. This is highly personal to your organization, but I’ll share some of my favorite profiles here

Slam Dunks

–   CSMs from similar tech companies

–   Consultants who were customer facing in large firms (MBB, Deloitte, Accenture etc.)

Different profiles I love + why

–   Recruiters- These folks have had to advise and influence senior leaders on one of their most important assets, their career)

–   Financial Advisors – If you have been telling people (particularly well off people) what to do with their money, you likely won’t get scared when they ask about how to optimize their tech stack

–   Military officers – I’m biased here (former Air Force officer). You should be careful to hire those that have wanted to ] change the system, rather than those that are ingrained in some of the slower processes and hierarchy of the military

–   Educators – like military officers, you want those that want to change the system – rather than those who have bought into slow processes and bureaucracy

How to find people

Now comes the FUN! It’s time to go find the right people and build your team. There are a lot of ways to go about finding to build your team. We won’t present an exhaustive list here, rather some of my favorite methods

–   LinkedIn Recruiter – If you wait for talent to come to you, it the best rarely will. Hiring managers should be sourcing talent in tandem with recruiters. This is time well spent as it helps the recruiting team align on desired backgrounds

–   Job Postings – Keep your postings based in the principles you have defined.

–   Internally – At least 1/3 of your team should come from internal resources. CS is a destination for high performers. Recruit high performers within your company, and it will become even more so

–   Referrals – Referrals = good. Go get them. Incentivize your team to refer folks. Everyone who is referred should get at least a phone screen. Not giving a phone screen to referrals will kill the morale of the referrer. If referrals aren’t a good fit, that feedback along with ‘why’ needs to be shared with the referrer. This will turn your whole team into recruiters

How to pitch and land your ideal candidates

Now that we have defined our profile and sourced the best candidates let’s think about how we pitch and land talent. There are 3 core principles to focus on when pitching candidates:

–   Absolute honesty. You will gain credibility by telling candidates the raw truth. For example, if a candidate asks about how differentiated you are from product support and you aren’t 100% differentiated yet – an ideal answer would be “We aren’t as differentiated as we would like. It’s something we’re working on, but when you come in that will still be part of the role”

–   Company first. Mos CS candidates are savvy. They know that company growth and mission will drive the value brought to their careers. If you are growing exponentially, play to that. If you have just recently stagnated in your growth, address that head on. You have to sell candidates on the company before you can sell them on their personal growth

–   Personal growth. Understand what the candidate is interested in growth-wise. If nothing in particular has come up in the interview process, candidates are generally interested in what their career progression will look like and what kind of new skills they will learn 

Next steps

Congratulations! You have found and hired the talent you need to drive your business. Now it’s time to onboard, enable, and engage that talent so we aren’t going through the same process every year. Some things to think about to help your team (which we’ll talk about another time) are:

–   Onboarding

–   Career progression

–   Setting boundaries

–   Operating rhythm


Hiring is THE most important thing you will do as a customer success leader. Take the same time and thought to build out your hiring profile and principles that you would take to build a QBR with a $3MM red account. This allows you to make calculated decisions about risk, open the aperture to find divers stars, and push your CS organization to new heights.

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