The First Five Customer Success Hires at 15 B2B SaaS Companies: An Up-Close Look

Are you a party-of-one Customer Success leader at a SaaS start-up? Or maybe a founder with the excellent problem of too many customers to handle?

Well, this one’s for you.

Vitally recently surveyed Customer Success leaders in the SaaS industry with the goal of answering these two questions: 

  1. What are the first five roles SaaS leaders should hire for when they’re building out a Customer Success function for the first time?
  2. What's the best advice you have for start-up leaders who want to make their first few Customer Success hires in 2024?

You can learn more about our research process at the bottom of this blog post, but we figured we’d cut right to the chase and show you what we learned. The infographic below lists the first five Customer Success hires made at prominent B2B SaaS companies. Use this data to inspire and inform your Customer Success hiring decisions in 2024 and beyond.

first customer success hires made by b2b saas companies customer success infographic

Digging Deeper: Here’s What Else We Learned

As you can see, there’s no one-size-fits-all, perfect formula for making those first few Customer Success hires. Every company does things a little bit differently. 

To us, it seems like “the perfect hiring decision,” if there is such a thing, depends on: 

  • What your customers need: Who would help customers stay on and grow?
  • What your team needs: Who would contribute exactly the expertise you lack?
  • What your business needs: Who would add to your company culture?

Despite the varying first five hires in the infographic above, there were tons of similarities between our respondents’ free-response advice about hiring Customer Success professionals in 2024. 

Here are three of the most popular recommendations from people who’ve "been there, done that" with early-stage Customer Success hiring:

#1. Find People Who Are Comfortable with Ambiguity 🔎

You want to work with people who are quick to say, “I don’t know, but I’m confident we can figure it out.” Whether you’re on the hunt for a great CSM or a stellar VP of Customer Success, hire someone who doesn’t need lots of in-place processes or crystal-clear job responsibilities. Start-up life is not for them if that’s what they’re looking for.

Instead, take this advice from Karlie Briggs, an early stage Customer Success professional at Lessonly (acquired by Seismic) and now Elate: “Hire someone with a servant attitude and a can-do, roll-up-their-sleeves mentality that can — and will — comfortably live in the gray area.” 

Tyler Diderich, the founding Customer Success hire at his current company, runZero, shares a similar sentiment: “Your first few team members need to be builders. They can be young up-and-comers or seasoned veterans, but either way, they need to be ready to build content, processes, or whatever else comes down the pipeline.” 

In short, find people who check their egos at the door and get excited about building a Customer Success function from the ground up.

#2. Choose People Who You’d Be Happy To Promote One Day 💸

This advice might feel generic at first glance — shouldn’t we always seek to hire people who show promise and growth potential? Yes, but it’s never more critical than when you’re hiring people who are building a department from square one. 

The first few hires within a Customer Success department quickly become seasoned experts about your personas, processes, vision, and more. Any candidate you consider hiring needs to be someone you could one day see leading the Customer Success organization.

Kristen Gray Psychas, a Sr. CSM at Banzai who previously was on the founding Customer Success team at Nutshell put it this way: 

“Talent hoarding at an individual contributor (IC) level can stifle departmental scale. Be sure to preserve space for growth opportunities for ICs to move into director positions. You’ll responsibly scale your CS organization, modestly increase profit margins, reduce employee turnover, and avoid 'rip and replace' customer success initiatives.”

We couldn’t have said it better ourselves. Hire people who you can’t wait to promote.

#3. Hire People Who’ll Focus on Scale and Prioritization 📈

If you’re building out your Customer Success team, either by hiring a leader or bringing on your first CSM, resist the urge to ask them to create a super white-glove experience for every customer. It simply won’t scale. 

Our respondents talked about sourcing candidates who have experience prioritizing high-value CS motions. Mahalia VanDeBerghe, a customer enablement professional turned sales enablement practitioner who worked at Socio (acquired by Cisco), says this: “Choose people who’ll focus on scaling for the future, rather than building everything to be high-touch. Ensure that as much as possible is self-service and intuitive; this will help you scale each rep’s reach and enable your team internally.”

Speaking of those scalable, high-value CS motions, the Head of CS, Support, and Compliance at Salesmsg, Ben Francis, has some advice for successful deployment, too. He encourages early-stage Customer Success leaders “not to deploy all of their CS motions at the same time (think onboarding, training, retention, growth, etc). Prioritize and measure your impact.” 

This reminds us of grade school and learning about the scientific method; in the same way we were taught that you’re only supposed to test or change one variable at a time in an experiment, Ben recommends only changing or implementing one new variable at a time for customers so you can measure what really impacts the bottom line. Ben (along with the world’s greatest scientists) takes a patient, methodical approach, and it seems to be working well for them. 

More Great Advice on How to Prioritize CS Hiring at Your Company

Here's what some of our other survey participants said when we asked them for their advice on making their first Customer Success hires at a B2B startup:

Linnea Olson, Senior Customer Success Operations Manager at, former Manager of Global Customer Programs at Jamf
"Start with a good operational foundation. If you hire too many CSM individual contributors without someone to support them operationally, you will end up with a fractured team doing a ton of manual work that wastes their time."

Tom Maxwell, Head of Customer Experience at Ignition
"Make sure you are hiring people who are comfortable with ambiguity and change. In the early stages, your historical data is limited so you'll probably be changing your processes and playbooks regularly as you learn and grow. Try to identify the core problems you are solving for vs. just hiring CSMs for the sake of having CSMs."

Mark Stagi, VP of Customer Success at Avoma, former Vice President of Customer Success at AppZen
"Think about the customer journey and do you need to split out the journey with different groups (implementation, renewals, account management) and what those skillsets are for people. Make sure you don't hire too broadly and set the foundation well from the very start."

Nina Wilkinson, Director of Customer Success at, former Director of Customer Success at AspireIQ
"Prioritize culture, and consider hiring folks that have the background or expertise of your customer base. At AspireIQ our platform was built for running influencer marketing programs at B2C companies. Our first CS hire was a former social media and influencer manager, and she has since become the company's Director of Marketing Strategy and has influenced their product and built out customer education based on her experience in the field. It was super helpful to have someone who could speak in our customer's voice and translate those messages cross functionally."

Corey Kime, Head of Customer Success at Singuli, former Vice President of Client Experience at Lessonly
"There's no one-size-fits-all right answer to this question, but generally speaking hire athletes, i.e. people who are able to check the box on a few different parts of the customer journey. How far they can go will likely depend on the complexity of your business."

Anouk van Tuinen, Head of Sales & Customer Success at Slite, former Senior Manager of Customer Success at Miro
"Get leaders on board that are excited to get their hands dirty, and do the work themselves."

Devyn Mikell, Co-founder at Qualifi
"Have a strategy first. It doesn't have to be all pretty and perfect, but have a repeatable process for the new CS person to step in and run. I would start by documenting everything you do as a leader to get the customer to value and to retain them (ex. kickoff calls, onboarding, service tickets, QBR's, etc.) then find someone who has experience doing those things.

"It's important to find hires who are really talented at doing the job, but also strategic enough to see where things could be improved. If you have the budget to bring in a CS person and hire a fractional CS leader to build the program with you, that would be really beneficial as well. Focus on nailing this from the beginning because it'll make the difference for you long term."

That’s All For Now

If you’re an early-stage SaaS founder or Customer Success leader hoping to grow your team, we hope this research was helpful to you and guides your decision-making.

In case you were wondering, conducting small studies like this one is a new motion for the Vitally team, and we’re curious if you’d like to see more content like this. If you like what you’ve read or found any value here, tell us what you think we should study next by dropping us a note at

About Our Research Process

We gathered the data and insights above in December of 2023 using this survey built with Typeform. To get the survey in front of the right audience (i.e. people who are familiar with early-stage CS hiring at either their current or a past organization), we distributed it via LinkedIn, email, and a couple of CS Slack communities. We gathered 16 total responses, and omitted one of them, as the respondent’s Customer Success experience was not with a SaaS organization. 

Special thanks to Lenny Rachitsky for inspiring us with his "First 10 hires across top B2B startups" infographic!

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