Customer Success Battle Scars: Don’t F@&k Around With Hiring

“I want your job”. Who has been in a leadership position and not heard that at least once from a candidate in response to asking about their career objectives? I was no different when I was younger but I was probably not as brash. I knew early on in my career that I wanted to run my own Customer Success team and had a mission of creating the best customer experience possible. I was very lucky to have helped do this at Eloqua (Oracle), Influitive, and now Bluecore but it’s definitely not as glorious as it seems. Don’t get me wrong, I love what I do but it’s a role that requires the right acumen and the drive to keep learning and improving. It’s not for everyone. You also need the right guidance – this is where I want to help.

I learned some of my most valuable lessons growing the Influitive Customer Success team from 4 to almost 30 people while our customer base grew 10X in just two years. These lessons are now part of my DNA and I have the battle scars (grey hair) to prove it. It’s important that Customer Success (CS) leaders who have lived through these experiences in fast growing companies not only share all of their great tips but also the challenges and the mistakes. I’m not ashamed at all to admit where I’ve went wrong – it’s these mistakes that have made me a better leader.


In the next series of posts I’ll outline some of my life lessons in a fast growing start-up.

Don’t F@&k Around With Hiring: Plan Ahead, Hire Fast, & Hire Smart

Hiring is one of my key strengths. I love interviewing and hiring amazing people and I’ve had excellent retention rates for those that I’ve hired in the past. I remember sitting around the table with my CS team at Influitive and one my team members said to me, “Chad, we have a great team here. Make sure you hire carefully”. I responded by saying, “it’s the one thing that keeps me up at night”. Which was true. I was proud at the team we built but conscious of not wanting to mess up the culture. Hiring the right people gets harder as your team grows and as your start-up picks up momentum which is why you need to be vigilant and prepared.

I’ve worked with some of the best teammates over the years and understand the right qualities that I’m looking for in candidates for the particular role at the particular stage that the company is in. However, as many CS leaders know, hiring Customer Success people is extremely difficult and you need to have a good pipeline of candidates. In addition, you need to carefully plan the hiring for this role to ensure that you stay within your hiring budget while ensuring you have the right amount of resources when sales gets on a roll. It’s a delicate balance.

During my tenure at Influitive, we had experienced a small lull in new deals and then suddenly had a massive jump in sales at the end of the year that my team was not fully prepared to handle. This put an enormous strain on the team and forced me to strap on my hard hat and onboard new customers. As an aside, the CS leader should not be managing customers directly after you hit a certain level of annual recurring revenue (ARR) (I recommend setting the bar at $5 million ARR). When you throw in some inefficiencies in our recruiting process which delayed bringing on new people, you have a perfect $h!t storm: your CS team is overworked and is only focused on executing, the CS leader is stuck in the weeds and the team doesn’t see any relief on the horizon. I also needed to shift my CS resources to meet the need of these new customers which impacted the experience of our existing customers and we began to see a rise in churn. The sad thing is that the sales team is doing exactly what it should be doing – kicking ass and taking names yet instead of celebrating, you’re Customer Success team is hyperventilating.

Instead of celebrating, you’re Customer Success team is hyperventilating

Here is what I would have done differently:

  1. I would have tracked the sales pipeline religiously and determined how much of the forecast was accurate vs. fluff. I would have worked more closely with my head of sales.
  2. I would have had external recruiters sourcing new candidates for me and not have relied solely on internal recruiters (even though they tell you that they can fill these positions for you).

NSR (Never Stop Recruiting)

Here are some additional hiring tips:

  1. Always have a pipeline of candidates – never stop recruiting (NSR).
  2. Be prepared to ditch the existing hiring plan and negotiate a new one with your CFO to meet the demands of new situation you are in. When money is flowing in based on more sales then anticipated, previous budgets go out the window.
  3. Always hire two people for a team. I had started a team to focus solely on onboarding new customers to meet the need that I anticipated but only hired one person for the role. This made it difficult for that person to both onboard new customers and revise the customer launch the process. Don’t make that same mistake.

Hiring will always be difficult so you should have multiple back-up plans. While I don’t recommend the head of CS own clients themselves after a certain revenue level, you should always be recruiting. I’m new to New York, I’ve started to network and attend local Customer Success events. I’m constantly on Angel’s List and LinkedIn looking for new talent. Hey – if you know someone who is interested in Customer Success and in NYC, hit me up. 🙂

In addition, you also need to know when to put a proper CS leadership team in place to free up your time more so you can perform better in your role as well as be a more effective executive for your company.

I hope you found this helpful. To the candidates that I interview and work with that want my job, I say: come take it. There is no better honour for a leader then to see their team succeed and ascend in their careers.

My next post will cover another area I continue to work on and is the achilles heal of many leaders: Communication.

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