From CSM to Director

Kevin Mitchell Leonor

Hello GGR team,

It's been close to 2 years now since I begun my customer success journey. It's been quite a ride and now I am looking towards the next move. I have many avenues I am looking at to continue growth and to become more and more of an asset to the overall Customer Success community. One of which is to build my roadmap to becoming a director of CS.

I would love to hear your advice to getting myself prepared and when you knew it was time to start applying for Director roles.

For context, I'll share with you my journey thus far:

Hand selected for the pilot of a Customer Advocate Partner program aimed at current Venture Capital customers
Created feature journey maps at Duetto and RingCentral
Established as a subject matter expert on Customer Success internally at Duetto and RingCentral and within the community
Developed framework for playbook creation at Duetto
and of course the contributions I have made in Customer Success thought leadership within the community at large.

EDIT: as far as people management, I can leverage my time as a sales coach at Comcast, Supervising Officer at Transportation Security Administration, and Assistant Store Manager at Sprint.

I look forward to hearing about your journeys and the advice you could give to an aspiring Director.


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Kevin Mitchell Leonor
Customer Success Manager
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Parker Chase-Corwin

Hi Kevin - good luck in your journey - sounds like you are on your way.  Two ideas came to mind after reading your post:

1) Learn the business and commercials of CS. Your accomplishments sound impactful, but largely tactical.  As a director and leader of CS programs, you'll want to have a solid command of the commercial aspects of CS so you can move from "working in" your program to "working on" your program. Challenge yourself to understand the economics behind loyalty and adoption. Be able to justify additional investment from your leadership into the program because of gaps you've discovered in the journey mapping and correlate that to revenue. As a director, you'll need to be able to advocate for the needs of the team and program and to do that, you'll need to be able to articulate financial impact.

2) People management. Building out a complimentary team, hiring the right CSMs, establishing goals and role clarity... lots goes into building out the right team to execute on the program you have designed.  Spend time learning out hiring techniques and what characteristics make for strong CSM teammates, and then spend time on learning coaching and management techniques. 

Hope that helps!

Kevin Mitchell Leonor

Love it. I've been reading the Customer Success Economy by Nick Mehta. What other resources would you recommend regarding the economics behind loyalty and adoption?

i have some experience in project management back in my Comcast days when I lead an initiative to cross sell Verizon Wireless and Comcast Cable. A lot of business justification for implementing key tech stacks, headcount, etc.

Kevin Mitchell Leonor

Also, another follow up question, what were the milestones you hit where you felt it was time to make that leap?

Shari Srebnick

Hi Kevin - 

Yes, good luck in your journey! 

I'd echo a lot of what Parker mentioned above regarding the tactical accomplishments, and also the understanding of and ability to create and manage budgets, forecasts, etc.  Also, you'll need to be able to prove and communicate the financial impact your team will have ... and how you will do it.

People management is also of massive importance.  Can you lead, coach, and develop others?  How will you hire and what kind of team will you build? Have you interviewed and hired candidates before?  Many in their first real leadership roles don't realize that they won't have their hands on the tactical pieces anymore and that a large part of the success (or failure) of their team is on their shoulders.  "Leaders eat last" as Simon Sinek would say.  You are no longer an individual contributor, you are responsible for people .. and that cannot be taken lightly.  You are only as good as the people on your team.

I often see folks spending a year or 2 in a CS role and then thinking, "On to the next level!"  But I'd really encourage putting thought into what that looks like for you.  Is it a Director from a Senior CSM role?  What about Team Lead?  Or could it be an Individual Contributor role but at a management level? (those do exist).  If you haven't already, I'd take a deeper dive into what is out there because CS has expanded so much over the years.  If you like being tactical, it might help to look at roles other than Director.

I hope that helps.

Kevin Mitchell Leonor

Definitely helps. I have had my eye on CS Ops Manager too. There are a lot of things I want to influence process wise. That role has been a target of mine for awhile. Any other examples you could think of for IC manager level?

The team building aspect is also something I miss from my days at Comcast as a supervisor/coach. I'm looking forward to those opportunities. Great idea on the IC manager level. Thanks.

Shari Srebnick

CS Ops can definitely be an option to consider if you're interested in developing and influencing process.  From all of the GGR conversations, it's obvious you know how to dig deep on the tactical aspects - this could definitely be a worthy avenue to explore.

As far as other IC roles ... I've seen Customer Success Director vs Director Customer Success.  The former is (where I've seen it) a management-type level role where you're responsible for owning a select few very top tier key accounts.  Many of these roles have a Jr CSM assisting on it, so you'll have the benefit of leading someone without the full responsibility of a team.  

All of that said, before deciding on anything, I'd encourage putting on paper your vision.  What is your vision?  What things do you need to do or think to make your vision real?  What do you *like* doing?  What drives you?  Where you do thrive?  These are just some prompts to help, but I believe if you spend some time on these, you'll have a clearer path to what's next for  you.  Don't just say, well I am here, and X is the next role so that must be what I go after.  Identify what drives  you and have that lead the way ....

Kevin Mitchell Leonor

I like that approach. I'm in an information gathering stage right now, so it was an ultimate goal to start building out a vision. However, the one thing I didn't account for is really asking myself what is it I like to do the most. That changes the conversation slightly which is why I think based on that reflection, I figured out that the maturity of the SaaS org is also a factor. Since I really enjoy scalability, it looks like I would enjoy a startup environment or a pre-scale environment where I can ensure a strong foundation before scaling. Great ideas and it opened up more discovery for me.

Brian Hartley

Kevin - great to hear about your career evolution so far.  It seems as if you have a lot of great experience but what I didn't see was what experience you have mentoring, managing, growing people?  Presumably being a director would also include managing people. That is a big part of your job - you have to motivate and inspire your team to help support all of the operational and tactical programs you wish to deploy.

How would/are you going to handle low performers on your team?   How are you going to provide opportunities for your top performers to keep growing, etc? How are you going to handle team and cross-department conflict?

From a CS standpoint you have tremendous experience in programs, operations, strategy, etc.  I would also be curious about the people management element as that is a huge piece in my opinion.

good luck

Kevin Mitchell Leonor

Thanks Brian.

I was a sales coach back at Comcast and particularly the agents that were underperforming were the ones that were assigned to me. Prior to that I was a TSA Supervisor who had to lead a security team. Coached underperforming and new hire officers and then also challenged officers to take on more responsibility en route to them become leads.

I forget to talk about these things when it comes to my experience because im so dialed into CS that I neglect the leadership hats i've worn and still do well with.

Brian Hartley

Sounds good, looks like you are checking a lot of important boxes.  Good luck!

Kevin Mitchell Leonor

Thanks Brian.

Tiffany Morin

I love everyone's recommendations. When I first took on a Head of CS role, I actually took a risk (and pay cut) with a company in order to take on the extra responsibility i.e. people management, etc. I took a step back to take a massive step forward. Thankfully, I enjoy people managing now more than customer managing and found it to be the perfect role for me. 

I will say; however, to take your time. Part of what makes me a great CS leader is my experience managing customer. I had a CSM once tell me I was the first manager she'd had with real-world experience. Prior to that, her managers could not help her navigate complex customer relationships or even properly forecast churn! This put her and the entire team at risk...basically swimming upstream without a paddle for support. 

Another piece of advice i'd give is to find a good mentor. As I took on more responsibility and started navigating situations that were new, I leaned on my mentors to help based on their past experience.