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CSM from the Trenches: Mentors – Jesse Brightman, Head of Customer Success, stensul

For those just joining our blog series CSM from the Trenches, welcome. This series, now a community for frontline Customer Success Managers (CSMs), discusses trends, best practices, and advice that can help the frontline.

Being on the CSM frontline allows us to directly influence the success of our clients. I love that; as our clients are successful, we’re successful. Each day we learn from the trenches what it takes to make clients happy and successful.

Mentor Questions

We recently launched a new segment of the series that focuses on 7 mentor questions for the frontline. The goal is that by sharing our experiences, we’ll be able to learn and apply more practical advice / practices to our careers.

Let’s get started with this week’s post!

FromJesse Brightman, Head of Customer Success
Location: New York City

Question 1

What is one customer success best practice you’ve applied in the last few months that has had a positive impact on your success in your role? How has it helped you?

Shrink variability to increase predictability. It all comes down to pattern recognition – you can look at patterns of what makes customers successful, grow, and renew, as well as what has made customers bad fits or not successful. As you test and gather more data points, you can start to distill best practices. From there, you test, get feedback, and fine tune. The more you can do this, your processes and operations become more repeatable and scalable, and ultimately allow you to accurately forecast the health of an account based on your operations.

In building CS teams, it’s important to not say, “this is Carolyn’s way vs. Kevin’s way of doing things,” or “this is how we do it for Acme Inc.” Rather, you can take full ownership and put yourself and teammates in the driver’s seat and say, “this is our proven methodology of doing things, and here’s why it will ultimately be a fruitful partnership.” Consistency and repetitions, like many things in life, helps create mastery. It also ensures that customers get the same excellent experience no matter who they are partnering with on my team.

Question 2

What are one or two things you typically do during the first hour of your day that leads to a productive day?

Monday morning 15-minute team stand-up to ensure we know the priorities for the week. Every single day, I create a to-do list and prioritize based off what is urgent versus important. After I do that, I pretty much delete everything except for three manageable tasks.

Question 3

What are one to three books, blogs, or thought leaders that have greatly influenced your career, and why?

The Score Takes Care of Itself by Bill Walsh. Bill was the master of getting everyone to steer in the right direction by focusing on the details. He held standards of performance that everyone bought into 150% and had the results to show for it. When you do this with your team and get people rallied around your mission, and then see the results from it, people get that much more excited and bought in.

Question 4

How has a failure, or apparent failure, during your time as a CSM set you up for later success? Do you have a “favorite failure”?

As a CSM, a significant learning opportunity was not setting executive commitments and expectations with new partners coming onboard. It’s great that someone signed a contract, but early in my career I failed to outline specific responsibilities I expect of them in a partnership (actions, communications, meeting attendance). They control budget, and the value story we create for them is drastically different from that which gets told to our users or main day-to-day contact. In a world of so many solutions, it’s critical that we land on a buyer’s top 3 solution list, otherwise we are toast. Additionally, holding that relationship right allows us to call in favors, or even better, become the solution of choice when she/he moves companies or to a different role.

Question 5

What do you find most fulfilling about being a CSM?

I love investing in my team’s growth. I see growth in their skill-sets manifest in better customer relationships and results. If you are a people leader- in any part of the organization – your top priority should be that you have people’s careers in your hand that you are responsible for growing.

Question 6

If you had to give one piece of advice to another CSM, what would you say and why?

1) If it’s good for your customer’s business, it’s good for your business and, 2) You cannot exceed expectations if you do not set expectations.

Question 7

What is one customer success principle you try to live by?

The best way to retain customers is to continue to grow them.


Want to share your mentor advice? Submit your answers here.


Here are other customer success resources:

Customer Success eBooks:

Customer Success as a Culture: Customer Success Leaders Edition

Ultimate Guide to SaaS Customer Success Metrics

Other CSM from the Trenches Posts:

Sam Feil, ClientSuccess – 3 Best Practices that Drive Powerful Customer Experiences (How to Avoid the Dreaded Car Dealership Experience)

Erica Newell, Marketware – 5 LinkedIn Best Practices to Build, Grow, and Improve Client Relationships

Mieke Maes, Intuo – 5 Keys to an Effective Customer Apology

Priscilla Zorrilla, 15Five – Asking the Right Questions to Challenge Customers

SoapBox Team Shout-Out

Learn more about how ClientSuccess can help your company develop a strong customer success methodology and strategy with easy-to-use customer success software by requesting a 30-minute demo.

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