skip to Main Content

CSM from the Trenches: Mentors – Sheik Ayube, Director, ESG (Customer Success as a Service)

Welcome to our blog series CSM from the Trenches, a community for frontline Customer Success Managers (CSMs) that discusses trends, best practices, and advice for 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

This segment of the series 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!

From: Sheik Ayube, Director
Company: ESG (Customer Success as a Service)
: Denver, Colorado

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?

“Helping will sell, selling won’t help”. The best advice I’ve received from a mentor is that authenticity always wins. And unless you have a GREAT relationship with your customer/prospect, I wouldn’t recommend saying “I need to hit quota, can you help me out?” Any experienced buyer can pick up on when they are being “sold”. As an alternative, genuinely wanting to help and being a valuable resource has lead me to success in every role of my professional career. Give it a try, consistently, and I think you’ll be pleased with the results.

Question 2

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

1. Caffeine
2. Organize & Prioritize the day/week – A concept I subscribe to is time blocking. With dozens of things to do during any given day, time blocking helps limit distractions, and avoids analysis paralysis. Looking at to-do list of 30+ things can be overwhelming, and can often waste precious time evaluating what to do, rather than just doing it. Examples of time blocks I use: Emails, Meetings, Thought Leadership, Outreach, Admin, Personal Development etc. I’m not a superhuman, and some days/weeks it’s impossible to do it all, so I would recommend reevaluating and re-prioritizing these blocks on a regular cadence.

Question 3

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

1. The Obstacle is the Way
This has been the most impactful book to influence my life. Every success story starts with a successful mindset. I subscribe to Stoicism to keep my mind in the game when life/work inevitably gets tough.

2. Let’s Get Real, Or Let’s Not Play
We’ve all been on both sides of the buyer/seller relationship. This book is critical in understanding WHY this relationship is often times dysfunctional, and HOW to avoid those pitfalls.

Thought Leaders:
+ Michael Harnum
+ Ed Powers
+ Natalie Fedie

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”?

In my opinion, failure is a better teacher than success. A good portion of my CS philosophy today, developed through trial and error. i.e. I’ve lost deals to my competition. Sometimes big deals. Rather than blaming it on one of the many, many variables that might be out of my control as a CSM, here is a thought:

  1. Taking some accountability will change your mindset considerably
  2. Don’t be afraid to ask for feedback
  3. Now that you’ve owned the ‘failure’, and have feedback on why – consciously try to avoid those missteps in the future. You’ve only failed if you are unable to correct the behavior that lead to the outcome.

Question 5

What do you find most fulfilling about being a CSM?

I love everything about the B2B world. The opportunity a CSM has to interact with dozens of companies, to intimately learn their business (if you’re doing it right), and to build a lifelong network are all WINS, and should be treated as such.

Question 6

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

Stay organized. And stay focused. Even if you’re a new CSM, and still learning the business – staying organized will help you get those early wins. Those early wins will build your confidence & build momentum, that will propel you further and faster than others who can’t manage to do this.

Question 7

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

Be a student of the game – never stop improving your domain knowledge, to best serve your customers and your company.


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 – 11 Books Frontline Customer Success Managers Should Read Right Now

Cole Sanders, ClientSuccess – 3 Principles I Learned in My First Year as a CSM

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

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

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.

Back To Top