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CSM from the Trenches: Mentors – Sara Masson, Senior Customer Success Manager, Loopio

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 CSM. The goal is that by sharing our experiences, we’ll be able to learn and apply more practical advice / practices to our customer success careers.

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

Company: Loopio
Location: Toronto, Canada
From: Sara Masson, Senior Customer Success Manager

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?

Our team has recently implemented a “top tip” sharing as part of our weekly team meeting, and it’s had a huge impact. Whether it’s a new calendar tool that shows multiple time zones at once, a great email subscription platform to stay on top of industry trends impacting our customers, or a new screen capture tool that allows us to communicate with our customers more efficiently, everyone on our team is constantly stumbling upon these micro-wins.

By taking 5 minutes a week to step back and share these with the rest of the team, we’re constantly improving as a team, gaining efficiencies, and allowing every team member to contribute to the success of our 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?

I’m a huge fan of blocking time based on how I work, to make sure I’m proactively setting up my day for success.

I get into the office early, and set aside my first half hour of the day for big, creative initiatives. The beginning of the day is when I’m at my most creative, and it’s important for me to leverage that time effectively, instead of diving right into emails or calls.

From there, I block off the next hour to do proactive outreach to customers. This is helpful for a few reasons. The first is that if I leave this for later in the day when I’m busier, it’s much less likely to get done — there are always too many things that pop up when you’re in the full swing of your day! The second is that I work with customers in a variety of timezones. By sending emails out when half of my customers are still comfortably in bed, I ensure that responses come back at a trickle throughout the morning, instead of all at once.

Question 3

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

My favorite book right now is Radical Candor. It’s a phenomenal read that speaks to open and honest communication, taking ownership, and effective communication. The communication methods illustrated can be equally applicable for anyone who needs to become comfortable with the art of the difficult conversation.

In terms of thought leaders, I would be remiss if I didn’t mention our CEO at Loopio, Zak Hemraj. Joining Loopio in the early days of our organization, it was immediately evident that we had top-down buy-in on the value of Customer Success. I’m constantly hearing from Customer Success Leaders who spend half of their time (or more!) trying to gain executive buy-in. For any leadership team that is looking to drive a Customer-Centric organization, the biggest lesson I can share is to let your Customer Success team focus on your customers by providing them with your support.

With clear top-down buy-in, we are able to focus our attention on strategy and execution, instead of splitting our focus so heavily into trying to gain organizational buy-in. With great focus comes great results!

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”?

Churn is everyone’s least favorite word when it comes to CS, but when you’re looking at a favorite failure, it’s the most obvious one to dive into.

For our team, any time a customer is lost, we like to ask the question — if we had unlimited resources and time, could we have retained this customer account?

If the answer is yes, it becomes a question of scale — what can we do today to implement those actions in a really scalable way. If the answer is no, we can rest confident that we already did all we could there. It’s a really effective question that allows us to prioritize and learn, and constantly improve our customer experience.

Question 5

What do you find most fulfilling about being a CSM?

I know that many of the people I work with have never had to implement a new software before. To help someone drive impactful organizational change is not only helping to solve the real problems they face day-to-day, but also a huge career milestone for the people I’m working with!

I love making being able to form genuine relationships with my customers, make an impactful difference in their day-to-day life, and be a part of a huge career milestone for them.

Question 6

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

My best piece of advice to any CSM is that any time your customer shares something new with you (whether it be a new workflow, goal, or use case), imagine you’re immediately going to have to explain it to a key internal stakeholder. Find someone on your team who’s inquisitive and always digs deep, and picture them. If no one immediately pops to mind, picture explaining this in a meeting with your CEO.

Imagine that you’ll be asked questions — how is your customer implementing this new process? Why did they decide to go the route they did? What are they going to be looking at when it comes to measurements?

If you wouldn’t feel confident explaining your customers concepts to this key stakeholder, you don’t understand it well enough.

When you ask questions because you care about the answer, and genuinely want to develop a deep understanding, it’s obvious — and your excitement is infectious.

Question 7

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

The one CS principle I try to live by is focus.

In today’s world, there are so many constant distractions — smartphones, email alerts, text messages and more. Everyone is constantly interrupted, and it’s incredibly rare to have 100% of someone’s attention.

When you’re speaking to a customer, don’t have email, Facebook, or any other distractions open in the background. If you give someone 100% of your attention, they can tell — and it’s incredibly valuable to drive productive conversations, and meaningful relationships.


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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