June 27, 2019

CSM from the Trenches: Mentors – Tyler Richards, Head of Mid-Market Customer Success, Lucid Software

CSM from the Trenches: Mentors – Tyler Richards, Head of Mid-Market Customer Success, Lucid Software

New mobile apps to keep an eye on

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What new social media mobile apps are available in 2022?

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Use new social media apps as marketing funnels

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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

Our "Mentors" questions are geared toward CSMs receiving mentorship directly from Director-level and above customer success leaders, in order to help them grow professionally. 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: Tyler Richards, Head of Mid-Market Customer Success
Company: Lucid Software
: South Jordan, Utah

Question 1

What is one important lesson you learned in your early customer success days that has had a positive impact on your career? How has it helped you?

I strongly believe CSMs should view themselves, and their roles, as strategic consultants. In customer success, we are ultimately responsible for ensuring the success of our clients by helping them reach their desired outcomes, however, that success may not always come in the form you, or the client, initially expected. When consulting, we often run into scenarios where customers, contrary to popular belief, do not always know what they want. However, their expectation when purchasing software is that they’re also purchasing expertise from a thought-leader in the industry.

Along these lines, I learned early in my career that my responsibility as a CSM was to help my customers successfully solve problems. It was not to simply make them happy. Happiness is not the strongest, or best, indicator of success, however, successfully achieving a desired outcome is. Sometimes, we may have to push back on the client to help them get out of their own way and where they, ultimately, want to be. We might have to tell them, “No, based on what you’ve told me you’re hoping to achieve, this is the best course of action I would suggest for you.”

It’s our job as CSMs to understand our customer’s pain and consult on how to solve that pain. We have to be confident experts to help them realize real value, even (and maybe especially) if it’s different than their initial expectations. Our clients are looking for someone to help them navigate through their problems. CSMs can, and should, be that voice of reason.

Question 2

I’m the first CSM for my company and have been asked to implement a “customer success” program. Where should I begin? What tactics have worked for you?

Previously in my career, I joined a company at a time where the Customer Success organization consisted of only two other individuals. The only CSM at the time had less than three months experience in engaging with our customers. Needless to say, we didn't know much about them, nor what made them successful. We had our work cut out for us to build a Customer Success organization and process without really knowing much about our customer base.

The approach we took was to first understand our customers better; how were they using the product, and what value were they attempting to achieve through our solution? In my opinion, there's really no substitute for getting your hands dirty, especially as a leader. We instituted a training program where my team and I simply began to speak with customers. Our goal was to better understand their challenges and the pain they were feeling, which we hoped would lead us to how we could solve for that pain. We hired a few more individuals and conducted hundreds, maybe thousands, of training sessions over the course of the next four or five months. The information we gathered, as well as the lessons we learned, were invaluable. The insights we gained helped us throughout the rest of the next year and a half of building out our customer success organization and process.

If you are  just beginning to implement a customer success program, there's no substitute for digging in and just talking with your clients. Set up as many meetings as you can to interview them and get to know them a bit better. Ask questions like “What pain(s) have you felt  in your business that caused you to seek out a solution?” or “What was it about our solution that made you believe we could solve this problem?”. This will teach you a lot about what you’ll need to solve for.

Question 3

What are two or three ways you’ve established (or improved) “customer success as a culture” within your organization?

One thing I have found to be very effective are regular meetings with sales leadership, or sales counterparts. Holding these meetings consistently has helped ensure there's an open line of communication between sales and customer success. Even as a frontline CSM, I would encourage regular feedback sessions with sales. You can discuss what’s working and not working, or what each of you are seeing that could be improved upon.

I think we often assume that our partners across the aisle, if you will, fully understand our processes and the value we can provide as CSMs. In reality, I think it’s actually different than you might assume. An open line of communication can help you learn some things about your own process, and you might be surprised at how much you haven't communicated, or how much has been misunderstood about your process.

I would also suggest aligning yourself with your product counterparts. Early in my career, I made it a point to get to know each of the product managers within my organization. Good relationships with product leaders and managers can help in delivering more accurate and timely answers to your customers on why a feature works a certain way, why something might be broken, or better anticipate upcoming enhancements.

Question 4

What are two to three qualities of a great CSM? And why?

  • The ability to be agile - in every organization I have been a part of thus far, there has never been an entirely established, fully-baked customer success machine with no need for improvement. Additionally, my experience has been such that CSMs’ jobs descriptions can be fairly fluid. We are often tasked with being the glue between product, sales, and support, filling in for the “grey” areas, or potentially needing to “quarterback” various projects to help them get across the finish-line. You need to be comfortable with ambiguity and willing to roll with the punches. I feel like it’s really important, especially in a younger company or CS organization, for CSMs to be agile and flexible.
  • Autonomy - as a leader, you want team members where you don't have to look over their shoulder. If I have to consistently coax a team member to do their job, or reach out to clients, that's going to be a huge drag on productivity. CSMs, in my opinion, are the CEO of their own books of business. If they can be entirely autonomous, while still being effective, that is something I find extremely valuable.

Question 5

Was there a time you messed up and felt like you’d failed within your role or career? How did you bounce back?

Before my customer success career, I was actually in sales. And, honestly, I wasn't the most successful salesperson. I let the potential earnings of a high-profile sales position pull me in a direction that I was not entirely comfortable with at the time. After two years in this position, I realized I needed to look elsewhere and seek another opportunity. Sales wasn’t the best fit for me, and I was headed down a path that just wasn’t the right decision. Lucky for me, I was able to find a career in customer success.

One of the qualities I feel I gained during this time, however, was perseverance. I had a lot of adversity those two years in that particular sales role, and I found that pushing through that adversity molded me into the customer success professional I am today.

Other skills I developed in that sales role have also served me well in my customer success career. I am better able to relate to my sales counterparts and understand the intricacies of the sales process. Some of the most successful CSMs I have known have come from sales backgrounds, and they too realized that sales wasn’t necessarily their calling.

Question 6

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


  • Drive: The Surprising Truth About What Motivates Us by Daniel Pink. Recommended to me by a mentor and former leader, Drive talks about how autonomy, mastery, and purpose are the three things all of us innately strive for. As I have managed individuals, and built customer success teams, these are three qualities I have tried to instill into our culture. Everyone wants to feel as if they are the masters of their own domain, that there is a higher purpose to what they're doing, and that they’re contributing to a greater good.
  • Start with Why: How Great Leaders Inspire Everyone to Take Action by Simon Sinek. Simon is someone I've admired for a while, but this is a book of his that I read recently. The primary premise is that the most successful leaders start with their own “why” for getting out of bed each morning, and are able to effectively communicate this to those they lead. It is a great book that helps to dig down into how you are as a leader and what your approach to leadership should be.

Blogs and Thought-leaders

Question 7

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

This actually comes from my days in sales. I like to call it “three layers deep”. One of the main principles you learn as a salesperson is to not give up after the first “no”. Instead, you actively try to find a way around objections, often times taking several “no’s” before walking away from the deal. As a customer success professional, I feel that same principle is critically important.

The reason why I call it “three layers deep” is because we run into adverse situations with clients all the time. Our customer’s initial concerns, or reasonings, are rarely the root cause of the issue. This is where you start to ask “why.” At this point, customers may not even know what the real root cause is. “Three layers deep” means to continue to ask “why,” at a minimum of three times, in a way that is genuine. Be genuinely curious about why they are not seeing value, or are having a particular issue.

Digging deeper into why someone might not be adopting, or might not be satisfied with your product/service, can be extremely valuable. It can even help the client more fully recognize themselves why they're having a particular concern or issue.


Want to share your mentor advice? Let's connect!

Join the conversation on our LinkedIn CSM from the Trenches group page.


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:

Steve McDougal, Preqin Solutions / Dynamo Software, How to Land Your Dream Job in Customer Success

Cole Sanders, ClientSuccess – How Valued Engagement Touchpoints Help Build a Proactive Customer Success Strategy

Himanshu Patel, Icertis – 3 Key Takeaways from My First Two Years as a Customer Success Manager

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