July 23, 2019

CSM from the Trenches: Mentors – Natalie Williams; Director, Customer Success; SmashFly Technologies

CSM from the Trenches: Mentors – Natalie Williams; Director, Customer Success; SmashFly Technologies

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: Natalie Williams; Director, Customer Success
Company: SmashFly Technologies
: Orange County, California

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?

One important lesson I learned early on is to truly listen and ask questions in customer conversations. Earlier in my career, there was a specific instance where a customer came to me with a business problem, and in that moment I was so worried about not having the right answer I just started throwing out potential solutions. Our Chief Customer Officer was fortunately also on this call and chimed in, asking questions like “talk to me a little bit more about this” and “explain the changes your team is going through”.

A light bulb went off for me and my customer success mindset was completely shifted by this experience. I think it's really important for CSMs to be able to slow down conversations and be okay with not having all the answers right away. It’s the nature of a customer to question what they can or can’t do. And while we can answer “yes” or “no”, it's more important to understand what they’re trying to achieve; consider asking “what is your desired state?” instead. The key is being consultative and guide customers to their outcomes. Often that includes challenges what they think they want in order to achieve something greater.

For example, if we go to our financial advisor or lawyer with a specific solution in mind, they could simply agree and do what we tell them to do. But what we really want is for them to understand what we’re trying to achieve and be consultative in helping us get there. To give us an even better solution.

Listening, questioning, and sparking dialogue has shifted how I interact with customers. This idea of change management requires that we try to understand what our customers are solving for. If we’re actively listening, we can help them achieve what they want and more, gaining their trust as a partner along the way. Trust is everything, especially as they realize we can help them achieve more than what they originally thought.

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?

Customer Success has evolved so much and continues to shift at a very rapid pace. If I were asked to implement a CS program today, the first thing I’d do is define what success looks like (both internally for our company and externally for our customers).

  • Internally - define customer retention rates, understand who your reference-able clients are, map out customer lifecycles and journeys within your organization.
  • Externally - understand what success looks like from the perspective of the customer. Ask about their goals. What are the challenges they're trying to overcome? Why did they partner with us? What are their metrics? How are they leveraging those metrics to make decisions and provide visibility internally?

At SmashFly, we’ve shifted our cadence calls to strategy sessions because we want that focus on being a consultative and their strategic partner that solves business problems. Quarterly strategy or business reviews allow us to present key KPIs, metrics, benchmarks, and recommendations to our customers. We then present a proposed roadmap of tactics that will help drive the overall strategy forward. Thinking ahead with the big picture in mind ensures we’re constantly moving the needle on their desired outcomes.

Another recommendation I’d give is to learn your audience and evaluate customers for the right level of engagement. Each customer is different but by going through that exercise, we engage with customers at the right frequency for both the customer and the CSM.. Key things to look at are level of engagement, ARR, expansion opportunities. This has worked really well for my team and our customers.

Question 3

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

True customer success takes a village. Period. CSMs can’t do it alone! So one of the things I’ve tried to and continue to do is instill collaboration beyond the customer success management team. Companies are stronger when customer success becomes more than just a department.

At SmashFly, we partner closely with our product management team. As a SaaS company our customers are in the product every day so it’s important we’re connecting them with the team directly in charge of the product. This allows us to have conversations on how can we make the customer experience better and more successful.

Additionally, learning how to be the voice of the customer to help navigate and prioritize business initiatives internally. Sure, we can share customer frustrations as they are provided to us but more importantly, we should be the team gathering feedback and data so we aren’t making decisions on assumptions. Customers want to be heard and we are the conduit to the rest of our organization, like the product, engineering and our leadership team. Companies need to centered around the success of their customers; it shouldn’t just be the responsibility of the CSM.

Question 4

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

  • Authenticity - as one of our core values at SmashFly, we try to exemplify this in every interaction. Our customers trust us because they know we're open, honest, transparent, and that we legitimately want to help them. This starts with our leadership and trickles down to the frontline employee.
  • Action-oriented - CSMs must advocate for their customers and take the necessary actions to achieve desired outcomes. As you're taking these actions, it's also important to communicate what you’re doing back to the customer so both parties remain aligned with current success criteria and next steps.
  • Resilience - it’s important for CSMs to understand they’re the conduit for the customer and to not take certain pieces of feedback personally. While this can be difficult at times because of how passionate one might be, you have to remember to work through it and engage with purpose. Be resilient in your desire to help customers achieve success.

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?

Every customer we lose comes with a sense of failure. There was a major customer in particular at SmashFly who was engaged and we thought everything was fine... until it wasn’t. It came as a huge surprise when they shared they would not be renewing. Surprise churn or intent to churn is probably one of the worst feelings one can experience as a CSM. In this case, it also came as a big revenue loss for our company.

For me, this brought with it a big sense of failure in my role and career. I felt guilty as if I had let my company down. While I knew that customer success isn’t just the responsibility of the CSM, it was still difficult overcoming this churned relationship.

The key is you have to bounce back; I always try to reflect back and think “What could I have done differently? What could I have done better?” If we let them, these moments can make us stronger success managers and renew our focus for our customers.

In this particular instance:

  • I made a goal for every CSM to conduct a strategy review with their customers and include members of our leadership team in order to strengthen executive relationships. We also started inviting other team members (ie product, engineering or support) to join such calls. These review sessions allow us to highlight the good work our customers are doing to their executives, as many who were involved in the purchase are not in the platform regularly. We focus on demonstrating adoption and ROI. Having executives join also makes it easier to discuss any challenges in the partnership which can help increase awareness at all levels.
  • We’ve also made it a priority to be more diligent in recording customer pulses. I think it’s critical for any Customer Success team to record the status of their accounts (like we do in ClientSuccess) because it serves as a log for customer temperature and feedback. Doing so has helped us manage our executive expectations for renewals. We’re planning on launching a customer health profile to increase our proactiveness regarding customer behavior (ie help us get ahead of renewals).

Question 6

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


  • Lean In: Women, Work, and the Will to Lead by Sheryl Sandberg. I read this shortly after having my first child and doubted whether or not I could do it all. With several friends who had chosen to be stay-at-home moms, Sheryl’s experience, advice and lean in mentality gave me reassurance that I didn’t have to choose between work and parenting. It reminded me that I could still be a great mom while pursuing my career and passion as a Customer Success leader. Balance is key; every day, week, month we have the opportunity to adjust and learn how to best work with all the moving pieces.


Thought Leaders:

  • Maria Martinez - CS Leader and author. Formerly at Salesforce and now EVP & Chief Customer Experience Officer at Cisco. Her vision of Customer Success over the years has been and continues to be inspiring.
  • Greg Daines - I had the opportunity to meet him in Boston a few years ago. His philosophy on strategy reviews was game changing for our team, as they’re now a regular part of our customer interactions at SmashFly.

Question 7

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

Be real. Don’t just try to say the right things to say something; say the things you would want or expect to hear from a person or company you are doing business with.

My father has owned and operated his own business since he graduated college and my mother has worked for the same company for over 30 years. At a young age, they instilled basic human and relationship principles that I carry with me today. I’ve learned to be genuine and appreciative of a customer’s business.

When we’re direct and challenge our customers in order for them to achieve their desired outcomes, we have the opportunity to build relationships that last. Because people value their time and effort, they want to do business with people they trust will help them succeed.


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

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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