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CSM from the Trenches: Mentors – Nina Wilkinson, Director of Customer Success, AspireIQ

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: Nina Wilkinson, Director of Customer Success
Company: AspireIQ
: San Francisco, 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?

I’ve learned that meeting with your customers face-to-face greatly helps to build relationships that last over the long run. Obviously you have to have the budget and resources to be able to do so, but you can never go wrong with meeting with your customers as early on and as frequently as possible. 

We were fortunate enough to have clients spread across the globe. While we couldn’t visit all of them, we did try to meet with as many as possible (especially those near our hub areas). We believed in meeting with customers so much that it was actually one of the reasons why we created additional offices. Offices in New York, Denver, and San Francisco made many of these visits possible. 

Ideally, I believe teams should set aside a budget for their CSMs to meet with their clients in person, spend time with them, get to know, and nurture them. It’s pretty easy in the world we live for things to become very impersonal, especially from a vendor perspective. It’s rewarding to foster real relationships because it reminds us to view each other as people and not as simply a service provider.

Here’s a specific instance where communication with a customer solely via email and phone was causing difficulty in the relationship and how getting in front of them helped change overall sentiment:

We had a kickoff call with a client in the Midwest that was being held over Zoom with no video and 13 total participants. The sheer size of this type of meeting made it really tough to ask questions and understand who was actually speaking, yet alone the context of the question being asked. We eventually got the opportunity to meet with them in person and it completely changed the onboarding and implementation experience. We were able to break down the meetings and have them based on the different departments and who would be interacting with our platform. This helped us better understand what objectives they were trying to achieve, and then afterwards we got to take them to dinner which was wonderful. That interaction changed our relationship with the client from that of a vendor, to a partner.

Through these interactions, I firmly believe it will help create stronger relationships, as well as increase our opportunities for upsell and renewals. Unfortunately, sometimes you are limited by the technology and resources you have, so you have to rely on things like Zoom. But if you are able, face-to-face interactions with your customers can create better trust in you as an advisor and each other as partners.


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?

I would definitely encourage a CSM in this position to look at the customer journey and map out what each touchpoint looks like from the customer’s perspective.

  • When I land on your website, what am I seeing from marketing?
  • When I get to sales, what are the conversations I’ll be having like?
  • When I get to you, what does the onboarding process look like? Are there technical elements to it? Does it involve a lot of heavy-lifting? Or is your solution pretty simple to get started?
  • What does the adoption process look like? What does the experience look like to be in your tool and actually be doing stuff?
  • What does it look like to be a successful client?

At this point, hopefully you’ve got at least a handful of clients you can interview to look into their product usage and understand why they’ve been successful. 

You can then look at other areas, such as the renewal process. Developing, documenting, and strengthening your existing journey can help you understand where and what you could be doing better. In an ideal world, what would your customer journey actually look like? What would be the experiences there? And what could you do to make things better for your clients all around, whether that’s on the website, platform, product, sales or onboarding process…there’s a lot for you to continually enhance over time.

In my career, I’ve yet to come across a company that’s got it perfectly figured out yet. So again, I would start with the customer journey and reconfigure or rebuild according to whatever it might be to get you to a more ideal state. Knowing the customer journey and who’s responsible for owning which pieces of the puzzle are critical for any “customer success” to actually happen.


Question 3

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

As is typical for most customer success teams, AspireIQ worked hard to always consider our customer’s experience all the way through their entire lifecycle with us. What was the deal cycle like from Sales? What was/is their product experience? What did they do? Did they have any support issues alongside that? What was their Customer Success experience like? And finally, what are the takeaways? What are we looking to understand and potentially not replicate in the future? How can we evolve or better our own services or platform? 

We put a lot of effort into improving these postmortems to better understand why our brands would or should stay. It was important for us to move away from Customer Success simply reviewing the client’s experience and why they churned, because reasons for churn can be so varied. That’s not to say the lessons learned from churn aren’t valuable, I just believe we often overlook the reasons why customers stay. 

Regardless of industry, we need to remember we’re not the only solution available and competitors are usually anxious to gain our clients’ business. So in cases where we do secure a renewal with clients, we should always ask ourselves “why”. What did our company do to earn the renewal? 

This kind of success analysis approach not only helps mature and foster your customer success team, but it also aligns other departments to “customer success”. The entire company can benefit in understanding why a client has renewed multiple times; there must be a compelling reason for them to stay. It’s every company’s goal for clients to find so much value in the product or services it offers, that we strive to become as sticky as possible.


Question 4

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

  • Patience – CSMs have to be patient on many different levels, especially in terms of working with clients and dealing with various issues. Whether it’s during an onboarding, working through billing changes, user or champion turnover, or shifting KPIs…the ability to be okay and comfortable with change is a must. 
  • Passion – I believe we are most successful when we’re passionate about the industry or space we’re in. To that regard, as a Director I’ve always looked for hires who are deeply interested in the subject matter they’d be working on as a CSM. One must be able to gain the expertise needed in order to successfully manage a book of business. Spend time learning about your respective industry and strive to stay up-to-date with its changes and current developments.
  • Persistence – as a CSM, you’re going to have clients that go dark which can be incredibly frustrating. If you can find new ways to be informative and provide customers with valued engagement touchpoints, you’ll be better off in your work. This approach definitely requires more work than passively reaching out to your customers. But if we’re able to provide value at every touch point we have, we’ll be well on our way to “customer success”. 

And for a fourth quality:

  • Perspective – consider yourself as a strategic extension of customers’ own team and put yourself in their shoes to achieve objectives with their perspective in mind.


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?

As a team lead, I’ve struggled a little bit with fully understanding the appropriate DNA of our team and what works best for business. Going back to what I mentioned previously about focusing skills on industry or vertical you’re in, while critical, is only part of the appropriate DNA. Your CSMs will be able to do webinars and trainings, as well as write playbooks; these skills can help your team build out great content for your marketing team. 

Something we didn’t have for the longest time was being proactive about teaching our team to also have a more proactive “sales” DNA. I’ve come to learn that we as customer success professionals need to be able to ask tough questions and sell competitively. While it may not be an inherent CSM skillset, leaders need to be able to spot teaching opportunities as early on as possible and layer them in trainings as necessary. I now try to think six months ahead and groom those I work with in order to best serve our customers and drive our business forward.

Speaking of driving the business forward, if you’re building up a CS team you need to understand it takes time to hire and train people to the point where both you and they feel confident in their own abilities. Thinking ahead of the game is critical, and something I again try to stay ahead of because in my early days it was just trying to keep my head above water and figure out the process. Looking back, I can see that being proactive and forward thinking earlier on would have saved a lot of hassle and headache.


Question 6

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


Other influences:

  • Pete Kazanjy – he runs a phenomenal group called Modern Customer Success Pros, that includes 500+ CS professionals…director-level and above across different types of companies world-wide. I love this group because you can put questions out to the group and get some of the most thoughtful, impressive answers. It really helps provide the most robust, contextual answers you could ever hope to imagine.
  • Kristen Hayer – she has a great website as well, and her blog covers a wide range of CS topics. She’s also a great connection and always thoughtfully responds.


Question 7

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

One principle I’ve applied to my teams is treating my CSMs as people, not employees. 

I’m really proud that at AspireIQ we were able to institute a consistent work-from-home day for our customer success team. Every Wednesday we gave them a break from their daily commute, which for some was two plus hours each way. We also had the team Slack us that morning what they were grateful for, and it didn’t have to be work-related. 

Customer Success is a really tough profession, but also one of the most rewarding. Things can change in an instant and not work out as you might have planned. The biggest key to all of this is remaining positive throughout it. When we remember that those we work with are people first, employees second, we can do a better job at promoting a healthy work environment.


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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