Thank you for inviting me to be a Monday Guest! I am honored to be part of this great initiative.
Hi folks! I’m Dillon, and I work in Customer Success (like you probably do, too). I think we’ll cover that more later on…
More importantly, I’m a husband, a father to a one-year-old little boy, an avid runner, and an aspiring golfer.
We asked Dillon to take us through a journey telling us about his career path, how he spends his workday, what advice he can share with someone starting as a customer success manager, and many other questions.
Enjoy reading this interview
Tell us about your career path?
Like all good CSM’s do, I went to school for something totally unrelated. In my case, it was audio engineering. Upon graduating college and surveying the many opportunities (that’s sarcasm) for sound engineers in the US, I ended up in New York City where I worked in the music industry for a short amount of time before I realized I couldn’t pay my bills with free concert tickets.
NYC’s version of Silicon Valley, “Silicon Alley,” was starting to percolate, and I was able to find a sales position at a start-up. From there and in no particular order, I held roles in operations, support, product management, training, and account management.
How did you join Customer Success?
Somehow, it wasn’t until 2020 when I read Ashvin Vaidyanathan’s and Ruben Rabago’s book, “The Customer Success Professionals Handbook” that I recognized all of my previous roles were, in whole or in part, Customer Success roles. I cannot stress enough the positive impact picking up that book on a whim had on me, and the way in which it has crystallized the direction of my professional career for the better.
So while it has only been since around 2020 that I have held Customer Success-specific titles, I typically introduce myself as having 10+ years of experience practicing Customer Success, title or not!
How would you describe the ideal CSM candidate?
A person who can:
1) Engender trust with a customer, thereby earning a “seat at the table” enough to ask questions and receive earnest and thoughtful answers in return. These questions can be about their customer’s future strategies, or asking for introductions to stakeholders in other lines of business that are expansion targets, or it can be in asking for transparent feedback about the CSM’s company or product.
2) Grasp the details around how their customer’s business operates – the industry, their go-to-market strategy, and how their company’s products or services might fit in.
3) Facilitate and/or contribute to very difficult conversations and do so dispassionately, advocating in equal parts for the customer and for the company, while managing expectations and operating with integrity.
What one piece of advice would you give to someone just starting out as a Customer Success Manager?
Keep the big picture in mind, both personally and professionally!
Meaning, focus your time and energy on the outcomes your role is expected to deliver. These are slightly different at every organization, so train your eye on what your company is expecting and not what the multitude of CS thought leaders, books, and trends tell you to do and say. From a personal standpoint, I recommend folks at all levels of CS learn and think about all the paths a career in CS can take you. You’re no longer destined for leadership, or Senior Enterprise CSM-land, necessarily, and specializations within the profession get deeper every passing day. You control your destiny, so spend time often thinking about where you’d like to end up.
Keep the big picture in mind, both personally and professionally!.
Can you take us on a journey describing what your workday looks like?
Any given day is probably 60% meetings, 30% emails and Slack, and 10% heads-down work. So much of what a CSM does is conversate with others, both internal and external, and my day reflects that. The topics of those conversations will vary widely by day/week/quarter, spanning the range from discussing business strategy with the customer’s C-suite and to demonstrating new product features with the customer’s operations team, along with everything in between.
Much of what CS does is reactionary – we might begin a conversation with a customer expecting to ask about their 2024 initiatives only for them to tell us they’ve got an entire cohort of users struggling to adopt our product, at which point your proactive strategy call turns into the beginnings of what might be a months-long success plan. In CS, it’s all about following the bouncing ball and always trying to return to the proactive conversations as time permits.
What makes you feel inspired or motivated?
Ideas, exercise, and time off. All work and no play makes Dillon a dull boy.
What’s one thing that people are generally surprised to find out about you?
I’m an open book, so it can be tough to surprise folks. I’ll have to go back in time…
During my early career in New York City, I worked with over 100 Grammy-nominated artists.
What are your top 3 priorities now?
Family and health, then wealth.
What advice would you give to Customer Success Managers to grow and develop their careers?
Understand your company’s KPI’s for your role and be sure you align with their purpose and viability. Once you do, attack them ruthlessly and at the sacrifice of motions that do not serve them. Measure your performance more often than your company does. Broadcast your successes loudly.
Lastly, and by far the most important, understand your worth through the lens of those KPI’s and your performance against them and never ever ever let anyone give you less accolades or money than the worth you have proven.
What’s your favorite book, and why?
Have you had your “I’ve made it” moment yet?
There have been so many, and I’d encourage others to always celebrate the small wins. But the true challenge is being brave enough to move the goalpost on yourself and begin the journey of leveling up once more. 🙂
What should I have asked you but didn’t?
Who am I to tell you how to run the show? 🙂
Where can people go to find out more about you?
LinkedIn is a great starting point:
Or, you can check out my podcast and look out for new episodes of the pod coming in the fall!
Thank you, Dillon, for sharing your knowledge and for the opportunity to know you more.
Do you have a Customer Success Leader, Expert, or Influencer you would like to know more about?