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Going From CSM To VP In Less than 2 Years (What I Learned)

Answers to some of the common questions I get about my career growth in Customer Success
Sydney Strader
January 19, 2021

Often I’m on the receiving end of this question “Syd, your career trajectory has been incredible! You were literally a CSM and within 2 years a VP of Customer Success. What advice would you give me to achieve the same?”

I’ve always found this an incredibly hard question to answer, but it has challenged me to think about how I got to where I am and what advice I would give. My honest answer to that question... “don’t try and achieve the same.” Here’s why: 

A Title Does Not Lead To Happiness

We are immersed in a society defined by status—led to believe that our job, our “title” is a representation of our worth and value. This creates the perception that if you are a VP, you’re incredibly accomplished. A success story. 

A title is empty. What defines you starts from within. It’s critical that what you are doing each and every day brings you fulfillment and a feeling of purpose. It should strike you so deep to your core that you are driven to continue challenging yourself, even looking forward to the next challenge. That drive may one day land you in a VP role, or it may not.

You can be given a VP title tomorrow but I guarantee you it will not lead to your long-term happiness. What leads to long-term happiness is doing things that you’re good at, you enjoy doing, and cultivate a sense of purpose. Are you waking up excited? Are you going to bed proud? Even on the tough days, your drive to push through is rooted in how much you genuinely love what it is that you do—challenges and all. 

Speed is the enemy

In addition to living in a society where our titles are so heavily emphasized, speed is another recipe for disappointment and self-sabotage. Mark Zuckerberg became a billionaire at 23... Kylie Jenner at 21 (errr, Forbes may have recanted that but you get my point). We all see this and instinctively our reaction is “how do I achieve their ‘success’?” “What did they do that I’m not doing and how can I level-up super fast because I’m frickin' 33 and already behind!?”

We are all on different journeys and speed is a vanity metric when it comes to measuring accomplishment. The speed by which anyone has accomplished anything should hold no significance. Are they happy? Are YOU happy and fulfilled by the work you’re doing? Put the stopwatch aside and solve for each day as it presents itself to you when you wake up in the morning. Lean into your strengths. Lean into the responsibilities that light a fire within you. Solving for that fulfillment will land you exactly where you’re meant to be. The title and the timeframe by which you do this is insignificant.

The Bigger The Title, The Bigger The Problems

After having experienced this rapid trajectory myself, I had time to reflect, and one of my major realizations was how lucky I was that I loved what I was doing because the bigger the title got, the bigger the pressures and the expectations. If you haven’t solved for you yet, there is no title in the world that will make the challenges to come easy to deal with. From my personal experience, challenges that come with a bigger title include:

  • An immense amount of pressure to get things right ALL THE TIME
  • An abundance of opinions you have to wade through and decipher in an effort to make informed decisions 
  • The insecurity of knowing you’re never going to please everyone and the crushing feeling associated with that
  • The demands of being everything to everyone—pulled in every direction from those across the business and not wanting to let anyone down
  • The extremes you put your mind and body through being on planes, trains and automobiles continuously while maintaining a workload as if you were working in an office 5 days a week (Pre-Covid-19)
  • The unsettled feeling (at least for me) of all eyes being on you, people leaning on you, depending on you, etc.. 

All this not even to mention the pandemic and other global challenges that arise. The bigger the role the more pressure there is on you to not mess up.  

It’s a lot. The pressure mounts. I’ve cried my way through it at times, but for me personally, there isn’t anything I’d trade this for in the world. I have found purpose in the pressures and in the challenges that I face every day, and that is what gives me the confidence that regardless of the title assigned to me, I’m doing exactly what I’m meant to be doing. 

Trust Yourself

You can seek all the advice in the world from people you admire and respect but the only person that has the answers you need is you. 

You know what excites you to your core. 

You know what absolutely bores you to death. 

You know when you’ve had those days of complete purpose and fulfillment and what made those days so special. 

The moment you shift your focus to solve for you and not for what you hope others perceive of you is the moment the magic begins. Each minute, each hour, and each day is an opportunity to learn more about yourself to make more informed decisions about your career path, and if you follow your intuition you’ll end up where you’re meant to be; whatever the title.

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