window.addEventListener("hashchange", function () { window.scrollTo(window.scrollX, window.scrollY - 100); });

Lessons Learned from My Rookie Season in Customer Success

Kelly shares her lessons learned from Catalyst's Coaching Corner.
Kelly McGillis
September 7, 2021

I could start this by saying that “I didn’t have a conventional background for entering Customer Success,” but at this point, I think that statement applies to most of the individuals that I have spoken to. I also do not think that I am alone in admitting that I experienced a level of imposter syndrome when transitioning from being a classroom teacher to joining an educational technology (ed tech) software-as-a-service (SaaS) company (I mean, the acronyms alone required a cheat sheet!)

I entered CS through a referral in my network, and found I was able to utilize many of the people skills that I had developed through working with students, communicating with parents, and collaborating with fellow teachers. When I started at my current company, it was recommended to me to join the CS in Focus Slack channel, which is where I found the Catalyst Coaching Corner. This program quickly became instrumental to my success and growth as a CSM. I would like to share a few highlights from my experience so far - please note that these are not direct quotes from any of the coaches, but paraphrases framed within my own context.


My first call was with Irit Eizips, CCO and CEO of CSM Practice. At this point, I was quite new to CS, and having an easy enough time finding resources, but a difficult time figuring out where to start. Irit gave me specific topics to study up on and recommended a variety of resources, including her Top 10 Must-Read Customer Success Books for CSMs. She challenged me to pursue ongoing learning, and to continue finding ways to network with CSMs.

Building Skills and Confidence

The second coach I met was Elisha Carsrud, who has both North American and EMEA client success leadership experience in B2B SaaS. Two pieces of guidance she offered that I have embedded into my day-to-day practices:

1. Important and urgent are not the same. It’s essential to build a framework that allows you to be not just reactive, but proactive to ensure that success can be duplicated across your whole customer base.

2. The best way to build trust and rapport with customers is sometimes to teach them to be independently successful using help centers and portals. The instant gratification of being able to provide quick support over phone or email benefits me more than the customer. Enabling individuals to achieve success not only proves that I am able to help the customer exceed their goals, it also allows me to better manage my time for proactive support.

Elisha also encouraged me to read “Measure what Matters” by John Doerr, which is helpful for setting both personal and professional goals. She frequently held me accountable to ensuring I was looking at big picture goals, and not just getting caught up with daily tasks and events. 

When a position opened up internally at my company, she coached me through the application, and I got the role! She also guided me through creating a transition plan so that I could make sure that I would not be straddling two roles long-term.

Making Strategic Decisions

My next coach was Junan Pang, Director of Customer Success at Slack. At the time we met, I had just started a brand new role, on a brand new program, with team members that were (you guessed it) brand new to the company. I was excited about the challenge but was struggling on how to focus my energy in a way that remained efficient and sustainable.

Junan recommended using a risk framework for problem-solving during this time period, and making sure that I could tie my comments and insights to long-term company goals. For many projects, risk management comes down to a balance between time, scope, and cost. My instinct has always been to focus on problems and offer potential solutions, while Junan encouraged assessing and anticipating objections in order to guide compromise.

Becoming an Advocate and Practicing Self-Leadership

My next, and most recent, coach is Alex Bakula-Davis, VP of Customer Success at ExTracker. With Alex, we focused on how to empower collaboration and visibility within teams in order to ensure continuous commitment to goals and metrics. We also discussed how to balance bandwidth and prioritization in order to ensure that goals could be met without burnout. He recommended an article called Give Away Your Legos which I have now re-read many times and shared with many other individuals in my network.

Alex challenged me to advocate for myself and my team when it came to a point when team roles were shifting. He encouraged me to adopt a strategy of including both front-end and ground-level (platform-based) success measurements, and to focus on tangible results more than anecdotal evidence. The result? An updated job description, title, and contract. (My new role is titled Project Specialist, which falls within our CS department.)

What’s Next?

I definitely plan on continuing with the Catalyst Coaching Corner for as long as Catalyst will have me. I am immensely thankful for all of the time and insights that have been shared with me, and I can’t wait to keep learning more.

I completed the SuccessCoaching CCSM Level 1 course earlier this year, and recently started Level 2 with support from the company I work at.

I have recently met my newest coach: Marta Montero, who is a Manager of Customer Success at Alcumus. I am excited to continue to develop my skills within CS!

Better relationships. Less churn.

What’s not to love? Try Catalyst today.
Request Demo