I am Brittany Casey and I am a working mother of two boys located outside of Washington, D.C.
In my 9-5, I am a Lead Customer Success Manager at DocuSign serving our marquee customers, and am excited to be coming up on my three-year anniversary with the company in July.
I am a passionate advocate for Customer Success, and in 2020 took my 10+ years of experience in the field to the next level by offering professional mentoring services for people looking to break into CS or grow in their current CS role.
Outside of work, I enjoy spending time with my boys, taking care of my physical and mental health, and exploring new breweries/wineries/restaurants with my husband of 5 years.
We asked Brittany to take us through a journey telling us about her career path, how she spends her workday, what advice she 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 many in Customer Success, I had an unexpected journey to the role I have now. I began my business career in sales specifically in the legal technology space.
In order to strengthen my technical acumen, I took a job as a Solutions Consultant for a leading contract management analytics company. Halfway through my tenure there I became a founding member of their customer success division and as they say, the rest was history.
I have worked in both individual contributor and people/department management roles in my 10 years in the space and developed a passion for telling a compelling value story to both my customers and my peers.
How did you join Customer Success?
When I was asked to join a newly formed customer success department, I actually did not know what customer success was.
In my past tech sales roles, there was always an account management aspect to my job, and it was my favorite part of the customer journey.
When I understood that CS was not high-touch Support but rather focused on that aspect of the customer journey, (proving value and strengthening the customer relationship,) I immediately accepted the position and have loved growing in the space ever since.
How would you describe the ideal CSM candidate?
Customer Success Managers come from a variety of backgrounds. Each learns and communicates in different ways, and most are effective if they are keying in on their strengths.
There are two types of CSMs I would define as most successful in SaaS:
* The Growth-Minded CSM- this CSM is competitive and has an awareness of the sales goals associated with their accounts. They excel in working alongside the sales team to ensure the customer grows the *right* way. They ensure the prescribed solutions will not only help the engagement grow, but that those solutions will help solve for the customer’s larger business objectives.
* The Data-Driven CSM- many times this CSM comes from a project management background or specializes in the industry in which they are CSM-ing. They approach the customer journey as a series of projects that need to be accomplished and excel in assigning timelines and tracking relevant KPIs to ensure the larger Customer Success Plan is always progressing. These CSMs are experts in conveying value to their customers and leadership through data storytelling.
What one piece of advice would you give to someone just starting out as a Customer Success Manager?
The first 90 days in a new role is a magical time where doors will open to you that may not always be available by stating two simple words, “I’m new.”
In starting a new CSM role, be a sponge. Soak up as much information as you possibly can. Ask for an intro meeting a week to understand not only how CS works at your company, but how all of the cross-functional teams you will be working with do as well.
Take every type of training available to you to become a product expert of the solution you offer customers. Once you know your Book of Business, set up Google Alerts for your priority customers.
Starting a new CSM role, be a sponge. Soak up as much information as you possibly can.!
Take the time to deeply understand the company, its goals, its financials, etc. If you come to your intro-to-the-customer meetings really knowing them and their business, you are already building trust and providing value to your customers.
Can you take us on a journey describing what your workday looks like?
🙂 I sign in and start my day by responding to high-priority emails and Slack messages from the last 24 hours.
Next, I usually schedule 15-30 minutes ahead of my customer meeting to prepare. These prep sessions may also include the internal account team that I am working with. I try to work on larger projects like deck-building that require a lot of creativity or brainpower before I break for lunch.
A couple of days of the week, I take a quick lunch and reserve the extra time for new mentee intro meetings. When I return to work, I usually have another series of customer meetings and respond to other emails between those meetings. I also use this time to check my customer’s key KPIs and report on them accordingly.
Toward the end of the day, I take a look at the calendar for tomorrow and the rest of the week and ensure I have everything prepared for that day and any large presentations/meetings coming up later that week.
What makes you feel inspired or motivated?
I’ve always been inspired by being able to take the knowledge or skill I’ve acquired and give it to someone else to help them succeed next or better.
Whether it in sports or in Customer Success, I quickly gravitate toward coaching and mentoring, and get a lot more joy watching those I’ve worked with take what they learn and succeed, more than doing so myself.
What’s one thing that people are generally surprised to find out about you?
🙂 I am 6 ft tall and because of this, struggled with confidence most of my young life. I found relief in playing sports and continued to do so through college.
When volleyball was done and I wasn’t sure what else to do with my life, it was through a series of unexpected events I found myself competing in the Miss USA pageant system.
This is where I finally learned how to be confident in myself, and own my height and other strengths. I learned how your body language/walk/posture can communicate whether you believe in yourself a lot more than what you say.
I also learned that you do not have to feel nervous speaking to someone in power, we are all people, and feeling intimidated by someone’s title or status is a wasted emotion. I would never have had success in tech sales and customer success without learning it through that highly unique experience.
Who do you look up to the most?
I have a lot of people I look up to in my life for different reasons. I believe we all have different strengths and if we recognize those and key into them, we can accomplish so much in this life.
What are your top 3 priorities now?
– Being the best mom I can be to my two boys
– Saving up to move to a lakehouse in the next 3 years
– Becoming CCO of a leading technology company by 2033
What advice would you give to Customer Success Managers to grow and develop their careers?
Indirect leadership is a skill that is vastly underrated in Customer Success. The ability to organize and assign resources (people, processes, and technology) correctly in order to help your customer achieve their goals is crucial to success in SaaS organizations.
Take the time to understand all of the resources that are available to you, and get creative in solving your customer’s issues where there are gaps.
Another skill that will make you stand out is the willingness to live and work “in the grey” on your customer accounts. This does not mean saying yes to everything you are asked to do, but instead understanding that sometimes going above and beyond for your customer is necessary and will usually pay off in dividends.
What’s your favorite book, and why?
I’m a big nerd and love the Harry Potter series. My favorite book is probably The Goblet of Fire because I was an athlete and it is often called the “sports book.”
I grew up with the series, and have fond memories of standing in line waiting for book releases, making t-shirts for midnight movie premieres, and even meticulously designing our sons’ nursery in a Hogwarts theme.
Those books will always have a special place in my heart.
» Check out the 10 Books a CSM should read to advance and improve their skills.
Have you had your “I’ve made it” moment yet?
My “I’ve made it” moments tend to relate to my personal life milestones rather than professional.
I was really proud of myself for getting my promotion last summer and took a little time then to reflect upon how far I’ve come and set new goals both professionally and personally to continue to strive towards.😊
What should I have asked you but didn’t?
What resources would you share with someone looking to grow in their Customer Success career or break into CS?
My favorite customer success book is called “Customer Success (How Innovative Companies are Reducing Churn and Growing Revenue)” by Nick Mehta, Dan Steinman, and Lincoln Murphy.
It tells the story of why customer success became a profession with companies like Salesforce that had a subscription SaaS model. It highlights the foundations of Customer Success as a discipline, particularly how customer retention truly drives the success of today’s technology companies.
It is important to remember where we came from as customer success continues to evolve to meet future customer needs.
Where can people go to find out more about you?
The best place to find me is on LinkedIn. I post Customer Success career advice and day-in-life scenarios alongside TikTok videos to poke fun at the life of a CSM. To find more customer success video content, you can find me at
If you are interested in learning more about my Break in CS/Grow in CS mentoring services, there is a link in my profile to send a request to get started. I offer resume review and edits, interview prep, and 1v1 mentoring services.
Whether it is the large number of tech professionals looking for jobs or the narrowing of opportunities to advance in current roles, the challenges outside of our control are more present than ever.
I work closely with my mentees to best position them to achieve their goals despite these challenges and help them stay focused on what they can control.
Thank you, Brittany, 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?