In this edition of our Ask a CSM series, we’re chatting with Brooke Simmons, Senior Manager of Customer Success at Outreach.

brooke_simmons.jpgWhat was your background prior to becoming a CSM? What attracted you to customer success?

My background was in management consulting at Deloitte. I was embedded in dozens of companies and was able to spend weeks at a time on the ground with clients working through challenging mergers and acquisitions, organizational design and development, and even restructuring and bankruptcies. After being on the road for years, I knew I wanted to put down roots and invest in building and growing a company, but I didn’t want to lose my face-to-face work with customers. Customer success perfectly blended my passion for client services and process design.

What does your typical day look like? 

As a manager of a CSM team, I spend my day reporting, coaching, and building. I’m responsible for key metrics regarding our onboarding, adoption, retention, and growth/upsell, and spend a lot of time working with our CS Operations data guru to build SFDC reports and DOMO cards displaying customer health and risk. I spend about half my day directly coaching or shadowing my team. I’m either handling escalations for challenging situations, or shadowing complex calls (like technical integrations or large onboarding kickoffs) to ensure the team is on point. Finally, I spend the last frantic hours of my day building processes and protocol. Thankfully, our process needs become pretty clear after shadowing the team and spending time diving into data.

What’s the most rewarding part of your job? 

When my team is successful. I love when they get the recognition they deserve for working so hard to make our customers happy. I am lucky enough to have a very motivated team of CSMs that regularly goes above and beyond for our customers, and I love nothing more than shouting about their wins throughout the office.

What is the most challenging part of your job?

Working through customer requirements. It’s always a good challenge to align customer needs with our product roadmap. I’m continually impressed by our Product team’s ability to distill what a customer really NEEDS us to build, instead of just building what a customer may be asking for.

Which team (outside of your own) do you work with most closely, and why?

We have an excellent Product Expert team who runs our inbound customer support channels. Without their partnership, there’s no way our CSMs could support our customers. We need their deep technical expertise and quick turnaround time in order to keep our customers on the path to success.

What advice would you give someone who is just starting his/her career in customer success?

Work with the little customers. I see CSMs get obsessed with working on “important” accounts with high ARR. I think people associate some level of prestige or power with being an enterprise CSM, and think that they have nothing to learn from smaller customers. I love working with our smaller customers. They often have the strongest use cases, the best ROI, the most challenging product feedback, and are the most passionate superusers. You can learn so much about your product and truly refine your customer management skills by working with small accounts. Just because they have lower ARR doesn’t mean they aren’t strategic.


In our Ask a CSM series, we’re talking with some of the industry’s leading Customer Success, Education and Training professionals about the ins and outs of their day-to-day. Stay tuned for new Q&As each month!

Want to be featured in a future Ask a CSM post? Email danie@skilljar.com!