Aspiring Ops with Chief of Staff at Terminus, Sydney Cummings
January 22, 2021

Have you heard about one of the hottest trends that’s taking the SaaS world by storm? More and more leading tech start-ups are hiring for the Chief of Staff role. Don’t believe us? First Round Capital’s recent blog advocating for when and why the position is needed might lead you to think differently.


With the Chief of Staff role on the rise, our team knew we had to hear from someone executing in the role about what it’s like to act as the connective tissue that holds the business together. That’s why we are so incredibly excited to welcome Sydney Cummings, Chief of Staff at Terminus, to the second episode of Aspiring Ops! 


Before taking on the operations role, Sydney was the first individual to carve out what Customer Success looked like for the team at Terminus. After successfully scaling that team to over $30M in ARR, a new problem arose around prioritization and team communication. Taking what Sydney learned in CS, she let the customer voice guide her as she stepped into the operational role of Chief of Staff.


For the full story behind how Sydney came to find herself in operations, as well as the key points she’s learned from taking on the role, you can listen to episode two of Aspiring Ops below. 



If you’d like to hit rewind and take down some notes on your favorite part, we’ve got the show details right here:


💻Sydney’s Background and Introduction to Tech: 0:00-3:33

⏸️ Parallels Between Pursuing a Ph. D and Customer Success: 3:34-6:00

💭Letting Vulnerability Drive How You Scale: 6:01-9:37

🙋Taking a Personal Approach to Understanding the Customer Journey: 9:38-13:15

🤝 Learning the Hard Way the Importance of Sales and CS Alignment: 13:16-15:44

🗣️ Having the Voice of the Customer Define the Path for Operations: 15:45-18:21

💥 Biggest Surprises after Taking on Operations: 18:22-23:06

📋 Top of Mind Priorities for 2021: 23:07-26:00

💡 Advice for Any Early Stage Employees: 26:01-28:24

😤 Taking Risks and Using What You Learn Guide The Path: 28:25-34:17


There were so many key points throughout Sydney’s story that are valuable for anyone at an early stage start-up, but especially those in the operations role. One of the chief takeaways that stood out to our team was the overall importance of communication and alignment, no matter stage of the company. Whether it’s making sure you have the necessary resources (and time!) early on, or managing company wide communication after two company acquisitions, consistently putting prioritization at the forefront of the business is critical.


Sydney, thank you so much for taking the time to share your wisdom with our team and the listeners on Aspiring Ops. Your mindset of always being curious and never settling for the status quo showcases what it takes to be successful in the role of operations. We are grateful for your help in building out a community that Strategy and Operations leaders can lean on.


Episode three of Aspiring Ops will feature an individual who has been on the forefront of early operations for dozens of start-ups. Any guesses who it will be? Look out for the episode next Tuesday to find out!

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