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Q&A: Cher on Being "Chief Optimizer" and the Power of Coaching

Can you share a bit about your career path and what inspired each transition point?

My career really began at Trilogy Education in 2016 (now 2U, Inc). I had no idea what was in store there — but I was inspired to tutor for The Coding Bootcamp across their university partners given that I’d just graduated from one. I was on a mission to mentor girls in STEM outside of that!

Tutoring transformed into a full-time role where I grew roots building the operational foundation for Instruction and Academic Delivery. The inspiration was simple: 1) Unbelievable people, and 2) A firm belief in access to education as someone who’d also experienced it.

I was “Chief Optimizer” for our instructional community throughout the years into our acquisition in 2019 by 2U, Inc. From onboarding to product operations to centralized learning support, I led three (absolutely baller!) teams as we scaled to thousands of part-time instructional staff serving more than 40K students worldwide over time.

In 2021, I had the opportunity to join another incredible team at The Grand as Head of Operations. With five years of EdTech experience, I was curious about bringing people together in a new way through group coaching.

You’re now leading operations at the Grand. Can you tell us a little more about the Grand and what your role entails?

The Grand offers group coaching to people navigating challenges at the intersect of work and life. In a small group of 8-10 peers, a coach facilitates discussion and shares exercises and coaching frameworks that put individuals in charge of their own success. Ultimately, they also feel less alone in what they’re going through. That might include a major career transition, being a founder, leveling up as a leader, or navigating a new identity in work or life. Our programs place a heavy emphasis on asking open and honest questions and listening empathetically since those are the foundational skills of group coaching and can drive powerful learning in sessions.

My role is centered on scaling our end-to-end group coaching product from enrollments and group curation to delivery and coaching success. As an early stage company, I am in charge of keeping our operations flexible enough for growth and experimentation, while also identifying key levers for improving our core group coaching experience.

Group coaching is a fairly new model for learning and development. Do you think the approach could apply to skills bootcamps and new university programs?

Definitely. Graduation to the workforce is a huge transition that students have to navigate, whether it’s a four-year degree or skills-based bootcamp. Only about 20% of undergrads reach out to career services for advice on finding jobs or applying to graduate programs (Gallup and Strada, 2017), and they look to other sources for decisions that might determine their employment: professors, friends/peers, and family. In other words, they turn to their support systems for coaching and new perspectives on big decisions without even realizing it.

The heart of group coaching is exactly that: A learner and a support system. The Grand’s group coaching experience is designed to empower individuals to find their own answers, experiment in ways that are aligned to their goals and values, and receive feedback and support from their group and coach.

It’s not enough in today’s workforce to say “Here is the way!” because work and life are rarely linear, and the decisions we make in our careers have a lot to do with our circumstances and self-discovery. Some deeper questions that students might explore in group coaching:

  • What are my limiting beliefs about myself as a new graduate, and how can I transform those into energizing beliefs?

  • What are the values I’m optimizing for at this stage of my early career and life?

  • What would a typical day look like if I moved to a city for more opportunities? Stayed where I live and work remotely?

  • What is a my preferred communication style in the workplace and how I can learn others preferred communication styles as well?

  • In the past, when you had moments of peak happiness, what were you doing, thinking, feeling? How can you ensure you can maintain that with this new job?

You’ve now been a part of a very early stage startup, a startup going through hyper-growth and a publicly traded company. Do you have any career advice for how to stay flexible and impactful at each?

Throughout hyper-growth, early processes start to break and considering more sophisticated systems to sustain that growth is helpful. Know what the most important parts of operations are to keep it moving, and consider reorienting teams as the needs change. It’s helpful to not lose sight of how the business is reorganizing itself, and designate the right owners to tasks to avoid getting caught up in blurred lines of responsibility.

To stay flexible in a public company, it can be helpful to tack on two weeks to any deadline because there are often more approvals necessary to make changes in the business. It's also a great place to practice honing your skills since most positions tend to be narrower with clearer opportunities to grow in a particular direction too.

I’m still learning how to stay flexible in an early stage startup! I’ve always been comfortable wearing a lot of hats, so that’s a plus. And I’m thinking a lot about how to build simple processes and structure our data in a way that will scale well! And I’m very close to our customers and coaching community — people truly matter.

I think that surrounding yourself with great people is the key to staying flexible no matter the stage of the company. There is no perfect company out there and those skeletons in the closet are a lot easier to overcome with smart, authentic people around you.


If you're interested in being a part of a community of operators and educators focused on supporting adult learners succeed, consider applying to the Learner Success Guild.


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