Meet Chloe Pi, Chief of Staff at Ro and Primary Mastermind Network Founding Member

Read how Chloe Pi's past experiences as a Technical Program Manager led her to her current role as Ro's Chief of Staff and the lessons learned along the way.

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As a CoS Mastermind Founding Member, Chloe has benefitted from the many professional and personal growth opportunities she's encountered from connecting with peers, colleagues, and mentors through the network. Interested in joining? Apply here.

Can you walk us through your career journey to date? How did your interests and/or values help shape where you landed?

In the early days of my career, I had worked as a Technical Project Manager at Arabella, a boutique software development consulting firm. Being one of the earlier employees there, I had the opportunity to build the team and internal tools to help scale Arabella itself, and to collaborate and build multiple startups with incredibly passionate founders and visionaries across all types of industries. Despite being a project manager in title, the experiences I gained had been extremely interdisciplinary and cross-functional. I’d often ask to sit next to folks from different domains, learning how leaders in Product Management, Product Design, Engineering, Marketing, etc would approach the challenges they face or capitalize on an area of opportunity. That’s where my deep passion for building and scaling products, teams, and orgs comes from.

How did you land the CoS role at Ro? How did you transition from your previous role as program technical manager?

As a Technical Program Manager, I essentially acted as the connector between domains and teams, all the while driving alignment across multiple complex initiatives and identifying areas of opportunities for future investment. In essence, a TPM’s responsibilities are not too different from what some Chief of Staffs do (of course, the caveat is that CoS responsibilities vary in terms of what the org needs). At the time, Ro’s Tech Org needed an individual with the skillset of a TPM who could act not only as the glue within the Tech Org domains and with its stakeholders, but also an operationally-driven cultural leader who can build and scale a collaborative environment that empowers teams to be effective and autonomous. Based off of my ability and interests in building and scaling Engineering and Product teams, I was given the opportunity to be a Chief of Staff, and it was truly a trial by fire experience. Whereas a TPM measures success primarily through the health and effectiveness of one’s program, a Chief of Staff measures success through the health of an entire org, keeping track of the ever-changing dynamic of people, process, and priorities. Needless to say, being in this role is an incredibly challenging and rewarding journey as you’re given a front row seat working amongst leadership and (at times) being a leader yourself in lieu of your principal.

What has been the most rewarding part of the role so far? The most surprising and/or challenging?

Having the ability to move between different levels, departments, teams, and even meeting room walls to learn and understand the health of the org and then tasked to identify risk and opportunities is what makes the role so difficult, albeit incredibly rewarding, for me. Whether a CoS is hired to maximize efficiency with minimal change, or be a change agent to execute significant operational agendas that bring an org to their next level of growth, we’re expected to build strong relationships cross-functionally, be the voice of reason and sounding board for leadership, all the while transform an org to tackle more complex opportunities. That’s absolutely daunting!

What advice do you have for others who are looking to transition into healthcare tech?

I believe the health-tech space is at a pivotal moment in utilizing technology to drive more integrative patient-centric healthcare experiences that can make meaningful changes to a patient’s health outcome, rather than being an ‘add to cart’ service of purchasing supplements online. That being said, if you are interested in joining a health-tech company and following its long term trajectory, look closely at how that company is investing in their architecture and platform. See if what they’re building aligns with their mission, and whether it makes an impact on their users.

How has networking amplified your career?

Networking is a crucial skill for Chiefs of Staff. I see networking as an opportunity to learn from folks outside of your industry and expertise, widening your breadth of knowledge of how others operate. At Ro, networking is a large part of what I do to gather intimate knowledge about different parts of the business, create a snapshot of how things are currently faring across teams and domains, and develop useful insight on where I might need to parachute in to help. Building and growing relationships with cross functional folks extends my ear into different parts of the org where I can learn about wins, challenges, and areas of opportunities to surface to the leadership.

Interested in joining Primary CoS Mastermind Network and growing your community of peers and mentors? Apply to join here!