What Does a Chief of Staff Do in the Education Technology Industry?

Written by Beth Jacobs

July 20, 2022

We’re stretching your definition of the chief of staff role by sharing Q&A sessions with our vChiefs working their magic and utilizing their skills in various industries, beyond politics. Last fall, we introduced a vChief working in higher education, who provided more detail on what her role looked like in that realm. Today we’re sharing the wisdom of vChief Margaret Jaques-Leslie and her experience working in the educational technology field.

Please detail your experiences in working as a chief of staff in ed tech.

I’ve worked as Director of Operations at a couple of ed tech startups, first at Persistence Plus, a mobile behavioral nudging platform, where I spent four years figuring out how to deliver our nudging model at scale and building the business processes to enable that (managing launches, client engagement, etc). At empowerU, a seed-stage social emotional learning platform, I helped structure assets and processes to speed our platform launches at school districts across the country. Overall, I’ve spent over five years in ed tech specifically, and about fifteen years at education organizations, from large multinational content companies to seed-stage startups to national nonprofits.

What were your key responsibilities as a chief of staff in ed tech? 

I’m currently chief of staff at CodePath, a national nonprofit that brings together employers, students, and colleges to eliminate inequities in tech education, diversify the field, and provide underrepresented students with a path toward economic mobility and generational wealth. I’m supporting the COO, VP of Programs, and Director of Corporate Partnerships in developing a partner success management function. This means doing a current needs analysis, working with a larger team to rank needs and developing consensus around focus areas and next steps, and then engaging the right team members, whether Development or ExComms or others, in developing tools and processes that will build efficiencies and ensure transparency in partner success management.

How do your responsibilities differ from chief of staff roles you’ve held in different industries? 

Actually there is some consistency in my vChief work in that I’m usually developing business functions for rapidly growing organizations. This means balancing the right amount of “design” for the function — you don’t want to overdesign a system for an organization of 10 people or an organization of 75 people, but you do absolutely need it to function for the different team members. So: Ford Focus version instead of Cadillac Escalade version when possible!

Were there any surprises along the way? Any experiences you weren’t expecting? 

Every organization has a different mix of revenue sources, and those revenue sources will determine how to think about partner success management, program or product launches, and data and reporting. Many nonprofits are now tilting toward models in which a more significant percentage of their revenue is from fee-for-service models or stand-alone products. For many, this can feel a little weird! It’s new to be a non-profit and think about having a “customer” but it’s actually a useful exercise in understanding how your particular offerings are valued, whether by students, higher education institutions, or employers. It took time for me to learn and understand that using the same corporate language and mindset (customer, market size, etc.) wasn’t the complete right fit for nonprofit or socially-minded organizations — so I’ve learned to think much more about end users, about opportunity for impact, and about evolving an offering in relation to user needs and engagement.

Please list your three biggest takeaways from your experience in ed tech.

Lots of ed tech work is about the multi-headed customer, which is a scary-sounding and corporate way of saying that you really have to design for a diversity of end users and profiles. Is it easy for students to use? If parents are involved, is it easy for them to say yes to and understand? Is it easy for school district leaders to use? What questions will an Institutional Research office at a college ask?
  1. Take some time to think about how many people will touch your implementation/technology. Have empathy for their needs and anticipate their questions.
  2. Design your service or product to be easily implemented! Districts, higher education institutions, and employers are highly bureaucratic organizations, so designing for easy implementation is crucial.
  3. It can be hard for people to feel a clear sense of “success” when using an ed tech offering or product. For example, if your model is that you’ll help graduate more students, it takes a long time for an institution to actually see that result. So, it’s really important to have some early wins to share with your partners, balancing a few select data points with anecdotes to tell the story of a successful partnership.

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