Megan Wheeler is well on her way to becoming a "master generalist". Hailing from a marketing background, Megan has over 15 years of B2B and B2C experience and the cross-functional skills to show for it. With plenty of experience in growth marketing, Megan has turned her attention in the CoS position at Moves Financial(shutdown) to fintech legal compliance, People Ops, Finance and a host of other strategic projects.
Like many in Chief of Staff roles today, Megan's career path and eagerness to learn outside a single discipline led to a dynamic role she's excelling in and likely will open a range of opportunities where she can put these new skills and leaderships capabilities to further use. As the East Coast Chapter Head between Toronto and New York, Megan has stepped us a major contributor to the whole CoS community sharing her learnings along the way.
Thank you Megan for sharing your journey with us!
__
How did you get into your CoS role at Moves Financial?
It was a matter of timing, luck and self-direction. I first heard about the Chief of Staff role from a First Round Review article around 2014. It immediately appealed to me with its variety of operational tasks, focus on being of service while remaining a quiet power player in the background, and opportunities for constant learning and growth.
Over the next several years, I deliberately took on as many operational tasks as possible while progressively leveling up in a marketing career. This positioned me well for the company I’m at now - although I was hired as VP Marketing, I made it known early that I was interested in an operational role (like COS) if the company ever saw the need. After some time, it became apparent there was too much overlap between me and the VP Growth, so he took over my marketing responsibilities while I transitioned into the COS role.
It’s been a learning experience for us all - since it was a brand new role at the company and the CEO had never had one before, much of it we made up as we went along. We had some general guidelines when we first created the role about what I would focus on, but it quickly became clear that adaptability is the most important quality. We’re a startup that’s moving very quickly, and “special projects” or one-off tasks come up all the time that naturally fall under my ownership.
That can make it difficult to measure things like impact or success metrics - because it’s such a general role that works broadly across the business and takes on a lot of things both big and small, I think we’d notice more if things weren’t going well than if they are. So as long as things are generally running smoothly, I know I’m doing my job.
What are you working on right now?
There are a few areas that I oversee in general: People/HR, Legal and Finance. I don’t fully own these - there is shared accountability among a few people. Then there’s Compliance - we’re a fintech serving solo entrepreneurs, and there’s a lot of regulations we need to adhere to. I’m responsible for ensuring that our products, processes, and policies are compliant, but again, there is shared responsibility and vendors who help us with that. And like many COS, I also take on “special projects” - for example, rolling out our Employee Stock Option Plan, creating our fundraising data room, onboarding new partners or vendors. It keeps things interesting and I’m always learning.
What were some of the key learnings or breakthroughs you had while working as a CoS?
With the items I oversee, it’s very much a background role - ie, I’m not working on the “core business” items (we’re a product company) - so my contributions are easily overlooked (unless something goes wrong). I’ve had to learn to be ok with that, but also to advocate for myself and put my hand up to take on the projects that will get noticed and make an impact. Getting comfortable with that level of self-advocacy and taking on large, complex projects with a lot of stakeholders and regulatory restrictions has pushed me out of my comfort zone, which is always a good thing.
What have been the most challenging and rewarding parts of your CoS experience?
With all the financial regulations we have to follow, the challenge lies in remaining compliant while making short-term tradeoffs that we know we’ll need to fix down the road. It’s all about being comfortable with discomfort.
What’s rewarding about the role is the opportunities I’ve been given. If you’d told me a year ago I’d be overseeing compliance, HR, legal and finance, I wouldn’t have believed you. The growth and learnings I’ve experienced since becoming a CoS have done so much for me professionally.
What’s your professional goal in the next ~10 years?
I think I still have lots of room for growth in an operational role. The broadness and variety are something I enjoy and am happy to keep doing. That could take me down a path towards COO or similar, which is always at the back of my mind.
On the other hand, since I oversee compliance, I could choose to go back to a specialized path and become certified, so a CCO route.
I’m not in any rush for either, as I want to maximize my learning and impact for the next little while before making any decisions. I’m also very cautious about chasing salaries and titles, as I’ve learned those don’t necessarily lead to career fulfillment. I’m more interested in the details of the role than what it’s called, and maybe what I want is something that doesn’t even exist yet!
If you could wave a magic wand, with 3 wishes for your role, what would they be?
CoS is a funny role - I think a lot of people fall into it because they were in the right place at the right time. Many CoS are hired internally because they’ve already proven themselves in another capacity. That makes it hard for people to be hired into the role when they’re external to a company. Also, there’s no defined career path or courses to become a CoS. I wish there was a more formal route to this role and that it was more widely known, because I think a lot of people would be great at it if there was more awareness that it exists.
And it’s also a role that a lot of hiring managers don’t understand - they underestimate the experience required, the value it brings, and when and why it’s needed - so again, just having more definition and awareness would help a lot of people who are interested but having trouble getting hired or pricing themselves.
What’s something that you want to learn? (professional or not!)
I’m taking sculling lessons this summer, and while it’s pretty fun, I don’t know about this whole going backwards thing. But I love the water and paddling sports, so I’ve been eyeballing outrigger canoes. If anyone knows where to take lessons in Toronto, hit me up!
What’s the best professional advice that you’ve ever been given?
I hear the words of a former VP Engineering in my head whenever I’m assessing a role:
- Am I happy?
- Am I learning?
- Am I making an impact?
The rest - runway, compensation, title, seniority - become less important. If the comp is fair and you feel stable, a job that ticks those three boxes is a lot more satisfying than a high-paying or impressively titled role at a place that makes you dread getting up in the morning.
What’s something that you’d like help with?
Since I’m thinking about the Chief Compliance Officer path, I’d love to talk to a few CCOs. If anyone can make an intro, it’d be much appreciated!
%20(3).avif)
