What does a Head of People do? Learning from Ada’s Chelsea MacDonald

Over the past few months, we have been running a series of posts where we profile one of the many incredible operators in our network. These operators are generous enough to share their expertise and wisdom, and we are lucky to do deep dives into unique topics. We’ve already learned about marketplaces from Bala Subramaniam, Head of Fulfillment at Instacart. And Sin-Mei Tsai, VP of Engineering at Shippo, discussed code quality.

In this installment, I’m thrilled to introduce Chelsea MacDonald, Head of People Operations at Ada Support. Chelsea started her first business when she was 12, and her first non-profit when she was 13. She was a data analyst and has been in People and leadership roles since 2011. She has grown teams from 140 to 550 and from 20 to 60 (twice). And she has just about completed 60 to 140 (Ada is hiring!). She loves sneakers, travel (50+ countries) and running very, very fast.

Unlike “traditional” departments such as Engineering, Product, Sales, Marketing, BD, Customer Support/Success, People is a relatively new leadership function. That’s why we’re so excited to learn about it from one of the best!

What does a Head or VP of People do? What are your responsibilities and priorities? How is it different from HR?

Chelsea: A Head of People sets an organization up to do their best work in a way that scales. It’s probably the role in an organization that requires the broadest and most diverse skill set, because you’re looking for skills in: marketing & PR (employee branding, communications, events), BDR and sales (recruiting), product (employee experience, diversity, data), customer success (employee performance), and legal (HR law, terminations). Throw in a bit of wellness coach, and you have yourself a role for a renaissance person (or alternatively, someone who knows how to hire for their weaknesses).

The difference between HR and People is really the difference in priorities. The question that keeps me up at night is: “Is everyone at Ada working on the most important things, at the edge of their abilities?”. I think traditionally with HR, what I’m supposed to worry about is if we’re going to get sued 🙂 I still worry about that, but the cost of a lawsuit is drastically less than the cost of our entire team working on the wrong things, or not working to the best of their abilities, so it’s not my first priority.

As a snapshot, here’s what one of my most recent days looked like:

  • Ran reporting on OKR updating and progression
  • Spent 45 minutes thinking through how to make it easier for people to update their OKRs and incorporate it into 1 on 1s
  • Interviewed a candidate for Head of Finance
  • Planned 2020 future salaries projections
  • Reviewed performance of BDRs and Sales
  • Reviewed data on bot conversion, had a discussion about % of future that’s managed services vs product
  • Spent an hour talking to people about an org change (3 separate conversations)
  • Did a 45 minute review of our IT infrastructure
  • Ran reporting on recruiting pipeline
  • Re-hashed salary bands for 2020
  • Posted new coaching pilot to our leadership team for feedback
  • Posted communications plan for marketing and product features launches for feedback
  • Talked to a lipstick company about Ada-branded lipsticks for recruiting events
  • Shared my thoughts with you!

What does a Head or VP of People not do?

Chelsea: Here are three things that a Head/VP of People shouldn’t do:

1)    Don’t just blindly follow HR best practices. I remember very clearly my first moment of imposter syndrome around HR things. I was a data analyst masquerading as a people person, and so I went to our local HR association to learn what I didn’t know. When I asked about the evidence behind best practices, they looked at me blankly. Thankfully, since then, HBR, Google and others have led the charge on measuring outcomes of many best practices. Even so, always ask yourself how this would be unique inside your organization, and how you’ll measure the success of anything you try.

2)    Don’t expect people to do something because they’ve been told to do it. We all know we should eat well, exercise and sleep more. Most of us don’t do it. Telling people how to be a better manager doesn’t work if you don’t figure out how to support the behaviour change. You have to understand what are someone’s competing priorities, and how does the change you’re asking for fit into their day-to-day. Then you make it as easy as possible for them to make that change.

3)    Don’t do it yourself. When things are moving really quickly, the People team can sometimes try and force the function by just doing it themselves. To scale, you need to be giving people the tools to drive their own performance and the performance of their teams. While you might get a momentary lift from doing something for someone, you won’t succeed long-term unless you make it easy for everyone to do it for themselves.

When and how do you measure success?

Chelsea: Often and with a grain of salt. For people initiatives, the data sets are often small, and the link between correlation and causation is often murky. The data tells you where to start asking questions, but it’s rarely a penultimate answer until you’re at scale (and even then, only if you’ve built the tools to measure across the organization).


  • I measure long-term performance of hires based on source. It actually broke all of the recruiting norms. The highest performing people at 12 months were people who applied for jobs (though they were the poorest performers at 3 months). Employee referrals were the lowest performing at 12 months, the highest at 3 months. So basically, the bias of employee referrals was super strong, and the key to accelerating performance is actually relationships. The dumbest questions answered the quickest! I have no idea if this replicates itself across multiple organizations (though I’m measuring now!)
  • Measure time to deliver, and not time to hire. So how soon after we decide we need someone is someone excelling in that role?
  • I measure everything against work outcomes. The point of management training should be the teams that receive the training perform better. If there’s no pick up in OKR outcomes, then there’s likely no point in management training aside from making people feel good (which could be enough reason to still do it)

When should an organization bring on a Head of People?

Chelsea: It depends on how quickly you’re growing. It’s the point in time where you’re no longer confident that your team is actually working on the most important thing. Usually it’s around 60 people for fast growing organizations, but you should plan on it taking about 6 months or more to find the right person, so you might want to start early.

What are the qualities/skills/experiences that an organization should consider for a candidate in this position? Where in the organization does this role sit?

Chelsea: You want to find someone that’s business-focused and data-focused. If you ask this person about their impact on the business, they should be able to answer it well! They’ll also probably tell you about all of the things they tried they *thought* would impact the business that didn’t work out. Also, you need a builder. A lot of HR work is going to be setting up repeatable systems. If they aren’t operationally minded, you’re going to end up with a ton of bloat in your organization.

I’ve always reported to the CEO. It means I can talk to other leaders as a peer.

What is the most challenging part about your work and how do you overcome it?

Chelsea: With all of the new focus on culture, this can often get cheapened to employee happiness. Is everyone happy? Are they playing enough foosball? Did they show up at the employee event?

Do you want miserable employees? No. But you want uncomfortable employees. Challenged employees. Employees who feel like they’re on the edge of what they’re capable of. Managers who will ask for a bit more than what someone thinks they can do. Some work days will be scary. Sometimes you’ll disagree with your colleagues, your manager or yourself. It’s easy-ish to make someone happy; it’s very hard to make them fulfilled. And it’s very difficult to figure out where that edge is, and how to build the trust and relationships that make that a mostly enjoyable experience. My tip is to be transparent with people about what you’re trying to do, and listen when they feel like you’ve pushed too far.

Any tips on diversity/inclusion?

Chelsea: Raze it all. 🙂

Really. You can’t get to diversity and inclusion through nudges. There are systems in place that have continually shown us to produce biased results. For Q2 this year, we wanted to include Diversity and Inclusion as a focus, but it wasn’t going to be P1, and so we’re waiting for Q3 when it can be P1. We’re going to redesign a hiring process from scratch that’s built for diverse candidates. I don’t actually know if that’s going to work, but I’ll let you know!



Many thanks to Chelsea for taking the time to share and deepen our knowledge on this emerging role. As always, please feel free to add comments or ask additional questions in the Comments section below!


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