SVP of People, Cover Genius: 'We can do hybrid work better than anyone else'

Like it was for countless businesses around the world, the post-COVID shift to remote work was a sea-change for Cover Genius. It enabled the insurtech giant to hire talent globally, and the benefits have been undeniable.

But global expansion has also introduced complexities, such as time zone challenges for team managers, prompting the business to begin a careful shift from remote-first to a hybrid work model.

Although the journey is still taking shape, Ann Watson, SVP of People at Cover Genius, is convinced the company can do hybrid “better than anyone else.” She speaks with HR Grapevine in an exclusive interview about how the business plans to “thread the needle” between a purposeful, intentional hybrid model and flexibility for unique employee needs.

You’re currently shifting your approach away from fully remote work at Cover Genius, is that correct?

Yes, it’s a great moment to be having this conversation because the model is still evolving. We’re continuing to evaluate what feels overly complicated and where we can simplify or bring more clarity and focus.

Our philosophy is to build an operating model that positions us as a hybrid-first business. For us, that means some teams and roles will be clearly hybrid, some will remain fully remote, and a small number will be fully in-office.

Why go heavy on hybrid?

We're responding to feedback and stories we've been hearing across the organization.

Post-COVID, the company went fully remote. People could work from almost anywhere in the world. Our hiring model was to find the best talent everywhere, with an undercurrent of thinking that there are cost savings when you’re fully remote.

But there’s an element of balance. If you fast-forward to when I joined the company about ten months ago, one thing that leapt off the page was how complicated the employee model was.

We’re not saying we want everybody in the office full-time, but having more structure allows us to create intentional moments of overlap, where we can count on each other and collaborate efficiently, while still allowing for flexibility in other moments and other ways.

Additionally, some roles in our organization right now require significant travel, and not everybody can do that either.

Can you share some examples of the unexpected complexity it was causing?

We had people all over the place, with multiple instances where an employee was in one time zone, their manager in another, and their team or collaborators spread across three more.

While the individual had remote flexibility and control in theory, the complicated nature of our model meant that it didn’t always ring true in practice. We’re bringing that back into balance, with more purpose and intentionality – those are my two favorite words right now – around how groups are structured and what they need from one another.

We often think of remote work as inherently expansive, but there are also real limitations. In some of our other markets, I’ve seen hiring managers struggle with where to place a hire. When the entire world is your talent pool, it can be overwhelming.

Instead, we’re willing to wait for the right person, the piece of the puzzle that truly fits. That creates a much better experience than the borderline burnout some people felt trying to manage the complexity of so many time zones.

'We often think of remote work as inherently expansive, but there are also real limitations' - SVP of People, Cover Genius

What’s the journey to hybrid been like so far?

We're going to see how this progresses as we move through the process. I’ve observed that at Cover Genius, we often make a decision quickly and everyone gets excited, but then there’s a long period of consideration, conversation, feedback, and unpacking what that decision really means.

We need to think about what this shift means for the organization, and for the leadership team to stay in conversation with employees, trusting them to deliver great outcomes. It might not always look like that first decision, but everyone’s comfortable with that because we know we’ll arrive at a better outcome in the end.

It sounds like there’s still going to be an element of flexibility, then?

Yes, we’re going to stay flexible with ideas and listen to everyone’s stories, because we’re trying to achieve multiple things at the same time, and a one-size-fits-all approach won’t work.

We started by looking at this role by role and group by group, thinking about how they interact, who they collaborate with, how often that collaboration happens, and where those people are located. We considered it both in terms of where we want to be in five or ten years, and then worked backwards from that vision to where we are today, positioning the pieces to get us there.

Our biggest challenge will be maintaining the flexibility to consider individual stories while balancing the talent we want to retain with the model we believe is best for our future. We’ll have to thread that needle carefully.

Are there any groups of employees you’ll pay particular attention to?

If you step outside of Cover Genius and look at what happens in organizations with very rigid return-to-office mandates, you’ll often see that entry-level employees tend to thrive, and the more senior leaders usually feel energized by the in-office collaboration, because it's what they experienced for most of their careers.

But then there’s this middle band of people who can get squeezed. That might be those balancing aging parents or children, or those just stepping into management roles. For that group, there's often a certain amount of trepidation, sometimes even bordering on fear.

Finding ways to help support that group will be a key part of our balanced approach as we shift from being a fully remote organization to a more hybrid one. And for anyone who sees this as moving from flexibility to something more rigid-more demand or power-oriented, what we’re really doing is shifting toward a bit more planned structure.

'I truly believe we can do hybrid work better than anyone else' - SVP of People, Cover Genius

How will this flexible approach to hybrid work help you attract and retain top talent?

A significant portion of our organization will remain fully remote, in roles and teams that work independently. Remote work continues to offer a major advantage for us, not only in attracting and retaining talent but also in the efficiency of the work being done. We're not looking to change that.

Take our team in Uruguay, for example. They’re incredible. We bring them together once a year for purpose training, collaboration, development, and relationship-building. That’s a model I don’t see us changing unless there’s a major shift in the market. It’s our core strategy for winning talent in that region.

At the same time, we have a real opportunity to lean into hybrid in a way that positions us as a market leader. I truly believe we can do hybrid work better than anyone else.

Quite the ambition! What makes you feel like you can do hybrid better?

This is the most dramatic shift I’ve seen in my career. Sea-change moments like this don't come along very often.

From what I’ve observed – whether it’s big names in the media or from smaller start-ups – companies succeed in navigating this when they have a clear and genuine purpose, and people can see the logic behind it. On the flip side, when it’s all about command and control, where leaders don’t trust what employees are doing, it creates tension. That’s the ugly side.

That’s when you get entrenchment, where one side clings rigidly to remote work, and the other insists on being fully in-office. When there’s no conversation, trust and culture break down. You get a much healthier, more productive experience when you say, ‘Here’s what we’ve noticed, here’s the theory we think might help it, let’s try it together and learn from it.’

It’s about being thoughtful about what’s best in each case – for the role, the team, and the work – and making space for unique personal stories to exist within that framework.

How will you go about improving and fine-tuning your policy over time?

We should talk again in six months, and I’ll tell you! For lack of a better way to put it, I hope it looks like a different bird, but it’s still a bird.

Because I think if we stay on this path, we'll find that some of what we anticipated won’t materialize, and some completely unexpected things will emerge instead.

There's also a bit of a settling-in period as people get back into the swing of spending time in person. It takes time to rebuild that muscle. It takes practice. And honestly, I’m really excited to see how it works out.