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This startup hopes remote executive assistants will be a big part of the new normal

But Double CEO Alice Default says she's focused on current clients during these "stressful, stressful times."

Double CEO Alice Default

"The goal for us is to make it easy to have someone help you out with any type of task, whether you expect to need help for two hours per week or three hours per day."

Photo: Courtesy of Double

Remote personal assistant service Double will soon come out of stealth mode — just as the rest of the world has embarked on a giant unplanned work-from-home experiment.

Founded in 2018 by former Microsoft employees, Double seeks to pair executives with human assistants who help them out digitally from afar for as few as five hours per month. Now the company says it's secured a round of funding and wants to be part of the conversation about the future of work.

Protocol talked with CEO and co-founder Alice Default about how her company's "Doubles" are helping their bosses through the coronavirus pandemic and if the crisis might leave workplaces more comfortable with remote workers.

This interview has been lightly edited for length and clarity.

So you're coming out of stealth mode, now, while many people are suddenly being forced to work remotely. How has the COVID-19 pandemic affected your strategy?

Quite a bit. Obviously, it's still pretty recent, but we've been thinking about logistics, and for the last two weeks, we're still tracking to see how this is impacting our business. And we'll probably make adjustments in the future. For now, what we've decided to do is put all of our outreach efforts, my client acquisition efforts, on pause for now and really try to focus on our current clients. It's the most important thing right now that they have the best experience, especially in these stressful, stressful times. Obviously, one of our missions is to help our clients save time and save mental load and bring them that service. So yeah, focusing on bringing value to our clients, stopping outreach.

And the last thing that we should do is focus on more long-term marketing efforts. With direct email, for example, booking a lot more on building content that can be valuable right now, but also be valuable later down the road.

What sort of things are your Doubles doing during the pandemic?

So we've been doing a lot of things for clients. I think the first one obviously is scheduling and rescheduling things for afterward. A lot of travel was canceled, a lot of meetings moved to Zoom. Just being there for clients to help them manage all this chaos in their calendar was obviously a big one.

We've had a lot of clients who needed help figuring out the best setups for their remote teams. So just like getting them on Zoom, finding and taking all their events — like talks or conferences they were holding — and finding the best way to convert that into a webinar or virtual conference. We've been seeing a lot of just sending packages to their team members or helping their team members buy things to have a good remote setup: a big screen, a better chair. Obviously, we do a lot of personal tasks, so there's a lot of food delivery, researching health care options, helping finding activities for their kids to keep them busy and ordering board games and things like that. And the last bucket was helping with self care — finding gym classes to work out online, canceling gym memberships.

Do you think that our current nationwide, unplanned work-from-home experiment will make people more comfortable with hiring remote workers long term?

I hope so. If that's what comes out of this, it could definitely be great, especially because there's so many great talents who are working remote today and who were working remotely before this crisis started. I think for companies it's a massive opportunity, right, to find people that are not just in their city. That being said, I also think that it will depend on how the crisis and remote work is being managed by each company. Right now we are doing a work-from-home experiment, but we're also doing a worldwide economic crisis experiment — a "you can't go out of your home" experiment, which is not your typical work-from-home experience.

There's a lot of stress, a lot of anxiety. People don't know they're going to keep their jobs. But I'm just hoping that this is not going to add a negative connotation to just being remote and working from home. Hopefully, people realize that work can still be done remote, that you can trust your employees to do really great work, even if they're working from home, if they have more flexible schedules. And that's something that I'm actually pretty hopeful that will happen.

One of the things that we've seen a lot of the larger tech companies come out with is doing virtual assistants that are based on artificial intelligence with varying results — and sometimes using humans behind the scenes to supplement. What made Double focus on connecting actual people via tools instead of moving toward AI?

There's a few reasons. First, I think humans are great and that you shouldn't hide that. And the good things humans bring should be front and center instead of putting them behind a wall as some sort of a dirty thing. But importantly, we don't think AI is there yet to really bring a quality service, in terms of executive assistant. When you have an executive assistant, a lot of it is knowing about you, knowing your company, and being able to anticipate your needs. We don't think that AI is at a level where it can do that accurately right now. It can't really deliver a great experience.

The main way AI is working within virtual assistants so far has been on superfocused tasks: scheduling, for example. And they're getting better and better at these vertical tasks. But we really believe that as a client, you don't want to have to use a different tool for everything. If you have your AI assistant for scheduling and your AI for travel, and you're just adding on even more tools, they can get overwhelming.

So we think we're able to bring a way better quality of service by having these humans and just empowering these humans with tech and tools that are going to help them do a better job. We're actually building tools for both the assistant side and the client side.

And then the last thing is, for us, delegation is about trust, right? When you're delegating something, you're sharing a task with someone else. You need to trust that person with information about you — what's your preferences, credit card information, all these different things — and that they're going to do a good job. And so for us, that human relationship to create that trust is super important, versus validating something with AI where you don't really know what's going to happen with this data or algorithm.

Are you dogfooding? Do you have a Double who's helping you manage things?

Of course! Actually all the team at HQ has a Double — from engineers to our operations team — though we obviously have different needs. I've had a Double basically since the start, obviously to test the experience, and figure out what it is like for a client. I think it's super important that teams dogfood and talk through whatever experience they're building.

What kind of assistant tasks are easiest to manage remotely right now?

So we do a lot of things for clients remotely, actually. Most tasks can be done remotely as long as it's not going to pick up the mail or bring a physical package to someone. And even then you could figure out a way to find someone to do that, remotely.

Right now, we focus a lot more time for clients on scheduling. Obviously, one of the biggest things people ask us for is travel booking and admin tasks, whether it's expenses and invoices, onboarding new employees, things like that. And then we also do a lot of just project management, I would say, for our clients, whether it's helping them with their hiring funnel, or helping them prep for meetings, things like that. There's a lot of projects that can totally work remotely.

How large is your current pool of customers? And how many Doubles do you have?

We're still in stealth mode, and we've been like this for the past two years, intentionally keeping our pool small so we could really focus on building the best experience possible from a human point of view and building up on the operational side of the business and from a product perspective. So we have a bit over 100 clients in our setup right now and we've been growing that 20% per month over the last few months. Obviously, it's a bit different now. And we have about 30 Doubles to support people in our current system.


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So what's next?

There's so many things that we could do. But for now, the goal is to focus on making an assistant way more accessible to executives out there, without having to hire somebody in your office. We think that all of us need help, no matter what you spend time on during our day. We're all working on things that we don't really value doing — and actually way more than we think. And the goal for us is to make it easy to have someone help you out with any type of task, whether you expect to need help for two hours per week or three hours per day. So that's what we're going to focus on, which obviously means scaling the operational side of the business.

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