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In a fifth article in a series with Slack Fund portfolio companies which explore their growth stores and the role they play in creating the future of work, Jason Spinell, head of Slack Fund, sits down with Paige McPheely, CEO and Co-Founder of Base, to explore her journey from running a remote executive assistant staffing agency to building the technology that’s powering the future of the industry.

See the first four in this series featuring Hopin CEO Johnny Boufarhat, Daily Co-Founder Nina Kuruvilla, MURAL Co-Founder & CEO Mariano Suarez-Battan, and Notion COO Akshay Kothari.

With more than five years of running a hugely successful remote executive assistant  staffing agency behind her, nobody understands the challenges faced by assistants better than Paige McPheely.

One major issue: the complete lack of software custom built for the executive assistant industry. It was a major efficiency drainer: Paige’s assistants spent hours cobbling together solutions from existing tools, often with sub-optimal results. Frustrated, Paige decided to build the software tools herself, and stepped away from her agency to co-found Base.

Base is a software and training platform that helps assistants and executives to work better together, building additional clarity, context and trust in every element of their relationship. The platform is used by thousands of assistants across the world.

I recently caught up with Paige to explore her journey, learn more about Base’s unique approach to fostering culture, and talk about the role Base is set to play in shaping the future of work.

This interview has been edited for brevity and clarity.

Jason Spinell: Let’s do a quick introduction — can you tell us a little about yourself, your journey to becoming the CEO of Base, and a bit about the company?

Paige McPheely: Absolutely. About eight years ago, I co-founded a remote executive assistant staffing agency, 33Vincent, alongside Casey Putschoegl, who still runs it. At the time, I was 20 weeks pregnant with my first child, had just been laid off from my job and was in the middle of moving to a new city. It was a tough time, but we saw almost immediate traction with our early customers.

In the first three or four years, we were growing rapidly. With no outbound sales or marketing, we doubled or tripled in size every year. By 2018, we had an eight-month waitlist. We eventually had to close the waitlist because we couldn’t find the raw talent to match the demand. That was hugely frustrating, but I spent a lot of time thinking about the reasons that were driving it.

In most organizations, Executive Assistants (EAs) are well-respected, and it’s not an easy job to get. And yet, most people end up falling into this work — there’s no training, no degree programs, and definitely no specialized software to help them do their jobs. Assistants were left to cobble together their own software solutions — it’s as if the whole industry had been forgotten about.

These inefficiencies were costing our clients a lot of money. So, we decided that we would be the ones who would build the software that the EA industry so badly needed.

I stepped away from 33Vincent and founded Base. Early on, I started working with High Alpha, a venture studio that was  puzzling the same questions about EA software as I was. We launched Base out of its startup studio in late 2018, raised a seed round in early 2019 (which Slack Fund participated in!) and have seen a lot of growth since then.

Jason Spinell: I love hearing that background and story — it’s such a great evolution to where we are today. You talked a little about how software enables this large portion of the workforce. What does this mean for you, and the team at Base?

Paige McPheely: We believe software gives us a way to standardize what excellence looks like for assistants. Many industries have done this — the way sales teams use CRM platforms is one example. But EAs are frequently on an island, and it can feel like they have to recreate the wheel every time they start with a new organization because the individuals  they support have such unique needs.

In the future, our mountaintop is helping more people to feel seen and supported in the work they do. Software is one aspect of that, but we also want to expand access to assistants, better define career paths for EAs and give EAs more choice in how, where, and when they do their work. Businesses are going to have to evolve if they want to keep their employees happy, and we want to be a major part of that. A lot of the data we’re seeing from sources like Future Forum back that up.

Jason Spinell: Obviously the pandemic is still ongoing, and I know you’ve lived through it and thought a lot about this. What do you think are going to be some of the long-term impacts of the pandemic on how we work together, collaborate, and engage with businesses?

Paige McPheely: I’ve been thinking about this a lot. This job market is one of the toughest I’ve ever seen. Before the pandemic, being remote was one of our big selling points to prospective employees. But coming out of the pandemic, I think people are less firmly in the fully remote or fully office camp — they want choice.

With that hybrid approach, we’re going to need to be more deliberate about a whole range of things — context, access, employee support, and more. Businesses that don’t embrace this shift will lose employees. People are realizing that they don’t have to stay at one company, put in their 40 years, and then collect their pension the same way their parents’ generation did.

Jason Spinell: Pulling on the thread of choice a little bit — do you think that’s the biggest challenge that companies are going to have to overcome as we make this transition to hybrid work? What other challenges do you think businesses will have to figure out, and how is the team at Base facing those?

Paige McPheely: Choice is definitely one of the big pieces of the challenge:  what are we working on, when are we doing it, who are we doing it with — people realize they have a choice in all that now.

When we talk about hybrid work, I think context is another huge challenge. If you’re used to working side-by-side with coworkers, context happens in passing. When you’re in a remote or hybrid setting, context all of a sudden has to become intentional, and you have to build processes and workflows to drive clarity.

At Base, our Slack integration is one of the ways that we coach our EAs to build context. A lot of aspects of context can be built into tools like Slack and Base, but this needs to be done in a way that’s clear, repeatable, and predictable. If you’re not doing that, hybrid and remote work is going to start to break down.

Another challenge that’s related to context is access — to people, resources, and software. We rely on Base, Slack, and Zoom on a day-to-day basis. Sometimes it can feel like Zoom meetings happen in a vacuum, but having an intentional approach to the context of the meeting helps ensure that everything runs smoothly.

Jason Spinell: You talked a little about culture, and how intentional you are about building culture at Base. Can you talk a little more about that? How do you think about employee retention and wellbeing, especially in this tight job market?

Paige McPheely: Right now I think of everyone we hire as a ‘cultural cofounder’ — people who help us to expand, push, and grow the culture, not simply fit in with the status quo. We want to work with people who bring different backgrounds and perspectives to the table, and we’re excited to see how our culture evolves. For me, culture is a really important part of our hiring process. Most of my interviews revolve around these cultural issues.

We see our employees as whole people who have a life outside of their job at Base. Unless they’re able to be that person in and outside of work, they won’t be able to do the best at their job. As leaders, we try to be as open as possible. Lots of people are struggling with mental health right now, and it’s important to us that we can be open about the challenges we face and the approaches we take to manage them. It helps our team to not feel alone.

Base has three core values, which are deliberately a little bit in contrast with each other to make our team very intentional about how they live them. They are 1) Thriving Team, 2) Ambitious Growth and 3) Courageous Help. These reflect the behaviors we see in our internal team but also reflect on our users and the way that we hope to support the world.

We’re also big fans of micro-bonusing and micro-celebrations. We use Bonusly in Slack for this, and it’s definitely helped with team morale.

Jason Spinell: I love that, and I haven’t heard about many businesses having values that are in some way competing against each other, but it’s a great concept.

You’ve seen the progression of EAs for a while now, but focusing on the past couple of years, what’s the biggest change you’ve seen in the role of EAs? Do you see other challenges on the horizon as we start to straddle this hybrid world?

Paige McPheely: Think back to the Mad Men era, where every executive had a secretary outside his office. We’ve done away with a lot of that, which is obviously really, really positive.

But I do think the pendulum has swung back a little too far the other way, to this place where we romanticize being busy. The proliferation of software has meant that we think we can do all these things on our own, and that we don’t need an assistant, but that’s not necessarily true.

The pendulum is swinging back to a more healthy place in the middle of these opposite ends of the spectrum. People are realizing that it’s okay to ask for help, and that takes a lot of strength and humility. Meanwhile, companies are starting to realize you can do this in a tech-enabled way.

With these changes, a lot of the executive assistants that have been doing this for a long time are scared. They’re working hard to learn the technology, but have this fear that their jobs are going to be automated away.

To be clear, I think that won’t be the case for a long time. The level of interpersonal intelligence that you must have to be a truly good EA is a long, long way off being replicated by technology. That being said, I do think we might see more tech-enabled assistants in the next 10 to 20 years.

In the last 18 months, we saw a lot of assistants being laid off by their companies in the wake of COVID-19. The result of that was that middle managers became even more squeezed, and were expected to do all these different tasks with little support. But as we start to come out of the other side of the pandemic, the demand for EAs is definitely coming back.

A lot of organizations I talk to are doubling the size of their admin functions this year, and they’re looking for people who can be a Chief of Staff or EA hybrid. It’s a more strategic position that can often be a springboard for leadership roles. It’s important for EAs to figure out how to become that strategic partner. That’s why we’re out there with megaphones trying to educate and upskill people.

Jason Spinell: What other advice would you have for teams when it comes to collaboration, in terms of embracing the hybrid world?

Paige McPheely: Once you get a grip on the choice and context pieces that we talked about before, I think you need to make space for people to be creative within certain boundaries.

We just had our first in-person team gathering — all outside, very safe. There were a couple of things we wanted to accomplish in our time together, but we also made sure to have a lot of free time so that people could have more free-flowing, interesting conversations.

We know big companies like Google give their employees a certain percentage of time to go and create things, and I think this is similar. We give people time and space to use their brain and tap into their talents, and that unlocks a lot of potential for interesting collaborations.

Jason Spinell: It’s the fallacy of being busy, right? Just because your calendar is full of meetings, it doesn’t mean you’re being productive. Some of the most productive days I have are the days where I only have one or two meetings, and have a lot of time to think strategically.

It’s essentially creating a safer space to push decision-making to a broader set of people within the organization. You’re not going to ruin the business if somebody makes a bad decision one time. Of course, there has to be safety nets, but giving people that ownership and space to test and learn and do experiments is actually really beneficial, and creates a better culture.

Paige McPheely: I love that. We talk a lot about leading with trust and taking time to think. We make sure our team takes time to unplug, to read books, to go for walks, and just think deeply.

The little green light by your name on Slack isn’t indicative of the work you’re doing. You’re responsible for your output, and the thought process behind it, and we don’t expect that green light to be on all the time.

Jason Spinell: Agreed. I’m curious to know what can you share from a product roadmap perspective that you’re excited about with Base, and where do you see Base going in the medium or long-term?

Paige McPheely: We’re about to release a calendar scheduling functionality. We’ve been working on it all year, and it’s a huge release for us. It’s going to transform the way people work in Base.

From here, we’re focused on building more internal integrations within the app. Once we’ve got the calendar scheduling functionality in there, we’ve got a lot more context, and can integrate all kinds of tools — it’s going to really round out after the platform.

Longer term, we want to create and train the next generation of assistants. We’ve got the tools, the community, and the training to offer people these leadership apprenticeships and create exciting roles for them in amazing companies.

Jason Spinell: That’s awesome. And finally, we ask this to everyone we talk to — what’s your favorite Slack emoji?

Paige McPheely: This is probably the question I’ve thought most about! I use the ? emoji a lot when something is awesome. I also love the one where Homer is backing into a bush — there’s a lot of uses for it! Someone on the team even created one of me dancing. I don’t know where it came from, but it gets used a lot!

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