Podcast Episode 25

The Value of Executive Assistants for Early-Stage Founders

Join Ryan Davies as he hosts an insightful discussion with Jessica McBride, the visionary founder of Tech Savvy Assistant. Together, they will explore the invaluable role that executive assistants play in supporting early-stage founders. Jessica is a thought leader in this field and will share her journey from a traditional admin role to pioneering the use of cutting-edge technology, such as AI and ChatGPT, to revolutionize administrative tasks. You will discover the evolution of the executive assistant’s role, the importance of strategic partnerships, and how leveraging AI can supercharge efficiency. Jessica will also provide practical insights into hiring the right assistant and highlight the diverse tasks that can be offloaded, freeing up time for founders to focus on the strategic aspects of their business. Don’t miss this opportunity to learn from a true expert and gain valuable insights into how you can optimize your administrative tasks and take your business to the next level.

Jessica McBride

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Ryan: I’m your host, Ryan Davies, and I’m hosting today’s discussion on the value of executive assistance for early-stage founders with Jessica McBride, Jessica. Thank you so much for being here with us today.

Jessica: Thanks for having me.

Ryan: I’m really excited to kind of branch out of just only talking about chatGPT and AI and really focus on something that, I think, is really important about supporting early-stage founders, later-stage founders, really anyone with the value of an executive assistant, I think this is going to be a great topic and we have a lot of our audience that falls perfectly into this again, as you said, whether it’s early stage, that’s how we’ve kind of title this, but it really, I think is going to branch across to talk about the role the evolution of the executive assistant, how people can really bring it in regardless of where they are in their journey and the importance for doing so. a little bit about you, Jessica. You’re the visionary founder of tech Savvy Assistant, and you’ve dedicated your career to revolutionizing the operations of administrative professionals. Jessica has a decade of experience in the field, seamlessly integrating cutting-edge technology like AI and Chat GPT into her work. Her primary mission is clear and straightforward: to create strategies and tools that can streamline administrative tasks. But also redefine the roles of executive assistants, administrators, operation staff, and virtual freelancers; you are a thought leader in this space and have invaluable insights into how to leverage AI and ChatGPT to supercharge administrative efficiency and foster strategic partnerships for executives and founders. I know you’ve led a master class on this. You’ve been a keynote speaker on this. You’re absolutely perfect for this. And we talk a lot here again about upskilling about a lot of grand ideas, but this is something with executive assistance that really, again, can provide such elite and immense value for founders or anybody on their journey. Before we dive too far into your background, it is as an executive assistant. Tell us more about what led you to build a tech-savvy assistant and your experience.

Jessica’s Background and Journey

Jessica: Yeah. So, I wasn’t always an executive assistant, but I’ve worked in a lot of various admin operations-type roles for most of my career. I started working at Enterprise, and I have built my way up since then. And then, in 2021, I had a really bad mental health-like breakdown because of a job that I was at. So I quit. Just one day, I was like, I can’t do this anymore. And so I had a friend who was freelancing on a pro website called Upwork. And I was like, OK, I’ll give this a go; I’ve got nothing to lose. And so I started doing virtual assistant work, picking up here and there what I could find. I eventually started working with the tech company based out of New York as their virtual assistant. And it was an early-stage company, and they didn’t really have anybody doing this work yet. So, it was a new role, and I loved it. I made it my own and, you know, became like a culture leader and worked on making a nice workspace for the staff. I got to run a bunch of different initiatives, and it gave me all of this autonomy that I’d never had in a role before. But it was very much a golden handcuff situation. I was paid really well in US dollars, and then it converted to Canadian, like 35% more.

Jessica: So I was having a really good time for a while. And then, in January this year, I was on vacation, and I slipped and fell on a resort, and I hurt my knee really badly, and it rendered me unable to walk for the rest of the time that I was there. And I had ADHD, so I was spending a lot of time on TikTok. It’s like a dopamine slip slot machine, and I was getting a lot of chat GPT videos. It was really cool, and I had never heard of it before. I would start testing it out. Started working. I was already in a bunch of different executive assistant communities just because it’s a really lonely job. You’re usually the only one, and you don’t have a lot of people to talk to. So, I started testing out a bunch of different scenarios that people were coming across in these different groups. And it’s often things like being asked to create standard operating procedures or templates. So they’re looking to see some kind of itinerary. But because everybody has such top-secret information, they’re guarded, you know, they’re guarding for their executive, it’s hard to give out that information. So, it’s hard to know what you need to create. So, chat GPT  works really well for this. For all these generalist one-off tasks that we need help with as executive assistants, chat GPT  can be that It’s worked better than Google in terms of giving you guidance on what you need to do. And so, I wrote a guided chat GPT  for executive assistance that caught a bit of traction. And it’s been building from there, but in February, out of the blue, I was laid off with like 30% of the company, and then they laid off another 30% right after. So it really was not a good situation. And So I immediately was like, ok, what am I going to do? I’m applying for jobs. I am picking up freelance work on Upwork again. And I’m also getting asked to do speaking events for chat GPT  and more educational programs for admins. So I started working on that, and I have a series of job interviews, and I hate them all. interviewing makes me feel like absolute garbage. I just can’t imagine going back into an office and doing some of the more traditional in-office executive assistant work. I’d had just too much freedom and autonomy by that point. And so a couple of months since this, I was just like, I don’t want to do this; I don’t want to be an executive assistant anymore.

Jessica: I don’t think so because I haven’t been able to find that. Like synergy and relationship, and it’s not for me. I’m going to lean into what I’m building with this ChatGPT education program. A couple of months later, I named it Tech Savvy Assistant. And then, by June, I’m ready to file for my corporation. I was like making enough money from speaking that it thought I felt like, OK, like I can do this. And I’ve been growing the community ever since it started out. Just like I had a Facebook group, and now, you know, I have all kinds of different social media pages, and we have a newsletter. and I was speaking at the admin professionals conference in Vegas back just this past October; I got to do a big keynote for like 850 people. So, at some point, I just realized that I had built a brand and a business, and all of it was just based on a fluke injury. But it’s been such an amazing experience. This is what I was meant to be doing because I’m working with the most amazing people. I love the people that I get to teach, and it’s expanded from there. It’s been a really weird year. I look at it’s November, and I’m just like, January May. I could never have anticipated where we would be at this point.

The Value of Executive Assistance

Ryan: That’s wild. I talked to a lot of founders, a lot of people who have started their own businesses, his own revolutions, if you will, at times and changed so much. It seems like sometimes fate just finds you, and it’s almost like you got pushed over on the resort to do that to be like, well, at the time, you’re probably like, wow, my vacations ruined everything sucks. I hate everything. Then come back to what is happening, and all of a sudden, it’s just like, no. These cards were just dealt to you in the perfect way to help you provide this not just for you but now for so many other people. With that in mind, I want to talk more about the role the executive assistant plays. And a lot of us here, executive assistants. My mind always still goes; there is probably the traditional way of picturing the CEO in the office and the top tower that has the person following them around and is their eyes and ears type of a thing. But this is something that you really want to make sure is for everybody, as you said, for early-stage founders, because it’s so important to have somebody that keeps you organized and could be your eyes and ears when you’re trying to do 300 things at once and especially as a founder starting up. Wow, does that ever take place? So tell us a little bit more about how, you know, the importance of that executive assistant and maybe that evolution of the role away from, you know, maybe that traditional, almost Hollywood feel of the person following around with the clipboard to what it actually can do and how it can increase productivity.

Jessica: Something I find with this younger generation of executives and founders and CEOs is they really don’t know how to utilize an executive assistant. There is the Tinder dynamic where, a lot of times, the executive assistant is like 85% of women in the industry. And so, you know, there’s like, I don’t want to ask her to do things for me. My husband has an executive assistant; he’s like, I don’t know how to have her help me at all. And that’s not uncommon because we want to make sure that we’re asking them to do valuable things. But even as an early-stage founder myself, I got a virtual assistant back in June, like, four or five months into what I decided was going to be a business. I was like, OK, I need someone who can help me accountable and help all these little things that, like, I know that I’m letting slip because when you’re starting a business, you are your CFO, your CTO, your CEO, you’re all of the Os, and it’s a lot of pressure and just to be able to offload some of the admin tasks that you have to take time out of your day to do can be really, it, it frees up so much time for your creativity, for your thinking about what you want to do with your business. And people don’t even recognize it as an option sometimes, and it’s a lot of, it’s controlled, like not knowing what to let go of. But when we really look at it, you can start with a virtual assistant who’s going to handle basic tasks. They can help with your email and scheduling. They can start to learn your preferences and how you want to operate. Eventually, when this person gets to know you, they become more of a strategic business partner, more than just a virtual assistant; it’s really lonely to be a founder. And you don’t always have someone that you can toss ideas off of. But a good strategic business partner executive assistant can be that person for you because, especially as you bring on employees, you want to have your finger on the pulse of the organization, and people aren’t going to talk to the CEO; they are just not going to happen, it becomes very unapproachable. But a really good strategic business partner talks to everybody within the organization, and they assess the temperature.

Jessica: They’re getting an idea of this is something that’s going on internally that we should look at, you know, when I became the executive assistant and got really bored with just scheduling and just doing some basic tasks, I started to do that to get to know everyone within the organization and start to piece together different problems. I recognized that our CTO probably shouldn’t be mailing laptops out still. Why don’t I research a managed service provider, and we can start looking at how we rolled that out for an organization? That’s something that the CEO or a CTO doesn’t really have the time to do and research all of these other things. So, I always encourage founders to think about a strategic business partner or executive assistant as a second brain. If you can find the person that you really mesh with, it is going to be a force multiplier for your success because it’s like having two of you.

Hiring and Onboarding Executive Assistants

Ryan: I love that. So, with that in mind, let’s talk about how you get started in this. how do you hire your assistant? When is the timeline for it? Is it when you’re feeling that burnout? Is it when you’ve lost yourself, you’re not sleeping? Is it when you’re just, like you said, you’re letting tasks slip? What are the signs that you see where you’re telling someone? Look, this is, it’s time, and how, when somebody is already facing this burnout, do you coach somebody into it? Here’s how you go and hire one without creating more stress on your plate and things like that.

Jessica: I think this is when recruiters come in really well, like specialized recruiting, because it’s really hard to hire an executive assistant because it is very relationship-based. It’s you; you’re less looking for someone with a certain, you know, past experience and more someone that fits the way that you work that you can then mold to be your second person, your second person in charge. So, for me, like I’ve done some hiring work in the past, and you kind of start off with taking in information from the founder about their working style, what is important to them, what they would like, what they’re stressed out about. For me, it was that I was spending more time dreading doing my bookkeeping than it would have taken me just to do it. And it was like, ok, it’s time to like to get somebody to help. My bookkeeping was basic. So I could have a regular virtual assistant handle my bookkeeping for me. If you find that you’re constantly having to manage your schedule and it’s stressing you out because you’re getting behind on knitting, invite somebody to monitor your email for you and organize that is going to free up hours of time and stress in your life. And absolutely ask for help. It’s worth the money to pay for a good recruiter who knows what to look for within like an executive assistant than to try and just do it yourself because you’re not, you didn’t get hired and, or, you know, trained in HR or recruiting. We need to stop trying to be everything and start recognizing that there are people who are experts that we can utilize. There’s never been a time in history where, like, you could find such a niche person to help you. Like, if you need something, there is someone out there who is ready to help with that problem. It’s just we find them. Still, on LinkedIn, especially, there’s a really engaged community of executive assistants that are eager and like they’re looking to start branching out, and they want a challenge. They’re tired of just running the scheduled tests stand-alone, and they’re looking for the next level; this is such a great opportunity for them.

The Role of Executive Assistants

Ryan: So tell me more about, you know, the tech-savvy assistant itself, right? And what is role play, not just for you, but for early-stage founders for others, and how can any of our listeners kind of take advantage of that? What tasks can be taken off of their plate? Because we want to make sure again, we’re providing value for all of our listeners here in terms of they come here, and they go, ok, this is for me, I need to do this. Where do I start? What kind of roles can this kind of take on to help them in that process to move forward?

Jessica: There are obvious things like we can handle communications where you need to respond to this email, and you don’t have the time to respond to it. But also things like social media responses. You want your company to have a social media presence, but you don’t have the time and capacity to manage it, and social media is not your expertise. Well, you can have a virtual assistant do that kind of thing. There’s a calendar and time management of deciding honestly when I get so tired of just like burn out from business stuff. It is the decision fatigue that gets me more than anything where it’s like, I need to reschedule this appointment, and I don’t even know where I need to reschedule it, and just having someone that you can rely on to be like, can you take over and they will be able to drive that bus. There’s itinerary planning for travel if you do any business travel. I recently was working with the founder a couple of months ago, and you know, he wanted to go to a big convention in San Francisco. So it was, you know, finding hotels for you, finding flights, finding the restaurants, all those things that you’re going to need to do to be able to network properly and make those connections, you could have somebody research for you and plan out. And that’s probably one of our best strong points because we have really high emotional intelligence, and we can recognize what’s really important. 

Jessica: For networking events, expense reporting is really big. And I know that, like, so that’s a big struggle for me. I hate doing my expenses. So having them take that on and keep track of them for us is really great. Any special projects. So if you, for example, this is the time I rolled out for the CTO, the managed service provider, you can’t go and research all of these different vendors and figure out which one is best. So have your admin do that for you. Content creation is a basic one as well. Everybody knows what a virtual system can do for you if you want to create social media content. It’s really, I kind of talk about working with an early admin as thinking about what you can teach like a basic intern. What is it that you can offload, thinking about these small tasks? And that’s also how we talk about using chat GPT, for example, what are tasks that you can use chat GPT for. And if you’re not ready for a virtual assistant and you’re just like, I just want something to help me write emails or a thought partner. And that’s how I always encourage admins to use Chad G BT four is because Google is not great and hasn’t been great for a really long time because of, you know, SEO stuffing of, all these different blogs, is we can get a really straightforward answer on how to proceed with building a business. For example, I use chat GPT  for business advice all the time because I’m a new business owner. I don’t have an MBA. I didn’t grow up around people who had a business, and I sometimes struggled to know what the next move was. And so I’m able to use chat GPT  to talk through all of the issues that I’m dealing with and get some decent base-level guidance on how I need to move forward.

Jessica: And that is one of the coolest things that has come from using chat GPT  and then also teaching it to the admins. It is like when you get so frozen and scared because you need to decide on behalf of the person you support. Still, you don’t have good information to go on, like using chat GPT  to say here’s the situation, let’s talk through it together is incredible, and it really helps like embolden them to be able to do their job better.

Tech-Savvy Assistant and Chat GPT Usage

Ryan: I love that you gave a couple of examples there, but can you give us an example, like a specific, you said, like business decisions or things like that? Because that could be a thing all on its own, an episode we could have is using chat GPT as your assistant, right? To help you with that. But do you have a concrete example that you’ve used to say like, hey, you know what, here’s an exact question, here’s how that here was the result I got out of it?

Jessica: So I don’t remember the exact prompt, but essentially, it was, this is what my business does. This is the person who would use my business. Here are the products that I already offer, and here’s more information about what I do; tell me some other projects that I could create. So tell me more digital products that I could do or tell me ideas for presentations that I could create. Anytime I get asked to do a speaking event, they give me a vague idea of what the topic will be. I go to chat GPT, and it’s like, OK, here’s what I usually talk about. Here are my specialties, and here is the theme of the conference. Can you come up with a presentation theme that I can then use?

In the same way, executive assistant, they’re like, I need to plan for an event. Well, let’s use chat GPT to help us think about them because a lot of times, we’re given things like, hey, we’re going to do this company event in the theme of synergy. Can you create an icebreaker around synergy? And we don’t get paid enough to come up with things like that. Using chat GPT to be like, can you create some synergy-themed Icebreakers is a really great one. And then also, getting asked to do speaking events like podcasts a lot of times, they’ll be like, oh, can you provide us with some guiding questions? and then I just draw a blank, I just stare at them, and I don’t know where to start so I can ask chat GPT to kind of provide me with these like guiding questions that allow me to, you know, I can speak to that a lot easier than it’s going to be me just waiting and trying to come up with something actually to talk about.

Ryan:  Absolutely perfect. I’ve got stuff I can take away from here. I’ve been feverishly scribbling notes right now. If it is going well, my life could get easier from some of the nice information here. But I know for a lot of our listeners. That is the case that they’ve pulled away here, too. Before we sign off on this episode, I would love to get you to tell us more about where people can find you, connect with the tech Savvy assistant, and connect with you to learn, to learn more for sure.

Jessica: You can find me on LinkedIn under Jessica McBride. Feel free to send me a request. My website is Tech Savvy assistant.com, and I encourage everyone to subscribe to my newsletter, which you can find on the website. I often do free events for members of my community. I’m doing an upcoming event soon about how executive assistants can begin to utilize automation tools. We’re always building on the knowledge that we have. And yeah, you can find me on all the social media channels. I’m on Instagram and TikTok. And I have a Facebook community if anybody is interested in joining that as well. But yeah, you feel free to reach out.


Ryan: Absolutely perfect. Everyone takes advantage of that offer because, I mean, I think there’s a lot of ways that we could improve our work lives and, in turn, personal lives just by picking on some of the information that Jessica has given us here and has the resources she has available for us online as well. With that, we’ll bring this episode to a close, and I want to thank Jessica Mcbride for this amazing podcast on the value of executive assistance for early-stage founders. And I also want to thank our listeners; we cannot do what we do without you. So, until we meet again with another amazing TBR episode, I’m your host, Ryan Davies. Thanks, everybody. Take care out there.

About Our Host and Guest

Director of Marketing – Ekwa.Tech & Ekwa Marketing
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Innovative Founder @ Tech Savvy Assistant
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“I always encourage founders to think about a strategic business partner or executive assistant as a second brain. If you can find the person that you really mesh with, it is going to be a force multiplier for your success.”

– Jessica McBride –