Heather Cantor on What's Next for Executive Assistants

Heather · 0:00

Hi, my name is Heather Cantor, and my favorite leadership quote is, I'm never perfect, but I'm always genuine.

Speaker 3 · 0:15

The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.

Jeremy · 0:31

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Heather · 1:59

Thank you so much for having me, Jeremy. And first and foremost, thank you so much just for taking the time in addition to your full-time role to do this podcast and to build the Leader Assistant community and to share your knowledge with your book and your speaking engagements and everything that you do for our community. So thank you for that.

Jeremy · 2:17

Yeah, thanks for the shout out. You're welcome.

Heather · 2:20

Of course, I am actually a lifelong resident of Maryland. So I'm meeting with you from Maryland virtually today. And I, you know, from time to time, find that people are pretty surprised when they discover that I've never lived anywhere else.

Jeremy · 2:35

Nice. Nice. Where do you like to visit? What's your favorite place you've visited, traveled to?

Heather · 2:41

I think travel. So travel, I'm definitely a Caribbean, all-inclusive person just due to the natures of our roles. I love some just really good downtime of relaxation and having a team of people take care of me for once.

Jeremy · 3:00

Nice. That's great. Then what is your favorite thing to do when you're not working?

Heather · 3:09

Favorite thing to do when I'm not working? So something that's really, really important to me are fitness and nutrition. So about 20 years ago or so, I just really had this extreme interest in learning more about both and have continued that tradition in daily workouts. And also, I've been pursuing a precision certification with precision nutrition as well, just to learn a lot more about nutrition as a whole. So strength training is definitely something I really, really enjoy in my spare time. And then also, riding my motorcycle. So I got my motorcycle license last summer. I was the only woman in the class, and I went out and bought a bike a week later. So I love taking motorcycle rides.

Jeremy · 4:03

That's awesome. What type of bike did you get?

Heather · 4:05

I actually bought a Moto Guzzi. So it is an Italian motorcycle. Super unique, which is exactly what I wanted. I wanted something that didn't look like anything else.

Jeremy · 4:16

Nice. That's crazy. So have you had any, like do you like to ride in the city? Do you like to ride at the countryside? Like what's, where do you like to ride?

Heather · 4:27

Definitely in the country. I'm glad you asked. I live in a very rural area. So I am in the farthest tip top corner of Maryland and Northeast Maryland. And there's a lot of really great country back roads here. So I really enjoy that. And the longest, the longest ride, so to speak, I've taken so far has been about 90 minutes each way. And I headed up to Pennsylvania on back roads.

Jeremy · 4:51

Wow. Nice.

Heather · 4:53

A lot of fun.

Jeremy · 4:55

Yeah, it's I've never been on. I've been on dirt bike, but I've never been on a street bike motorcycle. So it's I don't know if my wife would let me, but, you know, it's a different topic for a different episode. So tell us about your career journey then. How did you end up as an assistant? You know, tell us a little bit about your. You've got over 15 years of experience. It looks like I'm looking at your bio. So tell us a little bit about your journey.

Heather · 5:23

Yeah. So a lot of my journey, I think, was influenced by my parents. You know, I grew up around entrepreneurship. My my late father had a small business for 30 years, which is actually still family owned and operated to this day. And, you know, since he was both an owner and operator, I learned finance and operations and sales and even marketing, right? And before I even realized I was learning it. So, you know, my mom, on the other hand, you know, she stepped into a career in insurance and was working full time and single mom and doing all the things. And so one thing I think I attribute to both of them is my work ethic and then just learning at a very early age. So, you know, I didn't go away to college, the traditional college. I stayed close to home, went to community college, and then I go right into work. So that said, my career path has not been linear at all. I've spent years building business generalist experience because I've had opportunities to be, you know, whether it was an operations manager or project manager, community manager, and then also an executive assistant. So I really, you know, I'm somebody who doesn't really care much about titles, so to speak. But I did find myself leaning into the executive support and operations space after having had the opportunity to kind of dabble in different roles. I've also had an opportunity to work in different industries and different business sizes, whether it's corporations or startups as well. And so I think that entrepreneurship shows up a lot from my childhood in that I love being in a startup where it's scrappy, you know, and you can really be in an operator and then also be making some strategic decisions as well.

Jeremy · 7:16

Yeah. So what was maybe, you know, it looks like you were executive assistant and you went to be, you know, community operations manager, director of operations back to executive business partner. And what's been maybe the one thing that drew you back to the support leader assistant role?

Heather · 7:38

So I am, you know, I'm also a certified scrum master. So when I, you know, learning more about servant leadership, you know, was very attractive to me. And so there's a lot of similarities with servant leadership and executive support and executive operations. And so it's really about that, that force multiplier piece and, and being and supporting others to help them show up. They're best and help them be successful. I really, really thrive in that environment. You know, whether it's front office, back office, what have you, but really being, you know, the operations manager, so to speak, of an executive to, to make sure that they are fully prepared and going into whatever and anything that they need to. I just was drawn to it. You know, in every role that I've had, I just really thrive in that environment.

Jeremy · 8:31

Awesome. So what's the, you know, your title is Executive business Partner and Leader Office of the COO. So what's, what are all those different parts of that title mean?

Heather · 8:46

Absolutely. So it's a very unique title. And I'm actually really glad that you, you know, called that out. So today, yes, I am the EBP to our co-founder and COO at Drata. And then I am also the EBP team leader. So I have six direct reports. You know, five of them are EBPs and one is an ABP. We'll talk about that in a little bit. But, you know, Drata is a continuous automation solution, right? That, you know, the product itself that monitors, it continuously monitors, remediates, collects evidence of controls from code to production. And ironically, there's a lot of similarities between what Drata does and what our EBPs, you know, here do at Drata. And so my role is very dual-hatted in that I am an operating EBP to, you know, an executive, and then I'm also leading a team of EBPs. And so I really feel like, you know, while that does present certain challenges, it really helps me relate to the team and see experience, maybe the same challenges that they're going through and to be able to effectively, you know, I guess, address the problems that we're trying to solve for and have a really good understanding of what's going on in the business.

Jeremy · 10:05

So what is, for those listening, that maybe they've heard Executive business Partner can be a title that is swapped out for Executive Assistant or Senior Executive Assistant. What is an Executive business Partner and what's the difference between the title and is it, what's the word I'm trying to think of, is it like a culture shift, title change? Is it because of the way that people see the word assistant sometimes, or is there an actual leveling that goes along with that? Tell us a little bit about how that works in your organization.

Heather · 10:47

Absolutely. So it's leaning more towards the leveling. You know, again, historically, right, there hasn't really been a solid growth trajectory for an executive assistant. You know, people tend to say, okay, I'm going to be an executive assistant, and then you end up being a career executive assistant. And that's okay. But for people that may want to venture into other areas or maybe their life changes or their interests change, what I love about the executive business partner role is here at Drata because it's not the same in every organization, but here with our team, it is a stepping stone. So the way that we're leveled is we have administrative business partners, which is more of an entry level role, and then we have executive business partners. And so I see that as a stepping stone to perhaps maybe a chief of staff role down the line, or perhaps I really think the possibilities are endless. So this could also be a stepping stone for an executive business partner to go into an operations type of role. So it really is kind of fueling that growth and the leveling that, in my experience in years past, has not been there for anyone in our space.

Jeremy · 12:05

Yeah, it's pretty rare still to this day, I think, for you've got all the levels and titles for the sales team and the engineering team and the marketing team, but then you get to the assistant team and you're like, well, we don't really have a path for you. Exactly. That's great. So then what happens if you're an executive business partner and you like the role so much, you don't really want to move in to achieve a staff, move into operations, move into, does that make sense?

Heather · 12:36

Absolutely. You can stay where you are. I mean, that's the beauty of it, to have the autonomy and the flexibility, and to be able to chart your own career path. And so that's another benefit of, I believe, me working with our team on their development and their goals. We're actually right in the midst of that season right now in identifying what they think they want to do today and the steps that it's going to take for them to get there. And the beauty of having this org structure in a startup, at least from my perspective, is that there are so many opportunities to dip your toe in the water with different things. So for example, perhaps one of the EBPs on the team has an interest in sales. They are encouraged and supported and they can go and shadow somebody in sales or learn more about the ins and the outs. And then obviously I would guide them to work on particular skill sets that they needed to work on to make that transition. It's just to me just kind of the next era of our roles and this industry in itself in that we have the same growth opportunities that others do in companies.

Jeremy · 13:52

Yeah. So what are the cons maybe to having an executive business partner like yourself lead the other EBPs?

Heather · 14:05

Yes, that's an excellent question. So like I said, this is actually top of mind for our team right now. And I solicit their feedback a lot because it's very important to me. And so, you know, I do think the benefits far outweigh the cons. And I think the only, maybe the only thing that could be present as a con slash challenge is just the dual padded role in balancing, you know, the EBP role itself and then also the, you know, people leader portion of the of the after actual opportunity. So I have an amazing, you know, communication and relationship with my executive. We have a great cadence together. And so we're constantly checking in on capacity, constantly reshifting priorities as needed to, you know, to kind of go with the ebbs and the flows of the business and the demands. obviously, as you know, in your role, there's, you know, there's busier times of year than others. So I'm just very agile and flexible in that I'm able to shift where I'm needed, sometimes like week by week, you know, and based on whatever the business needs, but most importantly, what my team needs. In addition, I mean, you know, one of the benefits of having, I think, an EBP as an EBP leader is, you know, being able to educate and grow EBPs, because that's also another piece, I think, that's missing as well as far as development. I host monthly working sessions with the EBPs, and they're a part of creating the agenda, and they kind of say, you know, hey, I want to learn about this, or I want to brainstorm about that. And so I offer educational opportunities as well as part of our team. And I think that's really important.

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Jeremy · 16:31

So what would you say is one of the toughest things that you've had to face and maybe the biggest challenges in? I'd love to hear if you can think of it. I'll put you on the spot. I'd love to hear your biggest challenge in your EBP role, but also your biggest challenge in leading the other EBPs. So maybe there's a story that comes to mind or an instance where it was a difficult thing to navigate through, or maybe it was in a prior role where you had to challenge with an executive you're supporting. So yeah, I'd love to put you on the spot there and hear a couple of your challenges.

Heather · 17:19

Yeah, I love it. I think a challenge for the EBP leader side of my role was, so the EBP framework, Adrata was actually brought in by my predecessor. And so the transition period of, you know, and this was last year, I was taking over the team, also working with my executive, but then also in terms supporting that particular individual's executive as well. So it was a lot. It was a lot of wants. It was a lot of change. And so, you know, I took it on and, you know, the feedback I was given is that I just thrived through it. So, you know, I think this is something you commonly hear, and I'm sure your listeners are going to be able to relate that most of us in this industry thrive in chaos. And so that is exactly what I did. So I, you know, I focus on what our team needs. I'm a people first leader and I focus on what the business needs. And so, you know, I think just again, managing your priorities and making sure that you have really solid communication with all stakeholders, including your executive, keeping them updated on what is going on, what is happening, allows you to have that autonomy and flexibility to, you know, reassess where priorities should be and where your time is being spent as well. Another thing that was really, really critical was delegating. So, you know, I put together a whole delegation plan for the team. I had people on the team step up and take ownership of various projects or initiatives. And so that those opportunities also allowed them to grow. So that was a win-win for me. So, you know, the most challenging time as an EBP leader actually ended up like resulting in, you know, I think one of the best times as well. I'm, you know, always looking to improve the team. But most importantly, you know, how can I be better? How can I show up and be better? So a challenge, I think, in the EBP role itself, I'll take it all the way back to when I first started at Drata. So, you know, I came to Drata because of the executive business partner org structure. I was absolutely just fascinated with it and thought, wow, this is a really great next step in stepping stone. And throughout the interview process, our talent acquisition team is incredible. And they, you know, kept saying we move very quickly here. We move at Drata speed. And I don't think it was until maybe my second or third day where I fully understood with that net. So it was extremely challenging. And I will add to I am in Maryland. Most of our executive team is in California and I am 100 percent remote. And so, you know, for those folks that think executive operations, you know, personnel need to come back to the office, I'm here to challenge that. So in almost two years, I've only been in person with my executive twice. So it can work 100 percent remote. And that has not been a challenge or a blocker. I just wanted to point that out that, you know, we've made it through all of these transitions and changes and challenges fully remote. So I think the challenge when I joined was, you know, oh, wow, like, I know you move fast here. But when you finally feel it and you're in it, you think, oh, my goodness. Right. So I quickly got up the speed, realized what expectations and turnaround times and things like that were like. And so it was it was just challenging, I think, at first to get into the the swing of things and the routine of things.

Jeremy · 21:03

What's maybe a specific example of something that you're like, wow, that's fast.

Heather · 21:11

Well, one, even before I started, which was really interesting, I mean, the whole offer process of my roller drada happened extremely fast. You know, I had been actually, you know, interviewing and that was very surprising to me. I think, you know, the speed in which we ship our product, you know, I'm going to go on the technical side. I think, you know, obviously running sprints and what have you. There's there's typical time frames there, but I'm really, really surprised at how quickly we ship products. I'm really, really surprised at how quickly Drata as a whole, as a company. So we're, you know, today, as we're talking, we're only three years old. And, you know, we are 400 to 500 employees, give or take with contractors. And so that's that's quickly scaling, but it's very mindful strategic scaling. So that's something we've also moved very quickly on as well.

Jeremy · 22:09

And what is give us a little bit of a taste of what Drata does, you know, software wise in that world?

Heather · 22:16

Yeah, of course. So Drata automates your compliance journey. So for your listeners, for the, you know, the companies they work with or they support and their executives, think about the audits, you know, that, you know, the meetings you're scheduling for audits and what have you. So Drata actually takes the audit process, and puts it on autopilot, so to speak. So we take everything from, you know, start to audit ready beyond, and then we provide the support from the security and compliance experts who built it. So we support over 20 frameworks. You know, what does, what does frameworks mean, right? So think about like, have you heard of SOC 2 compliance, ISO, HIPAA compliance, which is very big in the healthcare, you know, industry, which also really came into play during COVID, when a lot of people were pivoting to telemedicine and what have you. So we actually, we have over, we support over 20 frameworks now and we help companies get compliant, but then we also continuously monitor controls. So there's continuous monitoring, there's remediation, there's collection of evidence. And so what that does is it changes everything for a company. So typically an audit, you have auditors come out to your office, you know, think old school, people are taking screenshots of things, you know, and uploading them to a folder. And it's a lot of manual work. So think days, think weeks. Well, there's been instances where, you know, we've been able to do that very, very quickly. And when I mean quickly, it could be hours, it could be days. And so, you know, just having the product in place, and we have a lot of other excitings, the things that are coming down the pike, but having that product in place, you know, really frees up people's time in the organization to go focus on more important things.

Jeremy · 24:06

Love it. Great job. And I think your team would be proud of how you succinctly described the product. So nice work.

Heather · 24:15

Well, and I, you know, I describe the product and I compare it to the EBP team all the time. And like, you know, draw to continuously monitors. Well, EBPs continuously monitor the business environment, right? EBPs also, there's remediation. EBPs proactively address the issues before they arise. We're collecting evidence, right? We're little detectives ourselves. We're collecting information, data, we're synthesizing it. And so that is, you know, when people do ask me what we do here, if they understand our product, I'm able to really pull those two together.

Jeremy · 24:49

Nice. Well, this has been great, Heather, and I really, really appreciate you taking the time to share a little bit of your story. What's maybe your number one tip? If you mentioned working remote, what's your number one tip or two, if you have two, working from home and really staying connected to your team and your executives while in a different state?

Heather · 25:13

So that's a great question. You know, first and foremost, I would say take care of yourself. So the beauty that I have of being on the East Coast and the East Coast time zone is I have a jumpstart, I have a three hour jumpstart to everybody else on the West Coast. I just shared my secret. So I prioritize me in the morning. So whether it's appointments, errands, my workouts, you know, things like that, those are done in the morning. And then whatever else happens throughout the day, I know that those are done. So I am taking care of. I also think, you know, having, you know, time blocks on the calendar, that's also very, very helpful. When it comes to staying connected with the team, it's really important to have one-on-ones on the calendar and then also have, you know, those team meetings on the calendar as well. Anybody on my team would say this. I take a lot of pride in this. I very, very rarely will ever cancel a one-on-one because they trump everything for me. They mean everything to be able to connect with the team. So I think prioritizing your people and prioritizing the time with people is definitely key in a remote environment. There are opportunities, obviously, from time to time, once or twice a year, I go out to San Diego, where most of our team is based. Not a bad gig to be able to go out to San Diego, especially, but it's wintertime in Maryland. It's just such a treat and so lovely to be able to meet and gather with everybody in person when we do do that from time to time. But it's really, really key to just, we're a Slack organization. I do a lot of employee engagement efforts myself because it's really, really important to me whether it's in our team channel or company-wide. I think it's important for people to get to know each other on the personal level so we can understand one another and build those relationships virtually.

Jeremy · 27:13

Love it. Great tips. Thanks for sharing. Do you have any interesting stories about working remote where it's like maybe you did something that your team didn't think was possible from the other side of the country, or maybe you wish you were on-site, so you could have just run over and handled something?

Heather · 27:36

I would love that. There's so many times where I would love that. But that's a very long plane ride. I did have a case, it was last year where we do have some fluky weather here in Maryland from time to time, and I had lost power and made a really, really critical important meeting. I haven't yet gotten to the point of wiring a generator to my home yet, so I have a backup plan and again, and I live in a very rural area, so there isn't a shared workspace or anything like that right around the corner here. We have an amazing brand new beautiful library in my county, and so that is my backup plan when things go arar at home. I was able to very, very quickly, literally made it within two minutes to the library, got everything set up, got my security set up, and was able to just join the meeting, and it went off without a hitch and nobody knew. It actually happened to be an all company. We were doing a summer digital fun employee event where I was actually presenting to hundreds of employees as well. So the panic definitely set in. But in true executive business partner style, I had the backup plan in place and we made it all happen. As you know, with event planning, the key is to make sure nobody knows about all those hiccups that go on behind the scenes because boy, they do.

Jeremy · 29:01

Yeah, it's always nerve-racking when we get a storm coming through here and came to city and I'm like, I don't know, I've got podcast interviews, I've got webinars, I've got to hop on these meetings. But I think I've had to do it a few times, a handful of times maybe is where I'll have, because I've got a desktop but then I also have a laptop. So the desktop, if the power goes out, I'm SOL on that. But the laptop, it's like, okay, well, I'll pull my laptop out and I'll use my cellphone hotspot, and that's my no power, no internet backup plan that I just know. All right.

Heather · 29:41

I hope the batteries are charged enough.

Jeremy · 29:44

Right. Exactly. Exactly. Cool. Well, Heather, thanks again for being on the show. What's maybe your ideal, like if you were going to put a billboard together and have a message for assistance of the world or executive business partners of the world, what would you put in bold font on that billboard for the assistance of the world to see?

Heather · 30:14

I would say that nothing is impossible. It's something that I carry with me. I'm one of those crazy challenge accepted kind of people, like give me something super impossible to do. To the point where I can share a story where last year, my executive was planning a birthday gathering for his wife, and they found out that a dish was no longer served at their favorite restaurant. I went and found the chef who had went to another restaurant, called him, established a relationship with him, and then talked him into hosting a private chef dinner at my executive's house for his wife, which was unbelievable and went really, really well, so much that it's now an annual tradition, and they just had another one. So again, nothing is impossible. And it is, I believe, people like me and you and your listeners that make those things happen behind the scenes. Our executives come to us with a problem or a vision, and we are the ones that execute and make it happen. And one thing my executive always says about me is that when he thinks of me, he thinks unapologetic execution, because I'm also one of those people that I will just go get things done and then ask for forgiveness later. So just nothing is impossible. Keep doing what you're doing and the possibilities are endless.

Jeremy · 31:45

So I have to ask though, what was the special dish?

Heather · 31:50

It was falafels, but it was prepared in a very particular way that they were the best falafels she had ever had. And so, yes. So I heard that and I could tell he was scrambling a little bit, and I said, I got to go make this happen. So threw it out into the universe, tracked the gentleman down and made it happen.

Jeremy · 32:13

Well, nice work. Props on that. Yeah, falafel. My wife loves falafel. So she would be excited about that, too. Awesome. Well, Heather, what's the best place that people can reach out if they want to say hi and connect?

Heather · 32:28

I would love to connect with your listeners on LinkedIn. We will be growing the team at Drata this year. So I'm always looking to connect with like minded folks. And LinkedIn is the best place. I'm there a lot. I have a very active LinkedIn presence. So I would love to network, support, help. If anybody has any very difficult problems we're trying to solve for, I would love to meet your listeners.

Jeremy · 32:57

Perfect. And I'll put your LinkedIn link in the show notes at leaderassistant.com/287. For everyone listening to go check it out and say hi to Heather and reach out and connect. So thanks again and best of luck to you and your team at Gerada. And we look forward to staying connected.

Heather · 33:17

Beautiful. Thank you. Please review on Apple Podcasts.

Speaker 4 · 33:38

goburrows.com.