#15 - Success Stories: Halley Bennet

Success Story #1

with Halley Bennet

Maddie Duke  00:01

You’re listening to The State Of Work, the podcast by Lano. The State Of Work, about finding your place in the changing world of work as an individual or an organization. In each episode, we dive into some of the benefits and limitations we face when it comes to remote and flexible work. We talk about how we work, how we hire and manage people, and how we live in this increasingly global workplace. I’m your host, Maddie Duke. And this episode marks the beginning of a new series of mini episodes called “Success Stories” where we’ll chat to individuals about their lived experiences of working in remote or global teams. My first guest is Halley Bennett, Head of Marketing here at Lano. I chatted to Halley about what it’s like to kickstart your own remote journey as well as what skills are crucial to managing a team remotely. 

Maddie Duke  00:58

I’m speaking now with Halley Bennett, Head of Marketing at Lano. Holly’s joining us from Madrid. Welcome Halley. 

Halley Bennett  01:02

Hi, Maddie, thanks for having me. 

Maddie Duke  01:04

I want to talk to you about your experiences of working remote. So through your career, you’ve had the opportunity to both go remote and to start remote. And I’m really looking forward to hearing about your experiences of that. How long have you been working remote?

Halley Bennett  01:19

So I’ve been remote for coming up on three years now, during that entire time based from Madrid.

Maddie Duke  01:27

Okay, and what started your remote journey? Was it something that you pushed for from an employer, like, can we make this happen? Or is it something that you went into?

Halley Bennett  01:36

Yeah, it was something that I pushed for quite hard. And at the time, you know, it was, I think that idea about how remote work happened or what it would look like, was kind of had a bad rap 

just in that context of you know, that I would be sort of distant from the team. And I would probably be working fewer hours because I’d be on a beach somewhere. And so I kind of started my journey of pushing towards a remote position. It was motivated on my side by a lifestyle change that I was pursuing. I had, I grew up in the United States. But I spent quite a bit of time during my university studies in Latin America and in Europe. And when I kind of finished my studies and was thinking about where to start my life, I wound up in Madrid and actually have kind of accidentally fallen into the majority of my adult life has taken place here. So I kind of fell into life in Madrid. And after a number of years, I had an opportunity to go back to the United States to pursue some career growth, which was really fantastic. Spanning kind of two different locations, two companies, wound up working for a FinTech company called Prodigy Finance in New York City. And then had the opportunity with Prodigy Finance to spend some time in their London office, as well as in their Cape Town office. And kind of at the end of each of those stints where I was when I was supposed to go back to New York. And I was really finding that that was not that sort of that wasn’t exciting me anymore. I didn’t want to live in New York City anymore, I wanted to, I wanted to come back to Europe, I really was missing the lifestyle that I had in Madrid. And I was just so sure that I could make it work. And then and then in fact, it would be an improvement because I would be in a better time zone with respect to London and Cape Town,where the company that I was working for, Prodigy Finance, had their kind of main offices. And so I really went about kind of like building up a business case for what would my remote engagement with them look like? What kind of steps would they need to pursue to make that happen? How much of that would I be willing to take on…. which was a lot? But yeah, so it was definitely like a pitch from my side. And it was really fortunate to make it happen. And you know, you spoke kind of at the beginning about like the difference between going remote and starting remote. That was absolutely a scenario where I was going remote. So after spending two and a half years in the company, really trying to engage them on the idea that I could do my job even better, if I was based from a location that would make me really happy, keep me in the right time zone and be beneficial kind of all around for the organization, even though I wouldn’t be in the same location as the rest of my colleagues.

Maddie Duke  04:19

Well, good for you for making that happen and making that pitch. It’s you know, it’s really cool to hear about someone making a bold move like that. What are some of the things that the company has to do to make that happen? Like we’ve talked a little bit on the podcast about compliance. How did you go about working with them to navigate the kind of contract and tax system and find the right setup for where you were living and where their offices were based? 

Halley Bennett  04:47

It was a wild ride, I can say and I’ve learned so much since then. And really accelerated that in the last couple of months getting to know the products at Lano so much better, many of which I wish I would have known about when I made this change. And so on one hand, we spent a lot of time in the organization looking at how exactly as you say, like, how would the contract work? What kind of status would I need in Spain versus what kind of status would the company need to, you know, use to classify me as an employee of their London offices, is how we decided to pursue it. So I became employed by their London team, but living in Spain, and navigating the kind of tax environment for that, as well as the… we were really fortunate in that I didn’t have to, we didn’t have to navigate much in terms of my residence status. I already had a permanent residency in Spain. So that was kind of one fewer thing. 

Maddie Duke  05:49

One box ticked.

Halley Bennett  05:52

One less thing to worry about. Yeah, yeah, exactly. But the tax situation was definitely work in progress. We made an agreement as an organization that I would figure out on my own, how taxes would work for me and the company would navigate how taxes work for them. And I, we did not get it right the first time around, it was incredibly painful, including receiving, I mean, it for Harry Potter fans, it was like receiving a Howler in the mail… horrendous letters coming from Her Majesty’s revenue service on a regular basis, telling me that I was going to be blocked forever from entering the UK and calling my employer almost in tears saying, I don’t even think I’m supposed to pay taxes in the UK. How is this working? So over time, we certainly improved our understanding and really, you know, learned a lot together. But I think what I’ve learned now about how you know, how employer of record works, and how I might have set that up by more clearly differentiating between sort of, like a freelancer or a contract agreement with my organization versus a full time employment agreement with them, which I think they would have. Yeah, I know, they would have participated in and just don’t think we knew what the resources were at the time. So there was a lot of trial and error.

Maddie Duke  07:01

And how was that? How did that compare to your more recent experience of starting remote with a remote-first company, in starting your position at Lano?

Halley Bennett  07:12

Yeah, I mean, it’s such an interesting contrast. So at Prodigy where I was sort of dry, you know, I was personally motivated to make something happen. And I had the, you know, the real backing of the organization for which I’m incredibly grateful. But everything was green fields, right? So lots of research, lots of work to try and figure out how to make things happen. Lots of goodwill from all parties to make that move forward, I think otherwise, it might not have happened. And in contrast, or I guess, before I move on to kind of how it’s looking at Lano like the interesting experience that I was able to have at Prodigy was so I started working remotely well before, kind of the, you know, the global pandemic and before the significant shift to working from home kind of as a safety measure kicked in. And so also like seeing my colleagues transition to kind of a fully remote product prodigy went fully remote during the kind of majority of their lockdowns, both in Cape Town, London, US and India, where they also have a physical presence. So I learned quite a bit about how to help guide others and sort of sharing with them and creating community and trying to kind of bolster the normalcy of working from home during that time. But it also increased my empathy a lot to the kind of challenges of working from home. So where I was going remote, because I really wanted to make it happen. And I was in a, you know, privileged position really to kind of set that up for success, in terms of my home working environment, and the ability to kind of make that fit with my lifestyle, you know, really getting to see kind of what the other side of the coin is when when, you know, folks are forced to work from home and perhaps haven’t had that opportunity to really set that up in a successful way. And so now transitioning to Lano, which is remote-first, obviously, and, you know, by virtue of the products that we’re building, we think all day every day about how people work successfully together remotely. We’re also a much smaller team at the moment. And so I think in some ways, that’s quite a bit easier. But it is quite challenging actually to start a role remotely, maybe even more than I originally expected. And so it’s really, on one hand, been incredible to have the backing of the organization who knows what they’re doing, right, like the products and services that a lot of other organizations are the same ones that we’re using, in my case, for example. So Lano’s kind of core… one of their core products is to help others be able to attract remote talent by hiring them through an employer of record, who works with a vetted network of partners really, that gives us incredible global coverage. And I’m fortunate enough to be hired at Lano through one of those same employers of record, which means my contract in Spain is localized, so I get to benefit from, you know, all the normal kind of perks and and yeah, just kind of normal day to day stuff when it comes to how I get paid how my contract looks the you know, time off and the expected sort of Ts and Cs of working as a traditional employee in Spain are available to me through that type of arrangement. So not having to navigate that alone has been incredible to say the least, yeah.

Maddie Duke  10:27

I can imagine! Have you ever had any real kind of nightmare moments where something’s gone wrong? And you’ve been completely disconnected from your team? Have you got any fun anecdotes for us or maybe even like a contingency plan for when yeah, things like that happened?

Halley Bennett  10:43

Yeah, I mean, it was such an interesting experience. So when the kind of first wave of lockdowns hit, I was managing a team of five in, almost all in Cape Town in South Africa. And it just so happened that, you know, by virtue of the kind of this and the timeline and the time of year, I wasn’t able, obviously to travel and meet any of those members of the team. From the time I started managing them. So I started managing the team, we knew each other from social engagements, I’ve been at the company for several years as as had many of the team members, but so that we kind of started working together as a unit, and then kind of wave of pandemic hit, and most of them kind of then transitioned to working from home. And actually, exactly as you say, we had two members of the team who really lived in environments where, you know, fortunately, they had a comfortable home lives and plenty of space to work, but really, really, really difficult times accessing just good internet and just being able to kind of continuously participate in video calls, or, you know, in particular, I don’t know what it is, but like sharing documents on screen would totally blow up every single call we would have as a team. It was really frustrating. I mean, I think it was frustrating for the people in every aspect, right? So it obviously it’s it’s really disruptive, to the kind of flow of conversation, but it’s also just tremendously isolating, like the person that is on the other end of that and can’t really get connected to the tools that they need for the team to be, you know, to be successful on that team. Like, I just…. the empathy is tremendous. I think that’s just really unfortunate. And so we actually, we were really fortunate in that the organization made a budget effectively available to each of the teams to kind of problem solve for what they would need to sort of survive through the pandemic period. And we were able to upgrade, effectively, everybody’s mobile plan so that they could hotspot if their local internet connection failed. And that was pretty game changing for us. Like, you know, it sounds like such a silly thing. But basically putting everybody on like an unlimited data plan, having the company participate in financially backing that and that way, basically saying, okay, in the moment that your internet cuts out, switch to a hotspot, and everybody will be connected by hotspot, which will you know, it damages the quality of the call in some cases, right? Like, it depends on kind of where you are and what your mobile broadband scenario looks like. But, let us stay connected, right, like we would have had a significantly lower number of calls just get totally disrupted and thrown off course, after we did that. So it sounds like such a small thing, but it’s actually still my kind of backup is like, I’ve always got my, you know, kind of mobile hotspot budgeted into what I need to be successful in my role so that I can have that contingency plan.

Maddie Duke  13:53

It highlights an issue for me that I personally find quite interesting, which is also the range of access different people have to, kind of, different levels of lifestyle. 

Halley Bennett  14:04

Yeah 

Maddie Duke  14:05

You know, because obviously, in any company, you’ve got people in really junior roles, and then like C suite employees, and some people may be living in a share house and have like, other people making noise during calls, or maybe they have different I don’t know, there’s all these things that people have behind absolutely different costs that they they’re covering, and I think that the need for empathy and managing remote teams seems to be really, really key. Are there any other.. yes, soft or more technical skills that you would say are crucial to managing remote teams?

Halley Bennett  14:40

Yeah, I mean, I think the one you’ve highlighted there is a really big one, right? Like you need to be comfortable. Perhaps vocalizing or asking about boundaries in a way that might seem uncomfortable at first, because it’s not really naturally the way that we engage with each other as humans. But I think in a remote setting it becomes really critical. And so, I mean, I always think… we had a Scrum Master that I worked with in the past to just, I mean, she would stand up at like once a week in the middle of the office and say, Is everybody forming, storming and norming. This week, we just all kind of groan and roll our eyes and like, Oh, my gosh, the corn. But really, it’s a good it’s a really good kind of, I think set of skills to build up, which is effectively when you build a team, like, how do you get together as a symbol as an organization, you know, you set a mission, you decide what your purpose as a team is, you think about what rules or contracts you need to have in place about how you’ll communicate, how you’ll report back on progress, what documentation you’ll have in place, what tools you need to be successful. And then you work through the process of how will you resolve conflict, and you try to do that as much as possible, hopefully, with a facilitator where it’s where you’re able, but to kind of yeah, preempt effectively, some of the situations that you are guaranteed to get into in a team. And so even if you can, you know, adapt to that process, even if you don’t go through kind of the full set of actions, it’s definitely something that I think any leader and you know, it doesn’t need to be a team manager, but anybody who wants to kind of lead in an organization or have a leading voice, needs to think through what the authentic version of that looks like for them. 

Maddie Duke  16:25

Yep. 

Halley Bennett  16:26

And, ideally, document it and share it with others. Because exactly as you were saying, that’s not always intuitive, if you’ve, first of all, if you’ve never done that out loud, but also, if you are, you know, you perhaps coming in with slightly less work experience or a little bit less exposure, having someone you know, really kind of set down the guidelines, and establish how much you know how much of that is available to kind of create through consensus versus where you just need to kind of all be aligned, I think can be tremendously helpful. I definitely like the piece that you mentioned there about, you know, the experience that you have, giving you perhaps a different level of confidence in knowing what you need to be successful in a remote team, or how you would like to work with others can be complex, I can’t stress enough like the more I think the more we shift towards a world where remote is inevitable, in my opinion, but certainly going to be a growing part of how we communicate with one another and how we work together. Even if it’s in a distributed team, or global team setting for organizations to lean in really heavily on setting some of those guidelines in place, thinking about how they adopt, you know, programs of benefits and perks for their employees that are more suited to that type of environment. I mean, obviously, for example, right now we’re not we’re not really in a position where most of us can go out and find a co-working locally, or, you know, invest heavily in travel for us to be spending time on location with our teams. But those types of things in the future, I think will become really prevalent, or at least I hope so.

Maddie Duke  18:05

Yeah….before we wrap up, Halley, is there anything else you would like to touch on about your experiences of both going remote and starting remote/working remotely? 

Halley Bennett  18:17

Yeah, I mean, I’m sure there’s lots more we could talk about I’m I’m obviously really passionate about this topic, it’s changed my life tremendously to be able to work from the location that is well suited to the lifestyle that I want to have, but also helps me be a more productive and successful member of a team. I think I just I guess if I was like making a call into the world of the internet, where people are listening to ideas about remote work, I would say, I think moving away from this concept of remote being kind of black and white at one end of the spectrum, either everybody working from home and trying to juggle educating their children, walking their pets, cleaning their house, making their lunch and, you know, leading conference calls through to I’m a digital nomad, and I’m on a beach somewhere in remote. The Andaman Sea or something like the world of remote work is a much broader spectrum. And I think, you know, sitting down and conscientiously designing the model that will work for your organization or for you as an individual contributor, is an often skipped first step. And I just can’t shout enough about how I think the more we refine those models and create a common vocabulary for that. It will actually really improve the way we work together. Remote in person, globally, hybrid, whatever.

Maddie Duke  19:37

Yeah, that’s a great takeaway for our listeners to take note of. Well, I think then, let’s leave it there. It was really awesome to hear your stories and your experience. And I very much appreciate you taking the time with me today. 

Halley Bennett  19:56

Likewise, thanks Maddie, and I’ll see you on video call later this week. 

Maddie Duke  20:01

Yeah, exactly. 

Maddie Duke  20:02

The State Of Work is brought to you by Lano. The Lano platform has everything you need to grow your global team. Find out more lano.io. To read more about Halley’s remote journey, head to our show notes podcast.lano.io Thanks for listening and see you next time on The State Of Work.