How to Scale Human Connection - Alli Trussell

In today’s episode, I chat with Alli Trussell, Chief of Staff at Wunderkind, formerly BounceX. Wunderkind is a leading performance marketing engine that delivers tailored experiences for digital clients at scale. And in her role, Alli oversees the execution of the organization’s high priority strategic initiatives, operationalizes their vision, and manages communications for the CEO, executive team, and all other enterprise-wide messaging. 

It’s a dynamic role in a rapidly-scaling organization. 

And she’s an interesting person to speak with for those of us interested in the future of work. 

Discussions at the intersection of technology and humanity are a recurring theme on this podcast. And as organizations scramble to redefine their cultures, strategies, programs, tools, and processes, they’ll need to strike a balance between the two. 

Can personal touch be scaled using technology? Can we scale ourselves? Can we move beyond "performance management" to "performance acceleration"?

We tackled these questions, and many more in what was a really engaging conversation. 

It was a great discussion and I hope you enjoy it.

Alli Trussell

Alli Trussell is Chief of Staff at Wunderkind, one of the fastest-growing SaaS and Marketing companies in the United States. With proven experience in people management, talent acquisition and departmental development, Alli is at the heart of Wunderkind's extensive internal operations. She is passionate about employee success and has a professional mission to make "Career Pathing" the new "Performance Management."

 Alli is an expert in strategic assistance, PR and relationship management, having served as right hand to Wunderkind's CEO in the past. Today, she executes some of Wunderkind's most important strategic initiatives and is constantly innovating ways to harness and boost talent across departments.

With an unconventional story of success in the tech world, Alli Trussell captivates audiences with engaging stories about life and work in New York City, and managing relationships and people in fast-paced business contexts. Hosts and audiences alike will love her energy, vision and story. 

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Thinking Inside the Box

Constraints drive innovation. Each week we tackle the most complex issues related to work & culture.

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Matt Burns

Matt Burns is an award-winning executive, social entrepreneur and speaker. He believes in the power of community, simplicity & technology.

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Transcript

[00:00:00] Guest 1: It's the same thing with theater, every single tech week that I have been a part of has been an [00:00:10] absolute disaster costumes break. Suddenly people who have known their lines for like the past four weeks, can't remember like an entire scene, but then when it is go [00:00:20] time, something magic happens and the show happens.

The thing happens because. Throughout the rehearsal process, you've done enough, right. [00:00:30] To get the end result that you want. And I think that is like the single biggest frame of mind that I took with me in the corporate world.[00:00:40] [00:00:50] 

[00:00:56] Matt: Hey everyone. It's Matt here for another episode of thinking inside the [00:01:00] box, a show where we discuss complex issues related to work and culture. If you're interested in checking out our other content, you can find us at bento, [00:01:10] hr.com or wherever you find your favorite podcasts by searching, thinking inside the box.

In today's episode, I chat with Alex. Chief of staff [00:01:20] at wunderkind formerly bounce ex. Now wunderkind is a unique organic. They're a leading performance marketing engine that [00:01:30] delivers tailored experiences for digital clients at scale. And in her role, Allie oversees the execution of the organization's high [00:01:40] priority strategic initiatives.

She helps operationalize their vision and she manages all the communications for the organization, CEO, their executive team, [00:01:50] and anything else that is enterprise wide in nature. It's a dynamic. In a rapidly scaling organization. And that makes her a really interesting person to [00:02:00] speak with, for those of us who were interested in the future of work.

Now, for those of you who've been listening for awhile, you know, that discussions at the intersection of technology and humanity [00:02:10] are our recurring theme on the podcast. And as organizations scrambled to redefine their cultures and strategies and programs and [00:02:20] tools and processes of the future, they're going to need to strike a balance between those two things.

And that's not something that we've traditionally done very well in an organizational context, [00:02:30] can personal touch in a post COVID world, be scaled using technology. Can we scale ourselves and our teams using [00:02:40] technology? And can we move beyond performance management to performance acceleration in this new hybrid world of work?

These are the kinds of questions that I [00:02:50] batted around with Allie, and we had a really. Awesome. Engaging, thoughtful conversation that I hope you'll enjoy. And now I bring you Allie Trussell. [00:03:00] That's probably my new favorite way to start a meeting is when you have the privacy recording. Allie, how are you doing today?

[00:03:07] Guest 1: Hi, I'm great. Thank you so much for having me. Thanks 

[00:03:09] Matt: for [00:03:10] joining me on this Thursday. Um, we're going to talk about a lot of cool topics today. Um, I have a long list I've already started for us, but, uh, before we get to there, maybe just walk our [00:03:20] audience through a bit about who Allie Trussell is and what's your.

Oh, my 

[00:03:23] Guest 1: gosh, I love it. And you also got my last name, right? It's like Russell with a T um, people try to make it very, very fancy, like Tracell or like a [00:03:30] truffle. Um, but it's just plain old Trussell. Um, I'm Allie, I'm the chief of staff at wonder Ken for a fast growing tech company in the digital marketing space.

I like to say that we connect great brands with [00:03:40] great people. That's essentially what we do. And I've been the chief of staff here for about four years. I oversee our entire people function, which includes talent, HR, [00:03:50] our newly built. Foreman swinging or admin functions and our office operations and culture.

Before that, um, I was going to be famous. I was going to be an actress, still might be someday, [00:04:00] but my background is in theater. And when I got to New York, I did a lot of acting, but I also did a lot of producing, which I found translated really, really well into the corporate world. I tell anyone that I interview [00:04:10] that the great thing about producing is it's exactly like running.

An organization. You never have enough budget. You never have enough time and you have a ton of personalities you're trying to satisfy and then [00:04:20] put on this magical show. So that really, really prepared me for what I do today. And I love it. 

[00:04:24] Matt: And for those of you who have listened to this podcast for quite some time, you're going to know we're going to go in 16 different [00:04:30] directions with this conversation, given that introduction.

So thank you for that. 

[00:04:33] Guest 1: Um, any, any of those mentioned 

[00:04:35] Matt: way. Well, we're going to start with transferring skills from your [00:04:40] theater and artistic background into the corporate world. So you, you, you mentioned it there's a lot of similarities in terms of working within constraints around resources and obviously lots of pressure.

[00:04:50] Um, and having had friends in Vancouver here, work in that industry. I know it's a really tough slog for a lot of people in that industry. The glamor that [00:05:00] we see on the surface. Just that the surface, there's lots of happening. It's not what's happening in the background at three o'clock in the morning and a random field as you're getting a shot [00:05:10] for anyway, they're like it's 

[00:05:12] Guest 1: down or it's going to be ruined forever.

[00:05:14] Matt: Yeah. That being said the kind of people. That are attracted to that [00:05:20] industry are very similar to people who are attracted to the tech industry for, you know, similarly like creative pursuits. I'm curious for you, what are some of the big things that you [00:05:30] saw that were different between the two when you joined those two experiences?

[00:05:35] Guest 1: Oh, gosh, that we're different. There's just so much that's similar. Um, I mean, I, I [00:05:40] always joke with my talent team. They're, they're probably annoyed with me saying this, but I always say, look at people who are in production for that role, they can probably do it. Um, but. There's [00:05:50] really, there's not a lot.

That's different. I mean, you're dealing, you're trying to solve a different thing. Um, and I think the thing, the biggest difference, and this is actually something that I like. It was always [00:06:00] something that, you know, repeatedly excited me and then repeatedly broke my heart about film and television is it has a timestamp, you wrap things and you've built this family.[00:06:10] 

And a lot of times you're never going to see these people again. And so it was like you were so in the trenches together and you were doing all of these crazy things and you were in these high pressure [00:06:20] situations, which really bonds people together. And then it was done. Like your magic is released out into the world.

And with film, at least it's like a living breathing thing that you can go back [00:06:30] to again and watch on YouTube, but like theater it's like, it never happened. You know, it's like this tiny moment in time. And so you have all this buildup and that sort of, what's [00:06:40] amazing and beautiful about. But working in an organization, it's just your, you know, you're hitting a new target.

You're hitting a new goal. You're working with new people. You're adding people into the fold, [00:06:50] but it's not something hopefully that ever has this like end date on it. So that's the one difference that I really, really appreciate, but exactly what you're saying. I [00:07:00] think it prepared me so well for this. I also went a few years ago before I started working here.

I tried to produce my own series to get off the ground. And that was the [00:07:10] single most enlightening experience of my life. It was the only time except for now sort of where everyone's like safety and sanity depended [00:07:20] on me and like, did I have everything together? Was I prepared? We were here. We did our own fundraise for it.

We wrote it, we shot it, we edited it. We produced it. [00:07:30] And we employed a team of about 60. Um, so it was like running your own mini organization and it is, you're constantly working under changing deadlines. You're [00:07:40] working on. Weird external pressures that you could have never imagined, like suddenly it's raining or, you know, a chandelier in the place that you have rented for [00:07:50] way too much money suddenly just stops working and you can't get ahold of the owner, but you really need that light to shoot that scene.

So just everything that could go wrong usually does. Um, but [00:08:00] then if there is something that if you just keep the faith and you trust that you have built a good enough team around you. It works. And maybe this is just the tiny bit of like [00:08:10] pixie fairy dust that I believe in. And that maybe keeps me a positive glass, half full person.

It's the same thing with theater, every single tech week that I have been [00:08:20] a part of has been an absolute disaster costumes break. Suddenly people who have known their lines for like the past four weeks. Can't remember like an entire scene. [00:08:30] Lights break. Nobody can find their cue. Somebody's missing. This is like the first time somebody has run late.

There's all of this commotion. But then when it is go time, [00:08:40] something magic happens and the show happens. The thing happens. Throughout the rehearsal process, you've done enough, right. To [00:08:50] get the end result that you want. And I think that is like the single biggest frame of mind that I took with me in the corporate world.

You are [00:09:00] never, ever, ever going to get everything right. But get enough, right. And prioritize, getting enough, right. To have a good end result, [00:09:10] because then you can still have fun doing it. Yeah. 

[00:09:13] Matt: Yeah. And that's, uh, that's a message that that's a recurring theme in this podcast and this, and this ongoing conversation with the [00:09:20] guests we've had on, which is a lot of people's experiences, including my own include growing up in a corporate world where the differences between agile and waterfall [00:09:30] and the, in the way that we described them, the waterfall.

No toiling away behind the scenes in relative secret only to at some point in the future, do this giant [00:09:40] reveal and inevitably being disappointed when you find that there's misalignment between what you've created and what people actually need, because it's not a collaborative process [00:09:50] more often than not.

And it's usually not meant to solve a cross-functional problem more often than not. So. In an organizational [00:10:00] context, like switching to an agile way, where to your point you're producing, you know, for better term, like an MVP and accepting 80% of somebody's [00:10:10] best, but accepting it with the understanding that it's going to come a lot faster.

My team and I had this conversation. You talk about Chaz. People have that. They're tired of having the [00:10:20] chat that I have around the actual ROI on going from 81% to a hundred isn't worth the time we're going to spend to get there so [00:10:30] fast let's let's move quickly. Let's make mistakes and then let's refine the mistakes.

But the, also the mistake piece. And this is where I want to bring it back to your example. [00:10:40] The reason that model works, the agile model works where you essentially are introducing imperfection into other people's domains. [00:10:50] Constantly is a, is a social contract that you create that says a. What you're going to get.

Isn't perfect. So let's just create no illusion around the [00:11:00] perfection of what's coming down the pipe that you're not getting perfection. So please don't ask for perfection, please. Don't expect it. Part of the model we're building supposes. There's going to be mistakes. Secondly, [00:11:10] um, you will be key stakeholders in helping us refine whatever we drop into this environment to a place where it does make sense for everybody and just becomes part of the way [00:11:20] that we do things in this organism.

And you, your example from the motion picture, from the entertainment industry, if you will, as you mentioned, is very much about [00:11:30] establishing teams and building, you know, building relationships very quickly. And I have to tap to deliver a final outcome, but there ultimately is a timestamp on that. [00:11:40] At some point, relationships will, you know, separately.

You'll work. Won't work with the same film crew. You won't have the same people in wardrobe. You won't have the [00:11:50] same, you know, you won't have the same food services, people, all those things, those relationships, just that they go away. And then on the next engagement that you might have similar people, but just won't ever [00:12:00] really be.

How do you, as an organizational head now tasked with executing the strategy of a, of a SAS organization. How do [00:12:10] you adjust your thinking around teams and projects and work? Knowing that there isn't that ultimate timestamp that on Monday morning when the project ends, there's still [00:12:20] work to be done and you still have to work with bill down the hall.

[00:12:22] Guest 1: Oh, that's a great question. Um, you made me think of something when you were talking through this. Um, I actually just hired someone. To, [00:12:30] um, oversee a wing of the talent team. That's going to be very crucial for us this year. And the first conversation I had with him, I knew I was going to extend an offer to him.[00:12:40] 

When he started talking about exactly that he was talking about, he loved the job that he is leaving. Um, so we're very lucky to have him, but [00:12:50] he was talking about scaling very quickly and moving very quickly and they had, you know, massively grown during COVID. And I was asking him [00:13:00] what that was like. And he told me, he was like, well, you know, for a year I was just breaking everything to get it done.

The only thing I was doing was breaking [00:13:10] things and I was breaking things and we were having the best results. But at the end of the year, I had to take stock and I had to look back and be like, we broke every system, [00:13:20] every process, everything that we had set up that we assumed, worked at a different.

Stage of company. And so now I'm going back through and I'm having to [00:13:30] unbreak some of this stuff. And I think, I think my answer to your question is that I haven't adjusted my thinking a lot. I, I look for [00:13:40] people who share that mentality with me and projects have a timestamp on them. Right. They have a deadline.

There's always going to be a new one. And I think [00:13:50] it's more about keeping people's motivation high. Without perfection. I am a perfectionist. I tend to gravitate towards [00:14:00] perfectionist. And so it's how do you motivate someone knowing nothing's something nothing is ever going to be totally perfect. How do you keep them motivated and excited about their goal?[00:14:10] 

And I think it is just like celebrating the victory with them, to me. Um, we have a very eccentric CEO who doesn't like to talk in less than a hundred percentages to me, a good outcome as a [00:14:20] hundred percent. Perfection's like 1 25. And I think it's really important to make that good. I feel like a hundred percent.

I want to hire [00:14:30] people who are always going to like shoot for the moon and get almost there. Um, and they're going to enjoy doing it together and they're going to have fun doing it. And it's going to be a [00:14:40] collaborative process. I don't know any other way to work. Um, every work situation I have ever been tossed in has immediately been about relationship building has been immediately establishing.

[00:14:50] Okay. We're a team and what I do when I'm thrown in any new situation. I try not to talk too much for the beginning, unless I'm running the thing, I'll do a [00:15:00] kickoff, but you can really quickly assess like the extreme skill sets everyone brings to the table. It's sort of like in my brain, there's a matrix of like, [00:15:10] oh, wow, okay.

This person is super operational. The way that they're speaking, like they are speaking in a spreadsheet that is going to be amazing for. This piece of this project. Oh my gosh, [00:15:20] this person, everybody is gravitating towards them. They just have such a high IQ, so maybe they need to be working on like the coms of this project.

And so it's sort of like doing a quick assessment and building this puzzle together. [00:15:30] And that's what I mean by, um, ultimately at the end of tech week, you usually end up with a good production. Because you've done the right prep work. And then you have this one week where you're introducing [00:15:40] all of these new external factors and everybody freaks out.

But then because you've done the good prep work, you've put people in the right roles. They've rehearsed enough, they've practiced enough. They know what they're [00:15:50] doing. Eventually once that panic of like, oh my gosh, I have this weird corset that I have to like lace up in 25 seconds and then get back out on stage.

And I've messed it up the last five nights. [00:16:00] Or we have these weird lighting cues where I'm like nearly blinded. Every time I walk out on stage. It just works when you can like take a deep breath and then like when you have to deliver, you [00:16:10] usually do people's adrenaline kicks in. And so that's really the same way.

I think about my team. I think about it as like one long theater play. 

[00:16:17] Matt: So it has many of the [00:16:20] same benefits in that. You mentioned this before, just the ability to build relationships quickly and silly and going through a shared experience. There's this, there's this [00:16:30] sense of comradery. That's just, you can't replicate in a slack channel.

So that model is deployed in a lot of different areas. I mean, it sounds a lot like my MBA program that I [00:16:40] did a few years back, like in terms of the cohort model. And it's like, you know, the idea of. Being paired with groups of people for a very specific tasks where you each have to [00:16:50] rely on each other.

And there's all sorts of intrinsic and extrinsic motivation and all these different things. I'm curious, we're in an era now where there's a lot of conversation and [00:17:00] dialogue around fatigue, um, and around digital fatigue in particular, and the activities that you're talking about [00:17:10] are while effective in achieving their own.

They take, they take a lot out of. Yeah. Like they require a high degree of commitment. And [00:17:20] if you're operating in this current time where people are dancing around a global pandemic and childcare and elder care and financial and job related and mental health [00:17:30] and all the other myriad issues that are happening right now, how have you had to adjust your strategy knowing that maybe not everybody can give 100% all of the time.[00:17:40] 

[00:17:40] Guest 1: Totally. And I appreciate this question cause I can, I can be a little intense. Um, but I think the biggest change I've made is we talk about all that stuff [00:17:50] and it's, you know, I keep an open door policy. It's something that I know my team feels comfortable talking to me about. Um, if they are fatigued, I mean, I am like.

[00:18:00] As, as ruthless as I am about hitting a deadline and getting a project done, I am equally as adamant that when you are off, you are off, I will never, [00:18:10] ever, ever text my team at nine o'clock at night. And if I know someone is on PTO, as long as they've had coverage, no, one's going to hear from me [00:18:20] and I am.

I'm a stickler about that. Um, we tend to, I think a lot of tech companies do this and I'm certainly this way. We attract a lot of people who are kind of like all or nothing. [00:18:30] And when they're on their, like so on and you do see burnout in that environment. And so I think my biggest thing, and this ties back to what we were talking [00:18:40] about before we logged on the podcast in scaling companies, an extreme level of effort and attention is required to do what you need to do.

[00:18:50] You have to learn how to scale yourself with that company, or you will not make it, you will burn out. And I, you know, It's something I've done with my teams. We've brought on a lot of new [00:19:00] people and that should never be scary to anyone. If somebody is bringing on a new person, there's plenty of work to go around you and people have that panic that like giving away your Legos.

People have that panic that like, oh my gosh, I'm [00:19:10] not going to have enough to do. Even though they have so much to do, they are feeling crazy. Like they're on the edge of burnout, but that panic comes in and to recognizing when things are too much for you to [00:19:20] handle, you know, I, I, I have high expectations of people, but I do want to make sure that I'm giving them.

The correct resourcing to do it well and not make them crazy. I do not [00:19:30] believe that work is the most important part of your life. I believe it is an important part of your life in the sense that it enables a lot of your other life, but it should not be the thing that you're thinking about 24 [00:19:40] 7. I don't want you to be thinking about it 24 7, unless you're just thinking about how much you love your job.

And so it's something that we've talked about this year. You know, I, I talk weekly to my team about like, how are y'all doing. [00:19:50] Uh, mentally are you? I, I ask them if they're feeling burnt out. I mean, I know what their workload is. It seems like a lot. And I think I take a [00:20:00] personal approach with them and I think that's a hard thing to do with scaling a company.

But that means that like, I have to have the right level of support.[00:20:10] 

[00:20:10] Matt: Hey everyone. It's Matt here, and I hope you're enjoying today's discussion before we continue. I wanted to make you aware of our latest creative project, HR in [00:20:20] VR, every Thursday at 5:00 PM. Pacific standard time. All connect with technology pioneers, business executives from the world's most iconic brands [00:20:30] and industry thought leaders to discuss the future of immersive technologies like virtual real.

And their impact on future workplace. In partnership [00:20:40] with Microsoft we're broadcasting each episode on LinkedIn live and in front of a live studio audience in Altspace. Joining is easy for [00:20:50] LinkedIn users. Simply follow my account, Matt in VR and stay tuned Thursdays at 5:00 PM. Pacific standard time for the LinkedIn lives.

[00:21:00] Or for a truly immersive live experience, visit alt vr.com to download Altspace on your Mac, PC or [00:21:10] VR headset, and join us live in our studio audience. There you'll have a chance to ask questions, meet me and our incredible guests and connect with others [00:21:20] from the comfort of your own home. This is the future folks.

And I hope to be part of it. And I'll link the details for HR and VR, [00:21:30] along with all other relevant information in the show notes of this podcast. And now back to our discuss.[00:21:40] 

[00:21:40] Guest 1: I can't have 28 direct reports, which I did at one point this year. And I recognized very quickly. I was losing the ability to do one of my very most favorite things, [00:21:50] which was treat everyone truly like an individual. And I, you know, know the people. On my team who really, really appreciate me having amazing boundaries with [00:22:00] them.

And only when their slack light is green. Do I send them a message? I know those people. I also know the people who like prefer for me to email them on Sunday morning, because that's when they [00:22:10] sit there and have their cup of coffee and catch up. And that's when they'd like to hear from me, I was losing the ability to treat people.

Individuals. And I was going to, I had to go to this like model that [00:22:20] worked for like 75 or 80%. And I didn't like that. And I could tell they didn't like that. So then my biggest thing became, okay, how do I scale myself so that I can keep [00:22:30] something that I really feel is a strength about. How do I do that?

And so I had to hire a bunch of people. I had to hire a bunch of managers and you know, my favorite thing in the world [00:22:40] is becoming a team's fun aunt instead of their mom. I am a great fun aunt. And so introducing a management layer under me, enabled me to do that. I still see [00:22:50] all of these people. I still bring them a cupcake on their birthday.

But I now have a manager that can make sure that they're receiving the individual attention that they need and the [00:23:00] individual development that they need, because that's the other really, really big piece. And that's something that slips really, really quickly when you're focused on results at all [00:23:10] costs during 

[00:23:10] Matt: scaling.

It also raises a really interesting point. 10 interesting points. But the one, I think we'll key in, on, uh, in service to continuing this trend of just the [00:23:20] random spontaneous conversation. It's that the piece for me that I, I think about is how it just, how that environment obviously creates conditions [00:23:30] for individuality to exist in it.

And I think you've, you've referenced it like we're at a stage now where. We need to be able to have open and transparent conversations about [00:23:40] where we're at, like all of us, um, and where, um, if people need extra support or extra space to, you know, solve for any of the number of Misha issues, I may have [00:23:50] mentioned earlier and, and understanding that when you're working in the organization, In order for you to have the most contribution to what [00:24:00] the collective goals are.

We need like the intention and the effort in that, and in our organization. Now we're talking a lot about [00:24:10] how work is changing and how organizations while may have made the shift to hybrid work or even to a remote first work inviting. [00:24:20] Many of them before the pandemic struggled to build and sustain culture.

And now moving into a digital framework and [00:24:30] standing up a slack channel, a doesn't solve the historical problems and certainly doesn't solve the existing problems. And there's this kind of reverberation that we can expect to see in organizations [00:24:40] in the short-term as companies figure out how they try and do the best impersonation of a culture they possibly can.

Not really understanding the tools that they have available [00:24:50] to them to do that. Yeah. And you and I have worked in a profession human resources that unfortunately has a bit of a [00:25:00] label as a professional function that doesn't really understand technology and some cases resists it as inhuman. And [00:25:10] that the interface that's a digital interface is seen as either a, uh, a lower level of service.

And I'm using air quotes or is seen [00:25:20] as an inhuman, you know, proxy to maybe the traditional HR business partner, HR, like, you know, type model. And I'm just curious [00:25:30] as someone who clearly is working in an organization that has. A high rate of growth, very intelligent people, very dynamic and fast [00:25:40] moving problems in the environment that we're operating in.

I'm curious, curious about how you think about your human resources portfolio, as it intersects with things like [00:25:50] technology, wellness and how all those things tie together for 

[00:25:53] Guest 1: you. Well, it's so interesting because gosh, this is a big question. Um, I think they work perfectly [00:26:00] hand in hand. I think the day that you try to over-index on one and like give the other the shaft.

It's not going to work. We have a really, really wonderful [00:26:10] HR team who I think has really put this at the forefront and thought a lot about this. I mean, look at me as a person. I. I, I thought I was gonna like, lose my mind, [00:26:20] like most, most of the world dead, but I really, really didn't think I was going to make it through remote work.

I'm that's just not how I'm wired. I don't know how to just talk to people through a [00:26:30] computer screen. So, I mean, I've taken I'm, I'm also. I am fortunate in the sense that, like I only had to worry about myself and I realized that a lot of [00:26:40] people in this time didn't have that luxury. You know, there are people who are living with those who are immunocompromised people who had new babies, people who lived with their parents, people who [00:26:50] maybe aren't as healthy as they want to be.

And so I only had to take care of myself. So I caveat this by saying I was back in the office, as soon as I possibly could be. I [00:27:00] was like mask. I was gloved, but I was like, I have to see at least a few other people walking around. So it was really, really hard for me. Um, and I know it was hard for so many other people, but we [00:27:10] really, really had to totally change our playbook.

We were 100% in person. I mean, I think we have like three remote employees and they were sales folks [00:27:20] spread out across the country before the pandemic. And we're now. Completely spread across the United States. About 50% of our employee [00:27:30] base is remote and will continue to be remote even when it is like safe for people to return to, for people to have the option, to return to the office.

[00:27:40] And I think. Pivoted. Well, I think we're lucky. We're lucky. We're a tech company that inherently makes the internet nicer. [00:27:50] We, as a company, understand that technology is actually there to booster humanity if used correctly. And, you know, we [00:28:00] have a lot of offerings. We totally switched, you know, our gym offerings to being virtual.

It kind of made us be a little bit more innovative. And I think that's the silver lining of this whole time. [00:28:10] I think it's the silver lining of everyone leaving jobs. It's forcing companies to stay at a high level of innovation and rethink the way that they're doing things and make it work [00:28:20] for more people at the individual level.

You know, we flipped a lot of offerings virtually. We have a culture that does a lot of fun events. Um, every pretty much every week [00:28:30] prior to the pandemic, we had an in-person event. We had a guest speaker, we had pizza, we had a catchphrase competition. Um, we were doing something [00:28:40] constantly. And so very quickly after we went remote, I sat down with our head of culture and I was like, what, what are we going to do?

And it was so cool. [00:28:50] The way that, that team pivoted and I'm extremely proud of them. I mean, we had, we had, we found in Portugal, I can't remember the name of it, even though it was the most fabulous thing I've ever seen. We [00:29:00] had, we had drag Queens do, um, a Valentine's day cocktail making class and mocktail making class.

And it was so we, we were able to [00:29:10] keep that same spirit because of zoom actually. People were talking in the chat as if they were standing next to each other. And so I think the second you start [00:29:20] to ignore the benefits that technology has given us, particularly in this time, you just have to use them like you're human.

I mean, I'm I slack and email exactly how [00:29:30] I talk, um, speak in run-ons I type in slack and run-ons and I think it's just about humanizing the technology available to you. And I I'm, [00:29:40] I'm really, really grateful for that, but I also acknowledge that like our technology does that a little bit. So I don't think the bias that a lot of folks feel in this space really, really [00:29:50] applies to us.

Um, I'm just grateful. We have. 

[00:29:53] Matt: It's a really good example of how sometimes we can confuse the delivery channel with the solution. [00:30:00] And I can tie this both into this conversation, but also into tech in the sense that if you want to talk, we talked to individuals, we have this, I'll [00:30:10] call it a false expectation that deploying a delivery channel, like zoom is going to solve a problem.

Like. [00:30:20] It's not, it's not in the same way. Culture is about communication. We've been talking a lot [00:30:30] about offline, about the necessity for HR to take a page out of our marketing friends, playbooks and find the balance between the two, [00:30:40] because marketing is really good at using tools and really good at using.

To segment. [00:30:50] Audience demographics to find the right message for the right person at the right time to inform or to [00:31:00] influence in some way. I mean, that's really what marketing is. It's about getting people closer to the transaction point of the organization in the same [00:31:10] way, change management and HR in a lot of organizations is quickly looking a lot.

Like how do we get all the employees to the same? And a job [00:31:20] that's much more difficult when we don't have the benefits of all being co located. Because as you mentioned, zoom is a tool that can be used in a [00:31:30] really compelling way to propel that, or it can be a drain on it. It really depends on what we put into the delivery tool.

And [00:31:40] from an organizational perspective, it requires people to think different. And it requires people to, to look at problems that [00:31:50] historically haven't been solved for, but now, and now solve for them, even though they're more challenging to solve. And you mentioned this about like, just showing up and being human and how, you know, your [00:32:00] inside voice and outside voice are very congruent.

That's a really important point for leaders nowadays. And I'm curious, you know, as we pivot this to leadership [00:32:10] and whether that's individual leadership or team leaders, You mentioned the point about scaling yourself and using that to scale your teams. I'm just [00:32:20] curious, you know, in that dynamic, how are you thinking about scaling yourself as an individual?

Um, and at a time when most people, I think if we'd asked if we ask them, if they [00:32:30] have extra time right now, that that seems to be in short supply, you talk about scaling. It sounds amazing. Where do I start? What do I do? What kind of things were you [00:32:40] thinking about this timeline? Oh, 

[00:32:42] Guest 1: gosh, a lot. Um, one thing, a couple of things that stuck out, you just said, I tell everyone that they have to figure out how to be the COO of their job.[00:32:50] 

And I love, I love that you talked about marketing in that context. Um, I very, very much believe that you have to be able to [00:33:00] articulate what you're doing in a way that is good for other people. And if you can think about yourself and your function and your team that way. My hunches, you'll be pretty successful [00:33:10] to me.

Hot take cultures, get thrown out a lot as a buzz word. I think it's just clarity. People just want clarity. They want to know what's expected of [00:33:20] them, and they want to know how to get from point a to point B if they want to, or how to stay at point a in a way that is perfectly [00:33:30] lovely for them. Um, I think, you know, fun events, community, those are all components of culture, but you can get all of those.

Right. And if you don't have the clarity [00:33:40] piece, right, it doesn't matter. And I think that's the biggest key point in scaling yourself. It is being able to, [00:33:50] depending on the rate at which you're scaling, let's say it's really, really fast. It's the ability and it's, it's a learnability. Um, maybe some people have it naturally.

I don't, um, it's the learnability [00:34:00] to be able to look at a situation and rapidly prioritize. Um, you know, people have 90 million thoughts, a minute 90 million ideas, a minute [00:34:10] priorities can be rapidly changing, but if you can always focus in on like, what, what do I actually need to do? If I'm clear about where we're going as a company, if I'm clear about what we're doing as a team, [00:34:20] I've got a lot of stuff flying around me.

There's a lot of moving parts. What's most important right now. And, you know, good managers distill that down to their teams so that they [00:34:30] can do that a lot easier. But I think that's the way to not burn out. That's the way to scale. That's the way to help the organization. It's knowing what you need to do in any given moment [00:34:40] and making sure that it's within your bounds and you're correctly resourced to do it.

Um, it's something, but it's hard. Like I said, that's a learned skill. That's not something that I think everybody. [00:34:50] Is great at the first time that they try it. And our biggest moment of scale actually happened in the middle of the pandemic when no one was really [00:35:00] expecting companies to massively scale.

And so I think in a lot of ways, we were kind of unprepared for it. We over doubled in size last. And so it feels like we've been [00:35:10] like five different companies in one. And like I said, that learning curve can be really steep and there are challenging moments that helps that you're sort of all in it together, but there's a lot, you [00:35:20] have to relearn how to do, you know, stuff that was just kind of like.

Passed down through a few people and you kind of always knew what was going on. And you kind of like had this world of osmosis where you [00:35:30] knew who was doing what and what they were doing and what they needed to do tomorrow. That doesn't really exist anymore. Partially because we are way bigger than we used to be in partially, like you said, cause we're spread [00:35:40] across computer screens in different locales.

And so if you have a lot of clarity, I think it's actually a lot more inclusive. You're able to keep all of the people on the same [00:35:50] page. There is some beauty in zoom. I actually feel like our all hands are better, completely over zoom. Everyone's getting the exact same experience as opposed to like [00:36:00] all being crammed in a room.

And the person who's sitting way on the corner can't really see the screen. And they may or may not be able to hear the speaker. And, you know, the crappy recorded version is getting sent [00:36:10] to our UK office. I like. But it is this really like equalizing experience, but also something we looked at and something I knew was going to happen.

When I saw, [00:36:20] when I saw us tip into massive scale, I knew that this was going to be a hard thing. And so we built out an entirely new department of just in-house coaching. So anyone [00:36:30] who wants it in our organization can book a session with a coach who is in-house and isn't a third party because the coach then also understands.[00:36:40] 

What's going on with the organization, what's the priority in the organization. And I think that that is a unique vantage point to be able to help people [00:36:50] approach new opportunities and get over new hurdles and take on more or learn how to set boundaries and like keep themselves saying, [00:37:00] I think that my biggest thing is like, no one person wants the same thing.

And so figuring out. What, what is going to make someone happy? Because I firmly [00:37:10] believe that happy people do better work. And so it's something, I think it evolves over time. I'm not perfect at it. I've gotten a lot better at it because I've had to be. But I think if it's not a focus, if you're just focused on [00:37:20] scaling the organization and then if you're just focused on scaling your team, but you're not looking at like, how do I do my best work and how do I actually scale that and continue to do my best work.

You see all [00:37:30] these high-performers fall off. And I've seen it. You know, I've seen it in colleagues at times where they were a superstar at one level, but they [00:37:40] bumped up. And they didn't think about how do they scale themselves at the same rate. And so it is, it's a learning curve. It's it's, but it is crucial if you want to be a [00:37:50] person that scales through several different iterations of a company, which is really, really exciting to me.

[00:37:55] Matt: And I think one thing you mentioned earlier that stuck with me was. It was [00:38:00] clear that when you identify the opportunity around you having 28 direct reports, it was, you understood that there was an impact to you having supervision over that many [00:38:10] people, both in terms of the quality and the quantity of care that you could provide to the people in your organization, but in introducing a late.

Of people who were to [00:38:20] manage, you identified the importance of the competency of, and the importance of management and getting work done. [00:38:30] And didn't view it as a layer of bureaucracy. So there is a, like, there's a narrative out there where you look at, you know, modern day organizations are flat. Everybody [00:38:40] has equal say on equal things.

It sounds like in your view, when it comes to scaling organizations, You're actually doing a disservice by maybe going completely flat. In some [00:38:50] cases, there needs to be a level of coordination of work of goal, setting of prioritizing, of troubleshooting, of liaising between teams that you see as [00:39:00] being valuable in your organization.

Maybe just talk to us about that. 

[00:39:03] Guest 1: Oh, that's a great question. That's one of my favorite things to talk about because you're right from an org chart perspective and from a, who is giving who [00:39:10] direct attention perspective, you have to have layers. I, I. I would love to talk to the person who says a completely flat organization works.

And I would love them to tell me how [00:39:20] I'm not saying it can't be done. I don't see it because you can only have your, your, your attention can only be spread across so many ways. But where I don't personally take that [00:39:30] is that does not tie into who can have a good idea for me. My favorite thing about where I work is anyone can have a good idea and we don't put red tape around [00:39:40] good ideas.

And I. Always hire people who are better at their specific jobs than I am. I am very, [00:39:50] very, very much a generalist. I am perfectly adequate at a lot of different things. And, you know, I, by no means view [00:40:00] myself as any sort of special. But I hire a bunch of specialists and that to me is not I'm above them.

They're below me. [00:40:10] They're better at this one thing or these 20 things than I am, and they're the right person to be overseeing this. And [00:40:20] a lot of the decisions that made. Are going to be based on their feedback and you know, what they're coming to me with. They're the reasons that I do make the decisions [00:40:30] that I do.

And so I think, I think those layers are actually a beautiful thing because it pulls out the best in everybody. It allows everybody to do what they [00:40:40] want to do and what they do best and bring their specific strengths to the table. And I think that's the danger of a flat organization. You, I think you need a healthy mix of generalists and specialists [00:40:50] to make an organization have.

And in a totally flat organization, I, I don't know what the profile is, but I assume you get a lot of the same. Yeah. 

[00:40:59] Matt: [00:41:00] It depends on the size of course, in the industry, but yeah, it's, it is in my experience. They can, it can work with [00:41:10] a really small team. Sure, 

[00:41:11] Guest 1: sure, sure. We're you know, 800 now. So where it's like a 

[00:41:14] Matt: cooperative where there's like equal ownership in the, in the equity of the [00:41:20] organization kind of thing.

It gets problematic when compensation starts to. Because it has been it's like how much effort are you putting in given what you actually like? That's [00:41:30] when it changes for me. So it just, yeah, like a lot of the things you said resonate, and I'm curious for you, you know, you seem like somebody who is obviously very [00:41:40] mindful of finding the balance between performance and wellness and you're, you know, you understand that performance comes at a cost that requires an investment.

In the [00:41:50] environment and resources and self care and all the things necessary to optimize it. I'm curious for you as an individual, you know, what do you, when you look, when it comes to your performance, are you somebody [00:42:00] who's into biometrics? Are you somebody who's into, you know, looking at the latest AI enabled chatbots to make your administrative life easier?

Like, do you have any best care practices [00:42:10] about scaling yourself? Oh, 

[00:42:11] Guest 1: gosh. Oh, I love talking about this. Um, well, so my, my, the inside of my brain is organized for me, but it's [00:42:20] messy. And so I, I think the, the angels of the corporate world or executive assists. And, um, I they're [00:42:30] so underrated a good EA is so, so, so underrated.

So I, you know, I have a partner in an EA who I'm super [00:42:40] open with about my life and how my brain is feeling. And I also talk about like, if I know I'm super burnt out and I'm having a day. I make sure that I'm not, you know, I don't, I don't want to put my [00:42:50] bad day on anyone else. So if I have a meeting that I know is going to be very taxing or where somebody really, really needs a lot from me, they need a lot of support, you know, I'm going [00:43:00] to, if I can't move it, if it's time sensitive, I make sure that I take a walk.

Like I am big on physical movement and that's the only way sometimes I can get out of my head [00:43:10] and I'm pretty regimented in that I'm not a good manager and I'm not, I'm not a good performer if I don't have a little time to [00:43:20] myself and I love people, I'm a social person. We're on a big team, but I don't talk to anyone before.

Eight o'clock in the morning, unless it isn't [00:43:30] absolute emergency. I, I love group fitness because you can go and you have like all of these sounds going on around you and then you don't have to like, do anything. You don't have to talk to [00:43:40] anyone. I have like my moments in the day where I don't have to be social and I'm really protective of those because my job requires me to give a lot of energy to other people.

And I want to do [00:43:50] that. That makes me good at my job, but I have to have incredibly strong boundaries of time periods where I don't have to do that. And I get to keep a little bit of my energy for me so that I can continue [00:44:00] to show up for other people. 

[00:44:02] Matt: Alli, thanks so much for your time today. I had a really great conversation.

I really enjoyed how far we went in terms of various topics and look forward to keeping in touch. [00:44:10] Awesome. 

[00:44:10] Guest 1: This is so fun. Thank you for having me.

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