Become a Creator today!Start creating today - Share your story with the world!
Start for free
00:00:00
00:00:01
Sean Dazet on Global Hiring, Remote Work, and Modern Teams
11 Plays9 days ago
In this episode of MustardHub Voices: Behind the Build, Curtis Forbes sits down with Sean Dazet, Head of Partnerships at Oyster, to explore the future of distributed work, global hiring, and what it really takes to build high-performing remote teams.
Drawing from his experience scaling partnerships at companies like HubSpot and leading global growth initiatives at Oyster, Sean shares how modern organizations can unlock talent anywhere in the world while navigating the operational, cultural, and leadership challenges that come with distributed teams.
The conversation explores the realities of employer-of-record (EOR) platforms, why global employment is becoming a strategic advantage, and how companies can scale internationally without building costly legal entities in every country. Sean also explains why communication frameworks, intentional culture-building, and strong leadership habits matter even more in remote-first environments.
Curtis and Sean dive into the difference between remote and truly distributed organizations, the growing importance of follow-through and critical thinking in leadership, and how unclear communication can quietly derail teams. They also discuss how AI is reshaping productivity, hiring, and workforce strategy, while balancing the human side of work, flexibility, and quality of life.
This episode is a must-listen for HR leaders, founders, operators, and anyone thinking seriously about the future of global work, distributed teams, and modern workforce strategy.
About Sean Dazet:
Sean Dazet leads partnerships at Oyster, a global employment platform that helps companies hire and manage talent anywhere in the world. With more than two decades of experience scaling revenue teams across high-growth startups, PE-backed ventures, and global SaaS businesses, Sean has built the partnerships and ecosystems that drive market expansion and competitive advantage. He is known for turning strategy into growth engines, unlocking new revenue streams, and accelerating momentum at every stage of a company’s journey. Sean got his start at HubSpot in the early days of inbound marketing, and has spent the years since working at the intersection of go-to-mark
Recommended
Transcript
Introduction to Sean DeZette and Career Overview
00:00:05
Speaker
Welcome back to Mustard Hub Voices Behind the Build. In these episodes, I sit down with the people building, backing, and running better workplaces. I'm your host, Curtis Forbes, and my guest today is Sean DeZette.
00:00:17
Speaker
Sean leads partnerships at Oyster. A global employment platform that helps companies hire and manage talent anywhere in the world. With more than two decades of experience scaling revenue teams across high growth startups, PE backed ventures and global SaaS businesses, Sean has built the partnerships and ecosystems that drive market expansion and competitive advantage.
00:00:41
Speaker
He's
Sean's Early Career and HubSpot Experience
00:00:42
Speaker
known for turning strategy into growth engines, unlocking new revenue streams, and accelerating momentum at every stage of a company's journey. Sean got his start at HubSpot in the early days of inbound marketing and has spent the years since working at the intersection of go-to-market partnerships and distributed teams.
00:01:01
Speaker
Based out of the Boston area, welcome ah Sean. Appreciate you joining me on Behind the Build. Absolutely. Thanks, Curtis. Great to be here. Isn't it nice to like hear your bio read back to you? It really is. I felt very accomplished for a minute there. I was like, tell me more about what I've done. you know so i i do you know Point of clarification, I spent a lot of time at HubSpot, but I technically got my start.
00:01:26
Speaker
ah with Nextel cell phones back the day. You're dating yourself. Walkie-talkie. I'm dated. I'm dated. i'veav now Listen, if you look at my beard, am dated with the amount of gray that's popping in there. so i um ah i you know yeah HubSpot, its i mean well, let's get into all of that stuff. I'm actually very curious like about your career path. i mean You've been in go-to-market and partnerships for for a couple of decades.
00:01:54
Speaker
yeah and And that time, as like an early HubSpot person, back when inbound marketing was like kind of sort of still a new-ish idea.
00:02:06
Speaker
um yeah what What pulled you into that kind of work in the first place? Yeah. ah you know I'd spent... Probably eight or nine years in different roles prior to HubSpot, really early career stuff. you know Literally Nextel, I ran a franchise group for them at a new age. wow okay um I spent time in a couple of startups early on, product manager, running business.
00:02:35
Speaker
partnerships. I was a scrum master for a little while. So that classic, like early tech career where I had a lot of applicable skillsets and I would get pushed into different roles, particularly during, high growth startups that were also trying to find product market fit. Right.
00:02:53
Speaker
And i i was in the video game industry for a while as a biz dev guy, like classic marquee partnerships, working with Disney and AMD and Dell and like Post Foods and these big companies.
00:03:06
Speaker
But that was on the West Coast and came back to Boston. I'm a New England guy. And when I was heading to Boston, I took a really close look at what companies were there.
00:03:18
Speaker
and who was doing something that was interesting and that
Partnerships and Business Strategies
00:03:22
Speaker
resonated with me. And HubSpot was the top pick. Where they were in terms of the inbound marketing message really resonated with me.
00:03:33
Speaker
And I had enough of a network through friends, through people I knew, to get in there both as as a candidate but also as someone who knew some folks in there which is a classic way to get into a high growth company because at the time hubspot for years was harder to get a job at than it was to get into most ivy league schools from a percent of people they accepted type of thing so um you know i was lucky enough to get in front of the right people and i was really drawn to the mission i love the content from
00:04:07
Speaker
their founder and stuff, but you're absolutely right. It was early days, man. Like, you know, leading with, um, you know, thought leadership, leading with content, trying to pull people in with value that was free was feel feels elementary kind of today, but back then was actually pretty exciting and different than what a lot of folks were doing. so you know It attracted me and and luckily made made it in there and got in there. ah Started literally as a direct sales rep for for a couple of months because I was looking for a home. you know' um And your your journey into into partnerships is interesting, right? Because I see a lot of folks come in from either the product side or the biz dev side, right? I didn't realize you have a lot of that product background, which which yeah gives you a really interesting lens to look at opportunity through, right?
00:05:00
Speaker
for sure Because right a lot a lot of the folks that come in through the big bi dev side, you know they're evaluating the the you know maybe the commercialization aspect and then their next step is really to be hand it off to product. right And you're able to actually see it through both of those lenses from the from the seat that you sit in.
00:05:17
Speaker
um And it's funny because right it's it's not quite sales, not quite products, not quite marketing. right So from from that seat that you're in, How do you describe what you do to the people who think that partnership just means like, I mean, co-marketing deals? Yeah.
00:05:33
Speaker
Yeah. I mean, look, sometimes it does, but um it can be kind of an interesting nebulous function. And what what I often say is partnerships is this interesting intersection of the entire business, right? And that's what really attracts me to it is you have to almost be a generalist in every single function of a business in order to properly integrate a partnership because you're it's constant cross-functional navigation and you're often working with uh different functions at other at your partners too right so you need to be able to speak that language so
00:06:13
Speaker
You know, look at its core, ah partnership person is is a relationship manager and we are sourcing and we are stewarding relationships between organizations and we are bringing the right stakeholders in from both sides to ensure that what we're co-creating drives value and lift for everybody involved because If you're going in at one-sided, which, you know, unfortunately there are examples of organizations that take a really one-sided approach to this type of stuff. um
00:06:47
Speaker
It doesn't create the same sort of brand loyalty. It doesn't create the same sort of lift that a really effective bi-directional partnership can create for organizations out there. So yeah, it's, it's relationship development and it's developing tactical plays that are,
00:07:09
Speaker
supporting and driving long-term strategies?
Leading at Oyster and Global Employment Solutions
00:07:14
Speaker
um First of all, I know who I'm calling when I need to put together this ah my my dictionary on on on how this works. Because because that was really that was really well articulated, actually. it's incredibly well put. you're You're almost at this intersection of of business and product, but also sort of like general ecosystem function, right? Like you you're vetting all of these things, right, as ah as a manager of relationships. But at the same time, you have to be able to look at it through this like,
00:07:44
Speaker
exceptionally critical, both business and product, um you know, perspective, I guess. So you're your leading partnerships at Oyster and and I guess for for anyone unfamiliar, maybe we should start there. Tell us a little bit about Oyster. What is it? And and what are the general problems, right, that you're trying to solve there?
00:08:05
Speaker
Yeah. So um Oyster is awesome. We are about a six-year-old company. We're post-Series D right now, driving hard towards profitability, which is super exciting. Very high growth company. We're a global employment platform is what we are. So as you said earlier, our our our tagline is we help companies everywhere hire talent anywhere.
00:08:27
Speaker
What that means is we're enabling organizations to have global, remote, and diverse workforces in a really easy way. The core problem that companies face right now is the talent shortage.
00:08:41
Speaker
Talent for hiring across almost every role right now is sparse. People are staying in jobs longer right now and they're hesitant to make moves. So finding the right folks is a big, big challenge for organizations and companies that are addressing this with a global and remote workforce I think are able to tackle this a lot faster. And that's what it was to really allows you to do. So challenge you're located in the United States.
00:09:15
Speaker
You want to hire a full-time employee in Portugal. You either need a legal entity in Portugal, or you need an employer of record, which is our core product to act as your legal entity there.
00:09:30
Speaker
The reason you don't necessarily want to open an entity is it's expensive, it's cumbersome, and it opens you up to all sorts of liability and risk. There is tax, legality, et cetera, that you have to keep an eye on there. It's going to cost you six figures to open it It's probably going to cost that almost every year to maintain it.
00:09:48
Speaker
so we have massive legal team massive ai driven intelligence engine that uses our in-house expertise as well as out of house expertise that we work with and we've worked with for years to ensure that end to end we understand the compliance the legal the tax perspective on full-time employment in every country in the world save a couple sanctioned countries uh and every jurisdiction within said country, right? Every province in Canada, right? Like every state in the United States and so forth, because there's a multiple of complexity there. So we bring employer of record.
00:10:29
Speaker
We also allow you to hire global contractors anywhere in the world. And that really allows organizations to scale their teams remotely, diverse workforce, which helps with product market fit, which accelerates revenue and all that type of stuff.
00:10:43
Speaker
but it also lowers, generally speaking, your per headcount cost. And that's a core thing. We work with a ton of early stage organizations who are trying to extend that runway. And I think you know the reality is today, when we're looking at AI's impact on businesses, right? And how we're all trying to streamline, we are all cognizant of what our spend on talent is right now. And so thinking ah globally allows you to take advantage of highly skilled talent in other markets that may be within different salary bands around the world. And they can help you to extend your runway, hire an engineer in in Portugal versus San Francisco, way different economics there. So that's what we're bringing to the market right now. And it's working great for thousands of companies.
00:11:32
Speaker
I can imagine. I mean, it i and I see that really... distinct mission, I think, around keeping high paying jobs in a lot of developing countries or developed countries, you know, that, that, that have more accessible talent. And, and I guess I can see now, you know, where that comes from and why it matters, I think, to, yeah you know, i mean how using night with Yeah, look, our, our founder who, um, he was our CEO for while is currently our executive chairman, amazing guy, Tony Yamos. And, um,
00:12:06
Speaker
Tony, you know, displaced person himself, right? And he's ah he's a multi-company founder. And when he founded Oyster, it was exactly to do that, right? It is to keep high paying jobs in developing economies. It is to help democratize the world.
00:12:22
Speaker
and adjacent to that, We really want to be an example. Like we're eating our own dog food every day. Our team is dispersed across 65 different countries, right? So on a daily basis, I'm working with somebody from Africa, Asia, South America, you know, and it's, it's incredible. And it helps us to truly be ahead of where our customers are yeah because we are literally living the experience that they are having or they're going to have.
00:12:52
Speaker
But it also helps us, I think, to have a much more progressive and impactful culture, therefore a much more much more progressive and impactful trajectory as an organization yeah because we really believe in what we're doing.
00:13:06
Speaker
I can see that.
Remote Work Dynamics and Organizational Structure
00:13:07
Speaker
um I mean, um but obviously I can see it you really believe in what you're doing, but I actually can see how you know that that kind of impact you're talking about. A lot of people, sean I think lump...
00:13:19
Speaker
you know, employer of record platforms together. um um And i'm I'm kind of curious, you know, from your, from where you sit, what, you know, do most companies or people misunderstand about what an EOR actually does and where it kind of fits in the HR stack?
00:13:37
Speaker
Yeah. Yeah. We're, we fit interesting, right? Like a, like EOR for all intents and purposes is middleware between employer and employee. And so, There are a lot of players out there doing this and we we kind of broadly see the market in three ways. um There are very tech first players.
00:13:56
Speaker
They are tech platforms. They tend to be kind of wide and shallow with a bunch of different tech products in there. And the vulnerability that we see that creating is EOR in particular, global employment.
00:14:12
Speaker
It's a very human based business. There's a lot of complicated questions that come up. There's a lot of changes that happen to laws around employment, taxation, compliance, PTO, probationary periods, you know all that type of stuff. right It's evolving on a day-to-day basis around the world.
00:14:34
Speaker
So if you have a multi-product set and you're supporting all those, you don't necessarily have that baked-in expertise. And so it tends to create some vulnerability around them So there's your tech first players.
00:14:47
Speaker
There's legacy players who have great businesses who kind of started the EOR space for all intents purposes. And a lot of these legacy guys are really good, great expertise, but they tend to be kind of behind on tech and they tend to be um operating more like a consulting company, which comes with consulting company costs.
00:15:09
Speaker
yeah There's a middle category. Right, exactly, right? And there's a middle category that you know Oyster fits in really well. It's a balance of tech and people.
00:15:21
Speaker
And we are a human first EOR what we like to say, right? we're We're not the one you hear about all the time because you don't want to hear about us. if If an EOR is making making news and you're talking about it, it means there's a challenge there, right? Exactly.
00:15:37
Speaker
And so we have this great balance of a really nice consumer-grade software type of platform that an HR manager, an HR director, a people ops person can and your employees for that matter, your team members as a vernacular and EOR for the folks you employ, they can pick up and use with without a second thought, right? it's It's the same as picking up your iPhone.
00:15:58
Speaker
But we also have this incredibly deep human-based service engine that allows people to quickly and accurately get the information they need, get their questions answered, and ensure when those complex situations come up because They do. We've all, we've led teams and people, there's complicated stuff that comes up to people. Right.
00:16:20
Speaker
And when that comes up and you're like, how do I handle paternal leave in France? You know, which is, which is a whole different podcast in and of itself to get into the nuance of that.
00:16:32
Speaker
But, um, once you get there, you know, you, you want a person, you don't want, you don't want to just have a chat bot telling you this type of stuff. And so I think that's where that's the difference. I think broadly, like,
00:16:43
Speaker
Oyster allows you to do a tech first, but it ensures you have people behind that that are really going to answer your question. We have ah HR experts and HR business partners across the vast majority of countries that we support who are folks who are native to that country, live there, speak the language and understand and have literal people management experience that they can bring to the table and consult with you to ensure that you are providing the best experience for your team while also providing the best experience for your organization and candidly protecting your organization as well. Because again, there's a lot of vulnerability and compliance stuff that come into play with this type of space.
00:17:26
Speaker
You know, I want to, uh, I want to like lean in a little bit to this distributed work. You know you mentioned that your your own team is employed through Oyster, which I love. you You mentioned you're eating your own dog food, right? I love that. what What kind of things have you learned about distributed work by living it that you don't think people running offices or hybrid setups maybe be fully grasp?
00:17:53
Speaker
Yeah, yeah. I mean, there's... Look, I have a lot of experience with this. My sales team at HubSpot was the first one to go remote, like have fully remote employees. Oh yeah. So like I wrote some of the book on this type of stuff and umm I'm a huge proponent of it, right? Like I'm um'm ah um' a parent, you know, like all that type of stuff. like remote work enables me to do a really good job for oyster and it allows me to do a really good job for my family too and that's where i see remote work as being so critical to people to the world to development right so look one of the things that i think a lot of people miss is understanding
00:18:37
Speaker
how we work and making that a part of your culture and your onboarding right so you're in an office you get hired you go to that office there's kind of an ingrained rhythm of work that just happens in an office people work from 8 39 to noon they go to lunch they come back from lunch they get some coffee they work the rest of the day they leave there's some meetings everybody gets that right When you have a distributed team, when you have a remote workforce, it's unreasonable of me to assume somebody in South Africa is working the same hours as me.
00:19:14
Speaker
you know So um even ah my head of partner enablement, who's in Vancouver, working with teams that are in Portugal or wherever, right?
00:19:28
Speaker
It's unreasonable. We're not always on the same thing. So understanding how we work and really creating rhythm and systems that support that is one of the most critical things to success with a distributed team.
00:19:41
Speaker
That means how do we document things? How do we... set or don't set meetings for that matter how do we even write an effective slack message in order to ensure that i'm communicating what i need and i'm also communicating what the expectation is for the folks reading it right so that type of stuff is critical and we have something called follow the sun at oyster and It is thinking about wherever the sun is sort of shining, broadly speaking, summer hours can change this quite a bit. And so can if you live if you live you know near the pole. But ah look, broadly speaking, we think about it as, okay, if the sun's up there, probably this person is working. But that's not even always universally true, right? So when somebody joins us, we do this whole process about how we work, what our expectations are, how you should expect to communicate,
00:20:37
Speaker
um what type of timeline you should expect on responses and things like that, how you should document stuff, how you should leverage Slack for async communication, and how you should even think about whether or not you need ah an actual in-sync meeting versus an async conversation about something. So <unk> it's it's a framework question, I think, is also me what it is. And I think It's very easy to look past frameworks when you're in a location together because people just come together and you sort of the highest person on the totem pole within that place sets the rhythm, right? And so um very different async. I think it creates a flatter organization, which is good because that enables people to feel safer expressing the
00:21:23
Speaker
ideas, which is really, really important. we are We are better together than we are by ourselves. I thoroughly believe that within business. So um that's where I see so many advantages from this type of thing.
00:21:36
Speaker
I'll say one more thing and and we can dig in in a bunch of areas here, but the other thing is is the expectation part of delivery. And there there are questions like if your function is sales, right?
00:21:48
Speaker
You're async, there's nobody looking over your shoulder. Really, you got to understand what your delivery expectations are. And you got to have mutual understanding between you and whomever your, ah you know, upline type colleague is to ensure that you're delivering on things. And a lot of lot of the ability to nail that comes down to who you hire.
00:22:10
Speaker
And having a really good focused hiring process is essential to building an effective remote team, which is, you know, get part of that expertise we try to bring to our clients at Oyster is here's how you do this well. And we're constantly experimenting with it ourselves.
00:22:29
Speaker
I really like follow the sun. um, it made me, it made me giggle a little bit cause I'm picturing somebody in Alaska getting a message at 1am on in the, in the middle of the summer. That's where, that's where it doesn't work well. Yeah. Um, yeah but, uh, but yeah, no, by and large, I can, I, I,
00:22:47
Speaker
I appreciate that that visual. And I think sure you know this would be this would be helpful, I think, for folks maybe listening here. But I think a lot of leaders, maybe just gen and maybe this is more generally speaking, you treat remote and distributed like the same thing.
00:23:07
Speaker
So, uh, I'm curious, I mean, do you define them the same way from your vantage? What's the actual difference? Is there one? Why does it matter? Interesting. Yeah. Um, look, I think you could have, you have a remote employee and I think in,
00:23:22
Speaker
in the way that term has grown with ah the current generation of companies, that means that we have a mothership and there's a couple of people who are remote and they come into the mothership from time to time, right? So I think the implication there usually is that there's some sort of HQ that exists.
00:23:40
Speaker
People are going to come back. um A distributed team, i think, is... define more so, and I'll bet somebody like Boston Consulting Group has has a write-up on this, so maybe we're maybe we're misquoting something, but like ah I see that more as defined as your entire organization is is distributed and remote from each other, right? You don't have an office you're going to. And that's, I mean, that's our approach. Like we have locations, we have entities everywhere, right?
00:24:14
Speaker
and That's how EOR works. We have to have entities, but we don't have any offices. And so I think that's it. But to be honest with you, it's probably nuanced and it probably really depends on who's saying the words. Because I think a lot of people are probably going to assume they are effectively the same thing.
00:24:30
Speaker
But the way I see it distributed really leans into this is this is the the ethos of our organization is we are all in different places, but we're all working towards the same goals.
00:24:43
Speaker
So have kind of a question really about when this when this breaks down. and Because in some organizations it does. And I think that maybe let's starting ah ah start a ah level higher than that.
00:24:58
Speaker
and i think for a lot of SMBs or mid-market you know that are hiring internationally for the first time, I'm kind of curious what... What catches them off guard about managing people across borders, time zones, entities, right? For people doing this the first time, there's going to be things that they encounter that they didn't expect or that they're not used to dealing with. And then when that environment, when that distributed environment breaks down, what what do you see being the root cause? Is it the the is that the model? Is it the manager, the culture, or something else? Is it something that had...
00:25:36
Speaker
maybe originally caught them off guard that they weren't used to doing. Yeah. So i talk talk to me a little bit about those things. Yeah. I mean, look, I think probably the stuff that is initially harder for people to grasp. And, you know, I'm an American. I'm coming at this from kind of an American perspective. And a lot of companies, lot of our customers in the United States. And one of the things that you have to get used to and and this is this is true for for anybody anywhere in the world is that work is defined integrated and has different rhythms and cultural expectations around the world and i don't think that you recognize that until you truly work with a global team you know i could see that like you know i'm i'm in boston and i work with someone from california
00:26:31
Speaker
there's sometimes a different rhythm of getting stuff done, right? There's maybe a different casual nature to it. But working from as an American with people from Europe and other parts of the world, you truly start to notice how communication rhythms and communication norms are very, very important to um to acknowledge, to understand cross-culturally, because you can get into unintentional quagmires When I'm saying one thing and I'm a very direct New Englander who's going to just tell you how it is, whereas other cultures are not quite as direct, they're going to be less inclined for that sort of direct or potential conflict that comes out of sometimes disagreeing with folks. So I think first time going into it, you got to take the time. There's a great book that I'm forgetting the name of right now, but I read years ago that really helps you to think about how
00:27:30
Speaker
communication norms and rhythms are not the same and ultimately right where people communication is how shit gets done and if we're not communicating well we're not getting things done so that's a big big part of it um the challenges yeah know the the mistakes i've seen right not being clear on the mission is a mistake you know You don't get that same, you know, look, I've i've worked in offices and there are exciting times, you know, HubSpot, we were all in the office at first, right? And it was exciting because we all knew what we were doing. We all knew what we were driving towards, right?
00:28:07
Speaker
um At a remote level, if you're not clearly articulating your mission, if you're not clear about your goals, if you're not clear how you measure those, I think there's there's a risk sometimes of people sort of falling off the fallening off the train a little bit, not really feeling as as connected as they could be. And that that can stem from the top, that can stem from first line management as well.
00:28:35
Speaker
Because if folks aren't clear on why we're doing something, then I'm just sitting in my house, you know or I'm sitting in ah at a co-work space somewhere or something like that, and I'm like, well, I don't know why we're doing that.
Maintaining Work-Life Balance and Team Engagement
00:28:49
Speaker
And um there's nobody here to hold me accountable as far as I'm concerned if I just close this laptop. so Being clear about the why and the mission, I think, is is super important because it's not just going to come from sitting around with your colleagues, creating space for
00:29:06
Speaker
organic interaction is also really important. We have a lot of different social channels at Oyster, for instance, we have intentional, you can use a bot and it'll set you up on a quick coffee conversation with a random colleague every you know couple of weeks or month, depending on what you want to do.
00:29:24
Speaker
Things like that are really great because I don't have the opportunity to just develop a relationship with you because we happen to go to lunch together, right? It's not how it works. So you've got to be intentional about that. And you've got to find ways like we do with, with, you know,
00:29:38
Speaker
silly channels about like social yell is a channel where you go in and you type all in caps and whatever's on your mind, right? Like, I can't believe the school bus is late. You know, this is ridiculous. And everyone's just like pluses it and comments and all that stuff. So finding some ways to bring that silly energy, I think actually is important, right? Because you got to have a little bit of fun too. And I think if you're not having fun, it's a very easy not to, it's very easy just to focus on work.
00:30:03
Speaker
The last thing I'll say personally as a leader is I spend a lot of time with my people helping them to think about boundaries. And if you don't do that, you're going to have people who burn themselves out pretty quickly is is what I found. And you know I used to have this this colleague of mine and she'd be online nine o'clock at night. And I would, I would start to intentionally take a quick look at things and see if she was still on Slack and still green. And I would be like, stop working, please. And I know that I'm technically your boss and you don't expect that, but like you're overworking yourself right now. So trying to help people and modeling from the top down that you as a person matter and you need boundaries because
00:30:48
Speaker
you know, outside that door is my son's room and so forth. Right. And that's the really important things you got to remember that just because you're working from home or wherever you might be working from, you, you still need to be able to unplug and that's really important.
00:31:02
Speaker
So um it's a mistake I see people make where they don't try to ingrain that understanding and, and people burn out fast is what I've noticed in, in remote culture.
00:31:13
Speaker
This is kind of a good segue into this because I, I, we can kind of, click into something that I think you have some strong opinions on. And I know across your career, including partnerships work, you know, where deals live or die, you know, you've seen a lot of behaviors, I think, consistently get in the way of people doing good work together, I think. And I guess what I mean is, um you know, I'm sure things are probably coming up in your mind. One one pattern you flagged, I know, and you know, yeah is this this idea of lack of follow through. Yeah.
00:31:52
Speaker
Where, where do you see that breaking down? Is it getting worse? Are we just noticing it more because we have tools to measure that stuff? Yeah. And, and, and is that follow through problem different in distributed environments compared to in office ones, or is it the same one? Just fewer places hide. Yeah. I mean, I tend to think it's kind of the same. And, and I think, um,
00:32:19
Speaker
Look, i I think we're in an interesting moment right now where I have seen a lot of productivity gains from things like ai and tools and stuff like that that we're integrating into our into our professional settings.
00:32:38
Speaker
On the other side, that has led to changes in ah staff, right? Personnel changes and things like that. And so results right now, I think, is this idea of we can use AI, for instance, to do a lot, which might allow us to reduce our staff. Now we have a smaller staff doing a ton of stuff in addition to using AI to do that stuff.
00:33:06
Speaker
I think follow through comes when you don't try to meter the workload for people. lack of follow through, excuse me. and And so when I'm piling on, and I know I do this sometimes, particularly the one person on my team, and I literally a couple hours ago call myself out and in and a one on one with them. And I was like, hey I've asked a bunch of stuff from you. So I want to be clear. Let me prioritize it for you.
00:33:32
Speaker
So lack of follow through comes from sort of too many tasks in many respects. And I think it's easy to disappear right now into the noise of an organization into the let's deal with this immediate challenge in front of us as opposed to thinking about the long-term vision that we're trying to do and the long-term strategic plays that we're trying to do so my my advice if this is a challenge and we we have we've largely conquered this at oyster because we're very good at prioritizing things we're very good at communicating here's the priority
00:34:08
Speaker
here's what's urgent, here's the deadline, here's the things that are sort of allowed to fall off, right? And this is what I was trying to do today with with somebody on my team. it's It's really, if you dump a lot of stuff on somebody, you don't give them prioritization, you don't give a North Star, so what needs to be done by what date, you're not clear on expectations, I think you can run into a
Fostering Innovation and Problem-Solving
00:34:28
Speaker
challenge with follow through. I also think you run into a challenge with follow through if you're not clear on the fact that things don't need to be perfect right we need we need done not perfect everyone said that for years you know don't let perfect be the enemy of done you know i've heard that you know a hundred thousand times at this point in my career and it's valuable advice and i think if people have this expectation that they have to um deliver a perfect product every time not product but i'll say a perfect outcome every time they're not going to get stuff done yeah and then you're going to have tasks fall off
00:35:04
Speaker
you know Perfect, I think, also is the you know it is a moving target, you know as as i often is as I often try and and teach my perfectionist children that there's there's there's no such thing, because what's also perfect to one person is going to be different to another person. Totally subjective.
00:35:25
Speaker
Things are also moving so fast right now, man. yeah like i mean you know what What is a good idea today in in three weeks could be a terrible idea. Let me touch on that for a second. because you you One thing that was going through my mind as I was listening to you is this thinking about like people also –
00:35:48
Speaker
lob problems instead of bringing solutions. So totally what's actually going on there? Is it a skills gap? Is it a confidence issue? Is it a culture issue? Is personality? Is it something else? and and And as a leader, how do you train that out of a team, even when maybe that you don't necessarily sit next to every day?
00:36:06
Speaker
Yeah. Yeah. Yeah. Look, it's, it's, uh, it's common. And I see this with people at all levels of experience, right?
00:36:18
Speaker
Sit, successful executives and leaders, I see it a lot less obviously, right? But there's still in my career, plenty of folks I've worked with who you'd be surprised how good they are identifying a problem, but not actually trying to solve that. But they just want they just want to voice it to somebody, right?
00:36:36
Speaker
And everybody does it every in mean, I do it every once in a while and I'm like, ah you know like that's that's not helpful. you know But I actually think it is um it is a lack of... so So we train people how to do jobs. We give them technical skills.
00:36:52
Speaker
We teach you a sales process, a partner vetting process. We teach you programming languages. We teach you product development, project management, you know all this stuff. Obviously, thinking from my my tech company lens here, right? But what we often don't teach people is is critical thinking.
00:37:11
Speaker
is is how to be truly effective right and it's good leaders who spend the time to help their people to answer their own questions and to think through the problem from from what it is to what the long-term implications short-term implications e etc and what the solutions are so I think it's something that is skipped easily in terms of career and professional development. yeah And you are lucky if it's kind of ingrained from in you early from a boss, maybe a good professor in college, who knows, right?
00:37:57
Speaker
i the the The guy, one of the founders of of a company I worked for early in my career, was challenging but helped me to shape a mindset of i don't tell you what's wrong i tell you what's wrong and what we did about it you know and if i don't know what to do about it i give you options and i ask you and i tell you i need some guidance as to what we do about this There is a fear element in there. People are afraid to bring their own ideas to the table, right? So you have to, if you're not getting ideas, if you're not getting solutions from people, you got to think about if it's ingrained in your culture, you got to think about if people feel safe enough to actually express what's truly on their mind too.
00:38:40
Speaker
I mean, I think a lot of... There are a lot of organizations who purport this idea, I think, that they are that they want to promote risk-taking, right? Take risks, be bold. But then at the same time, right, when people do, often, you know, you're going to find out that they're going to get canned because of it. And so I think that that's where a lot of that fear can really germinate from. You know, you you you also talked before...
00:39:04
Speaker
about this idea that people think through things about really only 80% of the way. And I'm curious if that kind of if that's where some of it comes. They think about the problem, they sort of ideate around like what does better look like? And then yeah it kind of it kind of ends there. And and practically speaking, like what What would that look like if they pushed through the last 20%? And you just talked a lot about this this idea, and i'm I'm sort of summarizing what you said, but really about self-awareness, right? People who don't follow through, off problems, who stop short, who who yeah maybe don't even realize they're they're doing it, right? You're talking about the folks who get the training early on or have had those conversations or have had the boss that sort of walks them through that process, probably also own quite a bit more
00:39:55
Speaker
self-awareness, right? i think definitely. um Yeah. I mean, look, this is, you know, ah I'm an old sales leader at heart, right? And like, this was the thing I talked to all my sales reps about is you are, and it and this probably originated in like objection handling back in the day, right?
00:40:19
Speaker
You get an objection in sales, And most people think about 70, 80% around how they can solve that, how they can address that. And if you can get yourself to take a full walk, to give a 100% walk around this problem, that allows you to start to think about all the different perspectives on something, right? It allows you to understand where it's coming from.
00:40:46
Speaker
not just from your perspective, but from every perspective out there. So that might involve talking to other people. That might involve turning off and going for a walk and letting your subconscious run a little bit too, you know?
00:40:59
Speaker
And some of that comes from this do it, do it now type culture that we live in sometimes, right? And really discipline, effective people I've seen are really good at asking for time.
00:41:12
Speaker
They're really good at saying, I'm not sure, let me come back to you on that, because that allows them to do that 100% thinking. This is something that, you know, you think about what we're saying about partnerships in the beginning, man. I mean, that's it's the the the good the good, effective partnership people, because of how vast the impact can be on an organization, they're thinking 100%. They're going around, and they're saying,
00:41:37
Speaker
What is the impact on sales, on CSM, on product, on finance, et cetera, right?
Future of Work and AI's Role
00:41:43
Speaker
And that's 100% thinking that allows me and allows anyone who can practice that type of thing to be a lot more effective. And you do that in every single role. um I think UX researchers are really good at this type of stuff, right? Because it's part of their job. But we have to sort of think like a scientist in everything these days because there are so many quick implications, the market's moving so quickly on us right now. so
00:42:10
Speaker
you know, I mean, it's it's all a part of of knowing yourself, knowing your thought process. The self-awareness thing, I think, is critical that you're pointing out.
00:42:21
Speaker
And knowing where to ask for help, right? Like that is... my My weakness is asking for help, right? I know that's my weakness. So I'm able to kind of conquer it, right? And that's where sometimes I'm at 95% of thinking about things. So I go to our CEO or I go to our CRO and I say, you know what?
00:42:39
Speaker
I'm missing something here. Help me get this last this last leg of this thing so I can have a full picture on what I'm thinking about here. And then we're going to come to a better solution. Point of what I said earlier, we are stronger together in all things when it comes business.
00:42:54
Speaker
um I do want to make sure we have a minute to talk a little bit about future works. Let's kind of pull back the lens a little bit, right? When when you think about the next five years, what's getting too much attention? What's getting too little attention? Yeah. Talk to me about AI. Where are we headed? Give me your... Yeah. um So I think it's really interesting that at least here in the United States, all over all across like news channels,
00:43:21
Speaker
Right now, there were three different commencement speakers at college graduations who mentioned AI and got booed like crazy by by the graduates. Wow, really? so so I was kind of getting a kick out of that. So look, I think AI is awesome. I think we have to recognize that it's about productivity gains and it's about optimization. It's not about replacement, right? yeah And um look, ah ah BSG, Boston Consulting Group,
00:43:48
Speaker
I three, four months ago, I could be a little off at that time. They put something out that basically said, if effectively you have people doing more work now because they're asking you to do something and instead of just doing it. And then they got to review all the work from AI and get the job done. Right. So it is, i think it's going to be there. It's going to get better and better and better. Right.
00:44:10
Speaker
We have to figure out how to apply it in a really intelligent way to your business. You know, right now, ah you know thankfully, we're we're extreme you know this is this is the the oyster ethos is we are a thoughtful organization, right? And we are we're inserting it into all sorts of different areas for both our customers in terms of really smart ways that it can help to address, here's what the PTO practice, here's the best practice on salary within a given country, and then and then have a conversation about how you may want to optimize that.
00:44:47
Speaker
yeah But we're also inserting it into like our operating rhythm internally right now. And we are trying to open up to our staff in a big way of, hey, use these tools. Tell us what you did.
00:44:59
Speaker
But that's that's it. it's It's supplementing good work. it's not It's not replacing a worker or anything like that, right? It's optimizing. It's making us faster. So look, there's no question that's going to be there.
00:45:10
Speaker
You got to keep up with it in order to be there. i think I honestly think distributed teams are a big part of what the future is. um We already see the gradual shift in leadership to to to to your generation. My generation, we're probably about the same, though honestly. And then ah the the kids below us, right? The kids who are booing that commencement speaker, right?
00:45:35
Speaker
These are the future leaders. And these folks care about quality of life. yeah They care about flexibility. They don't want to sit in an office. They want to sit on a beach. Right.
00:45:48
Speaker
And so I think we're going to see a continued ah growth of distributed teams of the necessity to be able to address that need from your staff and acknowledging that companies are going to expand. Yeah.
00:46:07
Speaker
Hey, look, I think, ah ah you know, people have talked about this kind of SaaS apocalypse coming. I don't know where I am on that. And... But it's an interesting question when you look at all these tools out there that can kind of replicate quickly. You know, I, good friend of mine, i just had a drink with somebody. and She's like, vibe coded this entire app and it's a, it's a business now and I'm making money off of it. And I'm like, it's amazing, you know? creep So the speed is really, really interesting right now. And it's only going to accelerate. So we have to think about
00:46:43
Speaker
How does that impact core functions and staffing questions and things like that? And understanding that we're going to live side by side with things like AI is going to be really important as we think about what future organizations look like as well.
Conclusion and Listener Engagement
00:46:59
Speaker
And I definitely don't have all the answers to that one, but you know trying to, ah that's for sure.
00:47:06
Speaker
I mean, I appreciate that perspective. um a it's a good one, right? And i think you pretty much summarized probably what what what the majority of us are thinking or feeling. But yeah um Sean, thank you, man. I appreciate you joining me today. This was absolutely a lot of fun.
00:47:23
Speaker
Yeah. Appreciate it, Curtis. Really to be here. Yeah. And I want to say thanks to all you watching and listening. Mustard Hub Voices behind the build. Be sure to subscribe so you don't miss the next episode. Check out mustardhub.com to learn more.
00:47:36
Speaker
and discover how we help companies become destinations for workplace happiness and turn culture into a competitive edge. Until next time.