Chief of Staff to the CEO, or to the Business? with Ryan Kelly

0:09Welcome to the Chief of Staff podcast. I'm Scott Amenta, founder of the Chief of Staff Network, and I'm really excited to share today's conversation hosted by our Chief of Staff fellow, Tristan Lim. Tristan's guest is Ryan Kelly, the first ever Chief of Staff at Veramark, a Series B workplace trust company headquartered in London, with around 300 people working fully remote. The role didn't exist until Ryan pitched it to his CEO, and he then won it through an open process against more than a thousand applicants. He also sits on the leadership team as a peer, not someone reporting into it, which shapes how he works across the whole business.

0:41His path there was anything but linear. He started out as a welder, joined the JCB graduate scheme, quit to learn Mandarin in China, ran business operations at a London fintech, spent time at Skyscanner, and co-founded his own consultancy before settling in Singapore. In this episode, they talk about why front-loading trusts with their principal pays off, defining a brand new role from a town hall intro on what the chief of staff isn't, to whether you serve the CEO or the business, spotting the quiet problems nobody owns and how Verimark is approaching AI, and why Ryan believes the role is high EQ, low ego, and fundamentally human.

1:17Ryan is thoughtful, humble, and refreshingly honest about the messy parts. I think you'll get a lot out of this one. Let's get right into it. Ryan, welcome to the Chief of Staff Network podcast. It is wonderful to have you here with us. Thanks, Tristan. It's great to be here. I think the first time we met was at the second meetup that we did in Singapore for the Chief of Staff Network. Is that right? Yeah, it was a good event. Actually, I was pretty new into my new role with Veramark and it was a good opportunity to meet other people based in Singapore as well doing similar types of work. So yeah, it was a good event.

1:54I remember you quite well because I felt like conversations around you were buzzing. I feel like you were asking lots of questions and there was lots of energy sort of like pinging around. Probably that's because I was new to the role and I had a lot of questions as well. So I think with my role being a new chief of staff position within a business, there's so many questions to answer. And so, yeah, it was great to have some sounding boards. I particularly remember one of the chief of staff that attended Zen Fu. He had some great insights as well. So it was some good conversation. Zem was actually on the podcast, I think, two, three episodes ago.

2:26It was a really good conversation. And that was also my first time meeting him at that event. Very knowledgeable on AI. That's what I took away from that as well. The first question I love to ask everybody who comes from the pod is quite a common one, but I think it's just really important for setting the stage and helping us understand who we're talking to today. So I would love to ask you if you tell us a bit about your career story, some background that might help everyone listening from all parts of the world, from the US all the way to here in Asia? Who are you and who's sitting with us today?

2:58I would say my career has been quite varied in terms of the industries that I've moved into. And I kind of have described in the past my career journey as the stubborn millennial career journeys is kind of how I put it, whereby I found when millennials entered the job market, the senior managers that were bringing them into the business, they were quite puzzled by some of the desires and interests of millennials joining, you know, we would like this extra training. Can I go to this far off location two months into the role? And I definitely had that level of desire to, you know, see an experience as much as I could in the, in the businesses as soon as possible.

3:39So that's kind of been a thread throughout my career, just of every three years, moving on to a different either industry, location, role. Prior to going to university, I was a welder. So I thought that was my career. I was going down an engineering route and then decided to go to university business and management, moved into the sort of fabled graduate programs that everyone was trying to get in the UK back in 2013, 14 time and landed a role at JCB, Construction Machinery, linked to my past. I had a great exposure there moving around the business. Particularly, I think the good exposure that you get from moving around a business, I think certainly for a chief of staff down the line, that breadth of moving around, seeing how to function as a product team, doing some commercial work.

4:30So you get involved with contracts, negotiations, that got involved with sales work, account management. This gave me quite a breadth of understanding. And then left manufacturing. That was where I talk about the stubborn millennial. I quit my job and moved to China to study Mandarin. I'd been before with work and studying previously. And I saw it as my calling to try to learn a language at least. And I had a reasonable effort at it. But I always thought that I would end up working in China. And then in the end, I ended up working in London on my way back. So I moved into financial services. that's where I started to really move into the business operations type world, as I call it.

5:09So I think you get multiple types of chief of staff. You can get the chief of staff that's come up through the HR business partnering world, and they've got involved with leadership through that direction. In my case, it was a business operations route. So very commercial minded project management, getting involved with essentially reporting to the COO in this instance in my role at a company called ITRS Financial Services based in London, and getting involved with acquisitions. That was one of my first touches into the M &A world. And really that opened my eyes to see that business operations as a progression route was where I thrived.

5:50It was a generalist role. I wasn't a specialist in anything. and I got involved with M &A. I got involved with every single function. I got to do my commercial analysis, which I enjoy. I got to get involved with the budgeting process. So these were things that were pivotal in what I wanted to do next. Moved from there. I actually started working at Skyscanner after that. So I moved from B2B to B2C. And I would say that I still was in business operations, but it's a very different world moving from B2B to B2C or vice versa. And I think I noted that what I enjoy isn't the larger organizations, it's the smaller ones that you can really get a handle on, whether it's the chief of staff or in a business operations function.

6:32So I moved from Skyscanner after a couple of years, I moved to do my own consultancy, digital transformation with my co-founder. And that eventually led me to move to Singapore, where I'm based now, and led me to eventually find my role with Viramark after three or so years of running my own business. The word that stood out for me was generalist. And I think everyone listening can relate to that word. Obviously, being a chief of staff, there's a plethora of things that we were called to do. And we kind of figure out how to get it done. I'd be curious how, you know, you talked about that being sort of like in your zone of genius when you're being called to be more of a generalist.

7:17And what about having the variety of work spoke to you and like, what was that bringing out in you? I'd say it's probably my desire to help people. I look back and I think about my career and I wonder, I think I'd have liked being an accountant. I always liked Excel spreadsheets and I was very good at them. And I And I have too many other things that I want to get involved with as well, because there's so many other ways to help people. And you start getting into the realms of cross-functional working there. And that's more about dealing with people than it is about dealing with the specific problems.

7:51Because as soon as you get cross-functional as a generalist, you don't have the depth of knowledge to be able to solve each department's problems. So you need to work with people. You need to have high EQ. You need to be able to beg, borrow, and steal. Even in my interview for working at Viramark, I remember the private equity house that I've invested in Viramark. They had one of their talent specialists, the head of talent for them interview me. And he said, this role is going to be a beg, borrow and steal type role because you don't have any team reporting into you. How are you going to manage that?

8:24And I had a thousand answers for how I had to deal with that in the past in these roles. So it's definitely a balancing act as the chief of staff to be a good generalist and to not be put off by not knowing all the detail and knowing that you need help. You need help with the teams. And the more senior you get in your role, the more that becomes apparent. What was it then like to run your own business with your co-founder when you ran the consultancy? Kind of being in the employee seat to then being in the founder seat? I would advise or advocate for anyone to get some experience running their own business.

9:05I think it was a fantastic experience for me. We started it in the UK and about halfway through, I'd met my now wife. So I moved over to Singapore. It was a stipulation of the marriage that we closed that distance. So I changed the terms of my founder arrangement with my co-founder. And so I ran it from Singapore. He ran it from the UK. I think the thing you learn very quickly is nothing moves, obviously, unless you are moving it and driving it. And that takes a level of dedication and effort. Although I've always worked hard all my career, when you're running your own business, it's a never-ending thought in your mind.

9:43How do I improve things? How do I close extra sales? And you're thinking it on the weekend. You're thinking before you go to bed, you're dreaming about it. Because it's your own thing, you enjoy doing that. You don't question it. Or I certainly didn't. My wife did, but I didn't because it was what I was passionate about and what I was driving. So the thing that I took away from that, if I think about with Viramark, and I can reference what Viramark do in a moment, but I can much better work with my principal now who is a founder CEO. I can work with him in a much better way because I understand the mentality that's required now.

10:18and I'm sure I'd have worked with him before, but there is a difference now. I can appreciate why he is relentless in what he's doing because he lives and breathes it. And I know what that feeling's like. That kind of brings me to my next question, which is, you know, around Verimark, how you got involved with the team. And I know the chief of staff role was also a brand new one. So I would love for you to give us a bit of, I guess, an insight to how things are going, How do they get started? So Viramark is a business. We're in the workplace trust arena. So think about ensuring before you hire someone that they're who you want to hire.

10:54So that's your background screening, making sure they're not a criminal or they might be a criminal. You may choose to hire them, but you know who you're hiring is the key point. Coming into the business, it's about making sure that you trust who you have in your business. And so re-screening of employees to make sure as they grow a senior in the business, over time. People could be done for fraud or done for other convictions. And you want to just rescreen and make sure your team are still safe for your business. And then you've got the side the other way around of employees trusting the company that they work for.

11:26For us, that's a whistleblowing platform as well. And we're expanding out that workplace trust. But there's those sort of pillars pre, during and general workplace trust. It's an industry I never thought that I was going to move into. I could say that for a lot of my career, I've moved around. And I think what I learned, particularly from doing my own consultancy with my co-founder and the clients that we were dealing with, I found our client businesses and they were all SME size, under 500 employees. I found it was so interesting. It wasn't about what they did. It was about how they run internally.

12:01And that's when I knew the business operations world was my world. And that was what interested me, not what they did. And it's important to have a good vision from the founders or the leaders, but you can have that in any industry, whether it's pest control or background screening or manufacturing. And through my own networking, I met my now principal CEO, Daniel. I'd met him at a vendor event that I was going to. and just so happened as well that he also went to my gym nearby in Singapore. So that actually was just serendipity, I think, or synchronicity. I saw him a few weeks after at the gym and we grabbed a coffee and had a chat.

12:42And I was actually positioning some work for him. Essentially, I was quoting him for doing some work. We were at the time prior to me joining, getting involved with more M &A activity and that post-merger integration work is something that I enjoy doing. And so I was quoting for some work for that. didn't go any further beyond the quotes, some good conversations, but they decided to manage it internally. And then we had probably five months go by. And in that time, my wife and I had made a decision that we'd look for something more stable than the entrepreneurial route. And the honest answer there is from the Singapore side, the business hadn't been growing how I would have liked, but where certainly my wife and I were looking to grow our lives to and family and mortgages and whatnot.

13:26So I started to look around and I gave Daniel, I dropped him an email and I just said, Hey, I think you need this chief of staff role based on what I learned from the quoting process. And I think it'd do really well for your business. And he replied and he said, I've been thinking the same as well. Let's have a call. I think when you know what you're looking for in your own value, the value you can add, you know what that is and you know what you want in your next step of career, which for me, I knew I wanted a chief of staff role. I was very specific about it, oddly specific. I could therefore spot a need that they had.

14:02They were three founders that had scaled this business. One's the CTO, one's the chief product officer, and one's the CEO, CPO, and CTO, chief technology officer. And they scaled to 300 people. They just got their series B funding. And they were at a tipping point where cross-functional working starts to become unraveled. And that's where I felt I could come in without them needing to bring on a whole extra level of leadership. So take a CFO or a COO type role, which would then have a full restructure. They could maintain the structure that they have, bring me in to get them to the next stage of growth.

14:42And Daniel resonated with that. We had a call and the investors actually got involved in the end and said, this is an important, crucial role for the business at this juncture, they could see the value as well of the chief staff role, which was great. They actually thought it was a good move as well themselves, but they advocated it goes through a full interview process. And so in the end, I think they put out the job ad for seven days and it had a thousand applicants apply. Suddenly I went from being the only candidate who had kind of suggested this role to a thousand candidates. And I think Daniel did 34 interviews as part of it.

15:16And yeah, a couple of months later that I got the role. Kudos on following the thread or following the line. On your side, it sounds like from the quotation process, you could see the need, and then you could also see how you could be interested in filling that need, especially now that they were at that tipping point of raising a big round. And then as you try to speed things up, there's more pressure on the team. And then things tend to start breaking because expectations might not meet the capacity, which might not meet the current ways of working. things get a bit funky i just want to call it out because i think that's really a big one like it's such high agency to just you know reach out and propose the role i've had jobs in my career where i got them through my network and i've had jobs in my career where i've applied and got them through not knowing anybody there and i know it can at times come across as a controversial aspect perhaps more in early careers when you're looking over your shoulder at the people that are your peers and you're all trying to get ahead.

16:13And I think what I would advocate to everybody is the power of network. And I rekindled so many relationships through the three years that I ran 1801. I rekindled so many relationships that I'm now making sure that I maintain because over the long term, that's where they pay dividends in terms of intros to whether it's to clients, whether it's to new roles. So you're right, making sure that you're reaching out to the people you know and asking the right questions or asking for help is a huge asset a huge thing to be able to do as you said like a lot of serendipity can happen i mean the fact that you go to the same gym and you also saw each other there after meeting beforehand what was that like then to propose the role to have a lot of momentum between you and daniel around you being the fit for the job and then knowing that he opened it up and then did a whole bunch of interviews and you were part of this bigger process now.

17:08I mean, it certainly flipped the script a little bit, but I genuinely felt that I was going to get the job, not because of any indication from Daniel that I would, but to what we said earlier, I felt like I'd found where I could add my value in what their needs were at the time. And I think the way that I positioned it to Daniel wasn't just about, you've got to a certain size and things are starting to creak because that's kind kind of almost backwards looking in a way of what's broken right now. But one of the sort of things ahead of this podcast episode that I was thinking about was founder momentum.

17:44I have recognized is different to general CEO momentum. There's a different level of intensity. I think I alluded to it earlier. And the positioning of this role wasn't just to stop the business creaking as much as it is or was. it's all the speed and momentum that the founder wants to drive or founders want to drive in the business. My job is to better enable that. So it's not just to hold everything together. It's to enable the velocity of the business for what they want to achieve as well. And framing it that way is a very positive framing for a role that is coming in new to the business. It's a bit like the old adage.

18:24It's a lot easier to hire a revenue generating role because it generates something positive. And it's always good to look at it that way in a chief of staff role too. There's so much value and positive momentum that that role can drive in the business. When you and I had chatted before this call, we talked about a few things and the two sort of bigger threads I'd love to dig in with you. I think one is around what it means to be off service. The second one, which we can get to is what is it like to then come into a company where the role has not, well, you're sort of defining the role because it's the first chief of staff in the company.

18:57I would love to start with calling a bit back to when you just joined Veramark. And I know you had decided to fly out to Dubai to meet Daniel. I think that really stood out in the conversation we had before. And I thought it was worth kind of opening up and sharing with our audience. Could you tell us a bit about that? So Veramark are a fully remote business. I was just chatting to a couple of the team that we recently hired in India. And I said, how long is your commute? you know, Mumbai, the traffic's pretty bad. And he said, Oh yeah, my commute was one and a half hours each way. And I was like, okay, I used to commute into London, similar sort of thing.

19:35And then the next guy said, my commute was three hours each way. And so it's a little bit of a side tangent there, but we're a fully remote business. So there's a lot of people in the business that are adapting to being fully remote post COVID people are starting to go back to the office, but we've built a business that can operate remotely very well. However, coming into a chief of staff position whereby your principal is your key stakeholder, understanding them and how they work, what they expect, what makes them tick, getting that right as early as possible is how you can massively increase the velocity of the value you're adding essentially.

20:15And so although it's not the norm for us to travel across the world to meet each other so often, we do it a couple of times a year, I kind of put it in there as a part of my interview process to say, look, in my first 30 days, I'm coming to Dubai to meet you. And we're going to spend the week together. And I'm going to come with a list of questions, essentially. And that's what I did. During the four or five days, I must have asked 500 questions across a range of topics. this was all sort of transcribed, recorded as well. So I could go back over it with AI as well. But the irony was, I think it was only meant to be a three-day trip and it ended up being a five-day trip because at that same time, while I was there, the conflict in Iran had just kicked off.

20:59So it was a pretty tense time, but maybe a good bonding opportunity as well to be in an environment that was a bit stressful with your new boss. But we went through all the questions we covered, not just like, you know, what's your strategy for the business? We covered, what are you like as a person? What do you enjoy doing? What do you do outside of work? You know, understanding the person, but then understanding his career, understanding what motivates him, what pushes him into conflict. And I was building a picture of the principal and importantly, giving him an honest take on myself. We'd done the interview process and I made myself seem as glossy as you can, you know, with some honesty here and there as well, of course.

21:40But when you're about to start working with them, you want them to know where your weaknesses are, where you tick, you know, in certain aspects. And from my perspective, I said to him pretty plainly, there are times when I would probably need you to keep me focused on the results because I can be quite focused on the people and the sort of data side to things and the detail side. And I know that my principle, I know that Daniel is all about the results as a revenue sort of focus CEO. And so that's where we can complement each other. And we were able to draw out these sort of blind spots for each other.

22:14And that's where I found through this question and answer process, I could really understand where I could help. Whereas during the interview process, you're making a lot of assumptions. The interesting one as well, that for me was actually, certainly with my people hat on, was very important for the process. I threw out a bit of a curveball suggestion to him and I said, I actually think Daniel, it would be good to have dinner with you and your family. It felt like quite a bold thing to ask. You know, you're breaking the fourth wall type thing in movies. It's you're going into someone's personal life and mixing the two.

22:49I got a sense. I knew that he lived and breathed Viramark and therefore the sort of work life thing wasn't necessarily fully separate. There was a blurring there and I felt it was acceptable to ask, but I still had to justify it. And I said, I want to understand who you are at home so I can better support making sure you can remain like that as we grow. So one of the nights we went back to his home, I met his wife, his children, we had a nice meal. And that's when we really got to know each other and share a little bit more as well. I think that's built a lot of trust through that four or five days with bonds coming down or being intercepted, should I say.

23:25That trust has enabled as to in a new role within the business, it can become a state where you're having to justify constantly, if there's a lack of trust, the role's existence. And in this case, we haven't had to, we're seven months in and there's a lot of value I'm adding. There's a lot of progress being made. And so that trust is maintained. When I was just reflecting a bit back of you sharing your journey, even to get here to where we are today, you had Verimark as the chief of staff. and I kind of look back at you know your career story which you shared in the beginning of this episode going from being a welder and kind of going down that route and then going to business school doing and then kind of going the more corporate or desk job route but also you know the side quest to go to China and thinking that was what you're going to do I think what I'm picking up on is you following your gut of the different pivots and changes that you wanted to do.

24:18And just noticing how in the story you just shared of trusting that you're feeling that this could do a whole lot of good because it's such a unique opportunity and a unique role in order to build the human relationship, which it sounds like that's something you've already cared about so much in the past, the people side of things, how connections between humans, I guess, are impacted by changes in the environment. In this case, a company raising money as one example. So it's really beautiful to hear how you continue following that gut and how that also serves perhaps as a beautiful way to build trust between you and Daniel and a role that as we all know, it is the most important thing to have that trust.

24:58As a follow-up question, I'm kind of curious how, I guess, like how did he receive that, you know, when you had requested to meet the family and to have time, how was that conversation with him? with daniel he's very results focused he's a great guy outside of the results focus but when it comes to work related stuff there should always be something that we're driving towards by doing something we shouldn't just be doing something for the sake of it we're a very lean organization that's driving very fast and i think from his perspective by this point we're a couple of days in i kind of preempted this idea and then i doubled down on it while i was in dubai but he'd already seen from about a day and a half of the sessions we were doing that they were adding a lot of value, partly because it wasn't just about bringing me up to speed, the onboarding of Ryan.

25:43It was also clarifying things through my questions for him that maybe he'd not framed it in that way. He'd not thought about answering that question or he'd not thought, oh yes, I should make sure that the organization knows that this is what I'm thinking. So he'd already seen the value that this sort of process had taken us through. And going back to the trust, there was trust that, okay, let's try it. If you think it's going to add value, Ryan, let's try it. And I think that as an organization, still founder led with three very motivated founders who weren't from the industry originally, they've had to trial and error this whole time and see what works to grow to where they have.

26:24So he's definitely up for trying something. Thanks a lot for sharing that story. When I was working as a chief of staff as well, that was something that was very important for me to also try to meet the family of the founder that I was working for. it made such a big difference because I got to see the context in which he was operating in. As you said, that really resonated. The second big thread I want us to look at is actually, what does it mean to join a company as the first chief of staff? And what is it like to create that role from nothing? And what does it look like to then carry that ambiguity?

26:58It's something in the business operations space that I would say I've experienced before. I often say I kind of did a mini chief of staff job when I was at a company called ITRS. And there's the same level of ambiguity. You don't belong to a particular function. You're in a sense, you're creating a function. Then it was business operations. This is chief of staff to the CEO's office. What is the CEO's office? That's a new concept you're throwing in there. And for a company that isn't an enterprise size business of tens of thousands of employees, where chief of staff is probably a more known commodity.

27:34And usually you've got layers of functions that support the CEO. You'd have PAs, you'd have your EAs, you'd have chiefs of staff. There's various different levels to it. But in an organization where it's brand new, how do you explain a role when it doesn't fit into finance, sales, HR? So when I joined, I did interviews with all of the leadership team and some of the rest of the team, when I was getting a lay of the land. And through that process, I was being asked some questions that didn't surprise me, but they did make me smile at the time. I got asked, how does Elaine feel about you joining the business?

28:11Now, Elaine is our people and culture head. And it wasn't suggested. It was just, how do you think Elaine feels about this, your new role? And, but the point was, they thought that I was chief of people, not chief of staff. And so I imagine that's a very common one. So I had to explain, no, this is an individual contributor role, certainly for my business at the moment. And I only replied to the CEO. Lane doesn't reply to me. I was asked, so do all of the leadership team report into you? Again, thinking that it's a different type of role to where it is. Obviously, I explained around that. Another conversation I had with one of the senior people in the business, they essentially said, what are you even here to do?

28:53It wasn't said in a negative way. Thankfully, we're a company of very low politics and very healthy working. But it was said in a genuine, I don't know what you're here to do. And from an ego standpoint, it can be a bruising thing to realize that people don't know what you're here to do and what value you're there to add. And one of the things that I always advocate for and certainly try to practice daily is being humble. I think being humble is a huge asset for everyone as you move through an organization. And so when I was receiving these sort of probing questions, it's just realizing that you need to bring the organization on the journey.

29:31And how you bring the organization on the journey will determine how successful the embedding of the role in the business is. And so I had a challenge because I realized that this is a 300 person business. They've grown rapidly, doubling each year in size. And some of the team have been there since the beginning and maybe haven't seen these larger enterprise structures. So I've got to bring them on the journey. And the town hall was coming up and there's a segment in the town hall where we introduce new starters. And you just say a little bit about yourself. And I thought, if I go up there and I give this sort of boilerplate one-liner, I'm the new chief of staff.

30:10I'm here to help the leaders execute on turning strategy into execution, da-da-da-da-da, buzz wordy, buzz wordy, buzz wordy. If it's already gone over the heads of senior leaders that I've been working with, it's going to go over the heads of everyone else in the business. And recognizing that and just being humble about it and being okay with the fact that they may still walk away from that town hall having no clue what you do. And that's okay. You can prove it over time. But I decided to collate all of those questions I'd been getting. You know, what are you even here to do? How does Elaine feel about you joining the business?

30:43Do all of the leadership team report to you? There was a few other ones as well. And during my intro, I said, here are the three things that I'm here to do, which could sound a bit buzzwordy. I tried to make them as practical for people as I could for a role that was still being defined, you know, and it still is today because it's new in the organization. But then I had another section of what it is not. I literally said the questions that I've been getting asked because I know everyone else is thinking the same questions or at least multiple people would be. I did get feedback afterwards at that level of, you know, because it is being humbled by being able to say, someone said to me, what the hell are you even doing here, Ryan?

31:18You know, in slightly nicer words than that. It breaks the ice a little bit and it helps people realize, OK, I kind of get what he's not. I have some understanding of what he is. I'll give him the patience and time to show me over time and continue to bring the company on the journey. That's kind of what I was aiming for by it. And the feedback was positive on it as well. I think it surprised a few people. The thing I'm kind of connecting this to is breaking the fourth wall, similar to, you know, you asking Dan to have a meal with his family and to meeting them to kind of build a bridge to a part that maybe is less common to build bridges to what people might not expect.

31:57And in the same way, you sort of did that in this case, right? With just being humble about the sort of questions you've been receiving, even if it was, you know, a bit questioning, you know, I can imagine being a chief of staff, you know, only the only chief of staff. And then there's also not much clarity in the organization about what you do. And it's like, oh, do they want, should I be here? Like, do I have a role here? But then putting that on the open is kind of, oh, okay, there's another card you can play. And that is to be open with the questions that we all or a majority of people are probably sitting with and asking in order to build a bridge again, build a bridge to build some understanding about what it is, what it's not.

32:36I think that was really, really cool. One of the difficulties, obviously, with building a role from scratch is that you are building it from scratch, which also means that there's a lot of trial and error in figuring things out. And the call that we had before, you had mentioned sort of a self-check-in method that you use. How do you balance keeping things running how do you balance that with making sure everything on your plate is being done but also on the plate of the ceo in this case daniel is also being done how have you i guess been navigating that being at vera mark as the chief of staff and how's it going i would say this reminds me of another question i was asked and it was by one of the founders the cto he asked are you the chief of staff to daniel or are you the chief of staff to the business interestingly i after my 500 plus questions that I'd asked in Daniel in Dubai, even though I, my gut knew the answer to the question.

33:30And I said it to Angus, the CTO, I said, you know, I believe I'm the chief of staff to the business, but I think it's a good question for me to take back to Daniel, the CEO, and to just make sure we're aligned that that's where my focus needs to add the value. And I think it comes back to your question now, who are you there to keep happy? Is it that you're there to keep your principal happy on a day-to-day? Or are you there to add significant value over the longer term, which ultimately keeps your principal happy longer term? The obvious answer is it's both. And you can't get away with not working on the things that your CEO is throwing at you that happens in this line of work that we do as chiefs of staff.

34:12You have to keep making sure that you're dealing with the things on fire. So keeping all of the asks that have been thrown your way, being delivered as soon as possible, that will make the CEO, your principal happy short term. But what I keep making sure I check in on probably every month or so, we work in quarters, in quarterly planning cycles here. So I make sure at least every month I'm doing a real check on myself that I haven't just been dealing with the fires of the CEO, which keep him happy month on month. But then I get to the end of the quarter and he looks back at what he really wanted me to work on.

34:49Even though he may have really, really wanted me to put out the fire, if you ask him what was more important, that fire or the big objective I had for the quarter to deliver on, it's obviously going to be the big objective that takes three months to deliver on. And so my check-in that I do with myself is, am I just putting the fires out and keeping those things quiet? Or am I moving all the big pieces across the board at the same time? And you have to make sure you have a balance because if you only keep the CEO happy day-to-day, they'll not be happy at the end of the quarter. That's kind of the idea behind it.

35:22Because the true value of a cross-functional role, such as the chief of staff, is what you can deliver over the longer term, not the administrative stuff, not the firefighting, not the jumping in to support on something urgent. It's the helping the business change over time. What does that look like for you, in terms of keeping that balance of day-to-day, putting fires out, but also holding the longer term goals and projects. How have you been navigating that? I'll be honest, it's a tough ask. And it's the challenge of the chief of staff or business operations type functions to prioritize. You know, you're usually an IC, you're reporting to senior leaders within the business.

36:08And there is an expectation, depending on how the chief of staff or the role that you're in is structured, the more senior you get in that, you're expected to be able to make the decisions on your priorities and leave yourself open to be challenged by your principle. That's how I approach it. I say, I think these are the problems that I should focus on or the opportunities I should focus on and receive that challenge. We have our quarterly planning cycles. We put myself last in the order of the reviews that we do. We're going through them this week. Actually, this week's a very busy week for us.

36:40We're doing a retro on Q3 objectives and planning for the Q4 objectives. And we stick myself last because when you start to listen and hear all of the challenges that the different functions are facing, the areas you start to draw the dots on, this is a cross-functional matter. This is something that they can just take on themselves. This requires some oversight. This requires a little bit of BA skills. And that's something I sometimes get involved with, map out a few processes and such. Or this requires a light touch PMO, which often is a hat that I would wear in business operations roles or in this role.

37:19And through that sort of connecting the dots over the week we do these reviews, it then comes to me and we set these goals for myself. And it's either going to be I take on projects that I drive myself, or I take on projects that just require me to ensure that it keeps moving along. So back to the question on how do I manage that as well? The day-to-day stuff versus keeping those moving. It's just like any leader of a function is you have your objectives. And if you haven't met them by the end of the quarter, you're going to be judged on them. And in my function, those big objectives that are cross-functional, again, like I said earlier, that's where the real value gets added in this role.

37:56The more chiefs of staff I talk to, and the more these types of conversations I've been having, I'm seeing two really important traits, you know, one being high agency-ness, but also high compassion. The thinking in order to be of service to your principal, to the company, to different stakeholders, you need to be able to have compassion for the problems that they have, which means putting yourself in their shoes and seeing things from their perspective in order to then design and support them in representing them even in meetings from their perspective and what they may be going through. Sometimes it's not a pretty job, the things that we have to do as well.

38:38And I would love for you to tell us a bit about the story around IT onboarding that I think we talked about last time. I'd start by saying I think one of the superpowers for the chief of staff, or at least how I do the chief of staff role, is to operate with a very high EQ. I like to think I have a good EQ, but I think it's a superpower when you can display that. Because although there's a lot of talk around AI and replacing roles, and I can Google and there'll be a sign up to get your AI chief of staff with Claude. And I smile because I genuinely believe that if you do the chief of staff role well, and you operate with a high EQ, and as part of the leadership team, you're able to work with the people that have the influence across the business, that's how you make the changes happen.

39:28You don't make it through banging your fist on the table or using the power of the CEO's office to get stuff done. You get it delivered through high EQ, the beg, borrow and steal balancing act. So using that sort of emotional intelligence to spot when things are getting noisy or there's friction bubbling up, that's kind of what I'm on the lookout for, especially when we're doing, whether it's doing my interviews when I joined and that's probably something I'd be doing annually is interviewing the teams to understand the friction points. But also in these quarterly planning cycles that we do, listening for the bits between the lines, sitting on the sort of functional one-to-ones with the CEO and get to hear all of the noise in between those quarterly planning sections as well.

40:14And what often can happen is that because there's other priorities, noise, friction, stress points can be perhaps glossed over, overlooked because there's other pressing it matters. But when you drill into them, they're actually a much broader challenge or opportunity to fix that's going to add a lot of value that you don't really recognize in the day-to-day because it's not as loud as some of the big fires that you're trying to work on. In the case of the IT onboarding example that we previously discussed, over a lot of Slack channels that we have. And I'd recognize that as we've doubled in size every year, we are constantly revamping, improving, optimizing our processes and back office so that they're keeping up.

40:56And we'd started just as I joined around that time, we started to have a few laptops that weren't arriving on day one of the new starter arriving. And this at first was out of 10 new starters, maybe two of them, their laptops didn't arrive. And it wasn't noisy enough for it to be on the CEO's radar. It wasn't too noisy for it to be on the CTO's radar, who IT report into. But it was a real frustration at the HR side of things, because they're the ones having to deal with the new starter. And that onboarding experience, it's very well known that the onboarding experience, a poor one, has a really detrimental effect to attrition later on, So people leaving.

41:40And so I recognized that there was some noise. And for me, seeing perhaps because I sort of sit on that sort of people focus in how I like to think about things, I was recognizing that this was causing quite a bit of strain on the HR team. There were solutions that they were trying to come up with in the Slack channel. Okay, let's create a tracker. Let's do this. But they weren't looking at the end-to-end process. And my brain often goes to what's the end-to-end and wanting to understand something's falling down at multiple points if this keeps recurring. And so it was just a little bit of noise and wasn't going to be picked up.

42:15I could spot it and recognize if we look at the whole end-to-end, we could probably solve this for good rather than it keep recurring every now and again and being sort of dismissed. And that's what we did. It was one of our initiatives for the last quarter, those sort of quarterly planning goals I talked about. So because I was the one who spotted it, I was the one that had to run it. And I was happy to, because I wanted to do a bit of that BA work to map out what's actually going on and what we ended up coming out with. We worked with our MSP service providers who delivers laptops and sets them up.

42:49We actually worked out that there was these whole new service offerings that we could do that essentially cut out the need for the laptops to go via them. And IT didn't need to do any call onboarding and it could just be delivered straight from the manufacturer with all our security and compliance stuff already preloaded. These were just good outcomes that would never have at that time been addressed because no one was revisiting the process yet. So yeah, being able to put your hand up and go, I know this isn't noisy enough for it to be on your radar, but I'd still like to tackle it. And then the unforeseen added value that that brings.

43:23I think that's the thing is keep your eyes and ears open at all times because the CEO can't be expected to spot everything and the functional leaders are running their own functions you're the eyes and ears cross-functionally at that sort of bridge between the strategic and the tactical and so listen to the noise the little frustrations the little complaints that you might see on calls or on slap that's something maybe to dig into especially if you're in firefighting mode right you fight the fire you might not be doing like whole investigations like hey how did the fire start and how do we prevent this from happening in different areas in the company so i think that's something i'm definitely taking away as you're saying that like how to hold the urgency of needing to put the fire out but also communicating well to everyone else what you're seeing in order to understand that we are part of a bigger system like this fire exists within this whole ecosystem which seems to be you know a theme that you're very forward with how you say what's on your plate and also telling you perhaps your ceo and the rest of the team that it may not be super important for you, but this is still something which I think, you know, I might want to do.

44:29I think that communication piece is super crucial. The bit that I'd add as well is the idea that there are goals that you can set. And this is, you know, part of what I do is the quarterly planning cycles and the goals that we're setting and working with the teams to come up with these. And, you know, the first quarter I was here, it was very much sort of still learning about the business and stuff. So you kind of take a little bit of what people are saying, and often they will set goals that they can control, right? This is a problem for me. I can deal with this and I can control this and deliver this by end of quarter.

44:59I can commit myself to that. But if everybody was choosing goals that they can deliver within a quarter, that's within their remit 80-20, it's 80 % of what they need to do is within their control. It doesn't necessarily change the organization in a way that is materially improving it for the long-term scalability wise, for example. And so the value that I would say the chief of staff is there to do is to look at the bigger problems and be able to say, okay, if we were to take this large problem here and we've got four quarters to deliver it and it's cross-functional, let's break that down into each quarter.

45:36And then what would those goals look like in each function and how do they roll up into that bigger thing? And so it's trying to just get the line of sight to be a little bit longer term. I think that's that strategy translating into execution. It is about increasing the field of vision. I've got my HO empires or whatever with the fog of war. How much fog can you clear so you can break down those problems? Otherwise, people will focus on the problems directly in front of them. And that's the IT onboarding example is you've got what's directly in front of you. A laptop is late. But actually, there were multiple touch points that could be improved across that whole piece that added a lot more value but it took longer i like the fog of war analogy if all the fog of war is clear that we can anticipate what's coming you know so better plan for a resource management of what's coming or you know moves we want to make in the future being a podcast in the age of ai i think it's important to talk about ai and i wanted to get your take on every single ceo in the world most likely is wanting the team to adopt AI as fast as possible because of how fast it can help things move, but also the desire to not be left behind.

46:48I'd be curious how it's been for you at Veramark, setting the pace of how AI is deployed. And also how does that work, you know, between you and your CEO and that quality planning process? Yeah, it is the topic on everyone's minds. I'd say I'm privileged to get to be on the board meetings. I'm not a member of the board, but I get to be in there as the role of the chief of staff And certainly this business, that's some new exposure for myself, which I'm loving to be able to see how the board think about things. But AI is always a segment within that, you know, those board updates. I saw a stat recently, actually, I was reading a research article and it said 70 % of CEOs feel that they are the main driving force of AI within the business.

47:33And I thought about it and I thought about Daniel, our CEO, and how he's thinking about AI. And I would say we're lucky that we have three founders and two of them are on the technical side. So we've always had an AI automation focus with how we're doing development, how we're doing automation of our service delivery. Those two areas had always been quite well thought out. And so because if we automate our service delivery, we don't have to hire as many service delivery staff to deliver a higher volume of background screening checks in this example. The bit in between the product engineering, platform engineering type stuff and the service delivery stuff is the whole operating model of the business, the back office, the go-to-market function.

48:19And I would say that that's where the CEO's eyes are currently trained on right now. And there's been a huge desire to do more there. And from an investor standpoint, we're fortunate to have investors as well that have a lot of expertise within their businesses around AI and go-to-market functions. And through their portfolio companies, they've got visibility of what others are doing. And there's this good thing that they're doing right now, which is they're interviewing their portfolio companies, including ourselves. And they're sharing that output, running it through AI, I'm sure, and sharing that output to show what others are doing.

48:56So we've ended up with four areas of AI focus. We have the products and tech, engineering, product development type stuff. And they're very heavily using all the tools to essentially move to a place where we don't need to hire the traditional developers. We can hire technically minded product people and they can build the tools. Now, that's where things are moving to an extent, the product skillset and the ability to requirements gather effectively and talk to departments and then execute the changes. That's the sort of skill sets we're looking for. The service delivery automation, as well as robotic process automation.

49:34So it's not just all AI, it's just how do we automate as much as possible? And that's either with AI or other things. Those are the two ones that we've had for a while. The two that are new, and we started the initiative just after I joined. Daniel, the CEO, asked me to essentially set up an applied AI unit. And that Applied AI Units role is to look at all the bits in between those two areas that I mentioned. So go to market, back office, let's have a dedicated working group. So they dedicate a day a week. So we have a person from our revenue operations team. We have a person from our data team.

50:08We have a person from marketing, performance marketing. We have someone from our ops team who's great on the process and SOP side of things. And we've brought that team together. We're bringing in someone from L &D as well to join that team. And their job is just to solely think about each quarter, one or two high level value add projects that they can take on that will move the business forwards in those two areas, go to market, back office. That's the thing that I'm kind of chairing. I made the joke that I'm essentially just Nick Fury, who's got no superpowers and has just gone to all the great people in the business who are evangelists of AI already.

50:46They're doing things with it. And I brought them together and said, you're now the Avengers of AI. and it's been really valuable and we've done some really cool small projects it's the first full quarter they've had and the scale of what we're looking for them to take on is only going to grow each quarter and we're then going to start expecting them as a unit to be looking further down the line and clearing some of that fog of war of seeing what else is coming down the line in ai and taking on some of those bigger chunkier cross-functional tasks which you have to break down into quarters and smaller chunks to tackle.

51:20That's where they're moving to now because they've chipped away at some of the quick wins that are out there. There's loads of quick wins around go to market and back office. So that's the applied AI unit. And then the final one is the overall company maturity of employee AI maturity, as I would put it. And that's another area that I'm essentially looking at and going, we have our focus on product tech, we have our focus service delivery. But what about how we're 5X-ing our employees that maybe don't use AI very often, don't need to, but how could we help them overall if they had a better understanding?

51:52So our L &D function, we're starting to look at now, how do we just raise the bar and raise the level of AI understanding? I was talking to Zen Fu, who we mentioned earlier, and his focus around AI. And I had a coffee with him after the event, actually. And we talked about harness engineering and what are all the governance, the SOPs, the rules around use of AI within product engineering. That's the kind of usual way you'd look at harness engineering with AI. But actually, if we were to apply that across the whole organization, it will look slightly different. There's a lot more governance and rigor and structure that prod engine need to have when developing.

52:32But how do we translate that to all of our 300 employees? What are the sort of guardrails what are the parameters with which they can operate and how do we train that and how do we build their confidence but also constrain it a little bit as well because we don't want a proliferation of tools and there was only a few weeks ago we suddenly started having a proliferation of note takers and you know we use we're on the google stack and we use google to record and transcribe things but we started having note takers pop up and you know so that was an example where it's like, look, this is the approach.

53:07Let's stick to just using one source. And it's a lot more secure that way as well. Right. And as we come to the last bits of our chat today, there's a question I'd love to ask. How has being a chief of staff impacted your life outside of work? Well, as kind of introed with my entrepreneurial recent past, I think my wife was used to me being quite dedicated to my job. I think what I've noticed is when you join as a in such a role as this, or I'd say in any role really, but this role, you're in the frontline view of the CEO, your principal, and you've got to build that trust. And we talked about trust in terms of conversational trust of, you know, I go to Dubai, we ask you some questions, we build a bit of trust and that helps.

53:52But the other bit of the trust is ways of working. And you only learn those ways of working and learning what's working for you and what doesn't through working. And so So what I probably did at the start when I joined and not saying I have a solution for it, but what I would say is I would make sure that I was starting my day at nine because my contracts are nine to six contract. So I'd be starting my work at nine, but I'd be getting involved in so much stuff. I'm passionate about doing a good job. It's my first six months. So I'd be finishing maybe 10, 1030 by choice. You know, my wife would look at me and go, did you put that meeting in for 930 p.m.

54:27Ryan? I was like, yeah, yeah, because I needed to speak to this guy and they had a full diary. And so this was the only slot. And my brain, maybe I was still thinking as an entrepreneur, my brain wasn't viewing that as a problem. But my wife was pointing out, you're starting every day at nine and you're finishing every day at 1030. Although some days demand long days, you've got to make sure you're sustaining yourself and not burning out. And we talk about founder momentum. I've experienced it when it's your own business, you can push a lot harder and go for a lot longer and a lot less fuel. So over time, I've built more trust that I get the stuff done.

55:02My boss doesn't care what hours I work. We're a fully remote business. He'd have no way to know really. What he does care about is that I get stuff done. And over time, I've just gradually got a little bit more confidence in saying, I worked till 1030 last night to have some calls with the UK. So now I'm going to start tomorrow at 10 and I'll do that. And I'll feel really comfortable about doing it because I know that I've got the trust of my principal. He knows that I get stuff done. The balancing act in the work-life bit was just setting expectations with my wife that there will be more flexibility with time.

55:36But right now for this first four or five months, I just need to make sure that I'm doing what is contractually there, the nine o 'clock start. But yeah. Yeah. That makes sense. It's like setting like the foundation, the groundwork, and oftentimes that takes a bit more. And obviously the deeper we go, then it's also, perhaps something bigger can grow to be supporting that. I have a last, last question, which is what piece of advice would you give to someone starting the chief of staff role? I would say you've been hired because you presumably have a good understanding of cross-functional needs across a business.

56:14And you have an understanding of how to run leadership meetings and what works, what doesn't, and how to execute on strategy and all these things, but you don't know the business yet. And that I would say is 60 % of the role is knowing the business and how it works. And then the 40 % is applying what you've learned and what you can come with to reshape that slightly over time. And I think about one of my first leadership meetings that I was running and I was presenting how I was about to change all the operating rhythms within the business or the leadership meetings. I was saying, yep, so we've got these three levels of meeting weekly, monthly, quarterly, and because they have different purposes, the weekly and the monthly, when the monthly falls in a week, we'll still have the weekly because they're different purposes.

57:04And I was really like adamant about it because they're different purposes. That was my mindset. And the CTO in front of everybody, one of the founders, he essentially said, absolutely not. Absolutely not. And this was something I presented in my interview. So, you know, I thought a lot about it and I was like, there's no way that I'm going to spend this amount of time and this amount of time in the same week. Like we need to put them into one and somehow, you know, and I remember pushing back a little bit and being like, well, there's a reason they're different, but that's that piece we talked about humility, keeping your ego in check because I went away from that and thought about it, spoke to more people and recognized that if I did put all of that leadership time together in one week, for the way that our business operates and the speed that we should move at, it would have been way too much governance, way too much process, way too much time spent.

57:55So I look back at that, even though I defended my position on the call, I look back and I'm like, thank God I listened. Thank God I didn't just try to plow ahead because you have to be able to read the room understand the business you're moving into and not just apply a template as a chief of staff you can never apply a base template and expect it to work for everything to wrap things up like it ties in really well with what you had talks about in terms of the role of ai and for the chief of staff role and that the human relationship and like understanding the context of human relationships between each other between the people and the business like there's so much sense making that happens on a human level that we can have all the models we want of how to do things in certain ways but it's that piece right like the human piece of connecting the dots and seeing things and perceiving and having awareness and also having humility that i think really helps choose the stuff to like sense make of the situation and therefore be a good chief of staff the role is negotiation you are constantly negotiating between priorities across the leadership functions there There are constantly going to be conflicting priorities and people like to deal with people, but also expecting AI to, certainly for the time being, convince and negotiate with a leader to say, you need to put down this thing that you see as your priority and focus over here.

59:18And here's why, and let's talk about it and have an open conversation. That's the chief of staff role. It is negotiating priorities and ensuring that they get done because you can't do it all yourself. You've got to rely, you've got to beg, borrow and steal to meet the needs of the business. So yeah, I think AI is an accelerant. It's a supporting function and everybody should be using it and it will gradually do more and more. The chief of staff role is about people, in my opinion. So be a human chief of staff and you'll add more value. Ryan, thank you so much for your time today. It's been an absolute pleasure having you on.

59:52Thanks, Tristan. Great to have been part of it. That's a wrap on Tristan's conversation with Ryan Kelly. Two things I'm taking away. First was check yourself every month. If all you've done is put out your CEO's fires, they won't be happy at the end of the quarter. Second, listen for the quiet noise. The small frustrations nobody owns are often where the biggest wins are hiding. If you want to connect with Chiefs of Staff navigating the same questions, join the Chief of Staff Network. We're thousands of verified Chiefs of Staff across 25 cities with in-person events like Chief of Staff Connect, programs like Launchpad and the Chief of AI Fellowship, and a membership built for operators doing this job every day.

1:00:28You can find us at chiefofstaff.network. If you enjoyed this episode, please give us a like or comments on your podcast network of choice. Thanks for listening to the Chief of Staff Podcast. We'll see you next episode.

1:01:02We'll see you next time.