Leveraging Leadership

Wearing All the Hats: The Reality of Gaps in Startup Teams

• Emily Sander • Season 1 • Episode 187

Share episode

Sabrina Dhaliwal shares her unique career path from a Financial Analyst at the Canadian Coast Guard to Chief of Staff and Product Marketing Manager at a tech startup. She talks about landing her current job through a networking coffee chat, jumping into unexpected roles like head of marketing, and why learning quickly is key for Chiefs of Staff in fast-paced environments. The episode also covers work-life balance, building an 18-month roadmap, and the importance of community engagement for startups.

Free Resources:

 

Get in Touch With Emily:

 

Who Am I?

If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want. 

 

Time Stamps:

00:29 PTO and Work-Life Balance
01:53 Sabrina's Career Journey Begins
02:58 Transition to Strategy Consulting
04:15 Joining Remo Three
05:30 Challenges and Adaptations in a Startup
13:25 Evolving Role and Future Plans
26:38 Advice for Aspiring Chiefs of Staff

Speaker:

How's your week? It's going good. I'm actually on PTO this week and we go, I'm really enjoying it.

Speaker 2:

That's a good week. It is good. Now, are you actually taking time off or is it quote unquote PTO? But we're working a little bit.

Speaker:

No, no, no, no. I never work on my PTO, so I actually took this week off a couple of months ago, I planned it to start my vegetable garden, but I live right on the Canadian border. And if you know anything about this particular geography, it is, it'll be sunny the week that you're working, and then it'll be absolutely rainy and cloudy the day, the week that you have PTO. And then the week after, it'll be sunny. So, um, there's no gardening happening this week. Yeah, the

Speaker 2:

week you wanna do a vegetable garden, that's when it hales, is what I'm hearing. Indeed. It's actually

Speaker:

like freezing this week, but next week it's gonna be seventies and eighties. It's,

Speaker 2:

of course it is. When you have to be inside. Yeah. But good on you for like actually not working. I think that's like lesson one for chiefs of staff listening is like, Hey, when you take some PTO, like mean it and like take some PTO. So

Speaker:

work-life balance is really important to me. It's honestly probably one of the biggest qualities I look for. Just in terms of like career and how I navigate that whole thing.

Speaker 2:

Yeah. Also like secret, it makes you better at your job'cause you think that it does. Yeah. In the long run, better decisions. Hey, if anyone wants better decisions, um, better quality decisions, like give your brain a rest, but, alright. So Sabrina, we've, we've teased people long enough. You have an amazing origin story and it, it just showcases like the chutzpah and pro, I always get this word wrong, proactivity, proactiveness. You were proactive to get the chief of staff role? We'll say it that way. Can you, can you tell us a little bit about that?

Speaker:

Yeah. My career has not been the straight line that I sort of expected it would be when I was in high school. I'm sure a lot of people would say the same. I. I, so I started as a financial analyst for the Canadian Coast Guard. I started when I was 19. I was still in university, um, and it was a federal student work program. And then when I graduated, I ended up sort of bridging into a full-time role, but I always knew that I wanted to go into management consulting because I had a family member that was a partner in a management consulting firm. So pretty soon after that, I joined a strategy firm. And I think part of the reason was I sort of romanticized the lifestyle, you know, seeing my family member in this particular role when I joined consulting was right at the height of the pandemic. So consulting as it had been before the pandemic no longer existed when I joined. And I also sort of realized. Unfortunately, like women, a couple of months of joining this firm, that pure analytical, quantitative consulting was actually not for me at all. So I ended up focusing on a lot of digital transformation and customer first oriented projects, and I actually had to learn a lot of things like UX and UI design, um, customer experience design, even like marketing and branding to some extent. So even my. Strategy consulting experience is really unique in the realm of like consulting when you think of a management consultant, but I learned a lot from that job. I mean, it, it gave me a direction, it sort of. Gave me some semblance of what I'm good at and what I enjoy doing, and therefore how I can bring value in the workforce. And, um, after about three years, I unfortunately, like thousands of others, found myself in a career transition where I was looking for a new job. And it took a long time. Sadly, like this job market has been extremely brutal. And I ended up finally landing at a startup tech company called Remo Three, and it happened honestly, like completely by accident. I had a coffee chat with the CTO, which. Legitimately just led to a full-time job offer. And it wasn't a situation where they were trying to fill a, a position in their org chart. It was just, we want you on the team. So I ended up having a conversation with the CEO. Where we talked about the kinds of skills that I could bring, the kinds of experiences I could bring, and also the things that I wanted to do. And from there we ended up sort of devising a position and then slapped a position title on top of that. And it was so incredibly refreshing because I've never had the experience before where I can just sort of say, yeah, this is what I really enjoy doing. None of that fits into a nice clean box. So I think sort of as a convenience, we ended up putting Chief of staff on this particular position that I was filling in this company. Um, but I. Truth be told, I was never doing anything that, uh, a normal chief of staff, you know, would probably be doing in this company. And within maybe two or three weeks of joining the company, they ended up doing an overhaul of their marketing department and there was a pretty large gap in the marketing. So I ended up becoming the defacto head of marketing for the past six months. At this company, and I was also super involved in the UX and UI design and the community engagement for the product. So as of May, 2025. I am have now transitioned to the product team. I'm now product marketing manager. So I started as a financial analyst in the Canadian public sector and I'm now a product marketing manager at a really small tech startup.

Speaker 2:

Wow, that was a lot right there, Sabrina. That's a lot. I know. Like even at the very first thing you said, like, um, fp a analyst for the Canadian Coast Guard. That's an episode right there. So like you had me at Coast Guard, um, and then walk me through some of your. The pieces you mentioned. So you had the coffee with the CTO. How did you get that coffee? Again, it

Speaker:

was just a mutual networking connection. Yep. Okay. You know, I had a mutual networking connection who said, Hey, you should talk to Sabrina. And I talked to him. We had a second coffee chat, and from there I was like legit, just offered at a full-time position.

Speaker 2:

Wow. And like, I mean, that sounds like the fairytale, but break it down for people. Is it like. You were just chatting in general. I mean, you were looking for work, but it wasn't like you should have a CEO at Remo three, like da da or COS. It's Remo three da dah. It was just like, Hey, let's chat. And then something kind of clicked. Was there like a Yeah,

Speaker:

no, we had a conversation. I gave my standard elevator pitch.'cause at the time I had been job searching for about eight months. So I pretty well rehearse my elevator pitch and figured out what direction I wanted to go into. Um, and I, he was just legitimately interested in. My background and I started just sort of off the cuff giving some thoughts about how to scale the business, kind of hearkening back to the whole like strategy, consulting experience. Right. And he ended up inviting me for another hour long conversation with him and the chief marketing officer at the time. And I just had a feeling that something. Was there. So for the next week before the second conversation, I prepared a presentation sort of as I would for a client in, uh, consulting. And I presented to them, they recorded it, and that was sort of like the catalyst of Oh, okay. Like we're just gonna hire her. And I'm really glad I did. Like sometimes I obviously, when you are in this job market and you're searching for a long time, there's this thought of, I don't wanna have to do work just to get a job. I usually feel that way, but for this, I just had this feeling that there was something and I'm obviously really glad that I did it.

Speaker 2:

Yeah, well I think there's like pieces in there. Uh, the fact that you gave actual advice off the cuff, even in that first meeting, I think when you actually add value or you're just having an engaging conversation where you're. Like not, I mean, you gave your elevator pitch, but then it sounds as like you engaged in like, Hey, here's what's actually happening in your world and in the business. Here's my ideas. I don't know everything yet, but you were actually engaging at that level and he, and they picked up on it, and then you went kind of, I. Full blown, full, full court press. Uh, for the second one, which, which paid off for you?

Speaker:

Yeah, it was really organic conversation. It's sometimes your coffee chats sort of fall flat and sometimes they don't, and there's, you know, a little nugget that you can latch onto and sort of have a really organic conversation. And that was just one of those times.

Speaker 2:

Yeah. And then another piece you said it was like, I, I'm probably not a normal chief of staff and like the. Uh, it queued a movie quote from Forrest Gump, like, what is normal? Anyway? There's no such thing as normal chief of staff. But, um, you talked about bouncing around to different roles, but when you first got there, it sounded like there was like a functional. Gap or opportunity around marketing and branding, which played off of your previous experience. So was that kind of like, Sabrina, we need you to go do this and just jump in and do what you can for standing up this department, or what did that look like?

Speaker:

It wasn't at first. At first I was hired based on the presentation that I gave in this like quote unquote interview process. I was hired to develop the go-to market strategy. Ah, that's, and when I had the conversation with the CEO, we had talked about how I was. Really interested in UX and UI design and sort of giving advice on that side as well. So it was this, uh, position that we sort of devised that would bridge the gap between operations, marketing, product, and maybe even like sales. So it was this kind of strategic role. Um, and I think in a way that sort of fits into this. Chief of Staff umbrella, where you're sort of acting as the bridge between a bunch of different departments and figuring out how to execute a cohesive strategy. But I. Marketing, overhauling the marketing department, I think was probably not the plan, and then it just happened and there was a gap to fill. So I just ended up filling it and I had a lot of ideas. You know, I came in to the company, tried to do my due diligence about really interviewing everybody in each department, identifying what the challenges were. Um, again, hearkening back to the consulting really, which is figuring out what the problem areas are, doing some market landscape research, figuring out what customers want, and then. Trying to figure out how to bridge that gap. And so I had a lot of ideas about how to do marketing, and I spent a lot of time in consulting with a customer first mindset, just because the way that the market is today, the way that technology and AI empower. All users and all customers today forces businesses to develop business value by creating customer value. So I had this thought about how to do social media marketing in particular, and when they overhaul the marketing department, I just sort of applied all of these ideas as quickly as possible.

Speaker 2:

That's awesome. And I wanna go back really quick to one thing you just said. You said. I think you said during the interview process you spoke with the other team members. Did you get a chance to speak with

Speaker:

No, this was after I, I joined. Okay. Yeah.

Speaker 2:

Okay. After you joined, you did like a. Like a one-on-one listening tour. Some sort of like, hey, like, I'm here now. What was that? Pretty much, what was that first, like week or two? Like where people, like, who, who is this? Or like, had they gotten a heads up from people and it was like, oh yeah, no, we're glad you're here. Um, here's what I do. Well, it was

Speaker:

interesting because the, uh, the presentation that I did in my second coffee chat made the rounds throughout the company. Ah, the company is not that large. It's 30 people, but it had made the, the rounds already. So I think people sort of already had an idea of what I was here for. Um, but I really just spent the first, I wanna say two weeks doing due diligence and not presenting any ideas or not sort of coming out with, I know everything because. Obviously nobody does, but really just trying to understand what the business does and what the pain points of each department are, and then combining them together. The reality of startup is that everybody is so busy just trying to make everything function, that you often don't have the time to think strategically and sort of think cohesively. And I was trying to fill that gap a little bit.

Speaker 2:

For sure. I love that. That's, that's the quote of the episode so far. You gotta think strategically and cohesively. And a lot of founders, I mean, they're doing their best job, but they just get sucked into everything. And they're running a million miles a minute all the time. And for someone to say, let's. Lift our head up and look at the long term here. What are the long-term impacts to this short term decision? Or hey, you know, that makes sense for delivery and operations, but what about across the business over here in, um, product or compliance mm-hmm. Or what have you. So, um, someone having that longer term view and then broad scope. Scope is a huge. Advantage for a lot of teams. How have you seen your role evolve? So you mentioned go to market, uh, marketing, branding, and then now on the product side, is it just continuing to morph and morph as it as you go?

Speaker:

It really is. I was, I was actually listening to, uh, a recent episode that you did with, uh, Martian Dowling from Germany. And I think one of the things he mentioned was what he was COO, which was right hand to the CEO and he had this pallet of tasks. Yeah, and I just feel like I, I really re, it resonated with me too. I think just the palette of tasks just evolves and you sort of, again, in startup it's a situation, and especially in this company, every single person is legitimately doing the work. You don't have anybody who's just sort of supervising, everybody is legitimately doing the work and that leaves this pallet of tasks, these sort of like, you know, other things that just end up never getting done but are super value valuable to the business. And I think that, uh, palette has just evolved as I've moved through the company and sort of filling different gaps. And I'm really excited to now be in this product marketing manager role because I think. It will allow me to continue being that bridge, but it sort of makes sense for where I am and it makes sense for the experience and the skillset that I've developed. And yeah, I'm really excited for it.

Speaker 2:

And then would you say that your. Primarily working in these like functional roles or It is kind of, I have a functional role hat and then like a chief of staff hat, which is across the board and I kind of flip back and forth between the two. We've had chiefs of staff who definitely have two distinct roles in that, like I run this team and I have a whole, you know, team that reports to me, but then I also have to step into my chief of staff shoes and look at things across the board.

Speaker:

I would say it's more looking at things across the board. I, I don't run a team and you know what? I'm thankful for it. Uh, yeah. I'm more looking at how to enable, you know, product marketing and sales. I. Uh, together as sort of like this triad and figuring out what resources each of these department needs, and then how I can bring my specific skills and experiences to each of those departments, sort of help scale the business.

Speaker 2:

Yeah. And like as you go along, are you talking to the team about, you know, we're here now, but we do wanna have that intermediate or longer term vision. So if we wanna get to here in 18 months, we have to start doing these things and nudging people and reminding people to, to, Hey, we need to move in this, this direction. I know you like doing that, but we actually need to go over here now.

Speaker:

Yeah. The business has gone through a pretty massive transformation since I started in November. We've actually had. Quite a few launches, at least two. I think by the time this episode comes out, it'll be two. And when I was running the marketing department, I did a brand overhaul to sort of create a more cohesive brand look and feel, um, even down to like the colors and the fonts, um, the imagery of the brand and bring it all together with the UX and UI design of the product. And. Currently we're working on redesigning the UX and UI design so that it all sort of is cohesive with what the website looks like, for example, and I think. When startup, in general, you're sort of always in present mode, like just how to scale and how to grow like as quickly as possible. You're sort of always thinking about the present. And from this consulting background, I was definitely working on projects that were two or three years long. Yeah. And we were thinking about these 18 month roadmaps. With startup, you sometimes don't have the luxury of. Thinking that far out and I with, uh, quite a few other people in the company are now starting to think about how we can develop a, an 18th month, month roadmap and keep ourselves on it. Because I think at the end of the day, having a clear direction is really going to help you scale your business. But more than that, it is identifying where the market is gonna go and identifying what customers are looking for, what pain points they have, and what gaps there are in the market that you can fill.

Speaker 2:

Beautiful. And I'm curious, how do you interact with your principal, with the other C-Suite executives? It seems like you, like you said, it's a pretty small crew, so everyone might just know each other, but just what is that interaction day to day or week to week look like?

Speaker:

It's very informal. Uh, often quite a few chats, you know, teams messages or getting on calls. It's very informal and I think that is. Really beneficial. You know, having worked in both the sort of bureaucracy and hierarchy of government, and then the bureaucracy and hierarchy of consulting with these, you know, massive firms. Now I'm in this company with only 30 people and I. Hierarchy is a lot more flat, and I think that is probably to the benefit of the company because it enables people at any position within the org chart to deliver ideas and they're often really good. We have just incredibly intelligent people in the company. Again, I think Martin said something in his. In his, um, episode with you where it was sometimes you wanna hire the person that is not, doesn't necessarily have all the industry experience. That may be not the perfect fit. And I think that's where I come in. Personally, I don't have a lot of tech experience. I really don't know anything about it, but I had a lot of UX and consulting experience that I could bring and it was a very fresh perspective. We already have incredibly intelligent people in the company that know everything about tech and know everything about it, and I can sort of. Bring their knowledge together with fine. And I think that flat, flatter hierarchy really enables us to be more successful in this sort of startup culture.

Speaker 2:

Yeah, I love that, and I've heard that so many times from chiefs of staff where it's, I'm not the technical expert. But that's why I'm here because I'm not the tech worker. Exactly. Um, I can bring things together and that's a skillset that other people don't have and it's needed. Also, I think that like common sense goes a long way. Like if you can, if you have common sense and you can figure stuff out, that goes a long way that puts you, uh, that puts you, I. The above average category, in my opinion. Um, I

Speaker:

think it's also, it's, if you haven't started a business, I think sometimes, you know, the company that I'm working with now, the people in leadership, they've all either been in C-suite positions or have run other startups. Before. And I think if you have that experience for, you know, decades, you might sort of think this is the, this change management problem where, well, if you've been doing it for 20 years, the same way, like, and it's worked. Why, why would I change anything? And because I, in consulting, I worked on. A different project probably every three months, and I sort of witnessed the advent of AI and I witnessed the advent of this information age and how that changed how customers and users interact with the market. I think that brings a new perspective where it's not necessarily, oh, I'm so young so I don't have this experience. It's actually more just like bringing a new perspective to people who have. It's been really skilled at developing startups in the past

Speaker 2:

in terms of the crossover between chief of staff and consulting. I feel like there is some overlap for sure, and then there's some like, yes, definitely like distinction and differences. In your experience, what have you seen in like, yep, like this is a transferrable skill. I use this all the time. This can be used in both really well and like, oh, but these things are definitely different. I had to learn this or have a new perspective on this.

Speaker:

I would say. I think consulting and chief of staff is a very natural evolution. In fact, I know a lot of my consulting peers who have probably transitioned to some kind of chief of staff role over the years. Um, I think just like things like market research, um, things like making sense of the market or doing research on competitors and, um. Condensing, consolidating and making a strategy that is siloed among different departments, sort of cohesive for the business is super transferrable from consulting to some kind of chief of staff role. And you also develop that communication that just like comes along with it. Um, I don't know. I, again, my experience in consulting was so. Unique compared to what you would expect a management consultant to have. But I would say probably the UX UI experience didn't necessarily translate to a traditional chief of staff

Speaker 2:

role. But it helped you here. It did. It did. You never know. You never know. Yeah. Um, sometimes the underwater basket weaving experience can come into play. You never know. That's the joys of chief of staffing. Um, what are, like, what's up next for you guys? You have any big, uh. Updates or things you're excited about or things that you are thinking about as chief of staff? Okay. We're, we started that 18 month roadmap process. Emily like, okay, here's kind of what's on deck in our new opportunities and challenges and all those things.

Speaker:

Yeah. I'm really excited because we are. Very close to releasing a new plugin for, um, it's for, I, I guess I should give you a backstory about int uh, about Remo three first, which is we enable, um, users, IT admins and CIS admins and Intune admins sort of better manage their applications and their operating systems for enterprises. So we help them migrate to new OS systems such as Windows 10 to Windows 11, or we help them patch their apps so there's no security risks. And um, we also just enable Intune admins to make use of Intune, you know, and maximize their investment in Intune. And I'm really excited because we are launching a plugin for Intune and it appears that it is the first on the market. Oh, wow. So I'm really excited. It's the first, uh, tool for Intune that sits on top of the Intune browser rather than having users use a, a separate tool. And I think from a UX perspective and from a community engagement perspective, that's really exciting. And I think we're launching that beginning of June. And then after that, I really am hoping that we're going to implement this 18th month roadmap for the next obviously two and a half years for the next, for the rest of 2025 and all of 2026. Now that I'm on the product team and I really wanna focus on community engagement, think, you know, chief of staff is very internal facing and I'm now in this position where I really wanna focus on getting the startup sort of more. External reputation and growing that sort of external facing presence, whether that's becoming face of company or enabling somebody else to become face of company and really engaging with the, you know, quote unquote influencers in the company. So that's what I'm focusing on for. I hope the next 18 months or so,

Speaker 2:

just a few things here and there. Nothing, nothing much. Just a product launch. Yeah. Community engagement, you know, just 18 months graph. Um, all in a day. All in a day. Exactly. Yeah. The community engagement piece is really interesting. I was speaking with, uh, a chief of staff for, I. An NBA team and like a big portion of their job was coordinated with the city and with different initiatives that were happening at like the different local levels. And I was like, oh yeah, because you have this great forum and you're not always playing sports in it and you're, you're sharing that with the community. So that was just kind of a, it made sense once I knew about it, but I was like, oh yeah. So I think the community engagement piece, um, is something for a lot of chiefs of staff to think about. And it might not be like a natural like. Chief of staff community engagement. But for a lot of companies that could be, uh, a huge advantage and a whole area of focus.

Speaker:

It probably depends on the industry and the company you're in. I think people sort of view tech in particular as this like, you know, massive white whale. But when you're actually in it, tech is. Pretty small, honestly, like everybody knows everyone. The companies you realize are far more interconnected than they seem from the outside. And the influence that, um, particular community members have is massive. So for a tech company, especially a tech startup, to be successful in this industry, it's really important to have a really great reputation and a really good relationship with. Community members and community influencers. And that's what I'm sort of trying to bring us to now. And I think if you are a chief of staff in a tech company, especially if it's a startup, uh, community engagement would probably be one of the number one priorities, I would say to focus on.

Speaker 2:

Okay. Piggybacking on that, any other advice or lessons learned or like, don't do this or try this for aspiring chiefs of staff or current chiefs of staff?

Speaker:

I would say. Develop the skill of being able to learn pretty much anything. Um, there are so many skills that I've had to learn even in consulting, but particularly in this role and the roles that I have had in this startup at Remo three, where I've just had to learn a new industry or a new. Skill or a new product super quickly and honestly use leverage ai,'cause that's how I did it. But developing the skill of being able to learn and to absorb information and to apply it really quickly has been massively successful. And I probably operate and have the experience that would. Probably fit as a generalist category, but the ability to learn anything just goes a long way. Whether it's being successful in this particular position or thinking about my career 10 years from now.

Speaker 2:

And I, I think too that once you have confidence that you can do that well, like, I don't know about this and it's scary, but I can figure it out. That builds confidence in, in ways where like you do raise your hands for things like, I don't know all of that, but I can figure it out. And you raise your hands and that's how doors open. So I think building that skillset, I love how you describe that, but also increasing your confidence around that can open doors, um, for you in the future. So,

Speaker:

yeah, for sure. And it gives you an opportunity to show in an interview, for example, how you can actually apply that, because everybody will say, oh, I can learn really quickly. But if you can point to examples where you've actually done so in an interview or in a coffee chat, it goes so much farther. You know, again, I think about all the people that are currently in their job search or currently in professional transition, and that's one of the things that will definitely help you throughout your career is being able to apply. Learning things very quickly

Speaker 2:

and we've come full circle. So in that interview it was demonstrating that I can learn quickly and you probably incorporated some different things in the, in the second, in the second presentation you did. So, um, awesome. Sabrina, anything else that's top of mind or we discussed and it made you think of something that you want chiefs of staffs or principals to know?

Speaker:

I think I would harken back to what Martin said, which is. Don't necessarily hire the person who is the exact right fit. I think especially in this job market, companies and employers have all of the power and they're looking for the exact perfect candidate. So for people in the job market, it can become a little bit disillusioning because it feels like you're never going to check all the boxes from an employer point of view, from a principal point of view. Give that person who wasn't. The exact right fit of chance because chances are you already have the knowledge that you need, the industry knowledge that you need in your company, but you need a whole different perspective. You need an outside perspective for your chief of staff and then from the job seeker point of view. Definitely just try, just try this position or try that coffee chat. That seems like it's really out of left field because you never know and they might see value you in you that you didn't think you had.

Speaker 2:

Beautiful. Sabrina, thank you so much. This has been a wonderful conversation. I've learned a lot. And, uh, thank you so much for, for sharing your story. Thank you.