Allie Fleder on Changing Industries, How COO Roles Vary, Remote as an Extrovert, Clarity at Early Stage Startups, and Head Wounds

Allie Fleder

Michael Koenig: [00:00:00] Between two COO's is a podcast where phenomenal Chief Operating Officers from all sorts of companies come to share their insights, advice, and crazy stories. 

Allie Fleder: She opened the door. I was like, here are your suitcases have a great time. She was like, you're bleeding from the head. I was like, oh, I think I'm fine.

So much blood pouring out of my head. She was like, please like, let me call you an ambulance. You need to get to the A and E, you need to get to the emergency room. So I got to the emergency room. I was, they did all kinds of tests. I didn't know my name. I didn't know my birthday and the whole time. I'm like “what?”

Michael Koenig: Hello and welcome to Between Two COO's. I'm your host, Michael Koenig, and I'm excited to welcome our guests to Allie Fleder, Chief Operating Officer at SimplyWise, a FinTech company that helps people take control of their financial data. In addition to SimplyWise, Allie started a number of other [00:01:00] successful businesses and chairs EUROUT, Europe's largest LGBTQ+ business conference. 

Welcome Allie. Thanks for being here. I'm excited to have you on. 

Allie Fleder: Thanks for having me. 

Michael Koenig: So you're a two time COO first in the travel industry and now in FinTech. How'd you end up as COO? What was your path? And then maybe, can you tell us a little bit about the industry change from travel to FinTech?

Allie Fleder: Yeah, absolutely. Um, I had the very typical route to COO. I studied Latin American poetry in college. I then became a political speech writer. I then served as chief of staff at an NGO and a think tank that was based in New York. I then did an MBA where I started a British travel company and then rather naturally transitioned to a FinTech company.

Michael Koenig: Yeah, totally typical and traditional. And I know that there are tons of other COO's who have done the exact same thing. 

Allie Fleder: Yeah, it's definitely, definitely the, the regular route. Um, [00:02:00] but I do, I think I'm quite suited to this early stage startup COO because I am very much a generalist and, you know, being at an early stage company, I think everyone is in a way a generalist, but I do think that is the most true for a COO.

Allie Fleder: And I think that has been the one constant, um, through everything that I have. 

Michael Koenig: Interesting. So in terms of being a generalist, what areas have you found yourself gravitating to more in terms of your specific skillset? Because COO can cover a lot of different. 

Allie Fleder: Yeah, I think it's a really good question. When I first came on to my current company, I first came on to SimplyWise, um, our CEO, Sam brought me on to the team and I said, what do you want me to run?

Allie Fleder: And he was like, well, what do you want to run? And so we kind of went through the different verticals and he was like, what I would really love to have you do is accounting. And I'm kind of writing this in a notebook and finance, and HR are you go to HR sounds good. Customer support. Can you do customer support.

Allie Fleder: Yeah. [00:03:00] Recruiting, recruiting. Could you do recruiting human resources, maybe legal and actually it would be great to have you help out with product and maybe some business development too. And so I'm writing down everything and I was like, “so the business. What would my title possibly be?” Um, and he was like, what do you want it to be?

Allie Fleder: And we both agreed that COO was probably the best catch all term. Um, so I assumed that my, um, I think like what I am good at and what I felt like I would be doing when I got in is really the internal operations. I assumed that that would be like, I would just be focused on making the business run on, you know, making the gears right.

Allie Fleder: And, um, what I wound up doing, I was, as I was just telling you my goal, but I wound up doing I'm in my second or third week. Um, the company I wound up getting really involved in SEO, um, and a big part of our SEO work was in PR doing a lot of public relations work. And then by, I think it was within my first month, I was doing interviews on like local Fox stations and with like local radio show.

Allie Fleder: [00:04:00] Um, so nothing like what I thought it would be doing pro and frankly, like very far outside of my skillset, but I think at the end of the day, that's actually like, that's probably what I wind up gravitating to is anything where I can be learning a lot. Um, and needing to learn quickly to make something happen.

Michael Koenig: Yeah. Running the business, essentially, pretty much all aspects of the business. Save maybe engineering there. And you touched on a lot of the usual ones, which is G&A which usually includes finance and business development. So sort of the go to market aspect of this. 

Has your role changed over the growth of the company?

Allie Fleder: I would say definitely. I think, uh, I'm curious what you would say to Time Doctor, but I feel like my role changes probably like every three to four weeks. Um, and in some ways, like there are definitely some constants, you know, like I'm always sort, I'm always doing stuff on like finance and accounting.

Allie Fleder: There's always kind of recruiting going on. Um, in a startup there's always some like legal piece to what I do, but I did, I wound up spending most of [00:05:00] my, so before I came to SimplyWise, I think I spent about a week or two trying to do prep work to run the internal operations of this business. Um, so I spend most of my time in our QuickBooks trying to clean up the accounts and reconcile and use all of that to formulate.

Allie Fleder: Um, and I assumed that a lot of what I did my first few months would be, uh, you know, developing that budget out, making sure that things looked good with the CEO and, and using that to kind of pave the way forward and help develop a strategy for the business. But I actually think Sam and I spent maybe 10 minutes of that on my first day going over the budget.

Allie Fleder: And then he was like, right. What I really need you to work on right now is SEO. And like, we really like that's, you know, that is our growth focus. And I was like, Googling, “what is SEO?” And, um, so I literally quite literally spent my first month, like trying to like trying to make myself an expert, learning everything I can.

Allie Fleder: And I took a good General Assembly weekend course or something. At some point I'm trying to school myself up and, um, and literally spent like half of my time writing and like doing back to my speech, [00:06:00] writing, um, writing out blog posts and the other half, trying to figure out how to get them out into the world and link built.

Allie Fleder: And we, our strategy on it, changing from SEO after probably about like six to eight months. Um, and so that'd be gradually became less and less what I was doing to. One other constant I had though throughout my role was I was always where again, where I thought it would be kind of internal operations focused.

Allie Fleder: I actually spent a lot of my time and I continue to spend a lot of my time talking to users. So I spend a good portion of my time doing like what I would think of as more like a product role, like doing user interviews, talking to potential users, talking to our current customers. And I'm using that to inform a lot of how we build the product.

Allie Fleder: Um, and I would say that that has been a constant for me throughout, along with some of the internal ops stuff, but in general, like day-to-day as the product shifts as our marketing strategy shifts, so much of the role to. And 

Michael Koenig: You tend to find that a lot with early stage companies where you have to wear a lot of different hats [00:07:00] where the strategies can change. How do you find the constants though? And then at what point do you start to think and look at how you as a COO are spending your time and say “right time to bring on someone who can do this better than me?” 

Allie Fleder: It's a great question. Can I turn it back to you and ask, like, how do you find the constants? How do you think about that?

Michael Koenig: Sure. I mean, we can turn the table here. That's totally fine. In terms of finding the constants for me - and I think it's probably different for companies of all stages - the common thread would probably be the longterm vision of where you're going. So having that flag planted somewhere and looking at the different milestones that you have to hit along the way.

And certainly those milestones, the tactics you use to accomplish those milestones may change in my opinion, but at the same time, you still know where you're going. So you have that constant. [00:08:00] 

And in terms of when I decide to bring on someone to do a job better than me, usually it has to do with how am I spending my time. Is it really worthwhile doing XYZ that we could perhaps get someone who is less expensive, but has more experience in doing this and then looking at opportunity loss, where, where could I have spent my time and then kind of look at it and go, “okay, right. Rime to bring on someone, let's invest in some people and start to build this for long-term.”

Allie Fleder: How do I find my constant. I would say, so one of the first things that I did in my first week besides Googling what is SEO and trying to, trying to figure out how to make that happen was that I sat down with our CEO and I said, and we didn't have a mission for the company at that time. Um, and I was like, it feels, this feels like a really critical [00:09:00] thing before we think about hiring before we think about like going much further in the.

Allie Fleder: That we nail this down together. And so something that we wrestled with, I think for like our first, like two or three weeks in the company, we wound up, everyone was a part of it. We even had like some of our contractors that we were close to, like helping us out with some of like the exercises that we ran around it.

Allie Fleder: Um, but being able to come to a mission all together was some, you know, we had a vision for the company, but coming to like a mission, like so much more of like the why we are here and like the bigger, like the heart, I think it is the heart behind what we're doing that I found is something that I like that has been a constant for me and for the team and something that like we refer back to in like almost every week, sometimes every day.

Allie Fleder: Um, it's been something that like keeps me grounded and keeps me focused when it's really hard when you're zooming in and out. Um, and that's challenging. Um, the other thing is, and I know this isn't necessarily the case for every COO. It is more of a product hat, but is like being so close to our users.

Allie Fleder: Being able to talk to our users every day. I think it's something that regardless of where I wind up in the company, and I [00:10:00] don't necessarily know if that will always be the COO role. It's something that I would love to have as a part of my role, because as our product has shifted and changed, um, and wind and so doing as our users have kind of shifted and changed.

Allie Fleder: Being very close to them has also been like, kind of kept me grounded and been a very focusing constant. Like there is someone that I'm serving and I feel very aware of that. And that helps me even like within the internal operations, like helps keep me, um, keep me. In terms of when to bring someone else on.

Allie Fleder: I think I'm thinking about that constantly with every responsibility I have as I'm going into it. I think about what is the ROI here? You know, like, is, is this worth my time? Is there someone who could be, as you said, is there someone who could be doing this better? And so like for example, one thing that I've been, I've been working on, but it's currently taking up about 80% of my time is customer support.

Allie Fleder: Um, I am spending almost every day of the week and I'm spending Saturday nights at, you know, I step out of dinner to take a customer support email, or, or a customer support call. I'm spending a lot of [00:11:00] my time doing it, and I really love it. And as I said, I love being close to the users. And in a way I've been finding it kind of hard to give up, but I've connected with some other customer support specialists.

Allie Fleder: And they're like, it's time, Allie. Like this is not your primary role. It's time to hire someone new. Um, and so I've, I found it weirdly hard, but at the end of the day, I know it's not the right use of my time. And there is, I would be able to find an expert. Um, in someone who could be dedicated to this and really take it to the next level, 

Michael Koenig: Support is tough. It's often a thankless role as well. I remember the first time that someone cursed me out from support. It was in 2007. I remember it to this day, everything about it, man. That is tough. 

Allie Fleder: It is tough. It is really tough. I had, like, I learned early on my gut that I can not take anything personally. And I also found that as soon as you tell, so I now introduce myself and support emails, especially when someone's upset.

Allie Fleder: I'm like, “Hey Michael, I'm Allie from the [00:12:00] team. I hear you, you know,” and just introducing yourself, letting them know there's actually a human there. Every single time I get a response, “Oh, I'm so sorry for all caps. I didn't realize there was actually going to be someone who responded to this email.” 

Michael Koenig: So you spoke with some of your Support friends and they told you that, “Hey, it's time if you're stepping out of dinner and handling a support email, it’s time to bring on someone else.”

Michael Koenig: So in terms of building your team, how are you going about that? What are you thinking about in terms of hiring? How about location? Are you all going to remain remote or are you going to go centralized? How are you thinking about? 

Allie Fleder: Yeah, it's been a huge challenge for us. I am someone who is, I really need to be around people or like on a very personal level.

Allie Fleder: I need to be around people. It's where I get my energy. I always felt like I, you know, it killed me to be home during the pandemic, but, um, our team has become kind of distributed, like sort of naturally in the pandemic. Our CEO had a baby. [00:13:00] CTO on a painting to move to Boston, to be with his partner. And so we've just kind of become distributed.

Allie Fleder: So what we are doing right now is we're meeting in person every two weeks and we do like a day of work and then we do dinner. It has been really nice, but I will say like from my apartment, from my perspective, it is challenging. Um, and so it's something that we have been rested. I do think I I've been talking, I've talked to other CEOs.

Allie Fleder: I'm curious what you have to say on this too, Michael, but the one thing I've heard over and over again is just, it's important to be deliberate about whatever choice you make. So even if it's right now, like we're in this kind of gray period, like being very deliberate from a cultural perspective of like exactly what we're going to do, like while we're not really sure.

Allie Fleder: At some point transition to being back in person or back in person two or three days a week, um, or fully remote, like while we're in this gray period, at least like make it, you know, make a decision. Okay. So right now we're in this gray period and here's what we're going to do to set aside time to, you know, foreplay or set aside time for lunch or, you know, to do a Jackbox game or whatever it is, but actually carve out that time and [00:14:00] be, you know, be thinking more actively about the structure that you.

Michael Koenig: Right. So giving some clarity at the very least, it sounds like that's something that you have found to be key during times of uncertainty for your team. 

Allie Fleder: Yes. Yes. Yeah. Very 

Michael Koenig: much. Very nice. Very nice. And in terms of maintaining clarity, In an early stage company, you it's that famous word. You end up pivoting all the time, whether it's product, whether it's your strategy, which it sounds like you all certainly have iterated on your go to market.

Michael Koenig: How do you maintain that flexibility while still maintaining certainty on the team about where the company's going and how you're getting. 

Allie Fleder: Mm, it's such a good question. No. Can you tell me the answer to this was I have no. What I think the key is, is, is always communication. I think in [00:15:00] my, um, when I worked in the think tank, we, um, we purchased another, um, another organization.

Allie Fleder: So we had, uh, a merger and acquisition and it was a very fraught period. It was very confusing for the people that we were acquiring. It was confusing for like some of the overlapping teams within like, do I have a future here? What is the, what, what do these two organizations now look like together? And what we found was over-communicating on everything to the extent that that we could was the only real fix, um, in a time of uncertainty.

Allie Fleder: I think that's especially true in an early stage startup where like, there is no, there is no real roadmap. There is, you know, or you have a roadmap, but it's changing every day. I think like, just communicating as much as possible, um, with people up and down the organization. And I think that doesn't necessarily just happen in all hands, but a lot of that is like happens one-on-one and then, you know, like you build up trust, you've got people on board and then you're communicating things as a group.

Allie Fleder: Um, but I think like getting that communication right is key 

Michael Koenig: That last part, getting that communication right, I [00:16:00] wonder, do you ever run the risk of creating uncertainty by overcommunicating? Because you're constantly evaluating different scenarios. And how do you maintain that sort of semblance of certainty when you're facing uncertainty?

Allie Fleder: Yeah, I think that's a really good question again, like truly, I am curious to hear what you, what you would have to say on this. I'll tell you the way that we've been dealing with it, which is it's hard because I think like there are, um, on our team, there is definitely a divide and I feel this too, that, um, you know, like it feels like we know we're at the early stage.

Allie Fleder: We know things are moving and shifting around so much. But there is, there's also this sense of like, it just like the, the ambiguity can feel so overwhelming at times. And, and what we've noticed is that like, just like having a conversation and talking things out and being kind of stream of consciousness with the entire team, like that doesn't really work, it's better to have some of those, like, conversations, like either like at [00:17:00] the leadership level or just kind of, or keep them, or.

Allie Fleder: Or even for a sub-section of the leadership level to keep things kind of like isolated while you're sort of working things out so that you can have more like one more unified message to the team. Even if that message is like, look, this is where we are right now. There is some uncertainty, things are changing, but like helping guide people in one direction, it does like, that feels pretty critical.

Allie Fleder: But what has been your experience in that? 

Michael Koenig: I do agree with you that there are certain things that have to be done behind doors and behind closed doors that is. And that has to do with presenting a unified front as a leadership team, I think is, is very important. So

One of the questions I love asking, we've all had those moments as COO's where you wake up and you go, “well, never thought I'd see that.” Does one come to mind that you can share with us?

Allie Fleder: Um, okay. One of my craziest actually is when I was, so I was running this luggage delivery service in London and it was like a last mile delivery service. So we would pick up your bag from your Airbnb or from the airport and deliver it to one of the other, um, so that you didn't have to lug it around in your day.

Allie Fleder: And the, um, and I was, you know, essentially the COO of that company. And, um, so I assumed that I would be spending most of my time on strategy and our model and the deck and everything internal ops. And of [00:19:00] course that wasn't the case. And we had a lot of trouble. It was a two, we started off as a two-sided platform.

Allie Fleder: We had a lot of trouble recruiting drivers and especially good drivers who would provide a real, a real white glove service because it's a high trust transaction to take someone's suitcase from them that has, you know, all of their stuff. So we wound up for our first, I want to say for first, maybe like 1000 bags, I delivered a large portion of those bags as did my co-founders and I had at one point, I think it was probably in our first hundred bags.

Allie Fleder: I was delivering some bags from Heathrow area. To, um, sorry, maybe to Chelsea in London. And I had gotten to, I had gotten out of my car and there was a set of a long set of stairs. I needed to get up to, to deliver the bags, to there, to the customer. And there were two really, really heavy bags. And there were some old, like, does that like old Mulberry designer bags?

Allie Fleder: Like they didn't have wheels, nothing. It was just like really heavy. And I'm a smaller person. And I got, I don't really remember the whole thing. I think I got halfway up the stairs [00:20:00] and the next thing I remember, I was down at the bottom of the stairs with the bags on top of me, like, oh my God, like what, what am I doing with my life?

Allie Fleder: Like, how did I get here? These bags? Look, I have an MBA. Like these bags are on top. Like, why am I taking no salary? What am I doing? I'm just sitting at the bottom of the steps, like with these two suitcases on me. And then I was like, “you've got this Allie, you've got this”. And so I somehow, I don't know this part.

Allie Fleder: I kind of blacked out. I brought, I somehow got bags up to the customer. And then the next thing I remember the customer. Um, she was like, she opened the door. I was like, “here are your suitcases have a great time.” She was like, “you're bleeding from the head.” I was like, “oh, I think I'm fine.” So much blood pouring out of my head.

Allie Fleder: She was like, “please like, let me call you an ambulance. You need to get to the A and E, you need to get to the emergency room.” So I got to the emergency room. I was, they did all kinds of tests. I didn't know my name. I didn't know my birthday and the whole time I'm like, what am I doing? What am I possibly [00:21:00] doing?

Allie Fleder: And I was like, you know what? I'm never going to do. I'm never going to do that again. I'm like, this is crazy. Like maybe, you know, like this company is crazy. This is crazy that I'm doing this. Like I belong in an office. I don't belong, like delivering bags. And so we agreed that I would do that. And then of course, I think it was like three days later. One of our drivers, again, kind of canceled last minute. And there, I was like back at the airport, delivering bags. I think that one of my craziest moment. 

Michael Koenig: That's a story of persistence right there. Holy smokes. Talk about moving the ball up the mountain and then getting smashed in the face by it and bleeding.

Michael Koenig: I'm trying to imagine myself as your customer and having, like opening the door and seeing you just bleeding, but handing me my suitcases. That's gotta be one of, one of the stranger things, not just for you, but for this, this service. I mean, they really do put blood, sweat, and tears into it. And I think you probably poured all three [00:22:00] of those into making that delivery happen.

Michael Koenig: That's amazing. So in terms of a new COO moving into a new company, what advice would you give them as someone who has delivered bags with blood dripping down your head? 

Allie Fleder: Okay. A couple thoughts. The first I would say is if you, if you haven't gotten to the company, I do think it is really. It sounds, maybe it sounds obvious, but I do think it's really critical to find a CEO that you really, that you trust and respect and that you work very well with.

Allie Fleder: Um, I think like this job, especially in a startup, I think it is really challenging. I think it would be really challenging if you did not have that. Um, like with my, the CEO that I work with right now with Sam, we have a very like direct communication line. We, um, we have, there's a lot of trust between us.

Allie Fleder: Like I am great at what he is not good at. He is great at what I am not good at. Like, there's just, there's a lot of like give and take. [00:23:00] And I just, I can't imagine, I can't imagine having that can't imagine not being able to speak directly to each other and to have that kind of trust. Um, so I think that's the first thing I would say, like before you can take the role, don't take the role if you don't, if you don't feel like you have that, um, kind of, or that you could have that kind of.

Allie Fleder: The next thing I would say is to the extent possible. I do think you're the ability to try to connect with other COO's. I think you'll really benefit from connecting with other COO's and, you know, I was telling you before, um, I in taking this job, I didn't know other startups COO's and. And I, and I felt like I was really yearning for that advice.

Allie Fleder: And so I wound up literally going on LinkedIn and, you know, searching like COO fintechs, you know, CLO traveling, CEO, tech, um, and cold messaging people. And I called message probably like 20 people. Two people responded. They both gave me very different kinds of advice, but they at least gave me like some color for what the role would, um, would look like.

Allie Fleder: And I am not on cos, but I wound up creating in the pandemic. I created a [00:24:00] group of, um, female co-founder, uh, female founders and a slack group. And I have found we do a monthly call and I found that that is one of the most helpful things, because whether you're the COO or CIO or CTO or CEO in a startup, I think like being in a startup and being an early stage startup is kind of, in some ways, wherever you sit in the company, it can feel kind of isolate.

Allie Fleder: It can feel really overwhelming. And as we've been discussing, the ambiguity can just be overwhelming at times. And I think like being around, but you're, you're never, you're not the first person to do this. And so like being around other people, having the benefit of their advice and experience, um, and their wisdom is kind of everything.

Allie Fleder: And actually a third thing, I would say kind of off of that. Do not reinvent the wheel. I think I spent so much time in my first six months in this role, you know, recreating everything like designing processes, designing a hand, you know, an employee handbook doing research, like what is the best employee, but what is the best?

Allie Fleder: Like what are the best rejection emails and creating like my template of like my emails through the recruiting. [00:25:00] Um, and spending so much time and research on that. And the fact is the, all of these documents are out there. They already exist. You know, you can, you should, you can and should tailor them for your company and your culture and what's right.

Allie Fleder: Um, but a lot of this stuff exists. There are templates for budgets. There are templates for quarterly reporting for your investors. There are templates for employee handbooks. Um, so. You know, don't, um, don't recreate that wheel. Talk to your investors. They'll often be able to share templates like that.

Allie Fleder: Talk to other CEOs, talk to other people in startups and get as much of that as you can just don't don't waste theirs. There's so much ambiguity in a startup. And so much of your job will be an ambiguity where there are no answers and there is no roadmap. There's no playbook. There is no template. Um, so for the stuff that does have templates for the more traditional operational stuff, you utilize those templates that are out.

Michael Koenig: Great advice. So make sure there's a good fit with your CEO. You have to be the yin to their yang. And then also, don't recreate the wheel similar to great engineers. Great engineers will go and [00:26:00] find open source libraries and integrate those so they don't have to build them again or find managed services.

Michael Koenig: So there you have it. 

Allie Fleder: I'm actually, Mike, I'm going to add one last thing. I would say I found this to be true as a chief of staff, and I think this is very true as in the COO role too. I do think your ability, like however, large or small your company is whatever your managerial responsibilities are. I think your ability to truly understand your people in the company and what makes them tick and what motivates them is I think especially in a CEO role is everything because at the end of the day, you're in a startup, you need to make shit happen and you need to make it happen fast.

Allie Fleder: And, um, you can't know when it's going to do that alone. And so I think your ability as the COO to support the CEO and getting the team to work effectively together is everything. You know, communication and collaboration are always, are never going to be easy going. And so it's critical to really understand people and to know how to, um, like politically like network within your own company to make things happen [00:27:00] and get stuff done.

Allie Fleder: But you just, you, you need to know your. 

Michael Koenig: And that is different than playing politics. 

Allie Fleder: Yes. Yes, exactly. Exactly. 

Michael Koenig: Right. Well, Allie, thank you very much. Thanks for coming on the podcast. Uh, where can people go to learn more about SimplyWise and keep up with you? 

Allie Fleder: um, check us out or@simplywise.com or in the app store or the play store, and please always feel free to reach out to me on LinkedIn. I love to. 

Michael Koenig: Thanks for listening to between two COO's I'm your host, Michael Koenig, and a very special thank you to our guest, Allie Fleder, for joining us. Tune in next time for our next COO chat on Between Two COO’s, and be sure to subscribe on Apple Podcast, Spotify or wherever you listen to podcasts so you never miss an episode.

Just visit betweentwocoos.com for more. 

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