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Reena Jarwala
Let's imagine a small business owner who is looking for access to working capital. If they went to their bank, they'd have to give their tax returns, their paycheck stubs, maybe a sample of their blood in their firstborn kid's name. Right? Like it's a very long process. It can take months of cycling back and forth only to potentially get denied. Right. Because the banks just don't service this area here at Unbox. What happens is, is because we are embedded in the different ecosystems that small businesses do their work in. Maybe their accounting book embedded into the Intuit ecosystem. Right. We are getting all that access to data around that small business upfront. We're seeing their cash flows, their inflows, their outflows and everything like that. We are able to underwrite them and offer them that working capital. And it's very little friction, it's very fast. Our underwriting decisions are done within minutes and they're getting access to that capital as quickly as same day with our real time payments.
Cameron Herold
Welcome to the Second in Command podcast produced by the COO alliance and brought to you by its founder, Cameron Herold. In the second in command podcast, we talk to top COOs who share the insights, strategies and tactics that made them the chief behind the chief. And now here's your host, Cameron Herold.
All right, our guest today is a firecracker. She is the COO of Fundbox, an incredible financing company based in the US Expanding globally. Reena Jarawala is the COO of Fundbox. She oversees a broad portfolio including partner and customer operations, sales support, collections and revenue functions. She also serves as the manager of the company's Dallas office. She's a small business owner herself and she combines deep operational expertise with a strong sense of empathy and for Fundbox's customers. And you're also going to get a huge sense of that empathy she has for employees and delivering solutions that are both scalable and customer centric. She's currently finishing her MBA with a focus on coaching and leadership. It's going to be really interesting to see what she does with that. She's got over 20 years of experience in financial services and a proven track record of leading high impact initiatives that improve service quality, optimal internal processes and drive growth. You're going to gain some really great insights into how to scale as a leader, how to build a great organization and how to operate as a coo. This is one you'll want to watch and you can also share this episode with your friends. Share this with your leadership team and you can Watch all of our Second in Command podcasts on our YouTube channel. See you on the inside. Hey Reena, thanks very much for joining us on the Second in Command podcast.
Reena Jarwala
I'm so excited to be here. Cameron, huge fan of yours and looking forward to the conversation today.
Cameron Herold
Thank you very much. I appreciate it. I want to ask you something really briefly and it's one just because when we were talking before, kind of coming into the call, you mentioned you've got two kids, one middle school, one's in high school. It feels like women have certainly broken through the glass ceiling. They're in every C suite. Sheryl Sandberg was kind of the queen bee coo, you know, the one that we all have aspired to be. But women still tend to have that predominant role in the family of caring about the kids, caring for the kids, trying to have the balance. How have you been able to balance all that and build such a successful career for yourself too? How have you done that crazy dance of being everything?
Reena Jarwala
Oh my gosh, Cameron, I love that we're starting the conversation with this because at the end of the day, my family, my kids are my everything, right? And why I show up every day to do what I do. I the secret I think to my success is I have an amazing partner in crime and the two of us just figure out how to make it work. We complement each other in so many different ways. Where I'm the organized one, I'm the one who makes the schedule, the list, who needs to be where, who needs to do what, and then he helps execute on the other side, which just makes things so much easier. My husband is self employed, so I think it's allowed us to have that balance in our marriage, you know, going on 24 years. And really I think that he's allowed or he's able to really help take care of the kids when they need certain activities. Driving in places now my son's driving. So it makes life so much easier, but it also allows me to spend time on so many of the different things that I connect with my kids on. For example, summer, my son's out in in Baltimore doing a summer internship and I'm spending the summer here with him, which just a one on one summer with my son is incredible. The flexibility that I get with working while also balancing with an amazing partner, that's amazing.
Cameron Herold
So one of the things that's always driven me crazy in the last 10 years ish on social media has always been the young influencer who's like, here's how to have the perfect day, you go for a walk, you do your breath work, you do your grounding, I go to yoga, I have coffee. I'm like, you don't have any fucking kids Like Jesus. Like that. Of course that's a perfect day. But you throw two kids into that and then your dream boss, bitch, career thing, like, do you think having kids has made you a stronger executive? Do you think that that has the ability to. Can you speak to that?
Reena Jarwala
Hands down, my kids, I tell you, Cameron, my kids have taught me so much about life. I feel like God gave me my daughter, who is a carbon copy of me almost. I say that I look at her every day and I'm like, oh, these are the things I do want to do and these are the things we're not going to be doing in life. You know, my kids have really helped me stay grounded. They show me a different perspective, which really balances things out. I think it also allows me to have empathy, right? Like whether you're caring for elderly parents, you have children, you're taking care of a friend, whatever it might be. We all have people that mean something to us in our life. And. And for me, my kids have just given me that, that sense of purpose, and it helps me be relatable to others as I'm working with them, talking to them, navigating things through it.
Cameron Herold
Love. That makes sense. I want you to speak to the empathy part. It's something else that I've been thinking a lot about recently, and I think I've always intuitively known. It's like John Gray wrote the famous book Men are from Mars, Women are from Venus. Right. Men are not hairy versions of women. Right. We see the world differently, perceive the world differently. I feel like women show up in the business as much more empathetic, caring leaders. I think they just give a shit about their people more. And I think it serves them much better than the men do, who are just. I feel like we're always drive, drive, dive, not necessarily chewing our way over top of people, but we don't stop and take pause. Do you feel that there's some. Some truth to that at all?
Reena Jarwala
I think that it is. Women can be both. We can execute, we can deliver, we can see results. But I definitely think that, like, the way that I lead is generally with care and with purpose, like, meaning I want to get to know the team that I'm working with. I want to connect with them on a personal level and when I have a strong relationship with them, when I understand what motivates them, and drives them. For one person, it could be, you know, a rise in their career. For others, it's having the flexibility to work. Just knowing those things that motivate and take each individual has really helped me surround myself with amazing individuals around me. And that empathy is genuinely what I lead with. And I think that there are a lot of people in this world that have really high iq. They are geniuses when it comes to, like, you know, just the IQ side of things. But I think the EQ is where things are sometimes missing and you want to lead if you want to motivate, if you want to grow, if you want to march in a direction and you need a team of people to doing do that. I think that EQ is what's so critical to rally the masses and get them going in the direction you need them to go in.
Cameron Herold
Yeah, I think it's. It's that. That women can have that drive and that leadership skills and the empathy. Not a one or it's not a. Yeah, but. Right. Whereas I just don't think men do. I think we're. I think we've really missed that as I see my sister as a very driven, very successful, very focused entrepreneur. And she cares about all these people, which I think is almost her superpower. Yeah. And it's. I don't know, I just, I've been. Been really watching it carefully recently. I think there's something there that. I don't know, I'm just intrigued with it. So tell me about Funbox. You're the COO of a really great brand. I wanted to talk about the brand a little bit and then we're going to talk about where you're going and how you're building it.
Reena Jarwala
I'd love to. So thanks for the opportunity. So let me start by telling Fundbox is really the pioneer of embedded working capital for small businesses. What does that really mean? Small businesses are the heartbeat of the American fabric system of our country. And these small businesses need working capital. They need money to be able to start up, grow to, you know, to thrive in this environment. And so we at Fundbox are really offering fast, simple access to that capital, to that working capital. And really our mission is to embed into the ecosystems that these small businesses already do business in and become that partner that can integrate and provide access to working capital. We've been around since 2013. We've helped over 150,000 small business owners. We've unlocked over 6 billion in working capital since our inception, which is huge. Being a small business owner, I Know how critical it is to meet payroll and to be able to grow and to expand. And it's the working capital that FundBox offers to SMBs that has helped us as we've grown throughout our businesses. So we're really that embedded financial partner in the ecosystem where our small businesses live and work every single day and offer access to different working capital products.
Cameron Herold
Interesting. I'm not sure if my understanding of the space is going to transfer because I studied law in Canada, and in the banking law, would you be regulated as a bank in the United States? Do you operate as a bank or are you just in and around the fintech space, but operating as some other kind of a financial tech company?
Reena Jarwala
Awesome question. Awesome question. So we actually work with two bank partners here at Fundbox that we are able to originate our loans out of. We do have our own license in California and originate on our own, but we do partner with banks to be able to do our originations of our products and services.
Cameron Herold
So you'd be more like a mortgage broker versus like a bank that would underwrite the mortgages. If I'm to try to pick an industry of similarity.
Reena Jarwala
Yeah. So I would actually say that we're originating in the bank's name, but then we're buying that loan over and putting it against our. And that type of thing. Yeah. So we're really the one that's ultimately doing the underwriting, making the lending decision, distributing the money to the SMBs, collecting the money back from the SMBs and growing with them as they. As their SMBs, their businesses prosper.
Cameron Herold
Wow. Interesting. All right, so I came across a company in Canada about seven years ago called Clearco. Is that similar space to what you're in? And what I understood about clearco was they loaned, I think, expressly in Canada, but also mostly to technology companies that were, I think they were almost like capitalizing against revenue. It was almost like. What's the financing called?
Reena Jarwala
Like revenue based financing?
Cameron Herold
Yeah. Revenue based financing is what they were doing, right?
Reena Jarwala
Yeah, yeah. So very similar. Let's imagine a small business owner who is looking for access to working capital. If they went to their bank, they'd have to give their tax returns, their paycheck stubs, maybe a sample of their blood and their firstborn's kid's name. Right. Like, it's a very long process. It can take months of cycling back and forth only to potentially get denied. Right. Because the banks just don't service this area here at Unbox. What happens is, is because we are embedded in the different ecosystems that small businesses do their work in maybe their accounting books. Like we're embedded into the Intuit ecosystem. Right. We are getting all that access to data around that small business upfront. We're seeing their cash flows, their inflows, their outflows and everything like that. We are able to underwrite them and offer them that working capital. And it's very little friction, it's very fast. Our underwriting decisions are done within minutes and they're getting access to that capital as quickly as same day with our real time payments. So it's just fast, quick funding.
Cameron Herold
And is that because you know the space or you understand entrepreneurs or how are you able to know or is it just an arbitrage thing where you're spreading the risk out over so many investments that you just have an idea?
Reena Jarwala
You know, Cameron, it's really all of the above. We have been doing this, like I said, since 2013. We have built all these data sets on SMB so we understand how businesses run, we understand industry types, we understand lumpiness of cash flows. And so all of our models, all of our algorithms have been able to synthesize all this information. So when an SMB comes over and they're sending their data over to us, we're very easily able to underwrite them and provide that decision.
Cameron Herold
And are you, are you mostly underwriting small, medium sized tech companies? Are you underwriting small mom and pop restaurants in Virginia, like, you know, Wisconsin? What's the industries that you don't go after or is it just you're after all of it?
Reena Jarwala
We go after all of it as long as they're not a prohibited business that we're not allowed to lend into. We're able to service all industries and all verticals. And we are right now primarily in the US but we are expanding internationally. So we're taking our product abroad as well.
Cameron Herold
Interesting. I know that there'd been some funding options for companies. A lot of the people that were running courses and masterminds were doing it where they were able to put financing mechanisms in place for their customers to buy the product. Are you on that side of the business at all or are you predominantly on the loaning to the businesses themselves, not the customers for financing?
Reena Jarwala
Yeah. So we're not doing consumer lending per se. We're really doing the commercial lending to the small businesses. But there might be a small business that is selling from one small business to another small business. Right. Like maybe they're buying a small business is buying inventory from a bigger company and we're able to Provide financing or working capital to either side of that transaction.
Cameron Herold
Interesting. And you guys partner with some pretty big brands as well for your growth. What's the kind of the flywheel that you're focusing on now for growth? I know you're going through a rebrand. Can you talk about where you're focusing now for your growth? And then even what do you focus on that's got the flywheel going?
Reena Jarwala
Yeah, really the most critical thing that is helping our growth is finding those platform and those distribution partners that serve a multitude of SMBs and think in the, you know, 50,000 plus SMBs on their platform, where those platforms have access to data on that SMB, where they're, you know, if you're an accounting software firm, you see the cash flows, the ins, the outs, you're seeing all of that information. If you are a partner that offers, you know, home contracting services, we're seeing all the data on all the jobs that that SMB is receiving, how much they're getting paid for all of those. So any ecosystem or any platform that has access the different types of data that helps us really understand that small business is the platforms we're going after. And that's really created this flywheel for us. Right. Like this word of mouth has started. Oh, I got my funding, you know, from Fundbox. And they offer a multitude of products where that opens doors to another conversation. Some of our biggest partners are actually the ones that are like introducing us to that next big platform partner because of what they've received from us. I work with such a brilliant team of people that we can walk into the room, talk to a partner, understand their needs, hear what they need, propose solutions. It might not be our, you know, cookie cutter product, but we are able to hear what they need, synthesize and then deliver the right product for them, which has been critical.
Cameron Herold
I know your partners with things like QuickBooks and with FreshBooks. I've been client of FreshBooks and know the founder forever in a day. Another great Canadian company. When you're partnering with these companies, is there revenue share that you're putting in place with these businesses? Is it just, just partnering? Because if you keep everybody in the ecosystem growing and happy, they'll stay. What's the, why do the companies partner with you? What's, what's the upside for them?
Reena Jarwala
Absolutely. So you hit the nail right on the head. Yes, there's a rough share component. Every, you know, part, every SMB that takes access to working capital does definitely that that company benefits, you know, through a rough share agreement. But really what these partners that we have worked with have learned is that there's a lot of stickiness when you've got a customer using your product but also using working capital through your platform. And it's all integrated and seamlessly working together. It's retaining that SMB in your ecosystem. You know, we can do white labeled offering of our working capital so it actually can come across as if it's a product being issued by that platform which just keeps that that customer recognizes that brand recognizes that company recognizes how to interact with that platform. And behind the scenes we're providing that working capital.
Cameron Herold
Hey, it's Cameron. I hope you're loving today's episode. Quick question for you. Does your company have a strong leadership training program in place to grow the skills of everyone who manages people? If you want to help yourself and your company grow, get everyone who manages people learning from my invest in your leaders online training program. There are 12 core leadership skills that I cover online and they're all going to really grow. CEOs pay me $78,000 a year to coach them one on one and now you can all benefit for 1% of what they pay me. These are the same leadership skills that I created and certified everyone in at 1, 800 got junk when I was there as COO. Go to investinyourleaders.com today and use promo code podcast10 before the end of the month to get 10% off each manager you sign up. Now back to the show. Yeah, it's interesting. It's very similar to our COO alliance. I have a lot of member partners for the CO alliance and the members, these COOs from 17 countries that have joined Mastermind together. Love all the introductions I make to them and whether I make a percentage or not, they just like that. This community knows all the who's they don't have to. There's that trusted kind of information flow. I used to coach a company called Media Temple and they got 15% of their clients from WordPress because they partnered with WordPress back in the early days. When you're a hundred million dollar company getting 15% of your revenue from one source, there's a lot of gross margin that drops to the bottom line when you don't have to deal with the sales people and the marketing costs. Even though you're paying that affiliate fee or that percentage fee. Can you speak to some of the growth you're going through with the organization? I know you're also fund. How many rounds of funding has Fundbox had?
Reena Jarwala
Yeah, we've Completed our Series d back in 2021. So we've gone through four rounds of funding. We have some incredible investors who have really helped shape the company that we are today and our growth in the last couple of years. Let me kind of take a step back and tell you a little bit about how we got to where we are today. It's going to take you back to 20, because that's where this journey really started. I joined Fundbox in 2021, really came in to help lead our sales and operations team. In the middle of 2022, we started to really enter a very critical point of transformation here at Fundbox. Like many FinTechs, back in 2022, we were rapidly growing. I remember every week our key metrics would come out and it was like Blockbuster Week and couldn't have hit better numbers. And we're just on this RO rocket ship. Growth, right? That was really taking off. But what we found was that that year, like many fintechs, as we were growing so fast, it was starting to expose some of our pressure points in the business model. Right. We found that investors started to really shift that mentality from growth at all cost to really focusing on profitability and making sure that this company can be profitable and sustainable on its own. So during a very critical time in 2022, we had to really narrow in on our focus. We had to narrow in on our strategy. We started streamlining our operations. We got to extremely tight execution with that laser focus. With that vision in mind, we started to really double down on where we were going to spend our time and energy, which was really in this embedded platform partner space. I'm excited. Three years later, we have really turned this around. Right. We had our first profitable quarter back in Q3 of 24, which was huge for us. We have over 10 years of Runway now on our books just because of how well we're doing as a company. Right. We've got strong margins, and so this has really helped us as a company. Direct our time and our energy and invest in those partners that can really help us with that scale and that distribution.
Cameron Herold
So it's interesting, you guys have raised money. Your Series D raised money to $1.1 billion valuation. I just pulled you up on angel list to see if there's, you know, deals flowing where you can buy on secondary, which I'm sure there will be when a company starts returning to profitability and driving, which I'm so glad is more of the trend, that also messes up two things. It messes up the opportunity for the early stage investors to get an exit because there's no reason to bring follow on capital. There's no necessarily reason to go public. So has the strategy for growth started to change or is it just build a better company and then at some point, if and when we want to go public, we will. I don't know if you can speak to that. And then secondly, internally it has to create a bit of a cultural shift, probably in a good way where build it, build at all cost and build or bust is this really crazy frenetic stage, but it doesn't necessarily build a better company. So can you speak to what it was like to get everybody in the organization to now start to care about okrs that we'd never talked about before? It almost feels like we're a meat eating family till we're vegan. It's like, wait, what?
Reena Jarwala
Well, I am a proud vegetarian, so that makes me happy that. So let me tell you, 2022 was tough for the team, right? Because we here at Funbox. Look, I've worked in Corporate America over 20 years and I have never worked for a company like Fundbox. And I truly feel like we are family. I am surrounded by the most brilliant people and I come in every day and it is all about how do we solve this mission of unlocking working capital. And I mean I don't worry about like backbiting or any like no drama like that stuff just doesn't happen here. It's like we literally all come in, roll up our sleeves, CEO all the way to our frontline team, rolling up our sleeves to really solve this mission every single day. And so in 2022, when we went through this inflection point and really had to streamline our team, that was hard on everybody, right? Because it's like you're breaking up with a family. And we had to rebuild trust with the organization where because we had been flying for so long and everything was going so good, all of a sudden to have this seismic shift in our organization was, I mean it created a lot of like tension and fear and anx anxiety. All the normal things that anyone would experience if they're going through such big change. Cameron, what we did as a leadership team, and I've actually shared this with a couple of other executives that I, that I've talked to in other industries who have asked for guidance and help is we as a leadership team, the exec team came up with what I would call some really cre key critical milestones and OKRs that we said are the only way we can turn this company around. Our originations number needs to be here, our delinquency number needs to be here. We want this much cash in the bank, very crisp, clear key metrics and we shared that with the entire company and we said company, these are the things we're looking at and we are transparently going to share these with you every single month in our all hands meeting. We're going to tell you where are we and where are we heading and then you can make the decision on your own. Is this the ride the way that you want to ride or is this, this one that you don't want to be on? You make the choice. I don't want to give you a whole bunch of hot air. I don't want to tell you something you don't want to hear. I want you to be in control of this. And I really think that's how we've been able to keep the culture and through this entire transformation. I've sat in organizations where I watch attrition numbers and I have a, I have a key performance metric. Keep attrition under this number. I don't even look at attrition attrition here because it just doesn't happen. Very few opportunities, people have moved on and I love them for that because it's growth in their career. But for the most part we're in it every single day creating this culture, creating this company because we all believe and know what it can bring to the world.
Cameron Herold
Yeah, I completely, a thousand percent agree. I, one of my, well, probably my best selling book of all time is called Vivid Vision and it's, it's writing down a four or five page description of what your company looks like, acts like and feels like in the future. And I like writing in a very polarizing way to push half the world away from it. I don't want everybody to want to work with me. I don't want everybody to be a customer. But the ones that do, I want them to be zealots. I want them to be vibrating in their seats. I want them to see the twinkle in their eyes because they're so excited about what we're building. And yeah, you don't want to find out six months in a year and that oh, this isn't really the right company. You should have known that before you applied. You guys really get. And that is where that cultural iconic, almost cult like vibe happens is when people are all joining for the right reason and they're all completely excited about where they're building. What were the tough parts around going to profitability, what were the real tough parts and what lessons did you learn from it?
Reena Jarwala
So many. How much time do we have? Let me focus in on a couple. I think in my role as a coo, one of my hardest points has been really managing the emotional load and of the leadership team. Right. So what I mean by that is I am always. How am I showing up to meetings, how am I responding, how am I conveying a message to the team? I have had to learn how to stay calm, how to stay steady, how not to be emotionally charged through all of these highs and lows and really convey a message of transparency and being authentic to the my team while also navigating this ride that we've been on. As I think about our transformation, really, there's been two areas that I'll focus in on. The first is that I see my role as that orchestrator behind the scenes. I had once had a boss tell me, you're Reena. You're like the puppet master who's just helping everybody bring things, make things happen and make things, you know, come together. And that's really what I think has really helped me stay grounded. As we've gone through this, as we've gone through this transformation is really serving in that space. I also think that, like, when your question was actually around, what was the hardest part? The hardest part?
Cameron Herold
Yeah, what were the hard parts and what did you learn from the hard part?
Reena Jarwala
I'd say what the probably the hardest part for me is the context switching. That happens to me all day long. I can start my day talking about capital for international expansion, then the next hour talking about, you know, how are we going to negotiate a rev share for our partner. The next hour is going to be about what product are we bringing to market and what is the feature that's missing. And like constantly being able to navigate the 10, the 15, the 20 different threads that are going at any given time. That is probably, I would say, the hardest part that I have that I experience.
Cameron Herold
I think COOs are almost like a working Wikipedia where we just. We do some work, we click on the link, we do some work, we click on a link, we do some work. But all those tabs stay open too, until they're completed and done. The ability to multitask and stay on top of projects and stuff is huge. Over your career, you know, you've had to evolve, right? When you were 10 years old, you were Reno. When you were 20, you werena 30 arena, you know, now you're still Reno.
Reena Jarwala
Mid 40 year old Rita.
Cameron Herold
There you go. So you're still, you're still growing as a leader, but you're still the same person. I'm curious what you have really worked on over the years to get into this role of a coo. What are some of those core skills that you've worked on?
Reena Jarwala
By far the biggest thing is execution. I think that so many individuals are really good at talking and strategizing and pontificating. But the folks who actually turn it into execution and get the job done right are the ones that doors will open up for. I, throughout my career have not shied away from the hardest of hardest problems. My favorite Cameron, I kid you not, is to walk in because I'm an operator. My favorite is to walk into an organization with a bleeding red scorecard. Give me an entire red scorecard because that is the place where I can start to make changes. We can start to collaborate as a team, figure out what's broken, fix processes and when that red turns to green, it just like it gives me chills right now. Those are the moments when you know that you're making the biggest impact and the biggest difference. And I think that has been critical for my, my career is not shying away from the hard things. Look, I'm not going to get it right, but what I'll tell you is that how much worse can it get if it's a bleeding red score? Correct card.
Cameron Herold
I love that. I love walking into companies that have a really good proof of concept but they don't know how to grow it. They don't know where to go. I'm like, I got it. Just show me the vision. I got it. Here's what we need to do. I can kind of give them the plan and the people and the skills and go and then, then get the heck out of their way. So what are you working on now as a leader? Do you have a skill or an area or a blind spot or a shadow that you're working on currently? Because at the end of the day it's like Ray Kroc from McDonald's said, when we're green, we're growing, when we're ripe, we're rotting. Right. I imagine you're working on something. Something.
Reena Jarwala
Yeah. So two years ago I took a vacation and it was the first time I was away for like 10 days from the office, completely unplugged. And it gave me a lot of time to really think from this company or forever from this company that like I had taken the 10 day period away and I was now we were, we were on water and it was just, it was great, right? And so I had a lot of time to think and something, Cameron, that had been on my list for a very long time that I wanted to do was go back and get my master's. And in particular I really wanted to focus on the executive coaching side of things. And that's because I've been in the boardroom, I've been in the C suite. I understand how it operates and how it works. And going back to what I told you earlier, I think there are a lot of brilliant leaders and executives around there that have the iq. But that EQ is where there's an opportunity to really make a difference. Difference. So I came back and I decided to submit my application and I enrolled in my master's program.
Cameron Herold
Amazing.
Reena Jarwala
And this August, I am two months shy of graduating with my Ms. In Leadership and Organizational Development with an emphasis in executive coaching. So.
Cameron Herold
Amazing.
Reena Jarwala
In addition to working, I do go to school at night, write papers, take tests, do the whole nine yards. And really that is like learning every single day is so important to me. Finding ways to grow, finding ways to learn from others, whether it's listening to a podcast, reading an article, meeting someone new. How can I take information, synthesize it and adapt it and grow from it? That's just part of who I am in my DNA.
Cameron Herold
I love it. I love the self driven learner. I just dropped into the chat a link to an online training that I wrote and launched three years ago show. It's called Invest in your leaders. I'm going to give you free access to it. Normally I charge everybody. I mean we have hundreds of thousands of people going through the course, but I'm going to give you access to it for free. There's six modules of the 12 that are tied to coaching. So there's one, there's one on situational leadership that I've done some adaptation for the entrepreneurial world. One on coaching, there's one on one on one coaching, one on delegation, one on managing conflict, and one on time management, all of which are kind of linked in the that one in classroom teaching. So there's seven of the 12 modules are related to coaching. I would love to get your feedback on what I put together in there vis a vis what you're seeing from the kind of executive side of things. Because yeah, coaching is a skill that most leaders sadly have had no training in. You know, you think about most managers and leaders have no idea how to adapt their leadership style, let alone like You've, you've bumped into, I'm sure, a lot of situational leadership stuff.
Reena Jarwala
Right? Right. Daily.
Cameron Herold
Most manage well and like the skill by Dr. Paul Hersey and Paul Blanchard or Ken Blanchard who wrote the One Minute Manager, like these are really, really deep skills that some of the best companies on the, on the planet train on at Starbucks. They train the management team on situational leadership alone every quarter and then yet most mid sized companies have managers out there that have never been trained on how to run a one on one. And they run them every week. Right. Or they're coaching people all the time, they don't know how to coach. Like, like it's, it's a really scary thing to me that, you know, let alone if you have the EQ or the iq, most people just don't even know how to be a leader.
Reena Jarwala
That's so true. And I think that if I look back on my career, I think one of the things that I feel so blessed by is the leaders that I've been surrounded by who have like shown me the way and given me opportunities, believed in me when I didn't believe in myself. Cameron, I think that who you work for and the leaders that help shape you can be the most critical thing in your success as an individual. Right. And so I think that it is so important that leaders get the right training to then be able to train their teams and help them be successful to create the world class organizations that have a thriving culture that are growing, that are, you know, strategically thinking about what's next. But it starts with that really sound leadership and getting that ground, that solid foundation.
Cameron Herold
Well, and maybe, maybe this is some of the golden thread that, you know, we started with talking about women in leadership roles and you even being a mom. And the golden thread that I've just kind of realized is my gut is that most women are better at coaching and developing people because they've been coaching and developing their kids, especially the women's that are moms. I'm not talking about like the gen Y doing yoga with my hippie oatmeal froth. You don't know shit yet. You're still a teenager like the rest of us trapped in adult bodies. But I think women that have kids have understood how to grow people and praise people and care about them and give them feedback and micromanage when you need to. But then, you know, like we micromanage our kid when they're two at teaching them how to pour orange juice and then when they like you're not praising your Kid in Baltimore on how great he did pouring orange juice, he'd be like, mom, you've lost your mind. Right. But that's. That's situational leadership. That's the ability to adapt styles. And I just don't think guys are good at it.
Reena Jarwala
So, so, so I have a. I have a funny story I'll tell you really quickly. I think it. It's relatable. So two parts. I'll tell you that when I took this coaching program, Cameron, it definitely, definitely made me realize that coaching is not what I thought coaching was. I thought coaching was. Somebody comes to me, here's a situation, help me and tell me what to do. But that I learned through this entire coaching.
Cameron Herold
Mentoring.
Reena Jarwala
That's mentoring. And if I were to tell them what to do, that's my ego speaking out and saying, here's what you need to do. Because I've treaded the path.
Cameron Herold
Coaching is the Socratic method.
Reena Jarwala
Yeah. And it's about asking the hows and the what's and really getting curious about the situation and allowing the person on the other side to do that deep reflection to figure out how they're going to solve, because they're very capable. At the end of the day, I sit out in the open at home here, anywhere. I don't put on AirPods. My family's going in and out of the house, and they hear me every call I take, every coaching session, and I do, even my night classes. I do it all through my speaker or whatever. And so there have been times where I'll start talking to my daughter and I'll try to get curious about a situation. And she's like, are you coaching me right now? And so, you know, I think it is. It has made me. This program has made me a better mother, a better leader, a better partner, because it's opened my eyes to a different way of doing things. It's not about telling people what to do, but it is about getting curious and getting, you know, like just innately in the other person's shoes to be able to get to where we want to get to.
Cameron Herold
I love that. Yeah, it really is huge. Years ago, we had Simon Sinek on our board of advisors four years before he wrote the book Start with why? And we're having lunch one day, and we were talking about leadership. And he said that when somebody comes into your door and says, you know, do you have a. Have a minute? He used to say, no, I have a minute tomorrow in my half hour. You know, open office hours come back. The then and the person would come back in that half hour period and they'd say like, can I just ask you how to do this? And he'd say, well, what do you think we should do? And they'd be like, I don't know. Well then go away and think about it and come back and tell me what you think. And then they'd come back and they'd tell him what he'd think and he'd say, then go do that. Like he literally just didn't give them the answers. I'm like, it's almost you get to become the lazy executive by forcing them to do their own thinking. And then if they're really hitting the roadblocks, then you can transition from coaching to mentor 100%.
Reena Jarwala
100% and think of how empowering that is for the individual. When they finally figure it out on their own the next time around, they'll try to use those skills to figure out the next obstacle because they start to trust themselves. So often it's the trust within that they don't have and why they want to lean on somebody else to ask for that help. But when they have that confidence, when they feel safe, when they feel like they can try something that is maybe controversial or different than what has always been done, it starts to build their stock. And I believe in me and I can do this more. Their confidence more than anything.
Cameron Herold
Well, yeah. I mean, at the end of the day, our job as leaders is to grow people.
Reena Jarwala
Yes.
Cameron Herold
And it's to grow their skills, their confidence and their connections. Our job is to. And if we can grow their skills, confidence and connections, then we can delegate more to them. Like our. Anyway, we get it. So I want you to go back to the 21 year old Reena and give yourself some advice. What advice would you give the younger you that you know to be true today?
Reena Jarwala
Everything's going to work out and be just fine.
Cameron Herold
Like definitely, definitely marry the guy like you're.
Reena Jarwala
Marry the right one, Marry the right guy. Everything's going to work out. It's okay if you make mistakes. I really think that my entire 20s and 30s was led by fear because it was fear of failure. I had such a big fear of failure that I was going to make a wrong mistake, that I was going to fail and that I was going to fall and stumble and never get a job chance again. That that drove me. I'm now in my mid-40s and I'm at a place where I lead with so much more confidence because I'm like, it's going to be okay. We're it's going to work itself out and in time it may not be when I want it to happen, but in time things the puzzle pieces will fall where they're going to fall. Opportunities will open when they're meant to open. Doors will close when they're supposed to close. And just like kind of really being able to embrace that process has been huge for me. Huge for me.
Cameron Herold
Love it. Reena Jarwala, the COO for Funbox thanks very much for sharing with us on the Second in Command podcast.
Reena Jarwala
Thank you. It was such a pleasure and that went by so fast.
Cameron Herold
That was great. Really appreciate it.
You've been listening to Second in Command, brought to you by COO Alliance Foundation, Cameron Herald. If you enjoyed this episode, please be sure to like, share and subscribe to us on Apple Podcasts, Spotify and our other podcast streaming platforms. For more best practices from industry leading COOs, visit COOAlliance.com.
Second in Command: The Chief Behind the Chief with Cameron Herold
Episode 494: Rina Jariwala - Bold Moves and Personal Evolution in the World of Fintech
Release Date: July 22, 2025
In Episode 494 of the “Second in Command” podcast, host Cameron Herold engages in an insightful conversation with Reena Jarwala, the Chief Operating Officer (COO) of Fundbox. Reena brings over two decades of experience in financial services, coupled with a profound sense of empathy for both customers and employees. This episode delves into her journey, leadership philosophies, and the transformative strategies she employs to steer Fundbox toward sustained growth and profitability.
[02:50] Reena Jarwala:
Reena begins by addressing the often-discussed challenge of balancing a demanding career with family responsibilities. She emphasizes the importance of having a supportive partner, stating:
"The secret I think to my success is I have an amazing partner in crime and the two of us just figure out how to make it work."
Reena highlights the complementary dynamics between her and her husband, which have been instrumental in managing both personal and professional spheres. This partnership allows her the flexibility to dedicate quality time to her children while effectively leading her team at Fundbox.
Cameron probes deeper into how motherhood has influenced Reena's executive capabilities. Reena passionately explains:
[05:22] Reena Jarwala:
"My kids have taught me so much about life. They show me a different perspective, which really balances things out."
She underscores the role of empathy in her leadership style, conveying that understanding and connecting with her team on a personal level fosters a motivated and cohesive workforce. Reena believes that Emotional Intelligence (EQ) is crucial for rallying teams and driving organizational success.
Reena provides a comprehensive overview of Fundbox, articulating its mission to simplify access to working capital for small businesses. She explains:
[08:51] Reena Jarwala:
"Fundbox is really the pioneer of embedded working capital for small businesses... We've unlocked over $6 billion in working capital since our inception."
Fundbox integrates seamlessly into the ecosystems where small businesses operate, leveraging data from platforms like Intuit to offer swift and frictionless financing solutions. This embedded approach allows Fundbox to underwrite loans quickly, often within minutes, providing same-day access to capital through real-time payments.
Cameron seeks clarity on Fundbox's operational structure, particularly regarding its banking status. Reena clarifies:
[10:17] Reena Jarwala:
"We actually work with two bank partners here at Fundbox... we are the ones doing the underwriting, making the lending decisions, distributing the money to the SMBs."
Fundbox operates in conjunction with banking partners, originating loans under their names while handling the underwriting and repayment processes independently. This hybrid model enables Fundbox to provide efficient financing without functioning as a traditional bank.
A significant portion of the discussion revolves around Fundbox's growth strategies. Reena attributes their success to strategic partnerships with platforms that serve large swaths of small businesses. She states:
[15:14] Reena Jarwala:
"Finding those platform and distribution partners that serve a multitude of SMBs... has created this flywheel for us."
By collaborating with established platforms like QuickBooks and FreshBooks, Fundbox leverages existing customer bases and data insights to offer tailored financing products. These partnerships not only enhance Fundbox's reach but also ensure customer retention through integrated financial solutions.
Reena shares the challenges Fundbox faced in 2022 when rapid growth began exposing vulnerabilities in their business model. She reflects on the strategic shift toward profitability:
[19:53] Reena Jarwala:
"We had to narrow in on our focus... by Q3 of 2024, we had our first profitable quarter."
This pivot involved streamlining operations, enhancing execution precision, and concentrating efforts on high-impact partnerships. Reena credits the leadership team's transparency and clear communication of key metrics (OKRs) as pivotal in maintaining organizational morale and focus during this transformative period.
Maintaining a positive and resilient company culture amidst significant changes was another focal point. Reena discusses the importance of transparent communication and fostering a sense of ownership among employees:
[26:23] Reena Jarwala:
"We shared our key metrics with the entire company and said... you can make the choice to stay or leave."
This approach ensured that the team remained aligned with Fundbox's mission and empowered individuals to take control of their roles within the organization. Reena emphasizes the familial atmosphere at Fundbox, where collaboration and mutual respect are paramount.
The conversation shifts to leadership development, where Reena elaborates on her pursuit of an MBA with a focus on coaching and leadership:
[32:41] Reena Jarwala:
"This program has made me a better mother, a better leader, a better partner, because it's opened my eyes to a different way of doing things."
Reena distinguishes between mentoring and coaching, advocating for the Socratic method of leadership that encourages self-reflection and independent problem-solving among team members. This philosophy aligns with Fundbox's emphasis on empowering employees to develop confidence and trust in their capabilities.
Reflecting on personal growth, Reena shares the advice she would offer her younger self:
[40:01] Reena Jarwala:
"Everything's going to work out and be just fine. Marry the right guy."
This perspective highlights her journey from a fear-driven approach to leadership to a more confident and trust-based methodology. Reena's commitment to continuous learning and personal development remains a cornerstone of her leadership style.
Reena Jarwala on Empathy:
"EQ is what's so critical to rally the masses and get them going in the direction you need them to go in."
[08:13]
On Fundbox's Mission:
"We are really that embedded financial partner in the ecosystem where our small businesses live and work every single day."
[08:51]
Leadership Through Transformation:
"We are transparently going to share these [key metrics] with you every single month in our all hands meeting... you can make the choice."
[28:37]
On Coaching vs. Mentoring:
"Coaching is the Socratic method... it's about asking the hows and the what's."
[37:14]
Personal Advice to Younger Self:
"Everything's going to work out and be just fine."
[40:01]
Reena Jarwala's episode on the “Second in Command” podcast offers a compelling glimpse into the intricacies of leading a fintech company through periods of rapid growth and transformation. Her emphasis on empathy, strategic partnerships, and transparent leadership provides valuable lessons for current and aspiring COOs. Reena's journey underscores the importance of balancing personal life with professional responsibilities, fostering a positive company culture, and continuously evolving as a leader. Listeners gain profound insights into the operational strategies that drive Fundbox's success and the personal philosophies that sustain Reena's impactful leadership.