What It's Like To Innovate At The Intersection Of Startups And Corporate Bureaucracy With Kara Kaplan

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Table Of Contents

In this episode, Mike Gardon chats with Kara Kaplan. Kara is currently the CEO of Moonrise. Prior to Moonrise, Kara spent her early career working in finance at Mesirow Financial and at Angel Street Capital (a boutique private equity and Investment Banking Firm). She then helped to spearhead the Business Development efforts at ShopTalk, a $30M venture-backed start-up delivering a direct marketing voice portal with 500,000 users. She also co-founded Giftbar, the largest high-end, semi-closed loop digital gift card marketplace representing thousands of SMB’s in 27 markets across the country until it was acquired in 2016. Kara resides in Chicago with her husband and three children.


  • Kara’s background
  • Moonrise - what they do, how it was started, and how it has evolved
  • Kara’s non-linear career path
  • Kara’s origins as an entrepreneur
  • How Moonrise pivoted during COVID
  • How Moonrise screens workers to maintain quality control
  • What it takes to cultivate a great team
  • What it was like starting a company while having a family


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Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

Michael Gardon (00:00):

Hello everyone. And welcome back to another episode of career cloud radio. I'm your host Michael Gardon. I'm on a mission to help job seekers build thriving careers they're choosing. And to do that, I try to have interesting conversations with people that approach careers a bit differently. In today's episode, we go behind the scenes with serial mom preneur and my friend, Kara Kaplan. Kara is a CEO of Moonrise, an employment platform with a mission. Their mission is to help everyday hardworking Americans make ends meet by giving them access to flexible on demand shift work. Moonrise is also near and dear to my heart as I was the team lead that helped bring Moonrise concept to life. And Kara was the perfect fit to build Moonrise and carry it into the future. Moonrise is also interesting in that it was developed using human centered design techniques and as a startup inside a stodgy fortune 300 insurance company, I talked to Kara about her origins as an entrepreneur. What it's like to start a company while having a family and how to get hired at a tech startup. If you're wondering what it's like to innovate at the intersection of startups and corporate bureaucracy, you won't want to miss this conversation with my friend, Kara Kaplan, Kara, welcome to the show. Great to see you again.

Kara Kaplan

Great to see you, Mike.

Michael Gardon:

I love a backstory. And so I ask every guest on my podcast what their first job was.

Kara Kaplan (01:18):

Yeah. Okay. Yeah. Well, it's good because we actually, I think had that at one point up on our website at Moonrise with what we'll get into, but my first real job was selling shoes in a shoe store in the local mall. And I learned two things in that job. One was that I didn't really like working retail and I really hated touching people's speed. Not for me. So yes, but my first true experience working was initiative.

Michael Gardon (01:50):

That sounds like a great fit for you then. How old were you?

Kara Kaplan:

I believe I was 16.

Michael Gardon:

Okay. Very cool. You kind of talked about what you didn't like. Did you learn anything from that experience though, that sort of influenced your later choices on the positive side?

Kara Kaplan (02:10):

Hey, you know, it was my first experience with obviously earning my own, you know, real money. I like babysat and did odd things, you know, prior to that, but earning like a true paycheck, you know, with taxes coming out and all that, I realized how hard it was to make money. Right. And how many hours I would go in and spend in that shoe store and come out with money that I wanted, whatever I wanted to buy at the time, whatever trendy item that my parents wouldn't buy me that I had by myself. And it was a members only jackets now I'm really dating myself. But yeah, I think I really realized how hard, you know, all of these individuals I interacted with in retail stores prior much older than I was. Right. I realized how hard they were working to earn money. Definitely opened my eyes to that for sure.

Michael Gardon (02:49):

So you and I are talking because we know each other from a few years back and we're going to talk about your company, the company that you run now called Moonrise. But before we really talk about that, I mean, one of the things that I really liked about you and we were working together was you were an entrepreneur before we ever really discussed Moonrise. Can you give our listeners kind of an idea of your career track? So you got out of retail and you got out of the shoe business, where did you kind of go and what were the different things that you've done so far in your career?

Kara Kaplan (03:24):

Yeah, absolutely. I'd say I definitely had more of a circuitous path to becoming an entrepreneur for sure. Obviously that was my retail stint. Then that's really where it ended. After college, I moved to Los Angeles and I worked in public relations. It was my first job. I love that job because I think it really sort of brought me out of my shell. Right. Obviously in PR you have to be really outgoing. You have to know how to communicate really well. And it was entertainment PR. So there was a lot of high profile individuals that I was dealing with. So it just kind of got me to get over my fear factor really quickly. You know, something that I say this day is if you want to be an entrepreneur, you have to get comfortable being uncomfortable. And that first job definitely did it for me.

Kara Kaplan (04:03):

From there. I'd say things just kind of started to take a turn. I realized pretty early on that being in LA wasn't the place for me to be the entertainment industry. Wasn't somewhere I wanted to spend the rest of my life. So that's when I moved to Chicago and my really got into finance, but I know it was a complete shift from BR, but I'm guided to finance and venture capital. That was sort of my first introduction to the startup world, right. Was looking at various investments, startup companies. And that just intrigued me, right. I always admire these people that were coming up with these ideas and writing business plans. And so I started coming up with various ideas. I wrote business plans. I even presented them to some people in various industries just to sort of get their take on my idea. And oftentimes it was like, this is great, but you know, you kept hearing that a lot, but I sort of stayed in the finance world for a while and then ultimately went to go work for one of the startups that we had invested in.

Kara Kaplan (04:54):

So, uh, jumped into business development at a venture backed company. It was, uh, Maveron back about $30 million called shop talk. That was my first experience with like a big startup back then. It was sort of the internet bubble hadn't kind of really happened yet. So here in Chicago was just all the talk. We had this crazy launch party. I still have my towel that I got from that. It was exciting. It was really fun, tons of young energy and young minds. And it was great. And then my career took another turn. My husband then fiance at the time, got transferred to San Francisco for his job. And so I had to go and obviously San Francisco was sort of, uh, the startup world going on. And so dabbled in various, you know, finance type related startups there, but always knew we wanted to come back to Chicago where our family was, but then had another run, throw into it.

Kara Kaplan (05:40):

And that I got pregnant with my first child. And, you know, at that point I was obviously elated to become a mom. And so I really thought that's really where my career path would end. You know, I was like, okay, I'm just going to be a mom. And I was okay with that. But then quickly realized that that entrepreneurial bug was just in me and it was something I couldn't really shake. And so while I was pregnant with my first child, I came up with an idea for, it was called the little pink book. It was essentially for familiar with the blue entertainment book that's been around forever. It was sort of a take on that, but it was for more local sort of women led businesses. It was called the little pink book and I went door to door and I got stores to sign up and offer a coupon in this actual book.

Kara Kaplan (06:19):

And it was little and pink and cute. And I wish I had one here to show you. Um, and I still have them and I sold them like in the stores, I sold them through charities, different partners. And you know, it certainly wasn't a huge moneymaker, but I learned a ton. I mean, I remember learning about printing, you know, the first run of books that got printed, the binding was upside down and the, the name of the book was upside down and it was sort of this freak out moment, like, oh my God, what am I going to do? You know? And finally I negotiated with the printer to reprint the book, a lot of lessons, but what I really formed were relationships, right? So I formed a ton of relationships with these local merchants in my area. So fast forward and had another kid.

Kara Kaplan (06:56):

And then another kid that's where it stopped three kids I'm done. When I was pregnant with my third, I tried to buy a gift card to a local store in the suburbs for a friend's birthday. I was in charge of getting the gift. And at the time they didn't have an online website to buy a gift card. And the only way I could do it was either fax in my credit card and this whole form that I fill out quite a physically drive out to the suburb, which is about 45 minutes away and buy the gift card. And it was just one of those aha moments for me, where I knew I could easily walk into any grocery store and buy a gift card for, you know, a big box retailer, but I couldn't get one to this local merchant. So it was sort of that aha moment.

Kara Kaplan (07:30):

If I have these relationships with these local merchants, I sort of understood technology and intersection there. And I thought, you know, could I convince these local merchants now instead of offering coupons, would they want to sell digital gift cards? So I started going door to door and asking them and seeing the answers. I mean, I literally built a fake website that I showed on an iPad. It was the first iPad ever. I believe I did them in stores and kind of showed them what it looked like. And it was started when I was doubting. Yes, I'm interested in this. So I quickly found a developer. I never laid eyes on him. I think he worked in some dark room in Boston and he built me my first website. And I signed up a handful of merchants here in the Chicago land area. And I remember when the website went live and I was waiting to see like a, someone going to buy a gift card.

Kara Kaplan (08:13):

And the first gift card that we sold on the website was $200. And I thought, oh my God, this is fraudulent. You know, like it's too high. It turns out it was a real gift card. And from there it just evolved fast forward. I ended up raising three rounds of capital for that business. We scaled in its 27 markets. We had thousands of independent retailers on the site and we were sort of the high-end websites for high-end luxury gift cards. You know, the average amount loaded on our gift cards was double that of typical big box gift cards. We were able to get between 15 and 20% of the revenue share with the stores and ultimately ended up selling that business. So it was just, I think, you know, there are a lot of lessons along the way, a lot of tears, a lot of learnings, a lot of struggles, as you can imagine, growing a business and scaling it, but I don't regret any of it.

Kara Kaplan (08:59):

It was one of the best experiences of my life. And it's ultimately what led me to my current role, which is how you and I met, which was Moonrise, which was really resonated with me about Moonrise was that Moonrise is a two-sided marketplace. And my last company gift bar was also two-sided marketplace. Right? I had consumers on one side and the individual stores on the other and Moonrise was very much the same thing and that we were going to have workers on one side and employers on the other. So I inherently understood sort of the challenges with building up a two-sided marketplace and what that entailed. And so when I learned about moving rise, it was just this sort of moment of here as I could take sort of what I've learned and apply it to a new model. And on top of that, Moonrise had a mission, right? It was very mission driven as you know, which was really about helping financially challenged individuals gain access more easily to supplemental income. And so that mission really resonated with me being raised by a single mom. So, you know, and, and I'm still has been raised today. So clearly it's been not your typical path to get here, but I've loved every part of it. And I wouldn’t change any of it.

Michael Gardon (10:01):

That's why when we were working together, I was drawn to you and your leadership of Moonrise because I have the same, same type of deal, very winding path, not linear, feel odd in certain conversations. Sometimes when you get that question of like, oh, what do you do? Or what have you done? You know, it's very difficult. So I love it. Can we take a step back and can for our listeners that aren't have never heard of Moonrise? Can you maybe talk, what is Moonrise, where did it start? What were kind of the origins of that and what is the mission?

Kara Kaplan (10:36):

Yes. So Moonrise has very unique origins, as you know, so ER actually owned by American family insurance and it's not always readily apparent why a large insurance company would own a staffing platform, but it actually is very much by design. So American family insurance, obviously large fortune 300 insurance company, many of are wholly owned subsidiaries as part of their enterprise. And one of those companies is, uh, another company called the general, which your listeners may be familiar with the general sort of non-standard auto insurance. I'm an American family. They had acquired the general number of years back and they started noticing some interesting behaviors work, particularly with policy holders of the general, the general is non-standard auto insurance. So the thought is these are individuals that are sort of less on top of their finances, most likely lower credit scores, things like that. But these policy holders were phoning into their call center on a weekly, if not daily basis kind of saying, Hey, I know my premium is due.

Kara Kaplan (11:28):

I'm going to be, you know, $25 short, can I pay that next Tuesday? And this was interesting tampon because, because of the thought that these were sort of individuals that are less on top of their finances, their behavior was showing the exact opposite. Hey, like I'm really on top of my finances, Sierra, I don't want to be late. You know, how can you work with me? So they thought let's kind of dig into this a little bit more. The general as a company had really strong brand loyalty, strong brand recognition thought, are there other services that we could potentially come up with to offer these individuals that would help them? So they ended up sort of leaning into that and spending the better part of a year sort of researching that exact problem. So they flew around the country, they met with dozens of policy holders in their homes or the asking them leading questions, like kind of what keeps you up at night.

Kara Kaplan (12:12):

What do you know, what are some of the challenges that you face? And they were just fascinating conversations. So they really learned some interesting things, mostly that these individuals, for the most part, all had full-time employment, but yet they were still struggling to make ends meet. So when they looked to them and said, well, you know, have you looked for another job or do you have a second job? You know, it wasn't easy for them. Right? A lot of them didn't have time to find a second job. A lot of them, if they had a second job, it was, you know, oftentimes a bad experience. Right. So they would go and work for it, Florida that wasn't that reputable and they wouldn't get paid. So just a lot of challenges there. So Anthem thought, could we come up with, with a platform that could help them?

Kara Kaplan (12:47):

So they kind of went and came up with a whole bunch of different ideas. You know, one idea originally was something called the weekend or so the thought was, could they offer them different types of jobs just on the weekend, but when they took that idea back to them, they were like, well, that's great, but I actually work a second job on the weekends. That's not going to work. Right. So kind of going back to the conversations again and iterating on that idea. And ultimately they landed on this concept for Moonrise, which was really offering these individuals a platform where they could be in control, right. It really gave them the flexibility to pick up shifts for reputable employers when it was convenient for them. So they could pick up one shift a week, they could pick up 10 shifts a month, whatever they needed to earn that extra, whether it was $50, $400, whatever it was.

Kara Kaplan (13:26):

So they piloted this idea in Madison, Wisconsin, which is where I'm going to headquarter for a couple of weeks. It was supposed to be longer, but due to insurance reasons, as you know, Mike, it couldn't, but it was very successful. And that these individuals were able to earn on average over a hundred dollars during that time. And employers are really happy with having access to trainable, reputable individuals to pick up these shifts. So after that pilot and fem said, this is really something that we want to get behind. And so they decided to launch Moonrise as a full fledged know wholly-owned subsidiary.

Michael Gardon (13:57):

Yeah. It's an amazing story. I was lucky to be part of it. Uh, there are a couple of things like I just want to add to that for our listeners. I mean, I think what's really interesting is the whole process that we went through is we use a process really called design thinking to have our potential customers lead us to the solution. And that was super cool from my standpoint. So if people are wondering about design thinking or wondering about innovating in a, in a large company, right? I mean there are teams at certain companies and they're trying to figure out how we can do things differently. And I think Ann, Pam was a great example of that, the venture capital team innovation team. And so I encourage people to learn a little bit more about design because design thinking and entrepreneurship. And if anybody's heard of lean startup, like they all kind of go hand in hand and it's really running small experiments, testing things and getting feedback to let your customers or your potential customers lead you to that.

Michael Gardon (15:00):

And I think, you know, in your backstory, you were really talking about that too, with gift bar. You're a, I made a fake website, right. And I would show it to people, right. Instead of spending five grand on building out an actual website, you were able to wireframe something that worked just good enough and spend maybe $0 on that. You know, that's an example of a, a skillset really that I kind of talk about and advocate for with people. I think that's a really important skill for the future, whether you're an entrepreneur or not. I mean, so

Kara Kaplan (15:29):

You, you touched on that, you know, at the end of the day, you know, human design research is really about, you're trying to solve hard problems and problems that you don't fully understand are really hard to solve. So unless you go directly to the source and try and get inside the mindset and the day-to-day lives of the individuals that ultimately you're building this product for, until you do that, you're really not going to get it right. What I love about what Anthem did is to your point is just that, I mean, they really went right to the source and said, what are the problems? What keeps you up at night? How can we help you? And then kept iterating upon what they were hearing and coming up. And they came up with, I believe 34 different ideas, you know, services and of those 34 only settled on one. It's not the other ones were horrible ideas, you know, but they really just, weren't going to work for this use case and for this type of customer. And so I think it becomes critical when you're starting these journeys. I mean, you're right. And then when I think back to my experience with gift bar and the, you know, I was really trying to solve a problem that I had, you know, so the question was, if I'm having this problem are other peoples having this problem, so let's test it out and let's see if I'm correct.

Michael Gardon (16:30):

Yeah, yeah, exactly. I think that what was also really interesting was I think the, the, the line that I heard in a big meeting was five years ago. If we would have said, we want to solve this problem, we would have spent $10 million and never talked to a customer and we would have built Uber for the general and we would have not nailed it. Right. But what we did is again, you can go out in the field and you actually talk to people and doing that is like the it's, it's empathetic. And it's the opposite of arrogant. It's us all acknowledging we don't know the right answer. And so we need to dig, instead of saying, I know what X, Y, or Z person needs. It's a massive change in how and how it's done. And again, I think in the world of startups in world of entrepreneurship, like that's common language, that's what happens at Amazon every day, running hundreds of experiments, right. It's not happening necessarily at, at other types of corporations. Yeah. So it's a really cool experience. I'm glad I was a part of it. And then we of course found a perfect person and you two to kind of lead, lead it on. So I want to talk about Moonrise as a company, maybe start with Moonrise as the platform. What types of jobs are people getting mashed with and how has that sort of working or how's it evolved since maybe, you know, the last time you and I have talked about

Kara Kaplan (17:52):

It? Yeah, absolutely. So initially when we launched Moonrise, um, we were exactly that we were an on demand platform meant to match up, you know, financially challenged individuals with reputable lawyers for shift based work. So that meant, you know, one of our first clients and biggest customers was enterprise car rental, right? So we worked with over 90 branches here in Illinois, and we were filling shifts for them, everything from car detailers to lot attendance, things like that. So, so hourly based work, right? That was very easy to train. We say that all of our shifts should be, um, trainable. And under 30 minutes that Pete really individuals that potentially had no prior history of working in enterprise car rental could easily do. So we onboard our workers. We do everything from a background check. Obviously in that case, there's an MVR, current valid driver's license, all that.

Kara Kaplan (18:37):

But once they're vetted and onboarded, we then match them up with those shifts that is all done via an algorithm, right? So we take into account their location, their availability on their preferences, things like that. And then they're matched up with these shifts. It's all via their phones. So we text them the shift. They simply reply back. Yes or no. They want it. They're given all the pertinent details when to show up what to wear, all of that, they show up, they clock in through their mobile phone, they work their shift clock out. And then they're also paid instantly. One of the big value add propositions that we had with Moonrise from the beginning was the thought was, could we pay these individuals upon completion of their shifts? So to this day, I think it's a huge value proposition that we offer because we do it free of charge.

Kara Kaplan (19:17):

So a lot of same day pay platforms that are out there particular for gig workers will offer same day pay, but they tack on a pretty egregious fee to have the workers do that. So that's something that we don't do. So with that, we work with large employers who work with, as I said, enterprise, we work with companies like Nordstrom's doing sort of inventory tasks. We work with 1-800-FLOWERS. We've worked with more local companies like moving companies. We also worked with hundreds of American family agents, right, doing administrative sort of customer service type roles in the agents' offices. So that's really what we were doing and kind of chugging along for a while there, I would say about a year and a half into it, what we noticed was the platform that we had built to facilitate this type of work, right? So really an end-to-end staffing solution.

Kara Kaplan (20:01):

So everything from recruiting, a worker, onboarding a worker, taking care of their paperwork, everything from their I nine to tax work, tax payroll, all of that, we had to build ourselves, right. There are other vendors we could use, but to do it in the manner that we wanted to, with a large on-demand workforce, it was easier for us to build it ourselves. So then once you onboard that worker, everything from matching up with the shift, the clocking in and out the invoicing to the client, paying the worker, all that was something that we had built. And we realized that this platform could actually be useful to other large companies that have large, hourly workforces that they staff. It can also be useful to other staffing agencies. So we kind of started going down this path of offering our platform. So a platform solution in addition to our on-demand business, and we were kind of chugging along and doing that, and then COVID hit.

Kara Kaplan (20:50):

So like many businesses, ours was drastically affected, right. As you can imagine, kind of overnight, we lost close to 90% of our shifts, right. In one of the first calls we got was run a race car rental saying, Hey, you know, we just can't have temporary staff coming into our ranches anymore with us. And we're like, okay. So, you know, when that happened, we're going back almost a year and a half now. Right. It was sort of like, like every company, you know, sort of panic mode sets in for awhile, like, what are we doing here? How do we help our workers for us? What was paramount was really that we had a huge supply side workers that were already living paycheck to paycheck. And we thought, gosh, you know, how can we really continue to help these individuals? So knowing that a lot of our clients had sort of closed down their businesses, we thought, well, the first thing we can do is offer our services free to any essential business that is in need of labor.

Kara Kaplan (21:37):

Right? So that was the first thing we did. We kind of put out the messaging there to essential businesses. So grocery stores, whatever manufacturers are still in business and whatnot, we did that for quite some time and were able to keep some of our workers working, which was great. But then I would say about six months into the pandemic, we started getting calls from the American family agents who said, Hey, you know, my office is closed right now, but I'm still really in need of someone to help me with really prospecting right. And lead generation. They said, you know, would there be a way for your moon risers to help me remotely? And at the time, to be honest, we said, no, because we did not have a platform that could facilitate remote work. Right. It's just not what we did. And we looked into sort of using a third party vendor to help us with that, you know, sort of have our workers be able to place outbound calls, things like that.

Kara Kaplan (22:21):

And just kind of cost-prohibitive the margins weren't there. So again, we said, no, we can't do it. And then we thought about it some more. And we said, you know, we have a really talented team of engineers. That's kind of sitting here right now without a whole heck of a lot to do. And we thought, you know, could we build something ourselves? And we ended up, um, doing a little bit of digging and sure enough, we ultimately ended up building out a cloud-based outbound call based platform to allow our workers to make outbound PCI compliant calls for these Anthem agents. And we piloted this at the end of last year and super excited to say that it was a huge success. And we are now scaling this out in the several other states with an Anthem. And our hope is to have the entire amp and agency force, you know, utilizing this platform going forward.

Kara Kaplan (23:04):

And obviously we're in talks with other large carriers to have them utilize the platform as well. So it's been sort of a win-win for us in that we're able, in some ways it's better because if you think about Moonrise prior, we really were a two-sided marketplace. And that we had to go market to market and build up a supply and a demand side in each market that we went into. Right? So we started out in Chicago, then we're going to Wisconsin, Indiana, and all these other markets with this, because it is a remote based business. We can onboard workers from anywhere in the country to do this type of work. So it really allowed us to expand upon our mission of helping as many people as possible. And same with the agents, you know, they can be in any state, we can facilitate that type of work.

Michael Gardon (23:42):

I had no idea. You guys did all. I mean, that is a lot of pivoting and being nimble on your toe. That's also like, it's also really interesting. Like, again, this is a, you know, a startup within a corporate structure. And to me it sounds like there's probably some, a little bit of relief there in that. Okay. The corporations actually finally bring in some, I don't want to say value, but like bringing an opportunity like this is actually, you know, you built a platform and now you can really solve a problem. You can kind of push a button and there's demand there. And it's really, yeah, it's really neat.

Kara Kaplan (24:18):

No doubt that it's a win-win and that, you know, Moonrise, obviously it's allowing us to offer shifts to our workers and for the enterprise, you know, for ramp bam, it's allowing that their agency to hopefully be more successful, right. And add those premium dollars to their book of business, which is great. You know, I think this platform, there's obviously other use cases, right? So it truly is an outbound lead generation lead nurturing platform. So we can work with any type of business that is in need of that. And we know that the most businesses that have to rely on a book of business, you know, their leads are drastically undertouched and under utilized in many cases, not touched at all. And so where we think we're a little bit different from a typical call center, that's out there or telemarketing company that may offer this, is that because of the way our platform operates, it really is turnkey, right?

Kara Kaplan (25:01):

So there's a long-term commitment, right? It's like, you can literally put it in a shift for three hours if that's all you want this week. So it's really about how they can augment their staff in a remote way when it's convenient for them. And we think that at our price point, because we own all the technology, we built it ourselves and we own our labor pool. We're able to offer this as a much more affordable, hourly rate than if you were to outsource this to another company. And right now, you know, because we built this with Anthem agents in mind, it's very much geared towards the insurance industry. We could certainly work with other industries as well, but I think we definitely have pretty good line of sight into what those agents really need out of this platform and what makes it easier for them, you know, to help them continue to build up.

Michael Gardon (25:42):

I imagine quality controls somewhat difficult. Like how does training work or how do you sort of manage quality?

Kara Kaplan (25:50):

Yeah, no, it's a great question. And yes, I mean, it's certainly important. Um, so we've a pretty rigid way that we screen our workers rights. So in some ways it isn't different from our on demand business, right? I mean, we have asked a series of questions online, they then move to a phone screen. We then some have assessment based tests that we give to our workers. And then we do some sort of dummy shifts, if you will, we can sort of engage with them and see, you know, is their voice friendly, all that. And after that, you know, we certainly give them shifts, but we're fully transparent. So the agent has full access to listen to those calls whenever they want the very first call that all of our moon risers make is to the agents. So they can go over the script with the agent. So the agent can decide, you know, yes. Or here's where I'd like you to say this. So yeah, I mean, QA is obviously really important. It's not to say we haven't had some issues, I think any call center would, but I think for the most part, we've really been able to maintain that caliber of worker, that

Michael Gardon (26:40):

The agent that the is looking for. Very cool. So I want to talk a little bit about Moonrise, the act, the company now, like for listeners were saying, man, this is a cool company. Like they got a mission and they're helping people, right? Like give us a little bit of what are the types of roles that you guys have had the staff for in scaling this business, um, that are important, right? Like I try to give the audience a little bit of flavor for the roles, the skills, like where's the job growth and what are the types of things that are needed at a company like Moonrise? Yeah.

Kara Kaplan (27:12):

It's sort of in some ways constantly evolving, right? In other ways, it's really having an incredible core team. That's super flexible and really willing to dig in. I think any startup will tell you that you really need team players first and foremost, right. Because every day is different. I mean, as I just described to you, we went from one business and then sort of pivoted to another. And it's like, you know, we have people that never worked at a call center. I mean, I didn't have any experience with a call center. I mean, to be honest, no one on our team had experienced in staffing when we started memorized sort of the irony of it all. But I've always said, you know, like if you honor what you don't know, it's really easy to find those individuals that you think are gonna be a great team player.

Kara Kaplan (27:50):

Right. And so we really worked really hard to make sure that everyone on our team is in the right place. So obviously we have our engineers and their, our CTO kind of has his own way of sort of figuring out who rises to the occasion. They're right. I can't call it. So I can't assess that. But, um, but I will say our engineers, you know, I've, I've often heard that engineer just want to build cool stuff, right. As long as they're building cool stuff, they're happy. And I think to a certain degree, that is true, but I have found at least with Moonrise that our engineers want to be a little more involved than I thought they would. Right. I mean, they're really interested in the business part of it and the customer's journey and how, what they're building is affecting them and, and they want to be involved.

Kara Kaplan (28:27):

And so having those types of discussions, I think our engineers are really engaging and, and want to be a part of the rest of the team on the other side of is really our, our moon riser side. Right? So we have a recruiting team, we have an account management team and then we have our customer success. Right. So obviously when we have workers that are out in the field, would you use to be 24 seven? Now it's mostly just during the day we have individuals there that are sort of Manning our helpline. If you will, around the clock in case, you know, they can't, if you're doing a remote call shift and you can't access the internet, right. It's a huge problem. Right? You can't certain pick those calls. So things like that troubleshooting, but I would say it's really about, you know, there's all sorts of different roles, right?

Kara Kaplan (29:03):

So obviously, like I said, you have sales account management, customer success engineering. We have typical HR finance, those types of roles. But for me, it's, there's two things, right? There's a process to get things done. And then there's, there's people and you can have the best process in the world, but if you don't have the right people executing against that process, the process doesn't matter. And on the flip side, you can have the worst process in the world, but just awesome people executing and they're going to get it done. And so it's really about, you know, how do you kind of find that happy medium, where you have a process in place, cause you do need a process or lead a scale things, but how do you ensure that you have the right team in place? And so, you know, I'm always mindful to my team really be cognizant of what are they doing on a daily basis?

Kara Kaplan (29:45):

What are they doing a weekly basis and monthly basis? And, you know, because sometimes, you know, I'll have someone on my team come to me and say like, I really hate doing this and I'm doing all the time. And, but then when you have them really sit there and write down, how often are they doing this? It's not as much as they think because they hate it so much. It's consuming their entire day in their mind. So really trying to decipher kind of what's going on in the lives of your core team and then figuring out, you know, how can we fix this? You know, because then you realize something that they hate doing. Sounds like it's an, a role, you know, maybe if someone in sales is doing something that account management should do, but you realize we don't really need an entire, we don't need a whole nother account manager.

Kara Kaplan (30:21):

We just need, you know, maybe it's just data entry. Maybe we just need to find a part-time person. Or maybe this is something that our customer success team can take on, you know, and do. And maybe it's really only an extra five hours of work a week. So really trying to always look at everyone on your team and what they're doing and what they like and what they don't like. We always say to our team, our goal is to have them be able to apply for the next job, you know, two years from now, three years from now or whatever it is and get that job at that next level. We don't expect people to stay with us forever. We want them to spread their wings and learn as much as they can. I mean, we've been fortunate that we haven't had a ton of turnover, but I think that's really a Testament to really allow people to find the rhythm within Moonrise and find out what works we've had.

Kara Kaplan (31:03):

People. We had someone we had an amazing Cassie was in our account. My account manager hired to be an account manager and she was awesome. And she's now a product manager because she was just amazing at it and really took an interest in it and wanted to move over the product. And she proved herself to be able to do so. And now she's in product. So we had to go and find another account manager that was as awesome as Cassie. But you know, those are the kinds of stories that I love because that's how you keep the team happy and engage. And that's how you get someone to sort of come to your company and look at all facets of an organization and really think about themselves and their role and what they like to do and what they don't like to do. And are there opportunities to learn and completely move over to a different role in that organization, which I think is really important when people are looking for jobs.

Michael Gardon (31:47):

Yeah. Building the infrastructure, if you will, to cultivate a great team and, and keep people happy and growing, I think is one thing getting great people right to begin with is difficult because I feel, I feel like today, there's obviously a lot of great smart people, but you hear all the time, like it's really hard to find the right person and there's technical skills and there's soft skills, right. Or there's technical skills in some other bucket of intangible. How do you hire that a player? How do you account for the intangibles? I mean, I want to bring it back to, like you said, honor, what you don't know. And you said something in the beginning of our conversation about getting comfortable being uncomfortable. I think those two things, it's sort of that intangible of what you need in a startup, but I think it's being, it's sort of increasingly more sought that flexibility. How do you hire for that? Yeah.

Kara Kaplan (32:42):

Look, I mean, it's not always easy, right? I think that with Moonrise, we've done a really good job with sort of adapting our hiring process. So with everything from obviously we post a job and people apply, we looked through the initial, like anything. I mean, you look through the initial screen of the resumes. And I think that to be quite honest, could be one of those frustrating parts for people, right? Because you just don't know what someone's screening for. We don't use an ATS, right. There are a lot of companies, as we know that just are screening for certain words on the resume. We're not big enough to where we have to do that. Right. But I will say here, you're getting a big influx of resumes. You've only have people read through so many. So some of it is just the luck of the draw.

Kara Kaplan (33:15):

Unfortunately, I'm sure there are resumes that we've skipped over unintentionally, but you know, we sort of narrow it down to those resumes that we think there's something within those resumes or the cover letter that have stood out that we really think, okay, you know, this warrants, you know, another, look, we have an initial RHR at a people, does it, this sort of initial screening and is looking for various things, right? Cultural fit, trying to glean from this individual, you know, what are they looking for? And then their next opportunity, assuming it seems to make sense. Our next is a series of interviews where it's really a series of interviews and we try not to make it too intimidating or too time consuming, but we try to give a great mix of different people in the company. So you're interviewing with folks that you may never really work with one-on-one or cross-collaborate collaborate really even, but it's important that you meet with this individual and they get a sense of what you're like, because ultimately it's all part of the culture.

Kara Kaplan (34:05):

Right. And so we do sort of these, these team integrase, we try not to make it more than, you know, two to three on one. And it's really a chance for our team to just get to know this individual on a more personal level. Right. I mean, we're not, we try to stay away from where do you see yourself in five years and you know, some of those patented questions and answers that you're going to get. So we try to look for more personal questions, Muley trying dig into, does this person, you know, sort of pass the mustard, if you will, how do they think, how do they problem solve? You know, obviously, you know, some of the questions that I guess are more patented, but are pretty telling sort of describing experiences and problems that they've solved for and how they've approached it because a lot of that, but I think it's, it's really, there's no right or wrong answer.

Kara Kaplan (34:46):

It's really oftentimes for me personally, it's sort of my gut instinct oftentimes, but I think we, you know, we've been fortunate. We have, you know, so many people on our team are just good and kind people, right? And they look for that in others. And it sounds crazy, but that can come through an interview. You have some people that come in sort of guns, ablazing, and they may be the smartest person in the world, but they just come in so aggressive. And so like that it's off putting and our team immediately is going to be like, whoa, you know, this is a little too much. So it's really trying to find those individuals that are just authentic, that just come in and can really be themselves. We think those are the types of individuals that will really thrive at Moonrise. I can tell you one point we were doing an interview and it was myself and our CEO at the time who was interviewing this person.

Kara Kaplan (35:28):

And it was a customer success role for manager of the CSS. And I realized everyone loved this individual. When he came into the interview with, and our CEO, he was crazy nervous. And I realized, you know, I thought to myself, you know, this is a really bad dynamic, right? You have the CEO and the CEO with this person, and he's really nervous. And he's, we're just not allowing him to shine because he's just so nervous. And we never did that again. We just realized that is just a bad two on one interview and it's not setting that person up for success. And so now we try certain roles, obviously I need to interview direct reports and whatnot, but otherwise it's, I just sort of pop in. Right. And I'm like, Hey, you know, I just kinda want to introduce myself and just make it seem less scary, right?

Kara Kaplan (36:09):

Like we're a family. Just want you to know I'm here and I'm available for any questions you might have. So I think I'm trying to make it a more relaxed environment. And, and we've been told by everyone that we've hired, that it was a great recruiting and interview experience. So while we're always looking at it and trying to make sure, and right now, as I'm sure you're hearing with podcasts, it's definitely a challenging environment. Things are just really different and things are still settling from the pandemic and definitely not over. And so no one knows where that's really going to shake out. But I think ultimately it's about being authentic, you know, in the process and the experience, maintaining those, those touch points, letting people know every step of the way where they're at in the process and being honest and giving that, that feedback.

Michael Gardon (36:49):

Are you guys back in the office, are you planning to come back to the office? How is that going?

Kara Kaplan (36:55):

So we are not really all back in the office. We do have certain in-office days. Now having said that people can go into the office, they've been able to go in the office if they want to, for quite awhile, in a sense that there was a sign up sheet. So we made sure that numbers were where they needed to be. But we have a lot of, you know, individuals on our team that live in one bedroom condos with no outdoor space and just really wanted somewhere to go and work. And you couldn't go to a Starbucks and work. And so we felt that we had to give that as an option going forward. You know, we renewed our lease for another year. We said we will keep the office. It is my hope that people, especially now that more people are vaccinated, that will start to go on a little bit more, but keep in mind, Moonrise as a company, we always had a really liberal remote work policy.

Kara Kaplan (37:37):

So even before COVID, we were all only in the office on Tuesdays and Thursdays and the rest of the time. Um, while I, and other people on the team were in the office, many social engineers were only in two days a week. So for us, when COVID hit it, wasn't that huge of a leap to fully go remote. We make, you know, generous use of slack there. Having said that, I think, you know, in-person meetings, there's definitely value there. I miss seeing the faces. I sort of take for granted those moments when you're just walking to the bathroom and you pass someone's desk and you stop for a minute to chat about their personal lives or whatever it is, and those moments are missed. And so I think to get those back, I think is important. So on some level we will look to, if we're not all back in the office, I think what we will do now that things are open up here in Chicago is look to do more in-person team events, fun outings, things like that. Yeah.

Michael Gardon (38:22):

Are you guys hiring? What types of roles are you, you know, are you looking to, yeah,

Kara Kaplan (38:26):

We are hiring. We have a couple engineering roles open right now. We have business development roles open. We have an account management role open. We have a, I believe a customer success roles open.

Michael Gardon (38:38):

Very cool. I wanted to ask you also, do you have any interesting stories about how somebody caught your attention in the hiring process or like one of your HR members? Like I came across a LinkedIn post the other day where a guy used Venmo and he, he Venmo to guy. This was, I think for a content position like writer, he Venmo's a request for $50,000 for this contract writing assignment. And I totally like caught the guy's attention. He wrote up this huge thing on LinkedIn and complete, you know, totally interviewed the guy immediately just because it was so different.

Kara Kaplan (39:19):

Awesome. You know, we don't have any stories is awesome. And that would mean rise. I mean, we've just had, you know, we've had some where I'm old fashioned in the sense that, you know, I mean, so many people now don't give a cover letter. So many people now send a up, thank you, email, which personally I think is tremendously important. So those stand out, but I will say not at Moonrise, but when I lived in LA, there was the company I was working for. Someone had sent in this box and when my boss at the time opened it, it was a shoe and it was a resume with the shoes that I hope this gets my foot in the door. And I thought that was creative. And you know, I I've always remembered that like, alright, you know, but, but you're right. It's sorta like my mom, you know, anything that I think is going to differentiate you and set you apart from the crowd nowadays by all means. I mean, I personally haven't witnessed anything as creative with that, but I would certainly take note of it and I wanted to interview

Michael Gardon (40:08):

Those people. Yeah. Oh, that's great. Yeah. I like that. Get the foot in doors a little cheesy, but I want him to work.

Kara Kaplan (40:14):

I mean, you need to take the effort once you, you know, what it in there.

Michael Gardon (40:17):

Awesome. Where can people learn more about Moonrise or you tell them where they can get ahold of you?

Kara Kaplan (40:25):

So you can go to our website, which is moonrise.works. You can email me at kara@moonrise.works. Um, and I'm on LinkedIn, but yeah, there's plenty of information on our website.

Michael Gardon (40:37):

Awesome. Kara, so great to catch up with you. Thanks so much for doing this. It was a pleasure. We need to get together in person next time I'm in Chicago.

Kara Kaplan (40:45):

Absolutely. Or hopefully I'll be coming to Madison one of these days in there a while, but I would like to, I miss my drive. So no thank you so much. This has been great.


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