Can Automated Smart Scheduling Help Hourly Workers? with Erika Wasser of Prospr

In the latest Uptech Report, CEO of Erika Wasser introduces us to her new app Prospr and explains how it is increasing productivity for businesses around the world.

Her suite of employee management tools allows companies to access all employee information in the same place. Prospr is known as “the one employee app to replace the rest”, and if one thing’s for sure, it’s that Wasser is definitely an expert on managing people. She is empowering both companies and their hourly workers alike.

Before founding Prospr, she ran a 14 store hair salon chain with over 100 employees. At the end of the day, she realized that there had to be a better way. So she created Prospr — with features such as automated employee scheduling, simplified shift monitoring, and real-time worker performance data, all packaged in one easy-to-use interface.

Erika Wasser is the CEO of co-founder of Prospr, the all in one employee communication and management platform for the deskless workforce. Trusted by brands like Dunkin’, Town Sports, Sodexo and Heyday, Prospr helps frontline employees succeed and stay connected while saving managers and leadership 60% of the time they used to spend in the weeds. 

DISCLAIMER: Below is an AI generated transcript. There could be a few typos but it should be at least 90% accurate. Watch video or listen to the podcast for the full experience!

Erika Wasser 0:00
What I like about SAAS is that you’re able to develop deeper relationships, they’re more consistent, you can actually really solve people’s problems over time. And there’s more of a history that you can have with the customer that you serve.

Alexander Ferguson 0:18
Welcome to UpTech Report. This is our applied tech series. UpTech Report is sponsored by TeraLeap. Learn how to leverage the power of video at Today, I’m excited to be joined by my guest, EriKa Wasser, who’s based in New York. She’s the co founder and CEO of Prospr. Welcome, EriKa. Good to have you on.

Erika Wasser 0:37
Hey, thanks very me.

Alexander Ferguson 0:39
Now Prospr is an employee management platform. Or as we were chatting earlier, earlier, you’re all focused on helping small business downsize their absolution. And in this whole frontline worker environment, I’m going to say what’s the problem that you saw and set out to solve?

Erika Wasser 0:55
So before founding prosper, I was running a 14 chain, hair salon, like a 14 store chain, nearly 100 employees and struggle was real. Um, you know, you get to a point where you’re trying to manage all these things and talk to the same group of people about all these different moving parts and a retail service business. And everything is falling through the cracks. Nobody knows where to go for information. And people look at you dumbfounded, like, I don’t know, nobody told me meanwhile, like, you sent an email, you talked about it in a staff meeting you like bought a skywriter, put it in the sky. And so nobody seems to know what’s going on. And so we kind of realized that there was this app fatigue happening across sophisticated businesses, there were Jerry rigging point solutions, right? It’s like scheduling might be over here. And time and attendance is over there. And learning happened here. And then, you know, documents storage was there. But there was no consolidated way for someone who in a split second needed information to do their job better to actually access that information in a way that was going to impact them as an employee. And then managers were spent essentially juggling and managing all of these systems, which ultimately then become more challenging than the problems that they were brought in to solve. And so I only know this after years of true reviews, by way of managing people.

Alexander Ferguson 2:29
You felt it you experienced it yourself when you tried to do I mean, for five years, it was called it was called Glencoe. Is that correct? That that you felt this pain of? And I imagined in an environment of frontline workers versus office worker? What’s the turnover? Like you’re always constantly hiring new people, right? And they’re more hourly or contractor like, what’s that? Their hourly? Right, so they’re in that environment? How would you compare that to other types of because we’ve looked at some other HR tech tools, we’ve talked to some folks that how is it different than in like the frontline worker type of space,

Erika Wasser 3:04
you’re dealing with a couple of unique challenges when you’re trying to create a frontline employer. Right? One is that the bandwidth of these employees is limited, right? And the, you know, amount of bandwidth you can require as an employer, um, has to be reasonable to what somebody is willing to get paid. Right? And so you have a lot of businesses really great. We want to pay you minimum wage now download these seven tools. What? Yeah, and then you’re wondering why people are jumping from job to job to job and not creating loyalty, because you haven’t been brought into the fold on anything. They’re not a part of communication. There’s really fragmented ways that people get information and highly political ways that people get information, these kinds of organizations, right, like maybe on Thursday, when the manager was explaining a new policy or procedure, they had a really great morning, but the group that worked on Friday, the coffee was too hot, he was late to work and his cars giving him a service thing. And now it was that in that group of employees actually isn’t getting the same fair shake at information or opportunities. Right and so when you have so much complexity, and how information gets from top to bottom, and then so much variance, that some of which is controllable, and some of which is not. Creating a democratized source of truth really allows people to take their own initiative and to succeed and when the you know the tide rises, the company does.

Alexander Ferguson 4:51
The take me back 2018 years old, running glam and CO did just one day you wake up and said I gotta fix this, I got to do something about this. What was that? What was the process.

Erika Wasser 5:03
So the process was before that the process was actually in 2017. Um, I used to wake up every single day at five o’clock in the morning, and sit there the giant list and start texting my employees, because it’s seven to figure out who wasn’t coming to work.

Alexander Ferguson 5:21
You’re texting him individually.

Erika Wasser 5:23
Ah, he sounds like I actually, I was I was a pleasure. And my co founder and prosper is in Berlin, five, six hours ahead. We met at a party after college maintain like a decent friendship, you know, he was this cool European computer guy. I was in New York during the hair thing. And our friendship actually got rekindled at five o’clock in the morning on Facebook, because I would go online to try to stay awake while I’m sitting here talking to all these people to try to figure out who’s not coming. And then Eric would always be online, because for him, it was noon. For him. It was lunch. And so finally he goes, You know, I’m gonna ask you, I am happy that we were talking again, but like, why are you always up at five in the morning?

Alexander Ferguson 6:21
And so you explain your situation? How does it How does he react them?

Erika Wasser 6:26
In typical Eric fashion, he went, Okay, you do things in folio exist the like,

Alexander Ferguson 6:32

Erika Wasser 6:36
be afraid now, I suddenly really started diving into the challenges that we had. And I believed that they were mine, and mine alone, right? That no other operator could be quite this miserable, or be dealing with this amount of nonsense. On a day to day basis, right? It must be that I didn’t come out of business school, or that I wasn’t, you know, backed by big capital, or that I didn’t have any experience in a corporate environment, I just thought, Okay, you just have to be that I’m an idiot. And I’m the only idiot. And that’s the way it is. And it wasn’t until you know, my network and sort of clout started to rise. And I got speaking opportunities and networking opportunities with other operators, unlike we’d be sitting at conferences, having drinks after the day, and everyone was bitching about the same stuff. And it didn’t matter if you were at HBS, or for background private equity, or if you were me, were managing this type of employee group, you were having the same challenges, right. And the aha moment was, it’s not so much that I was bad at managing people is that people are really hard to manage. And especially this working group in retail service operating businesses that also have a customer facing aspect to them. Mm hmm. Where the stakes get so much higher for every single interaction, like every single piece of information that doesn’t get to that cashier that doesn’t get to that service worker, that that front desk member doesn’t know, actually has a ripple effect to your bottom line, because it’s interacting with your customer.

Alexander Ferguson 8:16
So you start to realize that these after hours and dinners and like, you have the problem, you have the problem, you have the problem. We all have this problem. You have a friend in Berlin, who’s a tech guy, and then you decided decided to get together and say let’s let’s solve it.

Erika Wasser 8:34
So we had solved micro problems were examined go about like so when he said you know, Twilio exists. We actually did build like a call and response system for

Alexander Ferguson 8:41
your for your specifically cover. Yeah.

Erika Wasser 8:45
And it was web based and thinking doesn’t look or feel anything like what prosper does, um, but we built tools, internal tools that we realized later on had really broad appeal, and so much later, also on Facebook, I asked Eric to co found a company.

Alexander Ferguson 9:10
And he did okay, it was It wasn’t immediate. Yes, I want to does he have like a job at the time too. So it’s like being able to jump ship.

Erika Wasser 9:20
You just gotten promoted to head of product at this really well funded German startup? He said, leave me alone. No thanks. And it was just one of those things where like, I couldn’t shower, I couldn’t sleep. I couldn’t like, make coffee and not think about this thing, this thing that had to exist. And so then finally I said, All right, listen, I’m going to do it with or without you. So I don’t want to hear about it when you see it. I’d much rather do with you. And I don’t know if you’re a musical theater person, but I like to say he into the woods to me. He sent me on what he believed was a good Chase. thinking it would take me a year I burn out. Right? He said, Okay, fine. You want me to do this? I need you to get a customer who’s willing to pilot the MVP so that if I build something, there’s someone to use it. Somebody who is not you that thinks this is a good idea. Good advice, and $50,000 Because that’s what I think it’s going to take to build the MVP.

Alexander Ferguson 10:29
Okay, so you set to it.

Erika Wasser 10:33
Three weeks later, I come back to him. Three weeks, we had skin laundry willing to be our first pilot customer, which is like a 25 store brand in the US one in London and a camp on calm. We had the now CEO of mind body to validate the idea who also became our first angel investor. I totally lied about this grant. We never had it. And we did find

Alexander Ferguson 11:13
a ride but video like let’s let’s, let’s get the money. You basically fake it. You’re making some ways, but you saw the need you got validation? You got somebody ready to do it. So you guys jump in what year was this? What what timeframe is

Erika Wasser 11:28
Summer of 2018. And so then we got on a plane, went to Berlin, locked ourselves in his apartment. And envisioned what the first MVP of prosper might be. First MVP kind of from a web based perspective was ready March, April of 19. And our skin laundry pilot started just after that with our second pilot, which was with center plates a deck. So at the Miami Beach Convention Center to start in September of 19. So we had two pilots. Um, and then, yeah, kind of

Alexander Ferguson 12:16
that I love. It’s like thinking backwards. And and that was that we got it done. So basically, you spend less less than a year building MVP. If I understood if I got that correct. Then you get your first pilots, two pilots are going on in April and September. And then we’re coming up to 19 and into 20. Do you just get those pilots in? You just start rolling it out? Does it? Is that Is that how it started?

Erika Wasser 12:44
Well, I mean, it would have been.

Alexander Ferguson 12:48
And then yay, COVID There was a

Erika Wasser 12:50
small, flu like symptoms. I don’t know.

Alexander Ferguson 12:55
Yeah. Oh,

Erika Wasser 12:58
yeah. Um, so November, our first pilots turn paying. And we’re like, awesome. Customer. This is so flattering. And in that time, we were really primarily focused in the beauty space and selling into beauty in December, like a non non starter. And Susan, great, q1 2020, we go to market that is the only appropriate response.

Alexander Ferguson 13:23
Mm hmm. Yeah,

Erika Wasser 13:27
ah, and so we had gotten some traction and some things sign that we’re all supposed to actually hit in March, we were going out to raise an initial seed of 2 million, we were like, 1.3 1.35 of the way there. I’m really going into early March and then COVID hits. Um, we got very, very lucky that our pre seed investors did kind of redress versus like doing a real seed plan. We went really insular into product market fit, really being more thoughtful about what kinds of feedback were we getting, when we did try to sell right, what were the bottlenecks where were they tried to sell as much as we possibly could, but we are technology for in person teams. And a lot of people in a space.

Alexander Ferguson 14:30
So basically, for the rest of 2020, it was more of an inward sell where you can but focus on the product with the plan that once things opened up, we can scale.

Erika Wasser 14:38
Yes. Correct. Right. Um, you know, take the customers that we did have, how do we make them happy? How do we keep that kind of moving in the right direction. When we had opportunities, we first took them from a sales perspective. And then one of the biggest changes we made was pre 21. prosper was a one size fits all solution, where our kind of stance on the matter was you business owner, who clearly doesn’t know more about your business than we do, you might not know you need all of these tools, but you do. Right which like, nobody likes as like a sales psychology like nobody likes that. Oh, prosper became modular at the end of 20, to 21. And that change made all the difference, because we were able to become better partners, to the businesses that we serve and be much more prescriptive and how we sell, right? Because now it’s not about look at the great things that we can do. And tell me what your problems are. Right?

Alexander Ferguson 15:46
Where they are, at that moment, not saying now you need to just you need to solve everything. All right now with all of our solutions.

Erika Wasser 15:52
Yeah, I think what’s keeping you up at night? And do I have something that can solve for that, and there are times you know, 90% of the time, we do have something that consultant for that 10% of the time, I say, hey, that isn’t our expertise, but we have this quasi competitor over here that you should really take a look at. Right? And when you’re trying to solve these other things, then you give me a call, right. And so it really allowed us to, um, I think live up to the kind of I hate to keep using the word partner, but like, our customers really are hurt. Hmm.

Alexander Ferguson 16:33
And from your background, it’s like you can you just keep resonating, you understand their story. And you you want to play that that role for for the kind of going into the end of 2020 into 2021. Now, I feel like things are opening up again, how what was the response that like, what’s what’s been this last recording here in end of September? So last nine months, what’s it been like?

Erika Wasser 16:58
I mean, we’ve grown about five 600%, in 21. Which, and that momentum allowed us to go and raise a proper seed that we closed in August, just about a month ago. Um, which was like a surreal experience, because we like, everything kind of just came together at the right time with like, you know, the people that we had dreamed of working with. So yeah, a real like, I don’t even want to jinx it, because I don’t know, to what ever happened to me again, in my fundraising career. Um, you know, I think we’re seeing a couple of things like one is that businesses are getting this opportunity to clean slate, bad practices, right. So rather than come back to the show that they were before, they are much more apt to say, Okay, we’ve gotten this opportunity to kind of clean up our side of the street. Are there tools that can help me get to the outcomes that I want? I’m less than early or more easily, or faster, or easier or cheaper? Right, so you’re seeing a lot of interest in tools like ours, are operating businesses. And then I think short staffing is certainly playing a key role in businesses meeting ways to offer things like schedule, flexibility, and the ability to pick up more work. And on the go learning and development versus like, every Friday, you have to be here 12 to 10, right? Like, um, you know, we’re seeing the, we’re seeing managers who may be had one or two stores now to cover five. We’re seeing employees who used to be assigned to one home location and only work in allocation need to be cross skilled, cross trained, and more flexible across brand. Right, so we’re actually seeing more need for prosper today than we did pre COVID.

Alexander Ferguson 19:09
Wow, the powerful insights right there. And I think everyone’s has been seeing that the shortage of frontline workers in restaurants in different places you go and but the challenge as a business owner, I can only imagine operator of these would pull your hair out. How do you manage that? What? For you? This is your second business you run? You mentioned that the first one glam and go. Did you did you raise any funds for that at all? How did how did you accomplish that? And how was that compared to this?

Erika Wasser 19:39
Um, we raised a small amount of money in 2015, a year after we had started and it was a service business. It’s a brick and mortar business. It’s not one that gets venture capitalists particularly excited. Um, you know, and it’s not necessarily business at all. did write that kind of trajectory?

Alexander Ferguson 20:05
Did you see yourself one day being a tech company leader, I mean to see one or two or just kind of us falling into it.

Erika Wasser 20:13
So there was a tough that halfway through the D’Amico experience, I knew that I wasn’t going to do it forever. I didn’t know what I was going to do next. But I knew that the next thing that I did had to have three qualities, one was ability to scale really rapidly, really quickly, without me having to like be on a plane every other week, right? Like, I didn’t want physical occasions. The second is that I actually did not want to be in a service business, or retail business. Right, like get cursed out by a 13 year old, she doesn’t like her hair on her bat mitzvah. Like, once, that’s a once in a lifetime thing that I will link to put up.

Alexander Ferguson 21:06
He got like, done, I’ve received that I don’t need to make that happen again.

Erika Wasser 21:14
I mean, I’m sure the next one will be my own child, but like. Right. And the third is that I wanted to I wanted to grow in my own capacity and skill sets, right? Like I wanted to learn something new. And so prosper really checks all of those boxes, of like having really high quality people around me that I can work with and learn from that are way smarter than me all the time. Right that I can we can build something and like we have customers in Australia, we have customers in New York, we have customers in Bahrain, and everywhere in between. And you know, my whole life, for the most part is operated by SAS businesses.

Alexander Ferguson 22:07
All around us, around you. Yep. So why not? Why not be able to get into so now you’re really just the beginning of your, your, your adventure here. It’s just the two of you right now. Still, you’re about to scale up team wise, is that correct?

Erika Wasser 22:25
One customer success.

Alexander Ferguson 22:27
Okay, got it to be in a customer success. It’s kind of early to ask but curious, what would you share as far as learnings coming from a service business to a SaaS business for other entrepreneurs out there who are thinking about similar going from going from service to SAS? Any lessons learned you like, here’s a word of wisdom,

Erika Wasser 22:51
service and SAS. Um, so if someone is really trying to go from service to SAS to get out of the idea of being in service, then they shouldn’t do this either. Because?

Alexander Ferguson 23:06
Okay, why? Why do you say that?

Erika Wasser 23:08
Oh, well, you’re ultimately fine is it as a business, if you’re providing a value to a customer who’s paying you, you are always in service to someone, right? So we are still ingratiating Lee in service to our customers. And it is a different kind of service, right? Like so. You’re what I like about Sass is that you’re able to develop deeper relationships, they’re more consistent, you can actually really solve people’s problems over time. And there’s more of a history that you can have with the customer that you serve. versus, you know, the one off Rebecca Blumenthal in Miami Beach. Um, right. And so and it’s a different kind of service, right? Because they’re really, they’re not coming to you to bench they’re coming to you to actually, creatively problem solve together. And so it’s a very different kind of servitude, but we are certainly certainly still a service business.

Alexander Ferguson 24:07
Yeah. What are you most excited about? Looking ahead from here, anything you share in the roadmap? Like what’s coming up?

Erika Wasser 24:16
Um, we’re really excited that we’re working with a workforce that has been somewhat underserved by tech over time. Right. There isn’t a ton of focus on how do we make the day to day life? I really workforces and 80% of the global workforce, how do we make their lives better? To be on the frontier of what could ultimately lead to so much good? is really, really exciting.

Alexander Ferguson 24:45
You guys are focused on small and mid size, not to say enterprise set correct.

Erika Wasser 24:51
So it’s really more mid market, small enterprise. So any so businesses have anywhere from 50 employees to you know, 1000 2000 right now where they are not quite large enough to play in like the workday sandbox, but they are too large and too complex to have fragmented tech stacks that don’t

Alexander Ferguson 25:12
work. That’s where you finding your sweet spot of being able to serve that.

Erika Wasser 25:18
Too big for point solutions too small for HCM?

Alexander Ferguson 25:23
Where would you say if you were to imagine where the space is headed technology wise make a prediction in five years for frontline workers? What’s the technology going to look like?

Erika Wasser 25:35

Alexander Ferguson 25:37
Love you. Like, that’s amazing. But walk me through like a day in the life like what’s gonna, what’s it gonna look like 510 years from now is

Erika Wasser 25:49
510 years from now, I think I think you’re going to see a lot a more level playing field in terms of respect for all people and the work that they do, which is sort of our mission and value driver at prosper, right respect for the work all people do? And how do we elevate what has historically been like, oh, well, they’re just flipping and like, but that’s not true. Actually, they’re opening the store, they’re greeting the customer, they’re setting the atmosphere, they’re making sure the places burn down, they’re relaying real time issues that are affecting how you operate your company and how you derive revenue. Right? Like the only barrier between the customer giving you money is this person that you are choosing to ignore? Doesn’t make any sense.

Alexander Ferguson 26:41
I can sense the passion in your voice. Very topic. So it sounds like that. That’s one of your founding mindsets, going into this.

Erika Wasser 26:51
You know, it’s how you create productivity suites. For um, you know, I hate the term knowledge worker, because it sounds so douchey to me, right? Like, it really does like because knowledge is just something that your brain has to retain and execute on. And so, right, if you put me behind a Starbucks barista, and you told me to make, like some monkey, I couldn’t do it, right. Like, that’s knowledge that somebody else has, and I don’t, I’m right. But I think it’s going to be a reckoning of how do we really actually, like, what do we owe each other? Kind of a question. And I think what you’re already seeing is that the workforce is going to win, because they are the boss, right? Like, they don’t want to show up because they’re collectively saying, these aren’t wages we’re going to ascribe to or these are an hours that we’re going to be cool with, or these are not conditions that we’re going to participate in. Good luck, right. Like you. Good luck.

Alexander Ferguson 28:01
Good luck, that that if anything, I think the whole workforce has changed for sure of

Erika Wasser 28:07
the fact that they’re getting younger and like arguably more entitled, I’m sure

Alexander Ferguson 28:16
yeah, there’s there’s lots of buzzwords of course of, you know, the gig economy, etc. But it’s like how are we categorized catering so that if almost as employers you see your employees as consumers you serve them with the same technology and and forethought as you would a consumer to support them. And then mindset. This has been a fascinating conversation. I’m fascinated with where you are heading, the problem you’re solving is an absolutely needed one, you face it, you’re experiencing it, and I’m intrigued to see where you guys go next. For those that want to learn more, you can head over to prosper, that’s PROSPR.WORK. How was getting that URLs that uh, like, let’s take out a letter is like had the name cover. And your symbol also is the for those that are listening, Spock signal here have a piece.

Erika Wasser 29:09
So a couple of interesting things is a this is technically fair use because Gogan is part of the Webster’s dictionary. And so in Vulcan as a language was indoctrinated into this dictionary,

Alexander Ferguson 29:24
the Fair Use

Erika Wasser 29:26
Actually Star Trek didn’t come up with this. This is like an ancient Jewish Kohan symbol that the guy who plays Spock actually pulled from I don’t worry about this than I ever shut

Alexander Ferguson 29:42
but you it is definitely recognizable. I love the goddess again, and thank you again for your time. Erika, this has been fantastic. Thank you. And we’ll see you all on the next episode of UpTech Report. Have you seen a company using AI machine learning or other technology to train transform the way we live work and do business go to UpTech and let us know


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