Two Uber product designers raised $3 million, built a scheduling tool, and watched it fail for two years. Then they threw it out and rebuilt with Legos, and outsold the previous two years in the first month.
In this episode, Tito Goldstein reveals the brutal reality of finding product-market fit when you're too close to the solution, why composability beats cookie-cutter features, and how listening to what customers don't say became their unfair advantage.
Tito Goldstein is the Co-Founder and CEO of TeamBridge, a composable workforce operating system for hourly workers that serves over 500,000 employees across 200+ enterprise customers.
Tito Goldstein and his co-founder Arjun were two of the first principal product designers at Uber. After interviewing thousands of Uber drivers worldwide, they realized something powerful: drivers were choosing Uber despite lower pay because of the agency and self-service the app provided.
They raised a $3 million seed round to bring that same experience to the 60% of the global workforce who are hourly employees stuck with legacy tools. But after building their initial scheduling product, they hit a wall i.e. two years of near-zero revenue.
The problem wasn't the market. It was the product. Customers kept saying they needed to stand out, not use the same cookie-cutter software as their competitors. Their secret sauce lived in spreadsheets and manual processes, not in a fixed scheduling tool.
So Tito and Arjun made a gutsy call: throw out the scheduling product and rebuild as composable Legos. Customers could start with a template but configure 20% to match their unique workflows and differentiators.
The new product outsold the previous two years of efforts in the first month. Then it 3x'd, and 3x'd again.
Today, TeamBridge powers NFL stadiums like the 49ers' Levi's Stadium, medical staffing agencies scaling from zero admin staff to multimillion-dollar businesses, and enterprises managing thousands of hourly workers with self-service automation.
Key Insight
Key ideas
- Listen to what customers don't say: they kept asking for features but the real pain was "I need to stand out, not use the same software as competitors"
- Throw out sunk cost when the market speaks: 2 years of work became irrelevant when they realized the connective tissue (automations, workflows) mattered more than the core scheduling product
- Composability beats cookie-cutters in competitive markets: 60% of the workforce is hourly, supply-constrained industries need differentiation, and off-the-shelf tools make companies commodities
- Outsold 2 years in 1 month: as soon as they launched the composable version, it generated more revenue in 30 days than the previous 24 months combined
- Stay lean until PMF: Tito and Arjun kept burn low (team of 5-6) and maintained multiple years of runway, which gave them the freedom to pivot without investor pressure
π Chapters
00:00 Introduction and favorite quotes
01:18 What TeamBridge does and who it serves
02:29 Why composability matters for workforce software
03:35 Size of the business: revenue, customers, team
04:09 Origin story: interviewing Uber drivers
06:16 Going door-to-door to understand hourly worker pain
08:36 Raising $3M seed with just a prototype
11:07 Why it took 2 years to find product-market fit
12:56 The pivot: from scheduling to composable Legos
14:02 First significant sale during COVID
16:28 Biggest objections: explaining composability
18:46 Finding the right messaging and storytelling
21:05 Downsides of casting too wide a net
23:43 Moving upmarket to enterprise customers
25:34 How COVID forced TeamBridge to mature go-to-market
27:44 Cold email lessons: honesty and relationship building
32:05 Discovery-first selling: hold the pitch until you know the pain
34:29 Learning the nuances of each vertical
36:35 Lightning round: grit, curiosity, and fitness
π Key Lessons
- π― Listen to what customers don't say: TeamBridge's buyers kept asking for features, but the real pain was "I need to stand out, not use the same software as my competitors." The product-market fit breakthrough came from reading between the lines.
- π Throw out sunk cost when the market speaks: Tito and Arjun spent 2 years building a scheduling tool that failed. Instead of iterating on it, they threw it out and rebuilt with composable Legos - outselling 2 years of work in the first month.
- π οΈ Composability beats cookie-cutters in competitive markets: In supply-constrained industries (nurses, stadiums, staffing agencies), whichever company finds the worker wins. Off-the-shelf tools make you a commodity; customizable workflows make you a differentiator.
- π° Stay lean until product-market fit: TeamBridge kept burn low with a team of 5-6 and multiple years of runway. That gave them the freedom to pivot without investor pressure. Most startups don't have that luxury.
- π Your first product validates the problem, not the solution: The initial scheduling tool failed, but it uncovered the real pain: connective tissue (automations, workflows) mattered more than core features. Use early products to learn, not to scale.
- π€ Be honest in early-stage messaging: Instead of pretending to have all the answers, Tito pitched: "We built amazing tech at Uber, now we want to bring it to your industry." The right early adopters leaned into that honesty.
- π Focus narrows as you find product-market fit: TeamBridge cast a wide net (cafes, retail, healthcare, stadiums) to learn, but once they found traction with medical staffing, they doubled down. You can't prioritize everything, and trying to serve every vertical means delivering value to none.
Show Notes
Book Recommendations
- You Are Now Less Dumb by David McRaney
Episode Q&A
How did Tito Goldstein and his co-founder get the idea for TeamBridge from interviewing Uber drivers?
They interviewed thousands of Uber drivers globally and heard the same thing: “I know I'm making less money, but I choose to drive for Uber.” Drivers valued the agency and self-service of the mobile app over higher pay from traditional employers, which revealed an opportunity to bring that same experience to other hourly workers.
Why did TeamBridge spend 2 years with near-zero revenue before finding product-market fit?
They built a scheduling tool based on their initial assumptions, but when they took it to market, buyers said they needed to stand out, not use the same software as competitors. Their secret sauce lived in spreadsheets and manual workflows, not in a fixed scheduling product.
What was the “composable Legos” insight that led to TeamBridge's product-market fit?
Instead of building a cookie-cutter scheduling tool, they rebuilt TeamBridge as composable building blocks. Customers start with a template but configure 20% to match their unique workflows, automations, and differentiators – turning the software into their competitive advantage.
How much faster did the new product sell compared to the original TeamBridge scheduling tool?
The composable version outsold the previous two years of revenue in the first month, then 3x'd repeatedly. The initial product generated almost nothing for 24 months; the pivot changed everything.
Why does TeamBridge focus on hourly workers instead of salaried employees?
60% of the global workforce is hourly, and they're being asked to do complicated tasks with rudimentary legacy tools. Supply-constrained industries (nurses, forklift operators, construction crews) need to stand out to attract talent, which creates demand for flexible, differentiating software.
How did Tito Goldstein raise a $3 million seed round with just a prototype and no revenue?
Tito and Arjun leveraged their experience as top product designers at Uber, created urgency by condensing VC meetings into 2-3 days, and pitched the passion, grit, and product chops VCs look for at the seed stage. They had a working prototype and intimate knowledge of the pain point from Uber.
How did COVID change TeamBridge's go-to-market strategy?
They had been going door-to-door to cafes, movie theaters, and retail shops to talk to hourly workers and managers. When COVID hit in March 2020, they pivoted to outbound emails, cold calling, texting, and paid lead gen – maturing faster than most startups because they couldn't rely on in-person discovery anymore.
How does TeamBridge help companies like the 49ers' Levi's Stadium staff 3,000-4,000 workers for 20 events per year?
Stadiums send 30,000 emails to get 200 parking flaggers to show up. TeamBridge lets them build incentives directly into their mobile app (Playmakers) and broadcast opportunities to get people to claim shifts, turning email chaos into self-service automation.
What objection does Tito Goldstein hear most often when selling TeamBridge's composable platform?
Buyers are used to cookie-cutter software that does one thing well. When Tito says “TeamBridge does what you ask of it,” they struggle to understand, like asking “What does ChatGPT do?” The education moment is the biggest growth edge, but also TeamBridge's greatest strength.
Transcript
Omer Khan [00:00:00]:
Tito, welcome to the show.
Tito Goldstein [00:00:01]:
Thanks for having me.
Omer Khan [00:00:02]:
My pleasure. Do you have a favorite quote, something that inspires or motivates you that you can share with us?
Tito Goldstein [00:00:07]:
I actually have two quotes. One maybe I’ll paraphrase and the other I’ll say more directly. This first quote is from this Boy’s Life by Tobias Wolf. I think this quote is meaningful in a lot of different ways and maybe my second quote will add some insight to it. So the quote is, knowing that everything comes to an end is a gift of experience, a consolation gift for knowing that we ourselves are coming to an end before we get it. We live in a continuous present and imagine the future as more of that present. Happiness is endless happiness, innocent of its own. Sure.
Tito Goldstein [00:00:39]:
Passing pain is endless pain. So that’s like one of my favorite quotes. And I’ve had that quote since high school. And there’s another quote I’ll maybe paraphrase, which is basically that in order to become our best selves, we need to allow our former selves to die. And I think those both kind of play off each other, especially from an entrepreneurial sense where you have to have that kind of utmost optimism about the future, but pessimism of where you are today to be critical and focused and drive towards that optimistic outcome you’re hoping for.
Omer Khan [00:01:08]:
Yeah, love it. I didn’t expect that much out of a quote, so thank you for that. So tell us about TeamBridge. What does the product do, who’s it for, and what’s the main problem you’re helping to solve?
Tito Goldstein [00:01:18]:
Yeah, so when we looked at the market, we realized that 60% of the world’s workforce is hourly and they are being asked to do some of the most complicated tasks with some of the most rudimentary and legacy tools. So our focus is really on what we call like that forgotten demographic, those folks who need technology more but just have been given something honestly off the shelf that no one should have to use. So TeamBridge is a workforce operating system. It allows you to find, attract, manage, engage, and now even pay workforces in a way that helps you stand out. It helps you as a company leverage your differentiators, your secret sauce, to actually give the best possible employee experience and in doing so, win and increase your revenue. I think we have a quote from a customer who said, as soon as I signed up for TeamBridge, I took my admin staff and I took them off of keeping the lights on and I put them on revenue generating activities, the things that actually were the inputs to the flywheel and the way TeamBridge does that is with composable Legos and building blocks. So we let people start with a template but then stand out with unique features, products, experiences in the mobile app and in the admin experience as well. And it’s been a really exciting journey to date.
Omer Khan [00:02:29]:
Why is that composable aspect so important? Like why is it at a pain with other workforce management solutions?
Tito Goldstein [00:02:36]:
Yeah, if you think about it, you know, standing out is half the battle. And during COVID and even still today, nurses, forklift operators, construction crews, the some of the most in demand jobs out there. And so whichever company can actually find the worker actually wins. So how do you incentivize, how do you attract that talent? Well, if you’re using a workforce management software that’s off the shelf just like your competitor and that’s your main touch point with that, that employee, well then you’re a commodity now. And now you’re going to have to hire a lot of admins or do something or pay a lot more. But you know, if you can actually provide them a unique experience, a more self service experience, give them the agency and, and the only way to do that is with those composable Legos. Right. You can’t stand out if you have the same software as everyone else.
Tito Goldstein [00:03:21]:
And what we saw, you know, 10 years ago, Project management was upended by things like notion airtable Monday.com and we thought, oh my God, like there’s an opportunity here to give that same composability underneath a use case driven tool like a workforce management platform.
Omer Khan [00:03:35]:
Great. Give us a sense of the size of the business. Where are you in terms of revenue, customers, size of team?
Tito Goldstein [00:03:41]:
Yep. So we are about 60 employees. We are north of, you know, we’re multiple seven figures and we have over 200 enterprise customers and that accounts for over 500,000 end employees.
Omer Khan [00:03:57]:
Awesome. And I think you’ve raised at least 38 million so far.
Tito Goldstein [00:04:02]:
Yep. So we’ve raised you know, north of 35 million across three rounds. A seed, an A and a B.
Omer Khan [00:04:09]:
Great. So let’s talk about where the idea came from. I know both you and your co founder Arjun were at Uber at the time and part of the process you went through was you ended up interviewing like a hundred or hundreds of Uber drivers to understand some of their pains. And was that a customer discovery thing because you had this startup idea or was that something that you were doing as part of your jobs that led to a startup idea?
Tito Goldstein [00:04:38]:
Yeah, so that was just a core function of my day to day job at Uber. So me and Arjun were two of the first principal product designers Uber ever had. And we also owned large parts of the product, both the rider app, the driver app, and even internal tools that Uber was building. And that afforded us this amazing privilege to do a lot of our own user research to, you know, come up with our own product ideas. And because of that, we interviewed thousands of drivers all over the world. The United States, you know, east coast, central west coast, Brazil, Mexico, India, Singapore, Australia, you name it. Like, we went to all these markets to truly understand why the nuances of their communication habits and their riding habits, you know, changed the metrics in the Uber experience. And one thing we always heard, every single driver, they said, I know I’m making less money than I used to, but I choose to drive for Uber.
Tito Goldstein [00:05:31]:
And to us, that was like a, oh my God, like, how is this company, how is our company differentiating against a traditional employer who’s paying more and also giving probably more consistent hours? Because Uber drivers were, you know, working longer and longer hours and the pay, you know, honestly wasn’t great. But they were choosing that because of the agency and the self service aspect, the ability to go on their mobile app and work with a modern company and press a button and start earning. And we thought, how do we give that level of agency and self service to all these other employers that are competing now with the gig economy? So it really was kind of an idea that organically formed after all these conversations, usually more pointed around a specific feature, but a consistent theme that we saw as Uber became the behemoth it is today.
Omer Khan [00:06:16]:
Okay, great. So it sounds like what you heard was from these Uber drivers. The Uber app is actually pretty good compared to what I’m used to. And these are all the other problems I face with the other products that I’ve used with other employers. So that tells you how good the Uber app is and how crap some of the others are. But how did you then figure out what were issues with these other apps? Like, did you do more digging? Did you find hourly workers that were not Uber drivers? Like, how did you connect the gap?
Tito Goldstein [00:06:47]:
Yeah, so when we initially were, you know, starting out on this journey, we actually went door to door. We went to a movie theater, we went to cafes, we went to restaurants, we went to retail shops. And we started realizing how fragmented and how low quality the technology that they had in their hands was. Employees couldn’t request time off. Simply, they couldn’t even see their schedule. They couldn’t put their preferred schedule in. I worked at In N Out during the summers when I was younger and I remember I would commute an hour to the store and an hour home and I only worked a four hour shift because that’s what initially like the manager put me on. I’m sure he would have liked me to tell him I will work as many hours as you give me, but as a 17 year old, I don’t think I was ballsy enough to do that.
Tito Goldstein [00:07:32]:
So reducing the barrier to entry to allow employees to do oftentimes what a company needs and wants was like the key differentiator in if you want nurses to pick up another shift, giving them the biggest, easiest button to click in the app probably will increase that. Step one Product design and so I think we went out there, we heard about what was in the market and then we started designing because that’s what we and Arjun were inherently good at. We were product designers, we were product guys through and through and we said, let’s start with what we think is best in class and let’s learn from the market itself.
Speaker C [00:08:06]:
The reason we exist is because you cannot stay ahead of all threats. So what we do is we block by default. If it’s not on the list, it cannot run in your environment. And that is our core focus. Zero Trust principles. The core of threat locker is zero trust, 24 hour, 365 day a year support. We’ve got some of the most advanced threat intelligence team and this isn’t an outsourced offshore response, it’s our staff in our offices helping our clients directly who really understand the product and really understand the threats.
Omer Khan [00:08:36]:
You raised a seed round of around 3 million, but you didn’t generate your first dollar or any significant revenue for another two years after that. Tell me about what, like how did you raise that seed round anyway? What did you have to pitch at the time?
Tito Goldstein [00:08:57]:
Yeah, so we’d actually been hacking, you know, nights and weekends on some ideas and, and then eventually we realized, hey, like, it’s time. And so we were lucky enough to be relatively high up at Uber, so there was some kind of, you know, brand recognition with the culture that Uber had, you know, at that time. And we, we went out to some of our like colleagues at Uber, they connected some of the dots and we sent out this kind of mass email to VCs. Now I think one of the important things we did is we said, hey, like we are taking two days, three days at most, you know, to like meet with folks and see, you know, what the interest is here. We did a couple kind of trial runs with some VC friends of ours. And then eventually we packed in two meeting days full from like morning to night of VCs. And I think that helped us, you know, create that urgency, but also helped us just really refine in that, that pitch. And the pitch was we have this like working prototype we had built.
Tito Goldstein [00:09:54]:
We have some folks who are actually using it now we’re giving it to them for free. And we’re, and we’re very intimately involved with this pain point, given our experience at Uber. And so I think, you know, any VC is going to ask those same questions. Are these the right people to be doing this? Like, do they have the chops, the grit, the understanding, the technical ability to be able to execute on it? Do they have, you know, the passion? Do they have the chip on their shoulder? Not to just from a VC perspective, right, sell out early because VC wants to return the fund. So I think, you know, we checked a lot of those boxes. We had significant experience. We were, we were, you know, top class in, you know, the one thing we did well, which was product and design. And so we were able to kind of tell that narrative.
Tito Goldstein [00:10:35]:
So I think at the seed round, a VC is really investing in the founders. They’re saying like, hey, you know, maybe that changes a little bit now with like the AI dynamics of the world. But still they’re investing in kind of this ethos, this idea, and the idea might even change. But if the grid of the founders is there, know, they’re probably willing to lean in. So we did kind of this very, you know, rapid fire, you know, VC round. We received a lot of term sheets and then, you know, it came to deciding on who to go with and we, we, we made it simple on the VCs, right? We had the kind of, you know, typical terms back then, which was like a 3 on 15 round.
Omer Khan [00:11:07]:
Okay, so you raised the seed round, but then it took you two years to generate meaningful revenue. Like in that, in that period, it wasn’t zero revenue, but it was almost zero. So why did it take so long? Was it about. You spent way too much time building the product. It was hard to sell what was going on.
Tito Goldstein [00:11:26]:
Yeah, so we, we built, we had our initial prototype, even the one that we kind of started with in those VC conversations, we took that to market. And then when we started talking to folks, you know, the actual buyer, not the end user, not the employee, we started hearing something that was a little bit different from that initial assumption. And it was, I, they basically said, it’s a super supply constrained market. Right. So we need to stand out to get there. And they all had their secret sauce. And usually that was in spreadsheets, usually that was in some other tool. So we started realizing that our core scheduling product, our initial product, was not like the, the pain we initially assumed it would be.
Tito Goldstein [00:12:02]:
And in fact the pain was actually in between those moments. So to answer your question, like we had this initial product and then we took it to market, but, but we actually used that to uncover that nugget of truth that would ultimately be, you know, what team bridges today. And it was that the connective tissue, the operating system, what happens after, you know, a shift is marked as late. All those cascading automations, all those sc, those cascading like actions was the more important and more valuable piece of the platform. So we then, you know, with this new insight, you know, basically pivoted the product a little bit and we started building based on that new core concept of composability, of flexibility, of giving our customer those Legos and building blocks. And that took about a year. And as soon as we went to market with that, it, you know, outsold the previous product in the first month. Like the entire two years it outsold in the previous month and then, you know, it 3x3x3x.
Tito Goldstein [00:12:56]:
So I think the whole kind of two years of what you could call the doldrums were really about listening to the market and then actually executing on what we heard rather than holding on to that initial concept and having like that sunk, sunk cost fallacy there.
Omer Khan [00:13:12]:
How much pressure were you getting from investors when you checked in?
Tito Goldstein [00:13:14]:
So I think that one, we were a super lean team. Like we, me and Arjun have always been kind of more on the frugal side. We will spend money when we see something working. But until then we’re basically, you know, just holding that in our, in our war chest. So I think we were very light on burn. We were probably a team of five or six. You know, our Runway was multiple years at every given time. So I don’t think the pressure was as much there from investors.
Tito Goldstein [00:13:38]:
And candidly, you know, like investors, they put more focus on the things that do have like the momentum. So we were probably like a little bit in the shadows. But I think the investors we chose gave us the grace to go and figure that out on our own.
Omer Khan [00:13:51]:
So tell me about the end of that two year period when you landed the first significant sale. How did that come about? What type of customer was that?
Tito Goldstein [00:14:02]:
Yeah, so it’s funny because as I, you know, I think we we briefly touched on, we cast a pretty wide net. We didn’t know a specific market we were going after and we were building such a flexible tool that in fact we were very unfocused in our go to market. And I wouldn’t suggest that for any founder, but it helped us learn enough about enough industries to create the right primitives inside our technology. But now, you know, from that moment, we actually had a couple key medical staffing companies come our way. It was like the height of COVID and nursing was, you know, printing money. And so we leaned in there knowing that, you know, we had something that they really wanted and that was the flexibility to create this Uber type model to Uber ify their staffing agency and make it very self service and help them scale with demand almost infinitely. So we signed a couple of these medical staffing companies and moved very quickly, quickly learned their language and learned what it took to succeed. So that helped inform the building blocks we would add to the platform.
Tito Goldstein [00:15:00]:
And so that has been kind of, you know, an ICP for us now for a while where we’re actually able to see folks spin up a new medical staffing company with little to no admin staff and scale this to multi, multimillion dollar businesses where they’re now saying, hey, I’m bored. What’s the next business I should start? Because TeamBridge’s operating system is able to operate so much of that kind of, you know, automatically, as technology should.
Omer Khan [00:15:22]:
What were some of the biggest objections you were getting from customers when you were trying to pitch the product?
Tito Goldstein [00:15:27]:
Well, I think that, you know, even still today we’re going into an industry that typically is used to like a cookie cutter software, something that just does one thing, it does it well. And we’re coming in and saying, hey, it can do what you ask of it with a. In the world of AI, when you know you’re actually prompting something, it’s not doing one thing what you can’t say, what does ChatGPT do? And in the same way, when people ask, what does TeamBridge do? It’s let’s say, hey, you know, it could be an amazing time tracking tool. It can be an amazing learning management system. People build the tools that help them stand out into the platform. So I think that objection and that education moment is something that is TeamBridge’s greatest strength. But it’s also kind of a growth edge or a learning curve where each of the industries we go into has to be kind of, you know, rewired to think, wait a second, my scheduling tool can actually make me money. My scheduling tool can help help me incentivize staff to pick up more shifts or whatever metric I’m tracking towards.
Tito Goldstein [00:16:21]:
And that’s something that I think oftentimes requires a few objections and a few kind of educational moments.
Omer Khan [00:16:28]:
Yeah, I mean, I can imagine any busy business owner or leader kind of hearing that and saying, great, but I’m so overwhelmed with my job right now, I was hoping this was just going to be a plug and play thing that I can use right away. So presumably you had to find these early adopters, people who were actually excited about being able to do this level of customization. So how did you find those people within this kind of pool of potential leads and prospects?
Tito Goldstein [00:16:58]:
Yeah, so very early on we were kind of doing a lot of the typical things. We were subscribing and paying for leads from Software Advice, Capterra, G2, like these Gartner services that are like SEO aggregators. And, and I think that was good for us just to have those initial conversations. And I think those initial conversations allowed us to refine the message and say, what does this industry specifically need? For example, with a medical staffing company that does like, you know, shift based work, we could actually automate that away and make it an uber ified model. On the like, travel nursing side of things, we could get you to a place where you can auto submit travel nursing profiles. So I think we had to understand the language. And so the step one was the conversations. Once we had like the, the understanding of the industry and what would inflect their revenue, we could actually go out with that messaging in any channel, whether it’s calling, emailing, texting, showing up at conferences with that message, sponsoring, you know, dinners and events.
Tito Goldstein [00:17:56]:
There’s all these different ways you can, you know, get that message out. But step one was getting that message because we. You get zero traction if you’re screaming a irrelevant message into the void.
Omer Khan [00:18:07]:
Yeah. You know, I came across an article recently which was talking about how companies are really desperately looking for storytellers. And you know, I’m big on storytelling. We’re telling a story here today about TeamBridge and you and Arjun and how you came up with this business and grew it. You mentioned to me earlier that initially one mistake you made was you were trying to be everything to everyone and things didn’t really click until you figured out what your story was. So tell me about what kind of issues you were facing. I think you’ve talked about some of those, but maybe just summarize that and then Tell me about how you actually figured out how to tell a story here.
Tito Goldstein [00:18:46]:
Yeah, so I think, you know, when, even when we were showing up at conferences, my instinct as a builder, like Arjun’s instinct as a builder, is to be like, we can build it, whatever it is, tell us what you want. And that is not something that a business owner is going to lean into. So I think the hook was already missing, and I think the hook actually needed to be far more honest, especially when you’re in those very early innings and you haven’t figured out much yet. The hook was, hey, like, we spent a lot of our careers building amazing technology at Uber. We want to now build that to you, bring that to your industry. And so the folks who are the right customers for that stage of company will lean into that message because it is honest and true. So I think we, we switched that message, and all of a sudden we had these customers who were the right customers who were giving us ideas, who are excited. Who are those first early adopters willing to go through the pain with you because they saw that same ambition and that same future that they were optimistic about.
Tito Goldstein [00:19:42]:
Now, obviously, as the company matures, you know, our messaging and our, our kind of, you know, product obviously has evolved and now it is more focused. Now we’re like, hey, we’ve got this playbook. We’ve got this template. We’ve got exactly what a massive enterprise medical staffing company or an NFL stadium needs. And we will go to them and say, hey, like, based on everything we’ve heard in your three, here’s your template, and then here’s the 20% that you can start to, like, you know, configure and build and stand out and optimize for. So I think, you know, understanding that your messaging has to be true because a customer ultimately will see through the lies, like, and also the right customers will be attracted to the truth of what is going on today at your company.
Omer Khan [00:20:24]:
You know, you told me earlier that you cast a very wide net initially when you were looking, figuring out who your ICP was. And there was some upsides to that because you were able to figure out all of these challenges in different verticals and where, you know, how you could build the right product that would be horizontal, I guess. But this is a problem that a lot of founders have at this stage where there’s this reluctance to narrow down, niche down. And so you try to go as wide as you can. Just explain what were some of the issues that you experienced? You know, what was the downside of doing that, yeah.
Tito Goldstein [00:21:05]:
So I mean downsides to me were, you know, pretty apparent kind of constantly because even though TeamBridge is composable, even though we’re Legos and building blocks, one industry is going to ask for Legos A and B and another industry is going to ask for Legos C and D. And prioritizing one inherently means like you have to cut the other. But prioritizing both means you inherently have prioritized nothing and now you’re going to be the slowest moving player in that space and you’re probably not even going to deliver the value that you know, the segment you focused on wanted in the first place. So I think that yes, we benefited a lot from hearing from a lot of customers understanding how employee management at scale across many different verticals. But as soon as we found kind of that vein and that truth, you know, with medical staffing, healthcare, we started pulling that thread and we started building deeper into that, providing more and more value. And sure, we kept as product people, we kept an ear out to be like, are these agnostic components that any employee would benefit from? But we still had to focus both in our go to market and our product to make sure we are delivering the utmost value there. Now the cool thing about TeamBridge is that we actually are able to go into a new industry, hear from them and then compose usually 80 to 90% of the way. There’s oftentimes much better than the incumbents who are sitting in that space building vertical specific SaaS.
Tito Goldstein [00:22:24]:
But from a go to market perspective, we are always going to be like focused on like, you know, our icps, otherwise the messaging will get lost and distracted. And candidly, our customers, you know, won’t trust us that we are like leaning into their space.
Omer Khan [00:22:37]:
So that first customer was in kind of the medical field. Did you then say let’s just double down on medical or were you still trying your luck in different verticals to see what would stick?
Tito Goldstein [00:22:48]:
I think for a while we probably made the mistake of like, you know, leaving the, the doors wide open. And then as we started to bring on go to market experts, because me and Arjun candidly are just not that we started bringing on people who are actually successful, you know, salespeople who’d been there, done that at early stage startups, they were like, no, we gotta focus and we’re like cool. Then the conversations become much more pointed, they become much more focused and, and your product roadmap becomes the same. So I think, you know, we made the mistake of leaving that door a little bit open. But now it’s much more intentional. And we have, you know, medical staffing, we have, you know, other types of staffing. There’s kind of like that Venn diagram for us and we start to see these adjacent markets being the most logical next steps for us. So we actually aren’t even, you know, you know, expanding, you know, just experimenting willy nilly.
Tito Goldstein [00:23:36]:
We’re actually going after the adjacent markets that have a lot of overlap, maybe even sometimes overlapping workforces.
Omer Khan [00:23:43]:
Okay, great. So that makes sense. Tell me about. So you went from like having like your customers were like anybody who was interested, anybody who would talk to you, and mostly there were smaller businesses, SMBs. And then at some point you started to move up market to enterprise. When did you feel like you were ready to do that, that that was the right decision?
Tito Goldstein [00:24:05]:
Again, I think it’s been very organic. I think that we followed where the market was pulling us. So in this case we realized that a small SMB company probably is okay with something that’s out of the box and not super flexible versus a mid market company or even an enterprise probably has specific things that they want that no software can provide. And so because of this like we actually realized that our whole value proposal gravitated towards like the larger companies that had more opinions, that had more differentiation, that had the resources to probably hire people to do it manually, but now wanted to turn it into technology. Because if you think about this industry, these spaces, they have like the truth, they have this, the, the knowledge boots on the ground, but they don’t have like the product skill or the engineering talent to go and execute on them. And that’s you know, where TeamBridge and now, you know, this, you know, AI revolution comes in and is it shortens the distance between ideation and execution. And TeamBridge was that best of both worlds, build versus buy, where they could deploy an enterprise grade technology without spending millions and millions of dollars to whiff on an mvp.
Omer Khan [00:25:12]:
So you mentioned earlier that you started out getting customers just going door to door, doing a mixture of customer discovery and trying to do sales. Then Covid hit and that as you told me earlier, people weren’t opening those doors anymore. What happened to your go to market motion? What did you have to start doing at that time?
Tito Goldstein [00:25:34]:
Yeah, I mean Covid hit really early in the journey for us. I think we actually signed a new lease February of 2020 and then March of 2020 SF went on lockdown. So I would walk to the office by myself, kind of futz around in there, eat some of the snacks. I bought Till they were gone. And then luckily we were able to get on a month to month and eventually close that office until we reopened our HQ here in sf. Um, but to your point, like we thought, okay, you know, we’re scrappy startup founders. Everyone always says just talk to whoever will talk to you. So we’ll go just like we did early on, door to door at every cafe, find out what they’re using, maybe use that as a, you know, outbound.
Tito Goldstein [00:26:13]:
You know, hey, we talked to your, your employee like, and they hate this, like, want to see what TeamBridge can do. But since that was no longer afforded to us or possible during the COVID lockdown, we actually matured maybe faster than most startups do in terms of our channels. Like, we actually started outbounding, we sending emails, we started calling, we started texting, we started paying for lead gen sources to experiment and see what channel worked. And that was very kind of awkward at first. Again, not having any real go to market or sales people on the team and just two product guys who are like talking to, you know, business owners trying to learn. And again, it allowed us to be really close to our customers, but it probably meant that our go to market was like slower to gain traction than it could have otherwise been with someone who’s a pro. Hopefully that benefited us now because me and Arjun are still so close to our customers in that regard. But yeah, to answer your question, it made us kind of mature into maybe like a slightly more old school sales organization.
Tito Goldstein [00:27:08]:
But it works out when you’re going to an industry that is used to like legacy tech stacks that have been operating that way for a while. So it allows to kind of meet.
Omer Khan [00:27:16]:
Them where they were, you know, cold email. Every year we hear it’s harder and harder to, to get, you know, get that working. I’m sure you had your challenges back then. Tell me, tell me about what were some of the, the struggles in getting people to respond and what did you learn at the time to, to change that or improve the response rate?
Tito Goldstein [00:27:44]:
Yeah, I think, you know, ultimately it came down to the messaging, right. If you have something that’s very to the point and it’s the pain that they’re talking about that morning, afternoon and night, they probably will give you a shot. And, and to what I mentioned earlier, if it’s honest, if it’s, hey, like I was at Uber for five years and now I’m like, you know, curious about your space. Like you can be open about like where you’re at, the shortcomings and the wins And I think yes, email marketing is probably getting harder and harder and every channel will go through these like booms and busts as they get oversaturated and then people drop off of them and they have, you know, a, a dead count, dead cat bounce. But I think the, the, the messaging, you know, really is what matters. And then the second piece I’ll maybe double click on is that your first message is not going to be, you know, the oh my God, everyone’s clicked on this. But you’re actually building relationships that you don’t even know about. So when you then start showing up at conferences, when you then start, you know, running ads, when you start, you know, being More active on LinkedIn or wherever comm, whatever communities you’re customers are in, you actually start getting that recognition because like, hey, I remember your name because you sent that email.
Tito Goldstein [00:28:52]:
I remember a salesperson on your team sent that email. And that’s the icebreaker that you need to ask them a genuine question and dive into the discovery to see if their pain matches your solution.
Omer Khan [00:29:03]:
And for the people who responded, how, how easy was then to get a meeting with these people and how easy was it to turn that into a sale? I’m sure it was like this was just, was like, okay, I’ll listen. But then you’ve got the next level of challenges that come along. So what was your experience?
Tito Goldstein [00:29:22]:
Yeah, so I mean I think during COVID it was fascinating because I don’t think our industry was used to zoom calls, especially when we were talking about the mid market and SMB. So that was an entirely new ballgame for them. They were used to people like coming to them shaking their hands. And now we’re kind of, you know, back to that world a little bit where especially in the enterprise world, we want to be, you know, face to face with our customers. These become long term partnerships where their entire business runs on the TeamBridge operating system. Their operating system they’ve configured using TeamBridge. So I think that you know, folks were reticent, you know, especially in the small SMBs to take zooms back then. Now it’s more normalized.
Tito Goldstein [00:29:59]:
But usually when we got people on like calls, they were very excited about the product because of the flexibility, because it was a completely different ballgame than they were used to with legacy workforce management solutions. Payroll, scheduling, time tracking, they all not only looked antiquated, but they didn’t move the needle for the business. And then we came in and said, hey, this is not just a utility, this is your differentiator. This is how you actually pull the levers to make more money as a company. So I think that, you know, we’ve always, this has always been a case with Team Bridges. Once people were like on the call, they were, you know, very excited about the platform and usually kind of, you know, ended up being know customers of ours. But yeah, you’re right. Like, I think, you know, getting folks onto the demo, seeing the pl, the product is something that, you know, that is that first, you know, step in the funnel.
Tito Goldstein [00:30:46]:
You have to have enough value and you have to position yourself as that. I’m going to help share what the latest and greatest is. It makes sense for you to come check it out, right? I think question Based Selling is a great book to kind of, you know, unlock some of those nuances of how you message and how you don’t just sell, but you actually offer up insight. And if you are, you know, whether you’re podcaster, whether you’re a CEO, whatever it is, if someone comes to me and says, hey, would it make sense to see what’s the best, latest and greatest out there? Like, it’s hard for me mentally to say no to that. But that’s like, yeah, of course. Like I, that’s my job.
Omer Khan [00:31:22]:
Was this something that on the emails or on these zoom calls that actually really resonated with people because I guess many founders would go in and just start talking about how great the product was, how you can do everything, all the features, you already realized pretty quickly that that wasn’t the right approach and you needed to tell a story. But I’m curious, there’s usually something that once you figure out whether it’s a specific pain or some kind of outcome, that really lights up your icp. So back then, what was that? And you know, did you figure that out?
Tito Goldstein [00:32:05]:
Yeah. So the interesting thing about TeamBridge, right, is we have to figure that out for every industry we go into. So for like medical staffing, like there’s even within medical staffing, there is actually unique for sub verticals. So 30% of the industry is actually per diem, which is like basically shift by shift, claiming. You can think about it like, hey, I’m a nurse, I want to work tomorrow morning and I want to, you know, earn that money. Or you may be a more popular or commonly known is travel nursing, where a nurse will say, hey, I want to work for 13 weeks in California, or I want to work 13 weeks in Colorado. And because of that, like, they’re actually completely different in terms of what TeamBridge can offer them on the per diem side, we came in and said, hey, this is now the Uber, your version of the Uber app to be able to like, you know, self request and completely make the entire experience for the nurse self service and automated. Now on the travel nursing side, which is a little more high touch, we use our automation engine for something entirely different, which is putting together the packets of a nurse and then letting them submit as fast as some of the biggest, most tech enabled competitors out there.
Tito Goldstein [00:33:07]:
So even now, the mid market and smaller travel nursing agencies, or you know, the enterprise folks that come to us can be on the cutting edge of technology without spending hundreds of millions of dollars to staff that. So the messaging was completely different. That moment that you called out of, when someone lights up, completely different. And to that point, I think every founder should know that every sales call should start with a serious amount of discovery. Because if you just start selling your product and then at the end of the call they say, well, I didn’t want any of that, then you’ve just completely burned this amazing opportunity to have a conversation. So your discovery has to be very tactical and you should hold that point. So if someone mentions something that you do really well, don’t just jump at it because that’s the exciting thing a founder will do, but instead hold on to that and then when you get to the demo, make that callback to that very key value point that is most important to them so that your product and their pain kind of are very aligned.
Omer Khan [00:34:00]:
But it seems to me that it becomes really hard to sell to these different verticals because of these nuances. And if you don’t understand them specifically enough, you’re going to go out with this really watered down, diluted message designed to work across any industry or vertical. So when you went into a new vertical, did you kind of go through a process and say, we’re just going to do customer discovery again and we’re just going to try to go deeper and understand what these nuances are.
Tito Goldstein [00:34:29]:
Yeah, so that’s spot on. Yeah, that’s actually spot on, Omar. Like, so every time we’re in a new vertical, we know we’re naive, we know we don’t know anything, but we’re confident in our ability to provide, you know, an entirely different ball game than the legacy competitors. So for example, we now have the 49ers Levi’s Stadium on TeamBridge. And when we first went into, you know, the stadium space, we didn’t know what they did, but we learned that because it’s only 20 events a year, at the stadium, they have to restaff the entire stadium every game because it’s not a full time job, it is a part time hobbyist job. And so when they’re trying to restaff 3,000, 4,000 people across parking, guest services, custodial security, they’re sending out 30,000 emails to try to get 200 people to show up as parking flaggers. And they had no levers outside of emails to be able to do that. And their core workforce management software wasn’t going to be able to do that because it was just payroll and it was like, you know, the same thing for every.
Tito Goldstein [00:35:24]:
But. But now they can actually build incentives directly into their playmakers app, which they use to broadcast out opportunities and get people to show up. And so now we learned this playbook, we learned what, you know, a football stadium, which is very different than an NBA or NHL stadium needs. And so, yes, we go in very kind of, you know, eyes wide open, like, let, let’s figure this out. And we, we, we have to find partners that are willing to, to again, back to the core messaging, right? When we come into a new vertical, we say, hey, you know, we worked at Uber a lot. We’ve been doing a lot of this in healthcare and other industries, but now we’re interested in, you know, bringing that same opportunity to your space. If you want to be a first mover, if you want to differentiate yourself before anyone else does, like, come, let’s talk. And then very quickly, because of how fast TeamBridge can move, maybe on that same call or maybe on the next call, we’re actually able to deliver a solution that is more tailored to their needs than vertical specific software that spent 20 years building specifically for stadiums.
Tito Goldstein [00:36:20]:
And that’s the super exciting thing, is that when we can build something that beats another software at its own game and provides more value to the customer, on day two, we get super excited about what we can do with a couple more Legos or a couple more building blocks.
Omer Khan [00:36:35]:
Love it. Love the Lego analogy. I’m a Legos fan, so that’s great. All right, we’re out of time, so let’s just wrap up. We’re going to get onto the lightning round. I’ve got seven quick fire questions for you. You ready?
Tito Goldstein [00:36:46]:
Yeah.
Omer Khan [00:36:46]:
What’s one of the best pieces of business advice you’ve received?
Tito Goldstein [00:36:49]:
I think it’s all about grit. If the person who wins is the person who sticks with it longest, and the people who give up naturally don’t get that big payout, what book would.
Omer Khan [00:36:58]:
You recommend to our audience and why. And you can say the same one again. You mentioned earlier, if you want to.
Tito Goldstein [00:37:02]:
I think I’m going to say the book you are now less dumb. It’s a fun book about psychology that then goes into, you know, why you think something that’s actually wrong about yourself. And I think that helps you kind of open up about, you know, all the mistakes you potentially could be making.
Omer Khan [00:37:16]:
What’s one attribute or characteristic in your mind of a successful founder other than grit?
Tito Goldstein [00:37:21]:
Well, I mean, grit’s definitely top of mind, but I would say curiosity. I think innate curiosity to be able to seek out the truth, understanding that you could be wrong every step of the way and admitting that and moving forward with the new truth that you uncover.
Omer Khan [00:37:34]:
What’s your favorite personal productivity tool or habit?
Tito Goldstein [00:37:37]:
I think, honestly, fitness is the most valuable thing for me. I think that when I am healthy, food, fitness, like, sleep, all that, I am inherently better. I don’t think it’s actually like, you know, products or anything else. It’s just like if your mind is clear, if you are coming into the space with optimism, you can truly kind of, you know, unlock, you know, a different wavelength.
Omer Khan [00:38:02]:
What’s a new crazy business idea you’d love to pursue if you had the time?
Tito Goldstein [00:38:05]:
Oh, I’m not sharing that. That’s mine.
Omer Khan [00:38:09]:
What’s an interesting or fun fact about you that most people don’t know?
Tito Goldstein [00:38:12]:
I am a creator through and through. So I have brewed beer. I have made soap. I have made paper. I am currently converting a Mercedes sprinter van to a camper van in my free time, which is limited, so it’s a very slow project. Um, and I have a dog named Callie. She’s half German shepherd, half husky.
Omer Khan [00:38:33]:
Well, out of those, what’s one of your most important passions outside of your work?
Tito Goldstein [00:38:36]:
I think writing. So as a. As. As a child, I always really enjoyed writing, and I’ve stuck with it. I think, you know, if I got asked the question, what would you be doing if, you know, you stopped teenbridge or you didn’t have to work? I’d probably, you know, write both fiction and nonfiction.
Omer Khan [00:38:51]:
And I think in this age of AI, I think real writers are actually becoming a pretty valuable thing, hopefully. Yeah. Great. Tito, thank you for joining me. It’s been a pleasure. If people want to check out TeamBridge, they can go to teambridge.com. if folks want to get in touch with you, what’s the best way for them to do that?
Tito Goldstein [00:39:11]:
Yep. So you can connect with me on LinkedIn. I’m probably the only Tito Goldstein out there, so my SEO is usually pretty easy, but you can always contact TeamBridge through the contact forms. And I oftentimes are very close to our customers, so I love getting to work with all types of new entrepreneurs and business owners.
Omer Khan [00:39:28]:
Awesome. Thanks man. Appreciate the time and I wish you and the team the best of success.
Tito Goldstein [00:39:32]:
Thanks so much.
Omer Khan [00:39:33]:
Cheers.
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