Revolutionizing Construction Payroll Efficiency Digitization, Customer-Centric Trayd CEO Anna Berger

Welcome to the B2B Growth Blueprint podcast, where we talk with entrepreneurs, founders, and leaders at B2B services, tech, and SaaS companies to learn the systems and processes they've used to create success for their business. We'll also learn from marketing and sales experts to provide insights to help you grow your business. I'm your host, Mark Osborne, and the podcast is brought to you by Modern Revenue Strategies and their 10x ROI B2B Growth Guarantee. Schedule a free diagnostic call to learn the fastest path to double your B2B revenues in just 90 days. Hello and welcome to another episode of the B2B Growth Blueprint Podcast. I'm your host, Mark Osborne, and today I am very excited to welcome my guest, Anna. So I'm gonna read Anna's bio to make sure I get this Right. Anna Berger is the founder and CEO of Trade. Now, Trade is a construction payroll platform designed for same-day pay, which you can probably start to imagine why that's really valuable. Born into a construction family, Anna actually saw some of the back-office inefficiencies in the construction industry firsthand and its effect on sort of overall company health. I think that's probably part of what inspired her to, to Sort of found this. We're— we'll talk about that. As a result, the Trade team is focused on building the single back office operating system with payments at the core of the product. Anna has a great background. She's backed by Bloomberg Beta, Y Combinator, and the team is based in New York City. Prior to founding Trade, Anna was the co-founder of Curtain, which was a video dating app that was backed by Sam Altman and Joel Simkhai, the founder of Grindr. So Anna, thanks so much for joining us. Welcome to the show.

Thanks for having me. Excited to be here.

Awesome. So great background. Tell, tell us more about what you do there at Trade. Sounds like a really interesting challenge that you guys are tackling.

Yeah, the construction back office is so ripe for disruption, and it was truly born out of my dad's back office. I was spending time with him and his business in between Curtin and what is now Trade, and problem was right in front of me. I think it's not just his back office, it's almost every construction back office in the country. They're operating off of 7 or 8 different systems or manual pen and paper processes, and there's so much opportunity for digitization. So we're really trying to build kind of a business in a box for construction contractors.

That's really interesting. And I imagine that, you know, you being sort of like a second generation or maybe even more generations than that in the construction space, are you seeing that you're working with other You know, company leaders that are inheriting a business. And so now they've got sort of this, you know, mandate to transform digitally and all those things.

It is an interesting turning point. I do think we are starting to see the next generation taking over those family businesses. And for sure, those are the fastest moving sales conversations, right? Those are the customers that are like, I totally get it. I see the need for this and I want to adopt it quickly. I think the the people that have been working in the back office for 40 years are the people that are like, oh, a little resistant to such a change because if their process is working, maybe it's slow and old school, but it's not necessarily broken, right? They don't necessarily see the value of a tool that could save them, you know, 45 or 50 hours a week in manual work. So there's definitely that shift, but I think in general, Construction is at the highest demand it's been in recent years, especially in New York City. New York is on fire from a construction perspective, and these contractors are falling behind. So not only is it the next generation taking over, but it's, you know, everyone who's currently out and about is no longer able to keep up with the demand, and their back office is slowing them down. And so there's this increased curiosity and need for a software that can help propel them forward versus holding them back. And so I think from a macro perspective, there's this like more of a need to digitize and automate more than ever before.

So there's an interesting statistic. So we work with a lot of professional services and technology that is underpinning services. And the most common thing that happens when you don't win a deal is that they do nothing. You know, something like, you know, 40% of the time they just don't do anything. They don't change. The other 30% of the time is they will try to figure something out on their own, which is almost the same as doing nothing.

Yeah.

And you talked about that, you know, some of these companies that you work with, they've got a system that works, although it might be slow or it might not be as efficient as it could be. How do you build, you know, sort of the value in their mind to get to overcome that 70% that's either gonna do nothing or just try to figure it out on their own. How do you overcome that in the mind of your customers?

Every sales conversation is different. And I think this is something that like my sales mentor taught me is speak to their need, right? If you understand their business, you should be able to just like speak right to their biggest pain point. So for a lot of these, you know, older companies that have been operating for 100 or, you know, like literally 100 years, right? Like we have that were established in like the early 1900s, you know, for them, maybe it's like they want to save on overhead, right? Maybe they're spending $300K or $400K on their back office operations. So like, you can speak to that need first and foremost, right? Instead of speaking to maybe what's potentially frightening to them, which is like total digitization, maybe frame it as, why don't you want to like, let's save you a quarter million dollars a year in overhead and, you know, improve that bottom line, right? And start seeing the benefits that way. So I think I try to go in, once I understand a customer, I try to go in at the angle that makes the most sense to what their biggest pain point is.

That's so smart. And, and in fact, like the, you know, all the books, the best practices, everyone will tell you the way that you overcome that inertia is by connecting it to a real business outcome.

Yeah.

So it's not just, hey, you'd have the software and it would be great. It's, it's costing you this much money.

Yeah.

So that's just one thing.

Not only is the software costing you, but the people that are doing the software tasks and pushing, you know, putting the inputs in and out, that's also costing you, right? And so I think when you have those high-level conversations with the CEOs, with the comptrollers, with the CFOs of these construction companies, painting the picture and sharing those numbers with them, that's really when the door starts to be pushed open when there was previous resistance.

Yeah. Well, and, and also the, a thing that we've done that's been really successful is to not only put the cost, but even to sort of like turn that into every week that you don't have this in place, it costs you an extra this much, which really creates that urgency.

Yeah.

And, uh, sort of instigates the fear of, well, if we try to do it ourselves, um, we, it might take us twice as long. And if every week that we, uh, slide, that's costing us this much money, really builds that motivation.

Yeah, and I think as you go through the sales cycle, what's so exciting about Trade is it's not this pointed solution like so many construction tech platforms are. I think people have in the past historically gone in on time and attendance or have gone in on scheduling or have reporting or messaging software. And the benefit of Trade is it's this like holistic platform. It is an entire back office in one tool. And so as the sales cycle continues and you start to understand their business pain points, you can speak to those like needs and that kind of the where the real problems are and drill in with those specific proof points in the product. So like, for example, if I know employee onboarding is a struggle or like retention is an issue, right? And there's like if an owner is spending 10 hours a week trying to recruit, attract workers, retain workers, like that can be reallocated with a tool like Trade. And so It's just all about understanding the need as much as possible and then being able to say, here's a solution perfectly designed to address that.

Yeah, that's so smart that you, and it sounds like you've got sort of your discovery process or part of your sales process where you really tease out what their needs are rather than showing up and being like, let me tell you why this is the best software on earth. It's, well, what are your specific needs? Because then if it's around payroll or if it's around recruitment, as you said, you can really tailor your pitch to their most crucial need. There's an old quote, it's, you know, sell them what they want, then give them what they need. And so, you know, their top of mind burning issue might be X, they're gonna get all these other Y and Z benefits from implementing.

Yeah.

But if you talk about Y and Z, They might not give them the motivation to actually move because X is where they feel the pain.

Exactly. And I think this is credit to, we've taken a customer-centric approach from day one. I spent a year before I even like said the word trade out loud. I was interviewing hundreds of contractors and workers to understand the landscape and to be able to deliver on the need. So I knew like when I had like Recruited my co-founder to join me. I was like, we need X X X Y Z. Da da da da da. Like I we need this whole suite. We need we need to build this whole thing out. It's not just a one type solution. It's a it's a fifteen prompt solution in order to like truly deliver. And so there's been this you know feedback loop right from the customer all the way through, which has so helped with sales right because it's like I started building. with the customer in mind. I never said, oh, I think this would be a good idea. I like had it backed up by 15 or 20 interviews that I had already done. And so customer centricity from day 1 has allowed us to move to market as fast as we have.

That's really smart. Well, and, you know, obviously it's, you know, the best practice. You know, The Lean Startup says get out of the building and like have those conversations. So, so many founders though are sort of, what's the, what's the word, navel-gazing? Like they're, they can, they're convinced they can just look down and think about it and come up with the right solution. But the real key is, you know, all marketing starts with the market. You got to understand that customer, and you have a unique marketplace because you're almost two-sided because you have that end user that's the worker that's going to be getting the benefit, but the buyer is actually the, you know, the company itself.

Yeah.

Interesting that you started with, you know, understanding not the buyer but actually the user of the platform as much as the buyer so that you could, you know, build something that would have pull As well as push.

This is truly B2B2C. I think the initial version of Trade really speaks to that B2B product. The whole phase 2 of where we're going involves that end user. But I think the how I've gone about Trade from day 1 is creating a new type of feedback loop between this part of the ecosystem, right? And if you think about it, there's so many other players that touch Trade in this equation. There's The developers, the owners' reps, the construction managers, the GCs. And then once you start focusing on the contractor and the worker, it's a dynamic that's been untouched. And so that's really where we've drilled in to say, like, what can we do here that will make this person want to stay and come back and keep working really hard and then produce really good work and then win more bids? It's like, it's a— there's so much— what's the right word? It's a really, like, symbiotic loop.

Like a virtuous cycle.

Yeah, yeah, yeah. And super intentionally, right? Like, that's why it's such a meaty platform, because we needed to deliver on so much from day one.

That's really great. So you talked about, you know, getting out of the building and talking to potential customers long before you even, you know, sort of launched the business. So now you've, you've got this idea, you've, you know, built this thing. How did you go about, you know, sort of finding those first few customers? Did Did it sort of stem from your personal experience in the construction space? How did you move beyond your own sort of Rolodex of contacts into sort of those first customers that weren't friends of friends?

Yeah, I was lucky enough to have design partners through my family, right? We had our initial subset of users that, you know, I've known for a really long time. And I genuinely believe, you know, it was payroll, right? Like, I had to— like, no one does a favor of ripping out an ADP or QuickBooks as a favor to like their friend's daughter, right? So it was, I had to still really prove that we were capable and able to support their business. So that it wasn't even an easy feat to get those design partners, but we were able to build the barest bones MVP with really trusted friends and partners. And so that's what kind of got us to that P0 state. But I really believe like the The true test of do you have something worthwhile is if it's completely people that you don't know that are meeting you on the side of the road that start adopting your product and paying for it. And so really when we hit like our 10th paying customer, that's when I, who I hadn't known before, right? Who came through totally different channels, non-family connections whatsoever. That's when I was like, okay, we're, we're onto something here.

There's a there there.

There's a there there. If there are people that had no idea who I was, no idea who my dad was in this space, like, that's— now we're talking, right? And so now it's like, you know, let's keep it going. I try now not to touch my network at all. Like, now I'm going net new, completely kind of incremental, which is exciting.

So we oftentimes see that, you know, what leads to that success of getting outside of your network and really expanding is really understanding your ideal And the buyer personas and, you know, having a strong positioning strategy that can, you know, really help you differentiate from, you know, the other potential solutions in the marketplace. How did you go about sort of building that and refining that? Did you have formalized, you know, documentation on this is who our ideal customer is and this is who it isn't? Or did you kind of evolve it as you went through?

It is ever evolving.

Okay.

The, you build first for a specific customer, right? So I would say like P0, like MVP, barest bones of Trade was designed for a very specific contractor. I can like describe his entire business right now because I, we studied it, right? We studied everything about his back office operations. And then as you increase your customer base and start working with other types of businesses, the product starts to like shape-shift, right? And so because we're taking on like larger accounts and, you know, specific trades, we can, you know, the ICP now shifts too, right? So we are continuing to refine it. I think that I'll keep refining it. I don't want to ever put ourselves in a box. Of like, we only go after this person or this type of thing. Like, I think if we, we have a really agile, incredible tech team who can build and react quickly, and I think that allows us to keep feeling out the market and seeing where, you know, the most successful trade will be.

Do you use any sort of systems or processes as part of this refinement so that it, there's sort of like a regular cycle, or is it You know, is, and is it something that you bring your team around to collaborate on, or is it something that sort of you own in your role within the company? How do you, how do you keep it from not feeling chaotic if you're always evolving and, and not feeling like, well, we're chasing a different rabbit every day? But the team actually, you know, has a long-term plan and agenda. How do you manage that?

Yeah, well, we are like, early stage seed stage startup. So I think chaos is like our middle name, but it's like organized chaos. I would say we, we are, I think every person on my team feels super focused. We are building the all-in-one construction back office operating system. Clear, right? But I think the biggest insight within construction is no 2 back offices look the same. And so coming in, we knew that this would need to be a moldable, plug-and-play, customized platform that can slide into existing systems that could have potentially existed for 100 years, right? And so there is an element of like, we will be learning and absorbing edge cases for years to come. And I think that that's why startups have a chance to exist against incumbents like an ADP, right? ADP isn't pushing out, not to call them out by name, but they're not putting out updates every week, right? Like they stopped iterating on the product years ago, right? And that's why startups like Trade or like others in the space have a fighting chance. It's because we can continue to like innovate and I think that there's, in terms of systems in place, Notion is our best friend. We, we use Notion for everything. Usually, as I'm in customer calls and I'm out and about at association meetings, and I have like my ear to ground on the ground about what's going on in the space and what features I wanna build, I drop everything into like an Anna's wish list of product ideas. And then once a week, I'll sit with my co-founder and we will like triage, prioritize, and then, you know, create briefs and kick the team off. And so we have a product roadmap now through early 2025, right, of like everything we wanna build and how it slides into the overall timelines of knowing that we're also dealing with customer migrations every single day. So it's like, how do we juggle the present with like the future of the platform?

Well, and it's funny that you opened by saying it's, you know, sort of chaos and progress, you know, every startup is. But then you got to where you have a really pretty well-defined process where, you know, you capture ideas, but you don't call up your lead engineer at midnight and be like, I had a great idea today, you gotta change everything. Instead, you're taking the time to be thoughtful about it, to build this backlog of features that you think would be valuable. To then prioritize those to have a long-term plan. And that's something that's, you know, sort of so valuable that many founders sort of fall into that trap of, you know, it all came from my idea. So when I have a new good idea, it's still a good idea. Drop everything, change everything. Whereas having this system for evaluating it and then creating those backlogs is, you know, really valuable.

I think that the only time we would literally drop anything is for a really like unhappy customer, right? If there is something in their payroll cycle that has gone awry, we will go pencils down until we get it in a good spot. And it's nothing that new. It's not a new product feature, but it's like we're optimizing, we're fixing, we're iterating. Like we will— I've never said we'll be perfect from day one, but we are gonna like do our darndest, right? And so—

Yeah.

I think it's just like this hyper-commitment to customer service and customer success. That's when we would, you know, drop everything and get into that, like, you know, no movement until this is addressed.

Yeah, that makes sense. Well, so obviously technology is a big part of your solution. Obviously, you know, so product management and all those, all the things that come with a fast-moving technology. How do you, you know, what are other systems that you use to sort of keep your team aligned and going forward on a 2-year plan, but that pushes updates, you know, as frequently as weekly? I heard you say, how are you sort of create that cross-team alignment?

We are, it's the irony is I have been doing founder-led sales from the very beginning, but we've just brought on our first SDR to start really revving up our sales cycle. And with that has come the need to automate. So I, it's funny, I spend so much time automating construction back offices, but my inbox needed automation. And so, right, I was doing everything manually. So we've brought in a fantastic SDR who has just begun to like set up the infrastructure of sales for us. And so we're using sales automation tools for that.

Cool.

You know, already seeing like the volume increase, right? If it's one-to-many versus one-to-one and that would, you know, triple, quadruple our chance of success in deal flow.

Yeah. Well, and what we see is as companies grow is when you really understand who your best customers are, that gives you the ability to also understand who maybe your less best, least best customers are and implement systems that allow you to go, One-to-many for these, one-to-few for these in the middle, and then the— you can really swarm and put all of your best resources on those best opportunities because you've got a system in place that allows you to identify, hey, this actually has the potential to be really good. Too many times we see businesses that they don't have that system for identification. So everyone gets the same amount of attention. Which means that no one really gets good attention. Whereas when you have these systems in place that allow you to identify who gets one-to-many, who gets one-to-few, who gets one-to-one, then you can win those best opportunities. Because if you're not winning those best opportunities, you're, you're left with the scraps and what your competition doesn't want, and that'll really kill your business.

Totally. Totally.

So I know you have a background in, you know, sort of other marketing and sales stuff. How has that Sort of informed the way that you've approached growing Trade?

Yeah, before Trade, I was deep in the consumer lifestyle space and it's truly, if anything, it taught me like do things before even the Y Combinator mentality of like do things that don't scale. And it's taught me a lot about Trade. And so for me being in consumer and dating specifically, it was all about in-person events. and being where the customer is at the moment in which they're willing to engage with you. And that is, I think, just Sales 101. Like, if you have that insight and understanding of that truth, but then also exactly where they're receptive to meeting you and meeting you not even physically, but also just like mentally being open.

Yeah.

Then you're gonna be successful, I believe. So, you know, running a dating app for you know, 3 years and then working with the founder of Grindr on his next app for another year plus, it was all about in-person and street team activations and bringing people into the brand so they could feel it and understand it and, you know, interact with it in a way where when they walked away, they kept it with them. And I think that that's something I'm trying to bring into trade, right? Like, how do we make a B2B2C Totally software tech-enabled business feel like a community. And so I think as our strategy continues to evolve, all of my consumer experience will start to trickle in.

Oh, yeah. Well, and what's funny is, you know, we work exclusively with B2B folks and some B2B2C. But the thing that we see so often is that a lot of B2B companies forget that there are actually people on the other end of the decision and people are emotional animals. And so when you lose all of that, you know, sort of appeal to emotion or all of that sort of personal connection and just focus only on the logic of why this product is better than this other product, you really lose out on a lot of opportunities. And we always try to define, you know, for the buyer personas and, and, or even sort of the different champions that will be on, or members of a buying committee. So you will have a champion, a technical influencer, the sort of technical buyer. We'll identify what's their personal win from engaging with a particular solution, buying a particular product, as well as what's the professional win, like what makes it a right thing for the business and also what makes it right for that person. What's the sort of bigger Issue that they care about that they're hoping that this product is gonna deliver for them. And I'm sure that really helps in crafting your, you know, sort of go-to-market strategy and your sales pitches that you're using there for Trade.

Yeah, it really matters how you make people feel. Yeah, it really, really does. I think when you— and I think you can do that from a product-led perspective. I think what I'm seeing now Being so tailored to construction contractors, like we do have a really tight ICP, um, that it's not for a GC right now. It's not for a construction manager right now. It's not for the developer. It's for the contractor. And my product is like speaking to them and it's making them feel understood because they're like, oh wow, these, these features are like exactly where I struggle and exactly what I need. And then for there to be, you know, support and marketing and, and like communications and networking events that make him, that person feel like it's not just me that needs this, it's our whole network that needs this, and I feel understood. That makes a difference. That's when we're starting to get the phone calls of, hey, I heard about you from a friend. And that's what we're starting to really, really see happen. I've had calls where, you know, I was told, you know, reach out to this person, and I thought I was gonna have to do a full Full demo and full pitch, and I get on the phone. He's like, "No, all my buddies use you. I'm good. Let's go." You know, it's like, okay. Like, and that's especially in construction where everything is like quick, fast, word of mouth, phone call, this, that, call your friend. It's like that's where it's like, okay. When you make people feel understood and heard, that's when the product is gonna take off.

That's that's so great. So. Might have some folks listening that might be in a place to, you know, sort of explore a product like this. Give us the pitch. Like, tell us why they should work with Trade, why they should give you a call.

Yeah, we are saving contractors hundreds of hours a month and thousands of dollars in overhead on back office operations. So if a contractor is looking to streamline everything from time and attendance, scheduling, payroll, reporting, You know, we're the platform. We are, you know, all hands on deck in New York City and so eager to support. So any questions, you can reach out to support@buildtrade.com or me personally, anna@buildtrade.com, and I'd be happy to answer any questions.

So, Anna, thank you so much. Appreciate all your time and sharing all of your insights with us. We could talk all day, but I want to be sort of mindful of your time. So give us some closing thoughts. What's something that's either on the horizon that you're really excited about or some recent development with Trade that has been really exciting for you?

Yeah, we were just listed as a top 50 SaaS company. So that's really exciting by Bain Capital. So being recognized as a vertical SaaS player in the space this early in our journey is something really, really exciting and I think speaks to the fact that we are, you know, delivering on a need in a real, a big industry, I think is really exciting. And yeah, we're on the, we're on the road to $1 million in ARR. So we'll keep in touch and hopefully be there sooner than later.

That's awesome. Anna, thank you so much for joining us. Appreciate you coming on the show today.

Of course, anytime. A pleasure. Talk soon.

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