Role-playing and The Value of Practicing Sales Calls
March 31, 2025AltFinanceDaily asked several brokers over the past month about the value of role-playing with colleagues to prepare for real life sales engagements. Below are some excerpts of what they said.
Cheryl Tibbs, Commercial Capital Connect: “Before my broker life, I was a call center supervisor, so just really familiar with call centers making cold calls and that type of thing. So it’s very important [to role play], I think you have to practice. You don’t want to read a script, you don’t want to sound robotic, but you want to be engaged enough where you can have a good conversation with people without having to really think about it.”
Is there a point where practice is no longer necessary?
“Our industry changes day-to-day, little by little, things are changing. So I think it’s just always incumbent upon us to sharpen our skills. That means practicing at least once a week.”
Josh Feinberg, Everlasting Capital: “Role-playing is like stretching before going for a run. It makes it possible for you to be fast on your feet and really be able to have the answers when you’re talking to a, let’s just say, a construction company that does equipment financing, and they’ve financed all of their equipment. A lot of times they’re going to be more knowledgeable about the equipment financing and leasing product than a lot of the brokers that are going to be talking to them in regards to it.”
Is this something you do with your own reps?
“Yes, especially when someone is newer or starting out, role playing is essential to even a point just like on Equipping The Dream, we need to make sure that we’re call-coaching too. While we’re listening to them on the phone we’re in their ear telling them what to say, just to have them get used to it. And then we do a bunch of different role playing…we’ve done it hundreds and thousands of times over the years”
Adam Oster, Canyongate Financial: “We have a set list of questions: understanding the merchants needs and building that relationship. And if I know somebody’s really good but they’re not doing well, then we’ll go back and say, ‘Hey, let’s role play. Because there’s something—you’re too complacent, you’re missing something, or you’re not listening to the customer.’ So role play is very important.”
How does this take place?
“If they’re here locally, we’ll do it in-house a lot of times. I’ve got a couple people—one in California, one in Austin, Texas, so we have to do it over the phone. And if somebody’s thriving, I’ll ask them, ‘What are you doing? What are you saying to your dealerships or your customers that are helping you get deals?'”
How AI is Scaling a Veteran Small Business Financing Brokerage to New Heights
March 19, 2025“There are [AI] voice systems out there that have just blown me away,” said Cheryl Tibbs, owner of Atlanta-based Commercial Capital Connect. “So we are using those and I’m implementing some in my office in my day to day—we have an AI receptionist that answers the phone, it just frees up time.”
As a broker, Tibbs recognizes the value of being able to answer a potential client anytime, anywhere, but there needs to be time to sleep, train others, and expand as well. And thanks to the advent of actual AI, it’s now become increasingly possible to scale on multiple fronts where it wasn’t before. Tibbs told AltFinanceDaily that she’s been using AI to duplicate herself across anything she can.
“So we train these models on everything about our business, everything about us, and it can just answer questions, either through chat or having a conversation,” she said.
AI can call leads or qualify a customer through online chat at three in the morning if need be—not theoretically; it’s doing it for her already.
“Some mornings I wake up, I see full conversations between the conversational AI and somebody that filled out a lead form,” she said. “The chat agent has the ability to send them a text message with our full application link, or book them on our calendar.”
But more customers coming in the door means more questions from her team about where to place a deal. She’s got a solution for that, a bot she created named BrokerBuddy that can answer on her behalf when she’s not available to do it herself.
“I trained it on most of the lender guidelines that we work with, so they can just go in and just type a question, you know, ‘hey, BrokerBuddy, I’ve got a customer with a 680 FICO score.’ He says, ‘two years time in business, looking to buy a $40,000 skid steer. What else should I ask him? Which lender in our organization do you think will do this deal?'”
There’s a role for AI to just skip the questions and place a deal all by itself using advanced algorithms, something many tech companies tout these days, but the human nuance is a key component to her service, since any deal could be equipment financing, SBA, or working capital rather than solely one thing. It’s not always immediately obvious which one it’s going to be or what the customer would prefer. Way back in the day, Tibbs started purely with MCAs, back when they could only be done via a credit card machine. Since then she added equipment financing, working capital loans, and SBAs. For a long time now, she’s offered it all. She pairs up customers with the best fit and relies on her knowledge and relationships to know what’s going to work and what’s not.
“SBA is a hot button right now and merchants are really excited to know that this is definitely a possibility,” Tibbs said.
One opportunity with SBAs in particular is to consolidate MCAs, which, if the business owners qualify, can have a tremendous impact. Sometimes these business owners find her by seeing her posts online, and they reach out. Maybe it’s her they’ll get right away, or maybe it’s her AI. In any case, all of her experience has long since led other brokers to refer their own business to her, since she has a reputation for being able to get the deals done.
“I’ve been operating as a super broker most of the 20 to 25 years that I’ve been in this alternative space,” she said, “and as a super broker, I’m able to offer my broker partners more stuff than they even thought about. […] I study this stuff. I eat, live, and breathe it.”
While it’s unclear if AI qualifies as alive, her band of automated agents are beginning to breathe the rush of it all right alongside her. So many brokers (and lenders) are diversifying their product sets that her referral business is escalating, and she wouldn’t be able to scale without the assistance.
“Even though we get appointments, if we’re not on the phone with that merchant usually within three to five minutes, sometimes it’s hard to get them back on the phone. And even if they make an appointment, they may not show up. Having that instant engagement it definitely helps.”
Talk to People, Ask Questions, and Deals Are Everywhere
March 17, 2025“Well, when everybody says it’s tough, that’s when I start smiling, because I’m going to sit there and collect them all,” said Adam Oster, Director of Canyongate Financial. Oster was talking about financing deals for trucks in a tough market, though he’s known to be able to handle any kind of equipment in any kind of market. Part of the joy he gets from the challenge of the job is rooted in just how many great people he gets to speak with. Connecting, helping, and building relationships are his passions. And it never stops for him.
“I like to jump in and do everything. I have to have direction so I got to be talking to somebody,” Oster said.
True to form, when he’s taking a break from talking about semis, box trucks, and medical equipment, he’s marketing 3″ filled bones, beef cheek rolls, and gourmet treats for dogs.
“My fiancée has a dog food company, so Thursday, Friday, Saturday, Sunday, we’re out slinging dog food, we’re promoting her business,” said Oster. That business is called Abby’s Barkery, and he’s proudly featured on the company’s main Shopify page. Sometimes the two worlds overlap—in that he could be processing payments for treats while placing an equipment deal at the same time.
“…by 7:30 you get home and you’re like, ‘I think just every day is Monday.’ That’s how I’m going to look at it. Every day is just Monday in my life,” he said jokingly.
Oster began his career in mortgages, followed by a stint as the owner of a supplements store. He launched Canyongate right in the early days of the COVID pandemic after a colleague said he’d be really good in the field.
“When we came on we were strictly working capital, and working capital has its peaks and valleys, so I needed to fill the gap when working capital was down,” Oster said. “I’m like, ‘Hey, let’s transition here.’ So we started onboarding.”
Onboarding with equipment financing providers is precisely what he did. It helped that some of those providers were located right in his own neighborhood, which shortened the learning curve and helped lead to some great relationships. These days, Canyongate’s business is now 70% equipment financing and 30% working capital. Like others AltFinanceDaily has spoken to, not everyone who makes deals in equipment financing starts off by knowing everything about equipment.
“I knew enough in transportation, semis, trailers, that we lean there. But then I found very quickly that you got medical equipment—everything is a piece of equipment, essentially. So if I get a lot of invoices and I don’t know what they are, I have to Google it. I’ve got to look because the broker doesn’t tell you what it is. So I’m looking it up. I’m like, ‘Okay, this is a CNC machine… or this is a piece of yellow iron.'”
By now he knows so many things so well that he helps other brokers learn the ropes. As part of that he does coaching and training for large groups of people looking to break in. For example, they recently conducted an orientation for 500 people, where they started off by teaching them to focus on a niche. That could be semis or trailers or something else to get in the game. The deals themselves can come from anywhere, including simply knowing someone at the local gas station who might know someone who, in turn, knows another person—turning into a referral. It’s all about building relationships and asking the right questions.
“At the end of the day, it’s just conversation, ‘what are you trying to buy?’ And they’ll tell you. If I don’t know what that equipment is, I’ll say ‘what do you use that equipment for?’ They’ll tell you.”
For brokers already offering products like MCAs, they’re already on the call to steer the conversation in that direction if they so choose, but it’s important to do it thoroughly since the process to get a deal done is a bit more stringent.
“Ask if they need a truck, ask them what they need to finance,” Oster said. “When you’re submitting an equipment finance deal, it’s not an app and banks with no write up. You’ve got to tell me about the customer. Tell me about their experience. How are they going to use this equipment? There’s a lot of detail that goes into the deal before you even submit for underwriting.”
To that end, he said it’s important to set expectations for brokers looking to do equipment finance deals because it isn’t exactly the same even though it’s similar. On one hand if a broker can already sell a daily or weekly payment working capital deal then surely they’d be able to sell a monthly payment equipment financing deal. It’s a no-brainer when it comes to being able to offer the terms.
“Don’t fear it, ask the right questions,” he insists about taking the leap. And be prepared to ask them anytime anywhere. For example, he’s funded five MCA deals just through relationships he’s made through the Barkery.
“That’s a true story,” he said. “And I have pulled probably six or seven equipment deals out of the last year and a half from working at [my fiancée’s] business. So again, it goes back to it’s just conversation. Look at people’s needs. People tell me, ‘Well, I want to update my little shop and do all these things, I just don’t have the money.’ Well, what do you need? ‘Well, I need shelving, I need this…’ ”
Then he offers to help. Suddenly it’s the perpetual Monday all over again where he’s placing the customer while simultaneously processing payment for a good pup to chew on a lamb foot or a mammoth bone.
“And that’s how deals come about. Opportunity is everywhere. I love it. I get excited, man. I get all hyped up about this.”
How Mike Brooks Battled in the Ring and Won Top Broker in Equipment Financing
March 6, 2025
“Equipment Financing is HUGE,” declares Mike Brooks, CEO of New York-based Best Connect Capital and recent winner at Broker Battle 2025 in the equipment finance category at AltFinanceDaily CONNECT MIAMI. If his name sounds familiar, it’s probably because he appeared on stage as one of six finalists in the previous year’s competition. He refused to give up after his loss and returned this year for round two, leading to him securing a title and prizes along with it. To hear him tell it, it had been a long road to get there.
When Brooks got his start as a 27-year-old broker in 2015, for example, he had technically been battling in a ring for most of his life already.
“I had [boxing] on my mind in high school, without any influence,” says Brooks, “and I walked into a gym one day and the rest was history.” That history includes 60 fights in just amateur-level boxing, resulting in 45 wins and 15 losses. When he followed that at the pro level he went 11-2-1.
“I started fighting at the regular club shows, the Golden Gloves, the metro tournaments, national tournaments, and at one point, I was ranked number seven in the whole country,” Brooks recalls. “I beat some really good fighters, lost to some really good fighters and I made it to the highest levels in the country.”
Some of those fights even aired on live TV. As he bobbed and weaved for years in the ring, he started to think about what a possible career in business might look like afterwards. When that day came, he went to work for a local financial service company on Long Island who taught him about helping small businesses access working capital. Eventually he realized it was a business that he was uniquely suited for and now he runs his own company doing it.
First, there’s the endurance aspect, he explains. There’s a lot of calls, leads that don’t pan out, and heartbreak that hits when deals get declined at the finish line.
“A very small percentage of people can be a successful broker,” Brooks says. “You have to be able to take rejections all day long.”
To that point, Brooks noticed that as the industry grew he was not the only broker offering revenue-based financing to a client. Sometimes there were even as many as four or five other brokers talking to the same client at the same time, which meant that he wasn’t going to win every one and he did not want to bend his ethics just to eke it out. That’s when he started considering another approach and expanded his offerings.
“An equipment financing deal was my first big check during [the covid] lockdowns,” Brooks says. It was a $200,000 deal for a packaging plant. The terms were very attractive and he had the help of an equipment finance veteran who mentored him through it. When it worked out, he knew he had something very big in his arsenal and he’s been offering it ever since to anyone that qualifies for it.
“I said to myself anybody that needs equipment, this is a no brainer right here,” Brooks recalls of it. Now Brooks says when there is competition, he’s almost always the only one asking questions about equipment and the only one prepared to actually move forward with a deal tied to it. Of that experience, Brooks says he’s realized that some brokers have become so accustomed to the mindset of telling customers to take a specific deal, that they don’t stop to consider what they actually want. So his approach is to go in and diagnose what it is they’re trying to do first and then advise them of their options accordingly. And that’s what he does day after day.
At Broker Battle 2025, it was very much like time spent in the office. He was expected to be his normal self, but on stage in front of a large audience, while three judges played the role of prospective client and asked him questions about what they should do. The end result of it all was that Mike Brooks, former fighter in the ring, walked away as the Broker Battle champion in the equipment finance category in 2025.
“It felt amazing to be able to showcase what I do on a daily basis,” Brooks says, making it a point to say that even the venue took note of his win and offered him a personal congratulations on social media.
In the final photo-op on stage with his prize check, Brooks was the epitome of his dual life—the suit and tie spoke of business, while the cigar and sunglasses hinted at his former life in the ring. “I was a crowd pleaser,” he jokes. “You want to be like ‘bam bam bam’ and the crowd to be like ‘AHHHH!!!’ I want them to do that. I had a great time at AltFinanceDaily.”
Ryan Showe on Winning This Year’s Broker Battle
March 3, 2025
“What being a broker means to me is servicing your clients in the best way possible, really putting their needs before anyone else’s,” says Ryan Showe, VP of Sales at Long Island-based Lexington Capital Holdings. “Ultimately, at the end of the day, we don’t have a job if our clients aren’t happy, so just constantly doing the right thing, putting your best foot forward, and making sure that you’re doing everything ethically and honest.”
Showe was the winner of the 2025 Broker Battle at AltFinanceDaily CONNECT Miami for the revenue-based financing category, earning him the recognition of Top Broker and the recipient of some prizes along with it. Showe has been in the business for just a little over three years, starting at Lexington during its beginnings. Back then, learning the ropes while doing the work meant putting in 70-80 hour weeks on a regular basis. That included not only seeking out advice from the experts but also watching videos and reading books to fully immerse himself in the mindset of what it would take to become successful.
That effort is paying off and today Showe specializes in the most delicate part of the process at Lexington, helping clients who have applied get to the finish line with a deal while managing lender-side negotiations and communications. On the latter side, that means being highly familiar with the guidelines of more than 60 financial service companies at any given time.
“Anybody can get someone to apply and just fill out a quick one-page application, send over a couple bank statements, but really selling the deal, there’s a specific art to it,” says Showe. “It’s really important to be an expert in your industry and know all the lender guidelines, know what the backend process looks like, because every lender is going to have a different process, whether there’s certain steps that some lenders want, whether it’s a manual-login or DecisionLogic. There’s so many ins and outs to every different lender. And just being able to know all that off the top of your head and just really sound like an expert.”
At Lexington, one of the recent educational team-building strategies was to host an internal Broker Battle in which 30 employees participated in a double-elimination competition. The company’s CEO, Frankie DiAntonio, devised the format and questions—not only role‑playing scenarios but also testing general industry knowledge with trivia. Showe says it’s good practice to be put on the spot in front of a crowd, because a key part of sales is thinking on your feet and executing when it counts. Doing it together with colleagues made for a fun experience in a company that prides itself on a family‑like atmosphere, while also mirroring the competitive nature of the industry where many brokers vie to serve the same customers. It’s game time all the time.
“I even tell my clients, ‘competition is always going to breed the best results,'” Showe says. “If you want the best of the best, you have to make people compete. And it goes down to even selling a deal, right? So if I have a deal and another company has a deal, compare my numbers against their numbers. I’m going to do anything I can to win that business.”
By happenstance, Lexington’s Corey Digiantomasso was one of the six finalists selected to compete in AltFinanceDaily’s inaugural Broker Battle in 2024, where he put up a very impressive performance. This year was Showe’s turn where contestants weren’t given much background on the format other than that it would be roleplay-based. Showe kind of liked the mysteriousness of it.
“I’m best at showing up and just getting the job done,” Showe says. “So just doing what I do every single day made it easier for me at least.”
On his victory, Showe described the feeling as awesome while also recognizing that his opponent in the Battle, Joe Sasson, was a very worthy competitor. A large crowed showed up to support both of them during the championship.
“It was great to just see all the hard work that I’ve been putting in over the last three years pay off and be crowned #1 in the industry. It goes a long way for not only myself, but for the company as well.”
BROKER FAIR 2025 – NYC
February 27, 2025Broker Fair will return to New York City on May 19, 2025. The event is geared toward brokers, lenders, funders, vendors and more in the commercial finance and small business lending industries. Early bird pricing is now available at brokerfair.org.
Broker Battle 2025 Champions
February 24, 2025Broker Battle 2025 took place at the Fontainebleau on February 20th during AltFinanceDaily CONNECT MIAMI. Video highlights and more will be available soon. In the meantime, here are the results and the top brokers:
Revenue Based Financing
Top Broker: Ryan Showe, Lexington Capital Holdings
Runner-up: Joe Sasson, Advance Funds Network
Equipment Financing
Top Broker: Mike Brooks, Best Connect Capital
Runner-up: Yaro Yarema, Capital MBS
Cloudsquare Announces Its New Integration with Rapid Finance
February 18, 2025Los Angeles, CA – February 18, 2025 – Cloudsquare, the premier end-to-end lending platform powered by Salesforce, proudly announces its latest integration with Rapid Finance, a trusted leader in Merchant Cash Advance (MCA). This new collaboration is set to redefine how brokers and lenders operate, enabling them to process applications faster, streamline funding workflows, and enhance overall efficiency.
Bringing Speed and Efficiency to Brokers and Lenders
For brokers and lenders, efficiency and speed are essential to gaining recognition in the market. Delays in approvals, manual data entry errors, and complex submission processes can lead to lost opportunities. With Cloudsquare’s seamless Rapid Finance integration, these challenges have become a thing of the past.
Key Benefits of the Cloudsquare + Rapid Finance Integration
· Submit deals effortlessly via API – Say goodbye to manual submissions and data entry errors.
· Bulk File Uploads – Attach necessary documents directly in the CRM.
· Upload files with each submission – Attach the necessary documentation directly within the CRM.
· Generate tailored offers instantly – Present funding options quickly based on merchant eligibility.
· Provide Instant Approval decisions – Close deals faster and gain a competitive edge.
Why This Integration Matters
Cloudsquare has always been at the forefront of MCA technology, offering brokers and lenders an advanced, scalable CRM solution designed to automate, optimize, and grow operations. With Rapid Finance now part of its growing list of lender integrations, brokers can accelerate their workflows, reduce processing time, and increase funding success rates—all within a single, intuitive platform.
Seamless Implementation for Brokers and Lenders
New users can launch Cloudsquare Broker with the Rapid Finance integration effortlessly, ensuring quick adoption and a fast return on investment. Existing Cloudsquare customers can easily add Rapid Finance’s API through a simple license upgrade, with expert onboarding and support to ensure a smooth transition.
About Cloudsquare
Cloudsquare is the leading end-to-end lending platform, uniquely powered by Salesforce to deliver unparalleled flexibility and innovation for lenders and brokers. With a commitment to optimizing lending processes through cutting-edge technology, Cloudsquare provides robust, scalable solutions that empower merchants to achieve greater efficiency and growth. Celebrated by industry leaders, Cloudsquare has earned a place on the Inc. 5000 list as one of America’s fastest-growing companies and is consistently rated a top service provider on platforms like Salesforce AppExchange, G2, Clutch, and Manifest.
For media inquiries, please contact:
Cloudsquare Marketing Email: marketing@cloudsquare.io
