Secrets from Successful Sales Teams to Turbo-Charge Yours

It took five years of building a relationship and following up for Chicago-based decorator Rowboat Creative to close a sale with a large music industry merch group. “Another decorator had burned them, and it was finally our time to make it happen,” says Lucas Guariglia, CEO and co-founder. “We turned out 30,000-multi-location imprints in two days for two sold-out shows at Soldier Field. Our team’s persistence in earning the sale and then coming through like we did locked in the relationship, and we’ve been off to the races ever since.”

We asked some of the apparel industry’s top sales managers and salespeople to share their up-to-the-minute strategies for standing out, leading profitable sales conversations, overcoming cold-call jitters and objections, and making the big-league sales. Check out our favorite strategies for increasing your bottom line with your sales team’s help.

Start With How You Position Yourself

If the way you introduce yourself is as a “decorated-apparel salesperson,” you need to make a change right now. In reality, you’re a problem solver. Your business isn’t to just decorate apparel or design logoed merchandise. Almost anyone can do that. Your job is to figure out exactly what your customers need and how your shop can provide this to them. 

“It’s vital to ask your customers to give you a true understanding of what their business looks like today. Then be quiet, listen, and take a whole bunch of notes. Through this dialogue and conversation you should understand what your customers are focused on, and then modify your presentation to their needs, not just your company’s needs.” Charlie Bacon, alphabroder

As an example, Alex Fernandez, owner of Say It in Stitches, takes a consultative approach to selling that acknowledges that not every potential customer’s problems and needs are the same. “We start with a lot of questions and listening, because the customer will almost always tell us how to sell to them,” he says. “Our team finds that the vast majority of customers fit one or more buyer personas, based on their pain points and needs. Those include customers who’ve been failed by slow or late order turnarounds, buyers who’ve been embarrassed or hurt by decorator quality issues, or customers who experience difficult orders every time because of poor project management and lack of attention to detail.”

Then, as Fernandez and his sales team build a dialogue with a prospect, they consciously establish their subject matter expertise and credibility. “When we finally learn their needs, we’re in a position of authority and trust to offer specific solutions,” he says. “A one-size-fits-all approach is hit-or-miss at best.” 

This may mean that you work to attract a different type of customer. You don’t want clients who’ll nickel-and-dime you on every order with threats of finding the cheapest decorator in town. Instead, you want those customers who appreciate your ability to solve their problems, getting them what they may not even know they need to solve their branding challenges.

Create Relationships, Rather Than ‘Leads’

The best sales managers and salespeople know that hitting up a new contact with your pitch isn’t the ideal way to create a long-lasting relationship—or to increase sales in your shop. Real relationships build trust, and customers want to buy from people they know, like and trust.

That’s why you need to be as personable as possible with your customers. Find out their likes and dislikes (both at work and outside work). Find out what matters to them. Doing this allows you to make a personal connection and not become a faceless entity on the other end of the phone.

You can improve your sales relationships by:

  • Using social media. Share helpful knowledge as well as a bit about your life. This can include how much you love your job. 
  • Use video in your emails and in direct messages (some social media platforms allow video messages).
  • Create alerts set up for each relationship you hope to turn into a sale one day. Congratulate them when their company has a success. Show an active interest in their business.

It’s also important to hand-pick your prospects. “Qualifying prospects early on based on a specific set of criteria that can define a mutual ‘match’ is always a good idea,” Fernandez says. “Knowing when to ‘lose early’ and move on to more productive endeavors is also a valuable skill but requires some discipline.” 

Soon, you’ll have relationships that naturally turn into clients and referral engines!


In our opinion, one of the best ways to become an apparel sales expert is to meet with your trusted suppliers and see the newest styles, colors and fabrications in person. Visit alphabroder at the Northeast Expo, the largest apparel and promo products show in the northeast, on January 27-28, 2022. Meet with alphabroder team members, mill reps and decoration suppliers. See the newest styles in person, and pick up our 2022 catalogs and swatchcard books. Get ready to accelerate your apparel sales this year!

Create Better Sales Conversations

First, it’s important to remember that the decorated-apparel industry is always changing, but even more so now. “It’s a smart idea for a sales professional to spend time with ‘housekeeping’ at the beginning of all meetings,” says Charlie Bacon, regional vice president at alphabroder. “It’s vital to ask your customers to give you a true understanding of what their business looks like today. Then be quiet, listen and take a whole bunch of notes. Through this dialogue and conversation you should be able to understand what your customer is focused on now, and then modify your presentation to their needs, not just your print shop’s needs.”

“Let your prospect do the talking. Often, a sales rep continues to pitch a product or multiple products to a client without taking the time to listen and learn the client’s needs and where they are in the process. In some cases, the client has already done their own research and knows exactly what they want.”
Tom Rauen, Envision Tees

The seven steps below will increase your sales conversions once you adopt them:

1. Don’t use business jargon or inside terms. When you talk to your customers, be as “user-friendly” as possible and don’t use a lot of industry buzzwords. As soon as they start hearing terms like placket or yoke, their eyes gloss over and they’re looking for the escape hatch. The key here is to keep it light and simple.

However, it’s important to be conversant about current trends and to communicate those. Besides staying on top of changes and trends in the decorated-apparel industry, alphabroder sales rep Ashley Grenell likes to observe what other salespeople are doing. “That way, I can make it a best practice or come up with my own so I stand out or do it differently,” she says.

2. Focus on one aspect of your business in your sales conversation. You’ve heard of the “elevator pitch”—selling your business idea to someone quickly as if it could be shared in a short elevator ride. That’s what your initial sales conversation needs to be. Grab their attention so there will be follow-up conversations.

“Planning and research sets the stage for a successful conversation and presentation, and builds confidence to talk naturally and to be yourself,” says Helen Barbato, a sales rep at alphabroder. “Adding personal examples makes a sales rep relatable.”

3. Show your passion. Guariglia has been known to fly to another city to meet with a prospect to show how serious his shop is about earning their business. “If you want to tackle a large prospective client or partnership, you need to get to it and follow through,” he says. “Any sale is a partnership. It is a two-way street and relationship. You both need to know when to walk away or how to navigate as each partner is changing. There’s a ton of opportunity even between the lines of what you think you already accomplished.”

4. Listen to learn about your prospect. When you’re talking to a potential customer, don’t do all the talking. Instead, show an interest in what they do with their company. Ask questions about how their business works and emphasize they’re the experts in their field. Make sure they know that you’re legitimately interested in finding how you can help them.

“I can’t emphasize enough to let your prospect do the talking,” says Tom Rauen, CEO of Envision Tees. “Often, a sales rep continues to pitch a product or multiple products to a client without taking the time to listen and learn the client’s needs and where they are in the process. In some cases, the client has already done their own research and knows exactly what they want.”

5. Ask questions. Learn as much as you can about the potential customer and their relationships with their vendors. You want to know what they like about those relationships, what isn’t working, and what they wish they could have in the relationship. 

Here are four questions to ask to get these conversations started:

  • How do you like the apparel-print shops you’re working with?
  • Who’s your best vendor and what makes them your best?
  • What are you looking for in a decorated-apparel provider?
  • What’s an example of the worst vendor relationship you’ve had?

6. Follow-up. You may have heard that the fortune’s in the follow-up. That’s very true, since most people don’t buy when you first reach out. “Following up reminds your customers potentially about an opportunity you’ve presented them with,” says Chim Olisemeka, a sales rep at alphabroder. “Customers also always appreciate you following up and typically would be happy to tell you what happened to the opportunity and give you details on it if you lost. You set yourself up for success when you follow up.”

7. Be as efficient as possible: The most productive sales professionals understand the tools they have and how to leverage them. For example, alphabroder has developed tools to support its sales team and customers in finding inventory. “This is the number one stressor and time restraint for all right now,” Bacon says. “Over the past couple months, with the innovation of using spreadsheets on our website, automated alarms for when inventory comes in, and a new High Stock Search tool, we’ve helped our team become much more productive in responding to our partners. In turn, it gives them more time to be proactive in other areas of the business.”

“Having jitters because you’re about to connect with someone new is intimidating, when in fact that’s exactly what should give you confidence. You know what you want to find out or accomplish so plan for objections to your own questions ahead of time.”
Bryan Strum, alphabroder

Speaking of time, Rauen also suggests batching tasks together to be more efficient. “Designate blocks of time to make phone calls to prospects or nurturing calls to current clients, sending emails, and other day-to-day tasks, instead of jumping back and forth across multiple tasks and forms of communication,” he says.

It’s Time to Overcome Cold-Call Jitters

Cold calls can bring up anxiety from a fear of rejection or worse, anger by someone who doesn’t want to be bothered. There are steps you can take to greatly reduce and eliminate negative feedback (like those angry hangups) from cold calls.

You may even grow to look forward to cold calls. “I actually love cold calls,” says Gregg McEntee, an alphabroder sales rep. “There’s no downside to a cold call. Try to uncover any issues that your prospect has had in the past and let them know that you’re here to assist with anything they need.” 

Try these five steps to banish cold-call jitters forever. 

1. Get in the right mindset. For Rauen, believing that his clients will benefit from what his shop has to offer makes him pick up the phone. “It’s your moral obligation to let them know about your product and offer,” he says. “If you don’t, it would be a disservice to them to not know about what you have to offer. It’s a mindset shift from thinking you’re bothering them, to thinking they’d be upset and feel left out if you don’t offer your solutions.”

From a sales manager perspective, Bryan Strum, regional sales manager at alphabroder, reminds his team that they control the narrative. “Having jitters because you’re about to connect with someone new is intimidating, when in fact that’s exactly what should give you confidence,” he says. “You know what you want to find out or accomplish, so plan for objections to your own questions ahead of time. Remind yourself that you have nothing to lose. There are only gains, since you have no prior relationship to damage. Planting the seed might be all that’s necessary on that call, enabling a warm follow-up to get the win you desire on the next call.”

2. Prepare for cold calls. No cold call will be successful unless you’ve prepared in advance. Make sure you know the company inside and out. “It’s important to do the research before you reach out,” Grenell says. “Check their website and social media to gather information about them before you make the call. That way, it feels more like a warm introduction, rather than a cold call, so it takes away some of those jitters.”

3. Create and practice a script for cold calls. It’s fine to have a script to guide you on the phone call. But you don’t want to be reading it like a robot. You can rehearse the conversation ahead of time so you know what to ask comfortably. 

Include the following points in your script:

  • Introduce yourself and establish a friendly tone with the customer;
  • Why you’re calling them;
  • A few questions to make sure you’re talking to the appropriate decision-maker with the company;
  • A clear statement of what you can offer their company that’s different from their other vendors; and 
  • A clear-cut wrap-up that lets you set up a follow-up appointment or call.

4. Create a relationship with your cold call-ee. Once you have the caller’s attention and you know they’re interested in your services, make it clear you’re looking to establish a relationship. If the person you call feels like all you’re interested in is getting an order or a few sales and you can’t provide anything else, they can go anywhere for that. You can establish a relationship by creating great dialogue while on the phone with your prospect. It’s always more comfortable when you can get a good rapport going. 

“Remember, you’re a subject matter expert,” says Lori Donovan, a sales rep at alphabroder. “You want to be a partner and help your prospect grow their business. View yourself as a problem-solver, not an order-taker.”

To create a great rapport, try the following:

  • Ask open-ended questions, even if it’s something as simple as, “Do anything fun over the weekend?”
  • Know a bit about the company. If they’ve recently received an award or distinction, bring this up and congratulate them. Show a connection with the customer.
  • Don’t let the line go dead. Be an enthusiastic listener and be sure to ask follow-up questions immediately if there’s a lag in the conversation.

Finally, Fernandez keeps the concept of the sales funnel in mind, since there are different steps of each buyer’s journey. “The salespeople who try to aggressively slam a sale in one phone call will usually face the most rejection and negative energy,” he says. “No one likes to be forced to do anything. Start with a simple introduction and a 10-second explanation as to why your shop is different. Plant the seeds so that when they’re disappointed with their current decorator, they reach out to you.”

Need Help Overcoming Overwhelming Objections?

Many people worry about making cold calls because they fear rejection. However, even the best salespeople with long-term relationships need to be ready to address objections at any moment.

To prevent this, anticipate the following:

  • The prospect may not understand why they need your apparel-decorating services.
  • They may not understand why they need your services right now.
  • They may be cautious because they may not know your company, or have had a bad experience with another print shop.
  • They may worry that they won’t be able to afford your services.

“Being real with your sales team is crucial. Be there as a person and as a pillar. As a leader in a world on fire, you can’t crack. Let your sales team be in the driver’s seat of their own destiny, but also be an ally.” Lucas Guariglia, Rowboat Creative

Here’s advice for some common objections apparel salespeople get:

“I could advertise my business 1,000 other ways.”
A great response: “Yes, there are other advertising mediums,” Strum says. “My counter is always that decorated apparel is a highly effective way to market your business. You put a logo on a shirt one time, but then it generates hundreds or thousands of impressions as one person wears the garment over its lifetime. If the person posts a photo on social media, then the opportunity for impressions is endless. That offers a ton of bang for their advertising buck.”

“Your prices are too high.”
A great response: If your clients are upset about pricing, realize that’s a big challenge many have with selling decorated apparel. “Many buyers will bring up the fact that it’s less expensive online,” Grenell says. “I overcome this by bringing up service, hidden costs and get them thinking about what if something goes wrong with their purchase. Who’s going to be there to help them? I really challenge them to look at the loyalty factor of the buy.”

“You can’t get the apparel styles I want on time!”
A great response: Besides price, apparel salespeople get objections about turn time and inventory. “The biggest way to deal with any objection is to set a reasonable expectation that you can meet and educate the client about what’s reasonable,” Rauen says. “With Amazon, time expectations have really changed, so educating the customer of the process and timeline will help set the proper expectation for the customer journey.”

McEntee focuses on pitching styles that have a deep inventory. “I follow up with an email featuring those styles,” he says. “However, you also need to have backup product options at the ready.”

And over at Envision Tees, Rauen’s sales team has become more resourceful in just offering decorated apparel and promo products. “We added custom boxes for businesses and events,” he says. “That means we’ve expanded into sourcing and combining non-decorated products like coffee, popcorn and champagne to create a complete package beyond just what we’re decorating and producing.”

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Here’s how to overcome objections to your sales offer: 

1. Listen, as in really listening:

  • Listen to everything your prospect has to say so you fully understand their concern.
  • Don’t be defensive, and never take the objection personally.
  • Show your problem-solving abilities by working through their concerns carefully.
  • Don’t try to cut them off by anticipating their objections.
  • Be sure to give verbal confirmations that you’re listening to what they have to say.

2. Understand your buyers’ concerns:

  • Listen (and take notes) on their exact wording of their concerns.
  • Restate the concerns to them to ensure you didn’t miss anything.
  • See if there’s something else underlying their concerns, some lingering issue that you may be able to use to your advantage.

3. Articulate your response clearly and concisely:

  • Go through each of their concerns starting with the main objection.
  • Find a way to resolve these issues immediately.
  • Keep it short and sweet and don’t ad-lib your response.
  • Ensure that you have resolved their issues but don’t press them for a snap decision.

Don’t Forget to Motivate Your Sales Team & Get Ready to Soar

Strum says that a good sales manager can only motivate their team if they’re self-motivated. “Being personally invested in your sales team will provide you with the emotional intelligence to connect with them better,” he says. “If you take care of them, and they feel like they’re integral to your company’s success, they’ll strive to do their best. It’s our job as sales managers to promote and support that idea of purpose through positive reinforcement, engagement, information sharing, asking for ideas, coaching, and furthering their personal and professional growth.”

At Rowboat Creative, Guariglia stays far away from micromanaging his sales team, even as they’ve been working remotely for the better part of two years. He holds biweekly conversations with his staff to check in on a personal and professional level. “Being real with your sales team is crucial,” he says. “Be there as a person and as a pillar. As a leader in a world on fire, you can’t crack. Let your sales team be in the driver’s seat of their own destiny, but be an ally. We all thirst for success and we can all be there, together.”

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