Sales Experts Reveal The Wildest Ways They‘ve Closed a Deal

Dan the sales rep was sweating through his dress shirt as he hauled a bulky laser printer up to his prospect‘s front door. He rang the doorbell, silently praying the client would be home as promised to sign the contract before the end of the month closed out in 30 minutes. When no one answered, Dan set the printer down on the porch, pulled a pen from his pocket, and got ready to do what needed to be done.

If you Google "how to close a deal," you‘ll find plenty of lists filled with conventional wisdom and proven best practices. Have a well-defined sales process. Perfect your pitch. Create urgency. Overcome objections. Ask for the business. But real life isn‘t always so straightforward.

In the unpredictable world of sales, closing a major deal often requires equal parts persuasion, perseverance and creative problem-solving. When standard techniques fall short, top-performing reps find bold, imaginative ways to stand out from the competition and get the contract inked.

We asked sales experts at HubSpot to share the most unconventional ways they‘ve closed deals when the pressure was on. Here are some of their wildest war stories along with takeaway lessons any rep can apply to fill their pipeline:

1. Convince a telemarketer to become a customer instead

Caila Brandt, HubSpot‘s Associate Inbound Growth Specialist, once spent 20 minutes on the phone with a telemarketer named Ray who was trying to get listings for a family member‘s house. But instead of brushing him off, she saw an opportunity to turn the tables.

"I politely asked if he had heard of HubSpot, and used his prospecting time to add value and help with his process," Brandt said. "Ray admitted to frustrations in their system and a real desire for change and support. A meeting was booked that day, and after a demo and process run, the deal was closed."

The lesson: Every interaction, even unsolicited sales calls, can be an opportunity to find a new customer if you approach it with the right mindset. By actively listening to the caller‘s challenges and demonstrating how her solution could address them, Brandt was able to turn a cold contact into a closed-won deal.

2. Make a house call to set up the product yourself

Early in his career, HubSpot Executive Dan Tyre had an enterprise client who took a full year to make a purchasing decision on computer hardware. At the last day of the month, the customer finally called to say he would sign the deal, but only if Tyre could personally deliver and install the complete system at his house before midnight.

"I said yes. He specifically wanted to know if I had a printer cable to connect the computer to a printer. I did, and I got the deal," Tyre said.

The lesson: Sometimes you have to be willing to roll up your sleeves and go the extra mile to eliminate barriers and objections for the customer. By agreeing to an unusual last-minute request, Tyre showed his commitment to the client‘s success and was able to close the sale as a result.

3. Show up in person when you‘re being ghosted

When a hot enterprise lead suddenly went radio silent on HubSpot Account Executive Elizabeth Grip after a positive demo call, she decided to pay an in-person visit to their office. Even though the storefront turned out to be closed that day, Grip snapped a selfie outside the building and emailed it to her contacts.

"Knowing they are a small business, I figured if anything I would get to browse some nice-looking diamonds and hopefully get an update on the opportunity," she said.

The lesson: If a previously engaged prospect starts dodging your calls and emails, don‘t be afraid to show up at their doorstep (within reason). A surprise appearance proves you‘re serious about earning their business and can jolt the conversation back to life.

4. Win them over with food

Several HubSpot sales leaders shared stories of their reps sending pizza, donuts and flowers to prospects‘ offices to secure a meeting or nudge a deal over the finish line.

For example, Account Executive Ilias Pishev once hand-delivered a dozen donuts to his point of contact every Friday for eight months, until they finally signed on the dotted line. "384 donuts later, we won their business and a happy customer," he said. "We even celebrated the deal over a box of donuts together."

The lesson: When done thoughtfully, small gifts and personal gestures can delight potential customers, keep you top-of-mind and demonstrate your commitment to the relationship. Just be sure to tailor your approach to each individual prospect to avoid seeming desperate or tone-deaf.

5. Use props to make your proposal stand out

According to Dan Tyre, one of his former managers literally put himself into a deal when the printed proposal started to fall apart during a meeting. "He grabbed a stapler and then stapled the proposal to his tie – which was unusual, but we won the deal," Tyre said.

The lesson: Using physical props and leave-behinds in unexpected ways can make your pitch more concrete and memorable. Just keep it professional and relevant to the business at hand.

Closing thoughts

Unconventional closing techniques shouldn‘t be used as a crutch for sloppy sales fundamentals. But when you‘ve laid the groundwork properly and a high-stakes deal still hangs in the balance, a little out-of-the-box thinking can go a long way.

The common themes in these stories are perseverance, problem-solving, personalization and a willingness to put in extra effort. If you genuinely believe in the value of your offering and are committed to ensuring the customer‘s success, don‘t hesitate to take bold action to get the deal done.

In the words of novelist Paulo Coelho, "There is only one thing that makes a dream impossible to achieve: the fear of failure." So next time you find yourself in a difficult selling situation, summon your inner Dan Tyre, get creative and do what it takes to turn that "no" into a "yes."

Oh, and in case you were wondering what happened with Dan and the laser printer: when the client finally came to the door, he found the determined sales rep with the contract clipped firmly to his collar, ready to sign on the dotted line without delay.