Jon Grossman’s most outlandish prospecting strategy involved a tiny pair of shoes and a note saying: “Just trying to get my foot in the door.”

He didn’t think it would work. Even he rolled his eyes at the tactic when his manager at Xactly suggested it. But he had emailed and called the prospect to no avail. So, he gave the shoes a shot, and, to his disbelief, it worked.

The prospect sent an email back saying he got the shoes and wanted to set up a meeting.

“That’s probably the silliest thing I’ve done,” said Grossman, who now works as a business development analyst for Xyleme. “Hopefully, they chuckled and didn’t think ‘What an idiot.’”

Despite the tactic’s success, Grossman hasn’t made a habit out of sending baby shoes to every prospect he doesn’t hear back from. It’s not exactly scalable. But the experience did underscore the importance of infusing creativity into the prospecting process.

“That’s probably the silliest thing I’ve done.”

For most SDRs, persistence and volume of outreach are held up as the key ingredients for prospecting success. Managers reinforce that with daily 50 email and 50 phone call targets, and software accelerates it with automated email cadences.

But consider that an estimated 306.4 billion emails are sent each day, according to Statista. In addition, HubSpot found that the average open rate for emails to software companies is about 20 percent. Finding ways to be creative in how you prospect and what you send is integral to success, Grossman said. It’s how you stand out, and it can serve as an entry point into a conversation.

Fortunately, creativity doesn’t have to come at the cost of your daily KPIs, nor does it require purchasing outlandish props. Instead, it’s about research, personalization and letting yourself be a little goofy.

More on SalesLead Qualification Is a Waste of SDR Time


Women with email marketing illustration
Image: Shutterstock

Creative Prospecting Is About Personalization

Nikki Ivey was looking for a way to expand her network when she came across a Crunchbase article listing influential sales leaders to follow on social media. The safe play would have been to email the leaders and reference the story, but she didn’t think that would catch their attention.

Instead, she came up with the idea of creating a shareable, digital “card” for each leader. Using baseball cards as an inspiration and the Instagram app, Ripl, Ivey included an image of the sales leader along with a quote of theirs. She sent it to each leader, congratulating them on being selected to the Crunchbase list.

“It’s nailing the thing about that person that they themselves are proud of.”

The strategy worked, with thought leaders like John Barrows from JBarrows Training and Scott Barker from Outreach re-sharing her post and connecting with her.

While Ivey wasn’t actively prospecting those companies, the same approach has helped her find success as an SDR. It’s all about building personalized, relevant content for the prospect that’s delivered using some outside-the-box thinking.

“It’s nailing the thing about that person that they themselves are proud of,” Ivey said. “It’s a mix of hyper-personalization and relevance. Any strategy you use has to have those things.”

While there is no template for creativity, there are steps reps can take to integrate creative prospecting into their sequences.

For starters, Ivey suggests reps dedicate 15 minutes per prospect to research them. Typically, she’ll use that time to skim blogs, videos and company websites to find relevant information she can use to connect with the source. Podcasts are also a rich source of information, and tools like Headliner make it easy to find conversation highlights without listening to the whole episode, Ivey said.

That information will form the centerpiece of the outreach.

The next step is to package that content in an engaging way. In addition to baseball cards, Ivey has made Loom videos discussing a contact’s article, written social media posts highlighting a podcast clip and more.

The key here is to do something that is unique but that also fits the tone of the buyer, Ivey said. When Ivey sold to construction contractors, she knew that sending a goofy prospecting message would not fit the tone of their community social media pages. Connecting with them required posting serious, value-based content on their Facebook pages.

Meanwhile, following an outreach trend is a quick way to get ignored. Odds are the prospect has already seen it, Ivey said.

“You have to believe in yourself and throw caution into the wind,” Ivey said. You have to get rid of every eff that is making you consider what the person sitting next to you will think about the video and how goofy it is.”

Whatever content Ivey sends, she makes it a habit of leading off with “You,” as in, “You said something on LinkedIn that really resonated with me.” That little tweak helps to signal to the buyer that the content will be about them.


Try Different Outreach Avenues

It doesn’t matter how creative the content is if it ends up in a prospect’s spam folder.

Phone lines, email and LinkedIn inboxes tend to be overrun with salespeople, Grossman said. There are plenty of times where he’s reached out to sources on all three channels to no avail. So, he’s learned to be creative in where he reaches out to his leads.

Once again, this strategy requires understanding the source and figuring out where they are most active. When Grossman is researching for a new avenue to connect with a prospect, he looks at what professional information they share on social media.

“If you say what you’re doing, I think people appreciate that.” 

He once succeeded in getting a meeting with the CEO of T-Mobile by messaging him on his Periscope page.

“I knew that the CEO of T-Mobile was always doing these press conferences on different platforms, and he was on Periscope one time,” Grossman said. “So I put a comment in his Periscope, and he had his assistant call me when he got off.”

Twitter and LinkedIn can be useful avenues for messaging a prospect. Same with direct mail — however, that has become more difficult as people work from home.

The key is to go to where the source maintains a professional identity and to be authentic in the outreach. There’s no harm in being upfront about the fact that you’re prospecting someone and that you came across their page, Grossman said.

“A lot of people think that, if you’re too honest about what you’re doing and your intentions, the person will be turned off by that,” Grossman said. “If you say what you’re doing, I think people appreciate that.”


Man with email marketing illustration
Image: Shutterstock

Creative Prospecting Is Worth the Time Investment

Ultimately, creative prospecting doesn’t require quirky props. It’s often just about spending the time researching the customer and doing something different.

While it comes at the cost of efficiency, Ivey believes the advantages are worth it. Automated, formulaic emails are growing less effective with buyers and giving salespeople a bad reputation, Ivey said. Creative, customer-centric outreach resonates more with buyers and helps the rep build a better relationship with them.

“We can transform the sales culture and the buying experience when we engage in this kind of creative prospecting and genuine caring about what’s relevant to the people we’re prospecting.”

All it takes is an extra 15 minutes to research top-tier accounts and some outside-the-box thinking.

“We can transform the sales culture and the buying experience when we engage in this kind of creative prospecting and genuine caring about what’s relevant to the people we’re prospecting,” Ivey said. “That’s how we can all have more success and have more fun doing this.”

More on SalesAll Sales Reps Should Master Social Selling. Here’s How.

Great Companies Need Great People. That's Where We Come In.

Recruit With Us