Get Creative with Your Sales Prospecting

Each Monday morning, Steve McKenzie, InsightSquared Sales VP, asks the team one question:

Who has a Story from the Field to share?

Sales reps stand up and share the tactics they used to close their latest deal, the mistakes they think lost that one deal, and the creative prospecting methods that grabbed a great opportunity’s attention.

While the details of every sales interaction are always interesting and valuable to share, the most outlandish and funny tactics always get the most attention from the team. When a rep does something crazy to engage a prospect, everyone cheers, yells, and applauds their dedication and determination to close the deal.

This type of creativity and drive is a real asset for sales prospecting, especially for high-tech SaaS companies. Sales reps are always struggling to stand out among the hundreds of emails and multiple phone calls that most people receive each day. Why would a prospect open your boring email or take your standard call, let alone buy your product?

As a sales manager, it’s your job to empower your team to use their personality, their wit, and their creativity while prospecting to engage new opportunities. Here are the ways reps can stand out, get attention, and source more qualified business opportunities.

A Targeted Approach

When new sales reps start out, they’re often too afraid to get too creative. They stick 100% to the sales email templates and talk tracks that they’re given, and won’t deviate by more than a word. Some reps will start to feel comfortable and adapt the templates as they learn and grow, while other reps will never have the courage to change the wording without guidance from leadership. As a manager, it’s up to you to encourage reps to take the templates and talk tracks and make them their own.

Reps shouldn’t remove the important data points or value propositions, but that doesn’t mean that they can’t include some personality in the message. For example, if a rep is using trigger events to prospect, they should absolutely open an email with information they gleaned from a prospect’s LinkedIn profile or other social sites. For example, if the rep and the prospect both attended Boston University, the rep should feel free to say: “Great to connect with a fellow Terrier! Though I’m sure you don’t miss riding the Green Line every day.” Encouraging this lighthearted and conversational tone in sales emails will help reps more quickly build rapport, and hopefully, drive more conversions down the funnel.

An Intriguing Subject Line

As much as sales reps may not like to admit it, marketing has subject lines figured out. They’ve tested the type of subject lines that people are most likely to click, and exploit that to your business’ benefit. While sales reps may not have the same level of expertise when it comes to subject lines, they can do much better than a boring “Quick Intro” or “Our Product.”

As a manager, you should tell your team to put themselves in the prospect’s shoes. Would you open an email if the subject line was completely uninteresting and obviously a cold pitch? Probably not. But thinking of a completely original and interesting subject line is seriously challenging. Instead of just telling your reps to “think of something creative,” use the great content your marketing team has already written. If marketing wrote a popular blog post focused on New Data on the Best Time to Send Sales Emails, for example, have your reps use that content as the subject line. Reps should share the content with prospects along with a related sales pitch. Marketing has already proven that people will click on this content, so use their work to make prospecting easier for your team.

An Amusing Gif

That’s right, a gif! It depends on your target market, but if you’re prospecting into a company with a tech-savvy demographic, a gif is sure to delight and surprise. Gifs can convey the emotion and excitement that’s so often missing from sales emails. Depending on the context, reps can use gifs to convey surprise, happiness, frustration, and more. The opportunities are really endless, and only bounded by the creativity of your team.

Here’s a message that was sent to us as a great example of using a gif to prospect.


I’ve reached out to you a few times hoping to talk about MY COMPANY and YOUR COMPANY, but I haven’t heard back.


Neither of us want to be running in circles — if a solution like MY PRODUCT isn’t applicable to you or your team, then I’d love to know so we’re not wasting time here.

Do you relate to any of the following?:

I’m interested but haven’t had the chance to reply.

I checked out PRODUCT but it’s not a fit for my team at this time.

The timing is off, perhaps we can reconnect in the future.

Thanks for your time,


This email is different, fun, and eye-catching — all because of the gif. The message is pretty simple, and just asks the prospect for a response. This email is effective because it got the person who received it to reply. In fact, here’s what she said about it:

“I couldn’t resist replying to this sales email, even though I wasn’t interested in the product – so this person has done an excellent job!”

Never Cross the Line

While you do want your reps to have fun and get a prospect’s attention, you also have to make sure that they don’t get TOO creative. If a rep on your team is at all offensive or inappropriate in their messages to prospects, it will obviously reflect badly on the company. Again, the burden is on you as a manager to guide your reps. Make sure that your team understands the difference between amusing and unprofessional, and they never cross that line.

In a sea of B2B sameness, it is possible to stand out and delight your prospects. People want to be amused, inspired, intrigued, and enthused. You just have to let your team prospect with some creativity.

About the Author:

cara hogan insightsquaredCara Hogan is a Content Marketing Manager at InsightSquared, where she is a constant contributor to the Business Analytics blog and the host of the podcast Million Dollar Insights. Cara studied Journalism at Boston University and has written extensively about the intersection of technology and business.


Stay tuned for more of the latest in outbound sales best practices and methods.

This post was brought to you by PersistIQ.  Our software empowers salespeople to easily convert prospects into a qualified pipeline and create personalized outbound campaigns at scale.  See how PersistIQ can help you make your own sales efforts more effective today.

Try PersistIQ Today!

Share on facebook
Share on twitter
Share on linkedin
Share on email



Start more quality sales conversations with your prospects using PersistIQ. Increase sales activities by 3x. Spend less time on tedious work.



Discover how PersistIQ empowered Backerkit’s sales team to scale from 3 to 8 touchpoints and reduce implementation time by 50%.