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Are you and your sales team able to easily generate all the pipeline you need to achieve your ever-increasing revenue targets?

Sales prospecting seems to be getting harder for most sales professionals. The ability to break through the noise, get the attention of decision-makers, set meetings and create qualified opportunities isn’t easy. 

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It’s been 10 years since Aaron Ross wrote Predictable Revenue. In those 10 years, we’ve seen the emergence of the pure-play prospecting function with sales development reps and business development reps.

Unfortunately, most of the specific approaches described in Predictable Prospecting stopped working predictably years ago.

Now there are more channels than ever, and with technology that makes it easy to scale undifferentiated messaging, our prospects have gotten better at putting up walls and ignoring our outreach attempts.

All is not lost, though. There are committed professionals out there who have found ways to consistently set themselves apart and overcome these challenges. They’ve gotten creative, hyper-relevant, and even injected a bit of fun, to open the very doors that have appeared closed and locked to others.


Why is cold outbound prospecting so hard?

You’re competing with more sellers and they’re sending more messages.

According to HubSpot’s Industry Benchmark Data, since January of 2020, sales email sends are up roughly 62 percent. Meanwhile, response rates are down by about 30 percent.

Hubspot graph with total emails sent versus response rate

You’re also having to contend with the proliferation of channels. Daniel Disney recently listed 16 ways that salespeople can reach prospects and customers in 2021:

1) Phone
2) Email
3) LinkedIn and other social prospecting tools
4) Text
5) Referral
6) Post/Letter
7) Video
8) Twitter
9) Gift
10) Instagram
11) Clubhouse
12) Facebook
13) TikTok
14) Door Knocking (post-pandemic!)
15) Whatsapp
16) Networking/Events

I believe that the answer to breaking through all of this noise is not MORE. Instead, we need to be focused on BETTER. Better targeted outreach. Better personalization. Better messaging and relevance. Creating better experiences for those we’re reaching out to.


Top performers aren’t focused on quantity

Having interviewed over 110 active, quota-carrying sales professionals who are either the outright No. 1 top performers at their companies or at least in the top 1 percent of achievers, including over 15 top-performing SDRs on the Sales Success Stories podcast, I’ve learned firsthand that the best of the best aren’t focused on quantity. They’re dialed into quality. They’re not trying to get a response from .1 percent of 1,000 people. They’re working to generate double-digit response rates from a smaller number of high-probability, highly valuable potential customers.

As marketers have had to learn, batch and blast is dead — at least it needs to be. Loading up a spam cannon full of unqualified “leads” and blasting away just doesn’t work. Not only does it not work, but it tends to alienate people and tarnishes your reputation, making it even harder to breakthrough in the future.

Based on my own experience with the connect and pitch messages I get on LinkedIn and the frequent generic emails that come my way, I believe that all it takes to be in the top 10 percent to 20 percent of prospectors is 10-20 seconds of research. Given this person’s title and company, should I even be reaching out to them in the first place? What can I quickly learn to show that I did an ounce of research and have a sense of who they are?

It doesn’t take much to stand head and shoulders above the undifferentiated noise.

Taking it one step further and being better than 95 percent to 99 percent of all poor prospectors doesn’t take that much additional effort, either.

In an effort to inspire you and your team, I’ve pulled together seven sales prospecting techniques and examples that actually work in the real world. They’re creative. They’re different. They’re fun. And most importantly, they get their recipients excited and eager to engage. 

Would you rather continue to beat your head against the wall with mundane dial after dial after dial? Email after email after email. Or, could you make the process more fun and exciting for both yourself and your future customers through creative selling?


7 creative sales prospecting ideas


1. Leverage a unique platform like Cameo

You could do what Sarah Brazier from Gong did to get the attention of the team at Plixer who she was focused on. She went to Cameo and had Isaiah Mustafa (who is probably most famous for being the guy in “the man your man could smell like” Old Spice commercials) to record a customized message for them:


2. Create a hyperpersonalized video

A couple of months later we turned the tables on Gong in an effort to get the attention of their CMO, Udi Ledergor, around an opportunity to sponsor our own Sales Success Summit. After finding a video of Udi, who is a very talented pianist, playing this song. Alex Smith, who was helping us sell sponsorships at the time, wrote some custom lyrics and recorded this message for him:

Not only did Gong come on as a sponsor, but the feedback was tremendous. Udi replied back (while on vacation!): “Alex, I’ve got to hand it to you – that’s some creative prospecting :),” Gong’s director of marketing chimed in: “What an awesome video! Made my Monday :),” and after coming to the party a little later, one of its senior directors said: “Holy sh*t. I finally just saw this. Insane. Great stuff.”

Total cost to produce the video: $0. Just took some time and creative energy from Alex.

Video isn’t the only tool that can be effective in breaking through. While email, LinkedIn, and the phone have become very noisy channels, sending letters and packages is often overlooked.

Think about how many emails you receive in a typical day. Now think about the last time you received a handwritten note in the mail. You probably don’t get nearly as many of those.

That’s the kind of prospecting tactic can help you stand out, as these next two examples show. You can take your direct mail efforts to a whole new level if you just apply a bit of creative energy.


3. Be vulnerable in your outreach by sharing your real-time reality

In a recent NetHunt article, Hannah Ajikawo, founder and sales consultant at Growth Mode, shared how vulnerability and sharing our real-time reality is the key to breaking through and connecting with prospects in a personal way.

Hannah Ajikawo, Founder and Sales Consultant at Growth Mode

“Be vulnerable; yes, vulnerable. We need to admit that we do not know everything, but we are open to understanding, listening, and are keen to help. This is what helps us be more human and connect on a deeper level. When prospecting, we want our prospects to understand that there is an “out.” They must understand that we only have good intentions, that we are connecting with them because we have done the research and have found success with others like them.

Someone I consider to be a mentor, Cherilynn Castleman said in her book, “What’s in the CARDS” talks about blurring the lines between personal and business in the post-covid world. Buyers receive more messages, emails, and connections than ever before. Companies invest more in digital engagement and most prospects have become less responsive, according to research from Gartner.

Reaching out to prospects and sharing your real-time reality is both endearing and humanizes your interaction. For example, for me right now, writing this content, I’m making stars out of Play-Doh with my son, playing race cars with his Paw Patrol remote control car. That is my reality. It’s relatable and it gives your prospect permission to break through the business noise and engage with you in the same personal way.”


4. Apply the ‘crumpled letter’ approach

Here’s what Jeremiah Griffin did based on Dale Dupree’s “crumpled letter” approach:

Letters and handwritten notes are powerful, but what do you do when you have a truly hard-to-reach C-level executive who is likely being bombarded by your much more well-established competitors on a daily basis?

It might make sense to resort to a multitouch, multipackage experience like Nathan Offner demonstrates in the next example, using yours truly as the sample subject.


5. Try a multitouch, multipackage experience

At this point you might be thinking: Scott these are great, but they don’t scale. 

I would argue that making dozens of dials or sending hundreds of generic emails doesn’t really scale either. They’re undifferentiated and typically get ignored. Sure, these creative selling types of efforts take more time, but in most cases the response rates are well over 50 percent. They also create a far more positive initial impression.


6. Turn a ‘boring question’ into a connection

Let’s look at an effort by Jacob Gebrewold, account executive at Klue, and co-founder and executive director at Sales for the Culture. Here’s his story in his own words:

Profile photo of Jacob Gebrewold
Jacob Gebrewold, Account Executive at Klue, Co-Founder and Executive Director at Sales for the Culture

“I met an executive at a conference whose presentation I really liked. There were hundreds of people at the presentation and dozens he spoke with after. When I got my couple of minutes with him, I asked him what most would consider a boring question: what’s a book he read that isn’t super mainstream that somehow influenced that presentation and (crucially) why that book had that impact. 

The basic question is nothing outstanding, it’s what I did with the information that mattered. I ordered the book and sent him a picture of me holding it when I got it. Then I synthesized some key insights from it after a couple of days, particularly insights that related to what he said stood out to him. I tied that takeaway to how I approach business and my service and mentioned I’d be by his office a couple times in the coming couple of weeks and I’d love to chat more on how that common POV impacts how he’s dealing with challenges related to what I do. 

Doing something intentional with the answer to a “boring question” is how I got one of the most high powered executives in my ICP, in my city, to give me a 60 minute meeting. 

Afterward, he introduced his whole team to me and said if they ever have a need around my services, I’m who they should call — plus the book wasn’t bad either. :)”


7. Spice it up with your prospect’s product

Finally, one of my all-time favorite examples that has me laughing out loud every time I watch it is the video that Frankie Weschler of Dynamic Signal created for his prospect, Buffalo Wild Wings

Any time you can incorporate a brand’s own product into your pitch you’re going to see better results. Frankie just took it to the next level with this Blazin’ Hot account-based selling video outreach example:

If you found these examples entertaining and worthy of sharing, imagine how your own prospects will react when you send something creative and fun that breaks through the noise.

They’re far more likely to engage. There’s a really good chance they’ll share it within their organization and then you become known as that really cool sales professional who reached out with such a compelling and creative approach.

Beats the heck out of being ignored!

Got your own example? I’d love to see it. Feel free to send it to

Scott Ingram is the host of the Sales Success Stories AND Daily Sales Tips podcasts. He’s the author of three books: Sales Success Stories, B2B Sales Mentors and Finding Sales Success on LinkedIn. He’s also a quota-carrying sales professional who works for the professional services company, Relationship One, as an Account Director. Scott lives with his wife and two daughters in Austin, Texas, where he hosts the Sales Success Summit each October.

  • Originally published March 10, 2021, updated May 31, 2023