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Speak Softly and Carry a Big Gift: How Strategic Gifting Creates Opportunities

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When people ask me, “How do I become a more successful salesperson?” many are surprised when I don’t say something like, “Use data to get to know your customer better.”

Instead, my response is always the same: Build better human connections.

You can have all the data in the world. But it won’t help you if you don’t leverage it to actually develop and grow relationships.

I’m going to share my two biggest secrets for doing just that: listening and strategic gifting.

Sales: It’s not just a numbers game

“Sales is a numbers game,” is probably one of the most common phrases uttered by grizzled sales veterans. And while they’re not wrong, building human connections will always tip the odds in your favor.

Why? Because people buy from people, not from data points. 

Case in point: I’ve worked in tech sales almost my entire career. I was trained to send cold email after cold email. I was told that if I just send enough, I’d eventually hit my quota. And sometimes that worked. But more often than not, my cold emails fell on deaf ears.

At one point, frustrated with silence and rejection, I realized I needed to alter my approach if I was really going to succeed. I started doing two things that formed the basis for getting more responses, more meetings, and ultimately more sales.

How I revolutionized my outreach strategy

First, I started paying closer attention to my prospects.

I looked for clues to who they were: Maybe a sports team in the background of a profile picture, or a picture of their favorite pet, etc.

Second, I started sending them fun, personalized gifts that aligned with this knowledge: hats with their sports team’s logo, a chew toy, etc. Whatever I could find that would continue the conversation.

It turned out that this approach worked really well (so well that I went on to co-found Sendoso, a sending platform — but that’s a story for another time).

I realized that getting to know my prospects—and showing authentic interest in things they were passionate about—was a sure-fire way to keep their attention and eventually close sales.

It made them feel heard and appreciated. And in return, they often gave me their business.

In other words, I worked to develop real human connections based on real interactions. This wasn’t a data-driven process. This was literally me getting to know my prospects, and using that as a basis for building a relationship.

Today, adding an additional step in your sales cadence that isn’t an email or a call can more than double your response rate. Through strategic gifting, you are practicing how to actually get to know your prospects. Additionally, you will shorten your sales cycles and increase your close rates from your efforts as well.

No tech tool is the magic solution

It’s essential to make smart investments in the platforms you use to boost your sales efforts. Typically companies have no problem investing in tools to:

  • Make emailing easier
  • Make sending contracts easier
  • Make finding prospect data easier
  • Make using LinkedIn easier
  • Make sharing content easier
  • Make scheduling easier
  • Make getting intent data easier

But do all these tools guarantee sales success?

While they certainly can help, a human element is required to execute sales successfully.

As we all know, LinkedIn has long been a powerful social media platform for professionals. But just like any other social media site, it can be misused and abused.

Used well, LinkedIn can yield new connections, new doors opened, new sales, and more. Used incorrectly, you can send copy and pasted dry emails that go nowhere, blow through entire lists of qualified prospects, or worse–get locked out of the platform for bad sales practices.

My piece of advice: use sales tools well. Insert a human connection to your sales process. Build authentic relationships.

This begs the question: how can you do this at scale? I might be biased, but I believe investing in a tool that makes building relationships easier is incredibly important.

Two tips to build real relationships

No matter what tools you use in your sales efforts, there are two things you need to do if you want to be successful in sales. They are:

Develop your ability to listen

As salespeople, we’re often very talkative! We feel like we need to keep talking in order to convince prospects to sign on the dotted line.

But what we really need to do is to start to truly listen. Listen to our prospect’s needs, yes, but also listen to their pain points, their desires, and their hopes. We need to see them as people and not numbers if we’re going to build a human connection and translate that into a sale.

Learn to give in order to get

Another aspect of sales is that we are literally asking people to give us their attention and, ultimately, money.

But what we don’t do enough is giving. 

And strategic gifting can be a game-changer.

I’ve seen gifts open all kinds of doors at Sendoso, but I’ll share just this one story, because I was so impressed with the level of care and attention this team put in — not to mention the results they got out.

Boulevard is a platform serving spas and salons — point-of-sale, scheduling, and payments. Boulevard’s VP of Marketing, Bernice Lopez-Brennan, was literally running growth marketing while packing boxes for FedEx. As she admitted with a rueful laugh, “It was no way to scale.”

So the team got strategic.

After building out a budget for gifts, they created gift tiers for prospects in different stages of the sales cycle. When prospects registered for a demo, the Boulevard team sent them a $5-10 coffee e-gift.

Post-demo, reps followed up with an e-gift for a $25-50 lunch.

Sounds small, right? But the results were impressive.

The entire campaign was budgeted for less than $2k, but yielded 9x that amount in open opportunities, and 4x that in ROI during a single quarter.

Further down the sales funnel, reps followed up by sending boxes of cookies to their prospects’ salons — winning over the front desk staff and frontline stylists.

So yes, I’m talking about giving prospects a gift card to Starbucks or even a nice bottle of wine, but I’m also talking about giving them our attention. In my experience, that’s what people really want — and what they are often lacking when experiencing more data-driven sales approaches.

The takeaway

I’m sure there are plenty of sales veterans out there who will nod their heads approvingly to this approach, then go back to their offices and start sending out random emails without any personalization other than changing their person’s name.

But we’re living in a new era, where many of us are burnt out. The old approaches simply don’t work anymore. Ultimately, success in sales today—and in the future—will hinge on whether you understand how to develop real human connections. And maybe, like me, you’ll come to realize that building relationships is just as important as meeting sales quotas.

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      Profile picture of Roselynn2020
      @roselynn2020
      ( 170 POINTS )
      1 month, 1 week ago

      I totally agree. I have not sent out my first email as of yet, due to that perticular reason. I don’t just want to sell someone on something, it has to be
      what I believe can do them the most good but also beneficial for both of us. I have been cooking most of my life (professionally) due to a car accident no more. So I am definitely interested in helping people with all that (more another time) I am not going to keep going on this yoo long already. But I do totally agree like my first line said… Thanks for putting that out there.

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