Sales Best Practices

Four Dating Rules that Should Inform Your Multi-Touch Outbound Strategy

Chelsea O'Neill, Solutions Consultant's Avatar

Chelsea O'Neill, Solutions Consultant

Reaching out to potential buyers in the sales world is a lot like dating. Everyone who’s ever sent someone a request for a meeting, or gone out on a date, knows what I’m talking about.

As Vince Vaughn’s character says in Wedding Crashers: “You're wondering, ‘Do I have food on my face, am I talking too much, are they talking enough, should I play like I'm interested?’”

For sales development representatives, or SDRs, it sounds more like: “Do I call? And if I call do I leave a message, or should I email first to tell them that I’m going to call?” While the goal for outbounds sales is to get a response from the customer, you want to build a relationship with your customers without overwhelming them or coming across as a Stage-Five Clinger!

If you’re not sure where to start, here are 4 rules from the dating world to create an effective multi-touch outbound strategy.

Rule #1: Etiquette isn’t old-fashioned, it’s sexy

You wouldn’t send a text message at 10pm to someone you just met, and you definitely shouldn’t to your prospects either. Whenever you’re hoping to meet with a new prospect, be on-time, prepared, and ready to listen. First impressions matter, so don’t get disqualified by “people turnoffs:” anything that doesn’t put the customer first. Things like interrupting, being inattentive, or anything unprofessional will make your first meeting also your shortest because your prospect will quickly bounce. If in doubt about something, err on the side of polite and professional.

In addition, respect their requests after the meeting too. Honor all opt-outs and follow your company’s rules of engagement. If they opt-out of text, don’t text, but if you have Opt-Outs by Communication Channel, you can see which channels are most preferred by your prospects and then fine-tune your outbound strategies.

Rule #2: Mix it up a little

In both dating and sales, the phone isn’t dead. eharmony says that using the phone is still one of the top ways to engage a date, and the same is true in sales: more than 40% of salespeople say the phone is the most effective sales tool at their disposal.

But as the relationship continues, you’ll have to mix it up to make sure you’re reaching people on the right channel at the right time. Our customers with the highest engagement levels are constantly trying out new strategies to see which channels are most effective at each stage of the customer journey, and using A/B tests to continue optimizing their messaging and delivery. Why? Because what worked six months ago might not work today, and they want to keep being successful.

Outreach has integrated direct mail into our engagement strategies by including a general task into some of our sequences. We sent 448 prospects a personalized gift via direct mail, and the result was eye-opening: 40 booked meetings and a 26% reply rate--well above the typical 3-4% response rate. We saw this success as evidence that the tangibility of direct mail elicits an emotional reaction: 57% of people have reported receiving mail makes them feel more valued in a way that emails and phone calls can’t match.

Rule #3: Make it Personal

It’s never fun when you meet someone and all they do is talk about themselves. The same is true for outbound prospecting--be sure to listen and understand what they’re looking for, or like I said, it’s going to be a very short meeting.

At Outreach, we found that using custom or personalized messaging supercharged our prospecting. Our best-in-class outbound sequence begins with a heavily curated and custom email that we then supercharge with bumps (download template here).

This sequence focuses on customization at the front end, and resulted in 67% of responses received within the first five steps. In fact, this sequence was so successful that we ended up changing our internal team KPIs.
Screen Shot 2019 06 18 At 4 08 36 Pm

Using a hand-curated, customized email template was so successful that we got 67% of our responses within the first five steps.

This sequence focuses on customization at the front end, and resulted in 67% of responses received within the first five steps. In fact, this sequence was so successful that we ended up changing our internal team KPIs. The full sequence is below, and is a 38% automated, multi-touch strategy for 31 days and 16 touch points.

Chelsea Gift Chart

Our strategy was so successful we adjusted our internal teams' KPIs.

Best-in-Class Multichannel Outbound Sequence


  • Day 1: Manual Email
  • Day 1: Linkedin Touch
  • Day 1: Phone Call
  • Day 3: Auto Email
  • Day 3: Phone Call
  • Day 4: Phone Call
  • Day 4: Auto Email
  • Day 7: LinkedIn
  • Day 10: Phone Call
  • Day 14: Auto Email
  • Day 15: Auto Email
  • Day 17: Auto Email
  • Day 19: Phone Call
  • Day 21: Phone Call
  • Day 27: Auto Email
  • Day 31: Generic Task

Pro-Tip: When adding new prospects to any sequence, you need to make sure to diagnose the pipeline: go in and check if there were bounces in the custom email (or opts out) and clean up the data.

With really solid outbound multi-touch sequences that are front-loaded with customization, our reps have been tremendously successful in getting a response earlier than we ever had been.

Rule #4: Play like a champion

Not every date will go the way you might hope, and this is true for your sales. Remember that each lost sale is an opportunity to learn what might be done differently to make a connection next time.

As we say at Outreach… always #playfullout.