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Personalization, relevance, timing in sales outreach

A few merge fields for name, company name, and role, and everything is sorted, right? Not exactly.

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The difference between cold outreach that hits home and cold outreach that strikes out comes down to three key factors: personalization, relevance, and timing.

While incorporating each requires a slightly different approach, all three underscore the importance of understanding your prospect—who they are, why they should care, and when they’re most likely to be receptive to your offer.

These days, you can’t expect to get through to someone by just adding their name to a cold email. Personalization only works when you can develop a contextual understanding of their pain points, goals, and how industry news impacts them on an individual level (relevance and timing).

In this article, we’ll go over each of these areas and provide some insight into how you might incorporate these three critical success factors into your outbound sales strategy. Let’s dive in.


Personalization is the “easy” part of outreach. A few merge fields for name, company name, and role, and everything is sorted, right?

Not exactly. The more popular automated personalization becomes, the less effective it is. By now, everyone knows that “Hi, (name),” was accomplished automatically, we already skip over it as we read or ignore it altogether.

According to Instapage, over 80% of consumers want sales reps to take the time to get to know them and understand when to approach them and when to back off.

To earn your prospect’s respect and attention you have to dig a bit deeper. The more creative, the better. Find your prospect’s recent achievements, publications, comments, whatever you can connect with them about.

You want to show them that you’re a real person that’s taken a real interest in them, that you aren’t just taking shots in the dark. This ties in with social selling. Work your social media and whatever connections you can find.
Don’t doubt the power of personalization. 79% of companies that exceeded revenue targets report having a documented personalization strategy, while smart personalization engines that can recognize buyer intent are believed to boost profits by up to 15%.

With enough time and large enough accounts, personalization can become very complex and creative. Once you’ve done your due diligence for relevance and timing, you’ll have a better idea of how much effort you can afford to spend.


Salesforce’s 2019 State of the Connected Customer report found that 73% of customers expect companies to understand their needs and expectations, while 62% of respondents say that they expect organizations to adapt their outreach efforts based on past behaviors and interactions.

Relevance in sales outreach extends WAY beyond getting lucky with LinkedIn posts and bios. It’s about finding the right people, then digging deeper to find out more about the prospect’s background, company, and the industry they operate in.

Understand the defining characteristics of your best customers

Before you do anything else, you need to have a good ICP (Ideal Customer Profile) nailed down, so that you can weed out prospects that don’t fit. Characteristics might include:

  • Company size
  • Annual revenue
  • Industry
  • Job function
  • Location

We get into buyer personas in another recent article if you’d like to dig into this more.

Research prospects on the individual, company, and industry level

You’ll want to start your research process with a zoomed-out view of the prospect.

Head over to their LinkedIn page to get a sense of what this person—and the company they work for—is all about. How big is the company? What do they do? Who are their customers?

From there, you’ll want to dive deeper to learn more about the prospect as an individual. Check out the following to learn more about this potential buyer:

  • Social media profiles
  • Company news
  • Company website
  • Individual blog
  • Guest posts on other websites
  • Specific page visits and time visited, if possible

Initially, you’re trying to gain an understanding of who your prospect is and whether they match your ideal customer profile.

A cursory LinkedIn and Google search should help you get a sense of whether this person actually aligns with your target customer—i.e. will they find your solution valuable and are they likely to be able to afford it.

Essentially, you’re running through a manual lead qualification process to ID any red flags before reaching out.

From there, if everything looks good, you’ll want to start digging deeper to learn more about the prospect on an individual level.

You’ll want to learn more about their existing knowledge so that you can tell them something they don’t know (a hallmark trait of the Challenger Sales model).

For instance, it’s good to know ahead of time if your prospect is an industry thought leader with a library of in-depth content under their belt or someone who isn’t quite as well-versed in the goings-on within their industry.

Start your message by pressing on a relevant pain point

After you’ve learned about your prospect, their company, and the knowledge they bring to the table, you’ll want to do some research to uncover the highly-specific pain points that keep these folks up at night—or would if they knew what dangers were lurking in the dark recesses of the industry.

Don’t reach out before you fully understand your prospect’s most pressing pain points.
This includes looking for threats on the horizon, emerging opportunities, and potential black swan events that could undermine the prospect’s organization.

After you’ve examined current market conditions and how they’re likely to impact your target buyer, you’ll want to come up with a few strong hypotheses for what specific pain points your prospect is dealing with right now and determine how you can address them with your offering.

Cold outreach that doesn’t speak to your prospect’s current and pressing needs is likely to fall flat. No one has time to listen to your pitch just for the fun of it. If you don’t get the prospect’s interest in the first few seconds, your message will strike out.

This is why relevance is key. Your goal is to figure out which pains are most pressing for your prospect today, this week, this month, this quarter. Then shape your opening message around those pain points in a way that’s sure to grab your prospect’s attention.


Timing is the final and most crucial point.

The pain points you settle on might fit the prospect you’re working on, but if they’ve already dealt with the problem or it hasn’t started to bother them yet, your outreach is a waste of time. Likewise, if your prospect has just chosen a competitor’s solution, if they don’t have the budget, or are swamped with other work or higher priority problems, you’ll be fighting an uphill battle.

Frankly, all other challenges in sales pale in comparison to getting timing right, and it’s the hardest one to find out from research alone. Your best bet is to make educated guesses about when and why a prospect might need your solution and be certain to send your messaging when it’s most likely to get through.

Here’s a quick look at what to consider when it comes to nailing timing.

Actual time

Actual time refers to things that you have control over. Forget about your own offering, if your prospect was going to buy anything that they needed, when would they buy it? Think about your prospective buyers’ deadlines, budget planning schedules, and the best time to catch them during the day or week.

  • Time of day. Consider your prospect’s routine. What time do they arrive at the office (or hop online)? When does their day end? When are they most likely to answer the phone or take some time to respond to an email?
  • Day of the week. Do you know how this person structures their weekly schedule? When are they most likely to have meetings or deadlines? Again, which days are they most likely to respond to an email, a DM, or a phone call?
  • Months. Let’s zoom out a bit—are there certain months where your prospect is totally slammed (think accountants during tax season) or under pressure to hit a short term goal?
  • Quarters. Do you have a sense of how your buyer’s year is structured? While the practice of buying during certain times of year is becoming less and less common, some organizations still perform vendor research and make purchasing decisions during certain times of year. It’s good to get a sense of whether your prospect falls into this group before you start reaching out.

Trigger events

Understanding when a prospect might be ready for your offering can be difficult, but you can look to certain clues to make an educated guess. Even if you don’t hit the mark exactly, prospects will still appreciate that you’ve taken the time to look into their situation.

As a sidenote, one big advantage of quality outreach is that you don’t burn bridges. Even if your prospect doesn’t need your offering now, if you make a good connection, they will remember you if they need it later. And you’ll feel comfortable asking for a referral. (Always ask for a referral.)

Start with industry and organization news to find timing clues.

Company announcements like funding rounds, product launches, or new leadership could signal that your prospect’s organization is growing. For example, if the company is going on a massive sales hiring spree, they might be in the market for your sales enablement software.

In this case, you might keep track of industry trigger events using Google Alerts or any number of sales intelligence tools.

Additionally, checking sites like AngelList or Crunchbase can help you ID new prospects who have just secured a round of funding and now have some extra cash in their pockets.

You might also reach out in response to industry news like new regulatory requirements like the GDPR or the CCPA. Or maybe you have a video conferencing tool that makes COVID-era remote work easier on sales leaders.

Bottom line: sales outreach lives and dies with contextual understanding

You can see how personalization, relevance, and timing, build from one to the next.

Personalization means speaking directly to your prospect, not to an imaginary persona, and not sending bland, one-size-fits-all messages.

Relevance means that the offering you have fits the prospect you’re speaking too, it’s personalization taken one step further.

Timing means that your solution doesn’t just cover the right pain points, but that the pain points are affecting your prospect at the time when you speak to them and that they have the actual possibility to make a purchase.

Remember, your outreach needs:

  • “Who”, a real person that it’s addressing
  • “Why”, the reason that your offering is going to help the prospect
  • “When”, a good chance that your prospect needs the solution now

You can’t focus on any one of these areas without the others and expect your outreach strategy to be successful.

To learn more about personalization, relevance, and timing in outbound sales, tune in to our upcoming masterclass Tomorrow’s Outreach Today with Sales Development master, Justin Michael. Justin has been experimenting and pushing the boundaries with cold outreach his whole career, earning a reputation as a thought leader on the cutting-edge of sales engagement.

Justin will be breaking down sales messaging to explain how sales teams can go beyond simple merge field personalization to net the meetings that they need.

Tomorrow’s Outreach Today with Justin Michael ended on September 10. Watch the webinar replay now and increase your odds with your cold outreach.

B2B content writer & strategist

Grace is an experienced B2B content writer & strategist for SaaS, digital marketing, & tech brands from Los Angeles, California. With a knack for turning complex concepts into compelling narratives, she has assisted numerous brands in developing impactful content strategies that engage audiences and drive business growth. Her wealth of experience in the ever-evolving tech world has equipped her with a unique perspective on industry trends and dynamics, enabling her to deliver content that resonates with a tech-savvy audience.