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Playbook 12 April 2023

How to Create Personalized Sales Outreach That Gets Replies

Rory Sadler
Co-founder & CEO @ trumpet

Summary graphic about why you need to do personalized sales outreach

Toot toot, Rory Sadler, Co-founder and CEO of trumpet here. 🎺


2023 is the year of the buyer. This means sales has to do something differently. 


It all needs to be about your prospect, and you’ve got to do personalized sales outreach. 


There are so many channels out there. Buyers are being overloaded, and it’s causing indecision.  You heard it here first. 👇


So, let’s look at how you can work on your messaging to make it value-based. Use these steps to build stronger relationships (and higher reply rates).

Personalized sales outreach playbook

Step 1 
Cut the fluff in cold email outreach

You’ve got to just get to the point.


Particularly with cold emails or LinkedIn, if something doesn’t add value, just take it out.


I explain more about why you need to cut the fluff here. 🎬



Forget: “I hope this finds you well, I’m an SDR at X company”. Openers like this just make the message about you anyway.


Most people look at their emails on their phone. If an irrelevant subject line or email body preview takes up space, it’s going straight in the bin. 🚮 


Infographic about the do’s and don’ts of cold email outreach


💡 Need more tips on cold outreach? Check out these playbooks and articles:


Wanna put these playbooks into action? If you’re struggling to get accurate email addresses and phone numbers, you can try Kaspr for free.

Step 2 
Switch up messaging and make it personal

So how long do you really spend on multi-channel outreach? Voice notes and videos are often done too sporadically to make a big impact. If I get two voice notes, I’m way more likely to reply.


Too many prospectors still put 100 people into their sales sequences and think they’re done for the day. You’ve got to go the extra mile. 


  • Spend 5 -10 minutes on each prospect in your ideal customer profile (ICP).
  • Find out the information you need to add creative personalization to your outreach.
  • Consider your next steps depending on the action taken from your first touchpoint.


Remember, you need to iterate constantly. Your sales cadence will never be a final version. It’s so easy to stay in a routine once you find something that works for you, but different people appreciate unique forms of communication. So, consider the moves from the prospect.


Plus, channels quickly become over-saturated. Maybe videos will lose their novelty soon because everyone’s started doing them. It’s easy to stagnate if you never switch it up.


At trumpet, we evaluate messaging and sequences weekly. We go back to the drawing board and see what else we can do rather than focusing on what is working now. This means we always try new things, fail fast, and constantly improve.

Step 3 
Be the guide

B2B buying behavior has changed. Ten years ago, sales representatives would’ve been one of the only sources of information. Now, buyers do 70% of the research before they speak to a sales rep, and 72% prefer a rep-free experience.


They’ve also got:

  • Websites with ungated demos.
  • Review sites.
  • Social media.
  • Strong communities.
  • A network of peers on LinkedIn.


Let’s not forget all these available channels can cause indecision. 👇


You’re not taught how to buy software for your company. Sales needs to do the heavy lifting to guide their prospects through the buying cycle.


  • Introduce timelines. Give your buyers visibility of what’s ahead and how long the project will take.
  • Create mutual action plans. These add accountability, push deals forward and educate your internal sales champion on what’s involved in making this happen.
  • Clarity of the buying experience. Your buyer wants to know what usually happens, what you can help with, and what they need to do.


The big thing here is you’re helping them make a business case for your solution, in a way that can’t be done through other channels. Aside from being a good fit, you’re also explaining what needs to be done at every stage for the implementation to succeed.

Step 4 
Bring the elephant into the room

If there’s one thing I’d advise sellers to stop doing when it comes to personalized sales outreach, it would be…


⛔ Avoiding questions about competitors. ⛔


Prospects can get all the information they need online, including social proof. Maybe what they find is enough to make a buying decision. But even if they love your solution (or someone else’s), they’ll most likely be doing vendor analysis. It’s just common sense to shop around.


It’s better if you’re able to control the narrative. Be open about the strengths and weaknesses of your competitors.


Bring the elephant into the room by saying something like this.👇 🐘


“So with company X, who you’re likely to look at for these solutions, they are great at doing X, and are known in the market for this. The reason I believe we are a better fit is because you said a key requirement for you is X. This is an area where our customers say we are very strong in.”


This way, your internal sales champion can take it to their CFO or other decision-makers. We know that as recession uncertainties continue to loom, these stakeholders will always be asking their colleagues to have a full comparison of what’s available.


So, If you’re able to help with some of the research and heavy lifting, this is only going to go in your favor.

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