Outbound Prospecting

Tips and tricks for outbound prospecting that will fill your funnel. The do’s and don’ts (with examples), learn how to customize your messaging, and develop persona’s.

4 months ago   •   5 min read

By Bravado Staff

By: Mike Marg

The Definitive Guide to Outbound Prospecting

Entire books could be written on outbound prospecting theory, but the goal of this article is to distill it down to its most essential ingredients.

Here is why outbound prospecting works: it relies on individual sellers, who need to hit certain pipeline generation goals, to reach out to the exact right people, at the exact right time, with the exact right messaging.

It’s almost impossible to do this at scale, which is why marketing deploys relatively generic “mass appeal” messaging and campaigns, while sellers deliver value by bringing tailored messaging to the right people in their book of business.

What types of touch points should sellers be thinking about?

Sellers need to mix up touchpoints for the highest impact. When companies advertise, they try to hit you with TV ads, banner ads, Facebook ads, radio ads, billboards, etc.- the biggest brands in the world try to reach out everywhere with multiple touchpoints, and good b2b prospecting is similar.

You should think of a personalized email, an email sequence, a cold call, a voicemail, a LinkedIn message, a personalized video, a Sendoso gift as various tools in your outbound prospecting tool kit.

Where does most prospecting fail?

Most prospecting failures come from a lack of personalization. You see a lot of highly generic, highly interchangeable messaging that a prospect can read and say “oh, I can totally ignore this because this email is clearly not meant for me specifically.” Whether it’s a cold call, cold email, a Loom video, etc. - you need to have a personalized reason that made you want to reach out to this person, this company, this role. It needs to be thoughtful.

This means that prospecting becomes a factor of both messaging quality (multiplied by) messaging quantity. An enormous number of poorly written, poorly customized emails won’t deliver results. A tiny amount of highly personalized, perfectly messaged emails probably also won’t deliver results. So the best prospectors can figure out how to do both at once- relatively high volume, but in a way that is also customized and specific.

All things being equal, I’d prefer better customization and lower volume- that will drive better results in a world where everyone is desensitized to cold outreach.

How to customize

I personally recommend the reason/value/question format for most cold email, and this can be retrofitted to a voicemail, Loom video, or whatever you want.

I wrote about it here, but the TL;DR is that you need to accomplish 3 key things in a well customized message:

  • The REASON
    I’m reaching out to you specifically- that isn’t really broadly applicable, it should be something specific that can’t read as mass replicated
  • The VALUE
    I think the solution can drive for you, specifically (ie- if you share case studies or examples, they also need to be customized based on role/company type/persona)
    I want to ask to drive action- ie, what is my call to action? Without a clear call to action or question, it’s very easy to ignore you. Make it super easy for prospects to respond.

Develop your personas

The best sales orgs spend a lot of time and energy up front researching what type of users are the best fit for their product, and how they’re using the product specifically. This is important because, as a sales leadership team, sellers must be equipped to pattern match and bring the right message to the right person or company. Frameworks like MEDDPICC can help with this, but here's a helpful breakdown:

Here are some relevant questions for persona planning:

  • What roles (user types) typically buy your product?
  • What company types typically buy your product?
  • What companies specifically within each sector have bought that your sellers can reference?
  • What are the top priorities of these user types?
  • What pain do these user types have?
  • What gain do these user types typically get from your product?
  • What is the impact of solving this pain?

As time goes on, the sales org should build a repository explaining and mapping out these personas and examples so that sellers can bring tailored stories and example to their target audience.

Putting it all together

When building messaging, ALWAYS focus on the perspective of the person you’re writing to, not your own perspective. Meaning: don’t make your message all about you- prospects care about themselves, so don’t make them work hard to find the value in your message.

❌ Don’t

Start with  “Hey (prospect)- my name is Mike Marg, and I’m your account rep at (company name)." They do not care.

✅ Do

Focus on “you” - as in:

  • Hey {prospect), I was browsing through your {website, job page} and noticed {insightful observation}. Out of curiosity, {compelling question}?
  • Similar {role types} have noticed that {pain statement}. By {taking action} they were able to {drive key result}.
  • Does {painpoint} resonate with you as something that could be worth exploring?

The above framework is not at all “me” specific, I’m highly focused on the prospect. Simply shifting your mindset from “what do I care about” to “what do they care about” will work wonders.

Bad outbound example

Hi Greg,

I wanted to reach out and introduce myself- my name is Mike Marg, and I am Dropbox’s account executive at Clearbit. [reason- highly focused on me and not the prospect]

Clearbit is an enrichment platform that can enrich every single lead in a marketing database with firmographic information. That means no more incomplete records, or untargeted marketing campaigns. [value- this makes Clearbit (product) the hero, and not a similar buyer]

If you’d like to learn more about our enrichment product, please let me know, I’d be more than happy to share more. [question- no call to action, unclear what I’m asking for]


Good outbound example

Let’s try it again:

Hi Greg,

Your blog post on Dropbox’s product led approach was really interesting- completely agree with your point that the job of the marketer is totally different when you have thousands of free users. [reason- about the prospect]

A lot of PLG focused marketers (like you) find that enriching their userbase with firmographic information makes it much easier to craft specific marketing campaigns that actually drive response rates.

Dropbox users in the enterprise probably have a completely different set of needs than SMB or mid market businesses, and guessing your messaging would probably differ slightly for both populations. Similar companies like Box, Loom and Grammarly have found that enrichment tools (like Clearbit) can help drive a 15-20% improvement in response rate by powering better email personalization. [value- about how similar marketers took action to solve their problem]

Assuming Dropbox probably invests a lot in improving marketing email response rate, do you think database enrichment could be impactful? [question- easy to answer, clear what I’m asking]



Good prospecting is a function of bringing the right message, to the right person, at the right time. Quantity of outreach is certainly a factor, but it’s not nearly as important as customized outreach that cannot be mass produced- it’s incredibly easy these days to recognize and ignore non personalized outreach.

You’d be amazed at how much thoughtful personalization can help you stand out, so do the legwork upfront to identify key trends to personalize, and every message you craft will benefit.

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