Email Prospecting Playbook

The 1 Line Description

A simple guide to personalized prospecting emails.

When to use it

To test a new idea with a target audience who lives on email.

Key Ideas

Prospecting & 1:1 Emailing playbook

You have an idea but want to see if your suspected target audience will bite? Why not find some emails, and email them 1:1 and see what they say? This methodology works particularly well for Phase 1 of B2B marketing as described here.

The hack here is that while you make every effort to personalise the emails to each target audience, you use tools like Yet Another Mail Merge and/or Mixmax/ to do this in bulk as far as possible. 

Building a prospect list

1. Decide what businesses/people to target

It’s best if you start with a base list - this could be companies you think are the right targets or at the very least, a list of job titles+company size/industry that you think makes for a good prospect worth spending £s and time finding.

Think about the data points you’d like to do your analysis on when it comes to reviewing your effort. For eg. will it be good to say X people from the following 3 industries were emailed, Y people from Industry 1/2/3 clicked, and Z people people from industry 1/2/3 opened. Or do you want to test responses from varying job titles (aka personas)? Or is it the company sizesthat you are testing so you can guide your future marketing activity? Either make the effort or spend a bit of money and use the outsourcing tools mentioned below to get these data points from the web.

2. Get Email Address, First Names, Company Names as a Minimum

If you have prospect full names + domains already, you can use a tool like to find emails at bulk. Else, use LinkedIn to find people and a tool like to find the emails associated with the profile. 

A less scalable way is to add people on LI, and if they connect with you, you will be able to export the data and thus get their emails. Note that this often only yields personal emails.

Alternatively, spend the money and leverage an outsourcing platform like UpWork or PeoplePerHour to get the data.

At the very least you should have first names, emails and company name.

If this is your first time doing this, don’t be over ambitious. 200 people representing at least 50 companies is a good enough starting point that you will get a few good responses and hence learn something valuable. This will take you an hour or two set up and ~$40-50.

Typically ask the freelancer to find 2-3 people max per job title, give them a few job titles to seek out and thus get to an expected outcome of 200 people - as per the parameters of your test.

2a. Using UpWork

Upwork is Not built for email hunting - you’re essentially using it to hire a freelancer who specialises in ‘lead gen’ tasks. Create a free account, post a job (if it’s your first time keep it simple and select a short term contract), and basically pick the least stringent options like freelancers from anywhere in the world and not just ‘master freelancers’. You certainly don’t need to promote it as these jobs get subscribed to right away.

You will typically get 10s, if not 100s of people around the world keen to do the work. I’ve tended to optimize for people who have done email hunting previously and can start soonest. You can even insist that they will replace a few of the emails for you at no extra cost.

Hack: Get the person you’ve ‘hired’ to paste their findings into a Google Sheet that you’ve shared with them so you can check in on their work.

3. Verify list and Deduping

Without ‘verifying’ the emails (the tool pings the email server to check it exists) you will get bounce rates of 30-40% in most cases.

So find the balance between discarding all unverified leads and sending out to lots of rubbish/not working emails that will cause your inbox to be flagged.

Once you have all your prospects you’ll need to dedupe them against any existing sales list to avoid emailing contacts you’ve already contacted.

Here’s how to do it in Excel - Filter for unique values or remove duplicate values

And in on Google Spreadsheets - Google Spreadsheets Remove Duplicates Add-on

Congrats you’re a significant way to sending out emails to new prospects and hopefully getting some conversations going!  🙌 🙌 🙌

Crafting Emails and Sending

1. Create emails

This can have varying levels of complexity however a simple method to start with is 3 emails. 

Email 1 - General introduction

Email 2 - Simple reminder with the subject line as re: <email 1 subject line)

Email 3 - A different value proposition/alternative approach whilst also saying, I won’t bug you anymore.

Example emails 1

Example emails 2

Example emails 3

Generally a light and breezy tone works well. Remember these are meant to be personal emails so lines that say things like ‘You must be ___ so I want to offer you this new way to do things’ is the way to go.

Don’t be afraid to say you’re in the process of improving your app/business model and hence would like feedback. This will resonate with tech savvy, entrepreneurial audiences well.

Send these emails on a Thursday-Tuesday- Friday cycle (perhaps?).

2. Automate sending of emails

This can be setup via Yet Another Mail Merge or gmass. This software will link to a google sheets and can send individual emails via your gmail account to all the prospects. 

Interval: 3-4 days between emails is recommended.

If you want to build out smarter/longer workflows try a tool like or Mixmax.

Refrain from using traditional email marketing tools like MailChimp or Hubspot as these tend to send as non-personal HTML (newsletter) emails.