7 Steps to Booking Cold Meetings at Scale

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I’ve been asked by many founders recently how to book cold sales/discovery meetings. In this article, I’m going to show you how I leverage some key tools online to create meetings with cold prospects via email at scale.

These are the live templates, documents, and data I used when I was booking cold meetings for a discovery trip I did in San Francisco in 2018. I booked 22 meetings over 5 days from 250 leads. Contact details of leads have been removed for privacy.

Step 1) Define your prospect criteria

The first step is identifying the common criteria and search parameters of the prospects you wish to meet with. The tool I use for this is LinkedIn Sales Navigator (LSN). With LSN you can either search for Leads (people) or Accounts (organizations). Within each of these categories, you can filter by really specific fields such as Geography, Industry, Company Headcount, Title, Function, Seniority Level etc. It is helpful if you already know of an actual person you want to meet with and then work backward in figuring out what you would input to find them and their industry peers.

In this instance I discovered that the criteria of people I wanted to meet with had the following search parameters:

Geography = San Francisco Bay Area
Industry = Computer Software, Information Technology
Company Headcount= 201–500, 501–1000, 1001–5000, 5001–10,000, 10,000+
Title = Talent
Seniority Level = CXO, Partner, Owner, VP, Director, Manager, Senior

As you can see there were 456 leads that met these search parameters.

LinkedIn Sales Navigator results for my search criteria

Note: Some leads that your search returns may not meet the profile that you’re after because their ‘title’ technically includes what you searched for but it actually means something different internally at their organization. Try and identify if there is a pattern to these ‘non-prospects’ and instruct your freelancer in step 3 to exclude them.

Step 2) Identify the data fields you wish to capture per lead

Next, I created a Google Sheet with the column headers being the data fields I wished to capture for each lead. It can be useful to color code these headers with red being mandatory and yellow being optional. See an example here: Lead List Template.

I then completed the first three leads with the information I could glean from their LSN profiles; these profiles tend to have a bit more company data on them than personal LinkedIn profiles.

Example of Lead List data spreadsheet

You may find it difficult to find contact details on people’s profiles. To assist with this, I recommend using a contact scraper tool like Lusha or Hunter.io. I love Lusha.

Example of Lusha chrome extension doing its thing..

Step 3) Create an Upwork Job

Now, if you have less than 50 leads that fit your criteria, you could choose to go through them one by one and complete the fields in your spreadsheet yourself. However, if you have more than 50, then I recommend utilising some of the amazing freelancers that are out there. Personally, I use UpWork and highly recommend an UpWorker named Shubhashree Pai (aka Shubha); I have worked with her for 10 outbound campaigns now totalling over 1,000 leads. She charges US$0.50 per verified lead, has exceptionally fast turnaround and finds very high-quality information.

For this campaign, I created a job in UpWork for her and used the following copy for my instructions: Upwork Job Instructions template. Within the job instructions, I linked to the Google Sheet I created in step 2.

Step 4) Create your draft emails

Whilst Shubha worked her magic, I drafted the two emails I intended to send in the campaign. These emails were designed to be short, punchy and enticing enough to get a meeting.

Established thinking in the world of sales will indicate that you need to have far more than two touch points to run an effective sales campaign (9–12 depending on who you speak to), and I tend to agree with that, but this method is for when you need to move fast and book 20ish meetings in a week to run a discovery process, validate an idea, explore a new market etc.

Here are the emails I used in this campaign: Cold Emails for SF Talent Leads.

Note: If you wish to learn more about how to structure and optimize an entire sales campaign then I’d highly recommend getting in touch with Jacco and Andy at Winning By Design (a sales consultancy we used at Everproof).

Step 5) Send your first email

Once my emails were drafted and Shubha had completed the lead list data, I was ready to send my campaign. To assist in sending 100+ emails at once, I leverage a mass mail extension for Gmail called ‘Mail Merge with Attachments’. I find this extension is awesome as it doesn’t mess with the formatting of my emails at all and often avoids them getting caught in spam folders.

All you have to do once you have the extension added is:

  • Go to a new Google Sheet;
  • Select ‘Create Merge Template’;
  • Add the relevant data from Shubha’s completed list into this new Google Sheet;
  • Ensure that the field headers match the {{tags}} in your draft email;
  • Create an actual draft email with your first email copy in it;
  • Select ‘Configure Mail Merge’;
  • Configure it within the extension so that it matches the draft in your Gmail (the UX of the tool will walk you through this);
  • Then hit ‘Send Campaign’!

Note: To increase your chance of a response, send out your email campaign between 8am-11am Tuesday or Thursday. If you’re emailing CEOs then 3pm-5pm on Sundays can also work well (known as the exec window).

Another Note: there are other mass mail tools for other mail browsers.

Step 6) Monitor bounce backs and responses

Shortly after I sent out the campaign, I got a bunch of bounce-backs from dodgy emails (i.e. emails that weren’t correct or no longer exist). This is an inevitability as there will be some dodgy emails that weren’t properly identified by the data enrichment tool your freelancer used. The expected bounce back rate is roughly 25%. Any higher than 30% and you should find yourself a new freelancer (or use Shubha!), any lower than 20% and you’ve found yourself a real winner.

I usually highlight the bounce backs in a new column for Shubha and she will either find a new email address for that person or find a replacement lead that meets my criteria at no additional cost.

As soon as I got an actual response from a lead that I contacted I then commenced a bespoke email thread with them where I was either generally:

  • booking them in for a meeting if they were interested;
  • providing them with a bit more information; or
  • thanking them for their time if they weren’t interested.

Step 7) Send your second email

Lastly, 2–3 days after my first email I sent those that hadn’t responded a second email.

I tend to keep the second email shorter and with my available times and dates slightly reduced to show that I’m being booked up (even if I’m not..). I keep the email subject line the same (so that ideally it gets threaded under the first email) and I also copy and paste my first email under my email signature in the draft; just in case the threading didn’t work.

The template for my second email is in the same document as my first email here.

The second email always gets a much higher response rate than my first email and is what led to most of my meetings being booked. In this campaign, 17 of the 22 meetings I booked came from the second email I sent.

My total stats for this campaign were:

Leads contacted: 250
Leads bounced: 60 (24%)
Leads responded: 43 (22% response rate of non-bounced leads)
Meetings booked: 22 (11.6% booking rate of non-bounced leads)

This wasn’t my most successful outbound campaign but achieved my desired target of booking 20 meetings quickly.

Go forth and prospect

Okay, those are all the key tools and tips I can think of that have helped me book cold meetings over the years. Be sure to use this as a guide only and amend the copy, cadence etc. as you see fit.

If you found this article useful feel free to leave a clap or a comment and I’ll be sure to keep sharing what I’ve learned through my journey so far.

Final Note: I am not getting a cut from any of the products or people that I mentioned in this article. I am just a big fan of them/their services and I hope that you will be too :)

Chief of Staff @ Skedulo