Comprehensive Guide to Outbound Email Sales Automation

Published in

Captain Data

14 min readFeb 26, 2019

You want to build your outbound email sales automation process but have no idea where to start? Let’s build your sales machines!

This guide is for you if you want to:

Automate your outbound sales process but have no idea where to start
Build a powerful (email) sales stack
Understand how the best startups and scale-ups have managed to build sales machines
Stop searching manually for leads 🙂 and instead spend time qualifying them

We’ll be talking about:

Definitions: inbound and outbound marketing
Personas: smart targeting
CRM: you can’t go wrong with this tool
Email sequences
Manual testing: Trials & errors
Setting up your sales stack

Please remember that I’ll be talking only about B2B lead generation here.

Before diving into this guide, let’s go over some of the basics.

Definitions

In marketing, there are two big worlds: inbound and outbound, and it’s actually very straight forward.

For inbound, you want prospects to come to you.

Outbound is the hunting part, where you’re trying to seduce your prospects.

Keep in mind that you should not do outbound without inbound, but the other way around is not true. Hold on to that thought, we’ll get back to it.

Inbound

I won’t cover much about inbound, just the key points:

You need to write quality content: use cases, relevant blog posts about your industry … anything that might help prospects get to know you and what you’re doing;
Inbound is generally linked with SEO and e-reputation: the more you write, the better (always keep the quality high though);
Inbound is THE way to grow organically; some might argue that inbound is the ONLY way (though clearly you’ll be missing out on leads). Depending on your inbound strategy, this could lead to highly qualitative leads that convert easily;
Finally, inbound has a lot to do with your branding and the trust you’re building with your prospects.

Outbound

The big downside of inbound is that the effort takes a while to pay off.

You need to write content, share it and so on. You might need to wait several months before seeing any benefits.

Outbound, on the other hand, is very straightforward: got an email? You’re good to go. Got a phone number? Let’s harass that prospect ( just kidding, but you know how it goes).

We previously talked about hunting. The problem with outbound is that you want to quickly automate everything. But let’s say it from the start, you can forget about that.

A good outbound strategy is a mix of smart automation and people skills, because in the end, the sales game is a relationship game.

The main idea is to be constantly searching for leads.

You need to be very, very active. I’m not only talking about selling, but building long-lasting relationships.

That lead you’re talking with today might not be “ hot “, but it could definitely be activated in 3 months.

And always remember that a lead is (almost) never lost.

Don’t be afraid to be a little bit pushy, like planning a follow-up of 5 emails, minimum. Yes, at first you will be a bit scared and people will want to kill you.

But with time, that heavy follow-up will get better and better. And I mean, no one reads the first email, right?

With social networks and the web, outbound has been taken to a whole new level:

Target leads with LinkedIn
Interact and get to know them thanks to Twitter
Re-target them with Facebook
Enrich existing prospective databases
… there’s endless possibilities here, your imagination is the only limit

Know your prospect — Personas

If one thing is absolutely useless and counter-productive for both inbound and outbound, it’s definitely trying to operate blindly.

By that, I mean not knowing your customer. This is just a no-go.

Identifying personas might seem a bit tedious and boring, but believe me, it will make your life way easier.

*Credits to* *Putting Personas to Work in UX Design*

CRM: Your best friend

Whether or not you are automating outbound, please use a CRM.

If you don’t know which one to use, just go for Hubspot.

It’s still one of the best options available (and it’s free). You could also set up a spreadsheet or Airtable but I find that that quickly becomes a mess, and you don’t get to automate more than the bare minimum unless you’re tech savvy and not afraid to get your hands dirty.

There are roughly 3 techniques regarding CRMs and their management:

Account-based marketing: generally for > €50K deals
Upselling for < €500 deals
Multichannel prospection for > €500 deals

Obviously, strategies differ whether you’re targeting a big account or an individual. You need to be aware of this fact since it influences the way you hunt and build relationships.

Email Sequences

In this post, we will essentially talk about cold emailing. Even in 2019, it’s still the best way to reach out for leads!

A few basics before heading to next section regarding testing.

You need to read a LOT about follow-up email and practice twice as much. Although it seems “easy” to write emails, it’s definitely way harder than just starting to blast emails.

You need to thoroughly review and test them if you want to perform well.

You can find some follow-up templates that have proven to work if you want to get your inspiration flowing and start testing variations:

Consider reading some of the following blogs:

This is just to get you started; there’s plenty of material out there. And a few quick notes:

You will have to set up a minimum of 5 emails in your follow-ups
Use an automation software like Prospect.io or Lemlist (there are many more!)
Keep track of your stats & KPIs 🙂 and analyze each campaign: what works, what doesn’t and why, etc.
Consider that you’re reaching good stats with > 70% open rates and > 20% click rates
Always test and learn; you can always do better
Regularly check https://www.mail-tester.com/ or some equivalent to be sure you’re not falling into the spam box

In the introduction to this post, I wrote that you should not do outbound without inbound. Here are a few reasons why:

You need segmented content to share with specific prospects: use cases, stats, etc.
Inbound shows social proof (e.g. people that can vouch for your product)

For example, in your third email, you could send (manually) a specific blog post you wrote that you know will provide value to your target because you saw they liked something particular on LinkedIn.

It’s all about giving great value to your prospect and nurturing the relationship.

The key to email outreach is to open up the conversation.

Once the prospect is interested (replies positively), you can add that lead into your CRM and start having a real conversation to take them through your sales funnel.

That’s why you should never even mention your product / company in the first email but rather something that will make you connect more easily: a blog post, a like/share, about a subject you believe he/she is really into, etc.

Manual testing: Trials & errors

By now, you should have understood that:

You’re about to create a hunting process
You need to know your customers before doing so
You need to have a CRM to keep track and segment everything
You’ll have to send a lot of emails if you want to close

A quick note: You probably noticed that I never talked once about actually finding leads and WHERE to find them. The answer is pretty easy: LinkedIn.

There will always be companies trying to build B2B search engines (I know, we tried) and arguing that they have THE best data of the world.

Thing is, the only place I know where people really update their profile is LinkedIn (ok, not always).

There are always exceptions and there are obviously good alternatives on the market, but for the sake of simplicity, we’ll take all that for granted :).

Before setting up your sales stack and even thinking about automation, you must do it manually:

Take your personas
Buy LinkedIn Sales Navigator (in short: +++ search filters, +++ views, ability to save searches, and so on)
Decide whether you want to search for ACCOUNTS or PEOPLE

This is really important so I’ll make a quick stop on our hunting road.

There are basically two ways to approach hunting: accounts (companies) vs. people.

There are no golden rules, I’ll try to hand you the cards so you can choose.

People search

No matter the size of the company, everybody* finds value in our product.
Thanks Jane @Embedsocial for this awesome quote 🙂 (* given your persona, of course!).

As a rule of thumb, if your strategy is upselling or multichannel prospection (remember the CRM management above) you can’t really go wrong with a people search.

Indeed, with these two types of strategy, you put people first because the value you provide is primarily directed to individuals: you make their lives easier.

For example, at Captain Data, our mission is to help anyone easily access web data and automate stuff. The number one value we bring on the table is taking our customers’ pain away when it comes to manual work, so that they can focus on something more interesting and valuable.

If you feel that size doesn’t matter (I know, I know), you should start by searching for people instead of accounts. It’s actually a lot easier, because you generally draft your personas for people and not companies!

You can get started pretty quickly by referencing every job title that matches your persona.

For example, if you’re targeting “Office Manager”, you could also add the titles “HR”, “ Human Resources “ and so on.

One of the most powerful features of LinkedIn is the boolean search. You can combine titles to broaden your search (or exclude results!).

This might look like this: (DRH OR HR OR Human resources OR Office Manager OR RH OR RRH) AND (NOT assistant) AND (NOT assistante) AND (NOT consultant) AND (NOT consultante)

Accounts search

If you feel you’d be better off searching by accounts, no worries.

Start by filtering out the companies that interest you, then use the link “ See all 4 employees on LinkedIn “.

Got Sales Navigator? Awesome, check this out:

Way better, right? This way, you can filter by personas. I mean, you don’t want to shoot emails to the entire company, right?

The search URL looks like this linkedin.com/sales/search/people/list/employees-for-account/.

For example, using our LinkedIn Sales Navigator People Search you will be able to extract every profile from this search. It’s very easy to automate at scale.

Let’s get back where we left off:

4. Extract leads from your search

5. Manual data verification: Please don’t skip this step 🙂 No tool is perfect, even LinkedIn can introduce errors and you and your leads won’t be happy! No matter the size of your campaigns, you ALWAYS need to validate data 🙂

6. Start building your campaigns

For your first campaigns, you should have no more than 100 profiles.

So if you have 4 personas, you’ll be dealing with 400 leads. With so many leads, I’d say you’ll be good for the first month.

There’s a lot of reasons for this:

You first campaigns will most likely suck (unless you really know what you’re doing)
You might have over/underestimated personas or did not pick the right ones

Note: Before sending emails, the following steps are absolutely required — believe me, you don’t want to end up as spam (you might need the help of a tech person):

The address with which you’re sending email is correct; I know it sounds stupid but a DNS error happens more easily than you might think, especially if you just got a new domain (and if you don’t know what’s a DNS, ask your tech person)
Verify DKIM and SPIF are correctly set up
Verify every email to avoid hard bounces (which would damage your domain reputation). There’s a lot of cool tools out there like Hunter.io or Neverbounce (both with free tiers)

7. Schedule that campaign!

If you’ve never sent emails before, start gently. A good start is around 20 emails per day.

It’s fairly acceptable and will get you results pretty fast. Don’t start by shooting all of the 400 in a day.

A good tip is to progressively reach your cruising speed. Don’t try to eat too much all at once, it’ll make you sick. Increase the number of emails you send per day each week, and please do remember that with follow-ups you might send more than you thought, so try to take this into account!

As always, quality > quantity. You should prefer having 80% open rates on 100 leads rather than 10% on 1000.

Once you checked everything and your leads file looks great, you can import your file into your favorite tool.

They guide you through the entire process, it’s very well done.

Then you’re left with configuring the campaign.

You don’t need to be a genius to figure this out pretty quickly.

I won’t get into the details since it’s not the purpose of this post, but don’t worry, each tool provides you with step-by-step onboarding to help you get started.

Don’t rush it, take the time to modify the subjects or add small variations in the text.

Setting up your sales stack

First, know that there is no perfect one-size-fits-all sales stack. It takes time to love your sales stack and fully master it. It’s even more work when you’re scaling your sales team.

There’s a lot of work involved, most notably a lot of trials and errors.

This is what our email sales stack looks like at Captain Data:

Automated search & enrichment

So you’ve done it manually 2 or 3 times, your campaigns are starting to show good results and you master the process from A to Z (kind of).

But manual search is still a real pain, I’m sure you’ll agree on that.

You’ve got a few options:

❌ Buy prospect lists (please don’t do that!)
⚠️ Buy a SaaS that offers a B2B database where you can search for leads and build lists (remember what I said about LinkedIn being the best one?)
✅ Use a semi-automated chrome extension such as prospect.io
❤️ Use Captain Data

Of course, you could continue to do it manually. But it’s boring and not very rewarding.

The semi-automated approach works great. Even though you still spend time searching, manual data entry is limited and you can qualify on-the-fly.

If you want to automate everything in 30 seconds by just clicking a button and waiting for your results, you should check out our LinkedIn Sales Navigator People Recipe.

For each launch (we call them jobs), you receive a full extract of people with their email:

You’ve got a few options:

Searches for people
Extracts each profile
Extracts each associated company
Aggregates everything
Finds the email

It saves you a lot of time: the job above took 1h30min for 286 leads with our bot. Imagine how long you would have taken?

Leads verification

I shall repeat it again: whether you’re searching semi-automatically or you’ve completely automated the process, you should always open the results in Excel and verify them.

No tool or database is perfect, and there’s a good chance you’ll find a typo/mistake.

While you’re in there cleaning everything up, pay attention to qualification: are the results aligned with what you’re looking for? Don’t be afraid to delete lines (or save them for later).

Remember, it’s better to have 80% opens on 100 leads rather than 20% opens on 1k leads.

Finally, always verify emails. I talked a bit about Hunter.io and Neverbounce.

At Captain Data, we use neverbounce + prospect.io to double check every email so we never get hard bounces. We even integrate them as third-party (you just need to provide your API key!).

Follow-Up Email

We’ve already talked about it some, here’s where you import your leads and run your campaigns.

Depending on the CRM you’re using, you’ll be able to mark a lead as “qualified” (manually or with a trigger).

Don’t synchronize every email and lead that opens/clicks. It’ll pollute your CRM more than anything.

CRM & long-term work

Remember how I said that “ a lead is never lost “?. This is where your CRM is very helpful and it’s one the best reasons to use a CRM vs. a spreadsheet.

CRMs such as Hubspot can remind you to activate a prospect after X months, for example.

Some people could need more social proof of what you’re building with other customers, or maybe what you’re trying to sell is not really on their to-do list right now.

In startups, you probably heard people talking about “ market timing”.

Well, timing applies all the more with sales.

Remember, selling is about building relationships with people. And we’re not always having our best day, right?

You were too expensive but they just raised a $2M Series A? Might be a good call to re-activate this account
Account is hiring 10 new sales reps? And you’re selling the tool that will respond perfectly to XXX sales rep pain? Well, great!

Moreover, along the way, you’ll notice triggers: small things that say “ hey, that lead is ready to buy RIGHT NOW “, for example:

These are very general triggers, you could find something more specific to your niche/target. Try to pay attention to it, it’ll help you improve conversion.

Additional Tips

It’s always a good idea to:

Use something like Calendly to help schedule meetings and avoid back-and-forth emails (nobody likes those!). Check out my calendar if you want to chat with me about what you just read 🙂
Use something like http://appear.in or https://zoom.us/ for live onboarding/demo
Work with someone with a technical background (it’s not always easy to set everything up)

Conclusion

If you’ve read this far, I believe you have all the tools to properly start blasting emails and hunting leads.

I’ve scratched the surface to get you started quickly. There’s a lot more to know on the subject, and as always, it takes a lot of practice to master every step.

Remember that we’ve just talked about email lead generation and that there’s a ton of other ways to attract leads. We’ll cover this in some later posts 🙂

A few tricks you could think about are things like:

Automatically following a lead on Twitter when sending the first email
Automatically visiting a lead on LinkedIn to ping him
Send an additional message on LinkedIn if the lead has not answered 3 emails
As I said, your imagination is the limit…

Originally published at https://captaindata.co on February 26, 2019.