Automating Sales Emails: Tips for Effective Sequences

Posted by Lindsey Bowshier on Nov 8, 2021 1:32:13 PM

automating sales emails

Did you know Tribute Media hasn't had a real "salesperson" for more than a year now? While I wouldn't recommend that for most businesses, it works for us (as of this writing) because we've invested years of effort and expertise into building an inbound marketing machine that brings in enough leads who are already qualified, well-educated, and nurtured. From there, it's much easier for me to see them through to "closing the deal." As president of the agency, I wear many other hats and have much more responsibility beyond selling, so keeping track of active leads in HubSpot's CRM and using automation tools is essential to sustaining this model.

As I mentioned, we use HubSpot for, well, just about everything, including automating sales follow-up. Sales Hub Professional offers Email Templates and Sales Sequences which are the tools that I'll be specifically referring to in these tips. Still, even if you use different automation tools for your sales outreach, or even if you are doing things the old-fashioned way and manually following up with your leads, you should be able to apply these best practices to be more effective in your email outreach.

Subject Lines

OK, so most of these best practices are more or less about subject lines. What can I say? Subject lines are important. If you don't have a good enough subject line to get someone to open your email, everything else was a complete waste of time. Here are a couple of tried and true tricks to writing subject lines that inspire opens.


Using the recipient's name in the subject line can be really effective, but it's not a secret. This best practice has been around for a while and is made easy thanks to personalization tokens in most email software, so now it seems like everyone is doing it. Therefore, you have to do a little better than slapping a first name token to the beginning or end of whatever you wanted your subject line to be anyway.

Instead of: "[First Name], just following up on my proposal." Try: Do you think [Company Name] will benefit from those recommendations I sent?"

The Ellipsis (...)

We must know how the sentence ends! Between the three dots we see when someone is typing a message to us on iPhone and what we commonly see when text exceeds a character limit online (like in Google search results, social posts, and, well, email subject lines), technology has trained us to click to read more. This is not to suggest that you write long babbling subject lines that get cut off by character limits. No, you just end your subject line with "..."

According to a fascinating INBOUND session by Jay Schwedelson of, ending a subject line in an ellipsis is increasing open rates of marketing emails by 31% for B2B and 28% for B2C, and there's no reason to think the same or better won't be true for sales emails.

To Thread or not to Thread?

In your sequence settings in HubSpot, you can elect to thread all emails in a sequence so the subject line remains the same, and it appears to the recipient that you are continuing to reply to the first email. The benefit here is that they can see the entire thread and have all the context, so it's easy to slip in a few short emails that just say something like "Any interest in connecting on this?" (or something less cliche). However, when dealing with fizzling leads or trying to re-engage old leads, consider not threading your emails. This allows you to try out a variety of subject lines to see if you can capture their interest, including…

"Last Email"

It just works. When people think they still have a million chances to finally reply, they don't. If they have any interest at all and believe they are going to miss their opportunity, they'll often at least respond to tell you when will be a better time to follow up, and that's better than nothing. Remember, this doesn't mean you actually can't ever email them again (in fact, this even prevents people from getting so sick of you that they opt out and you REALLY can't email them again). It just means letting go of this particular follow-up. When there is something else you think might be compelling, or you see they've come back to the site, you can always try again.

Using Images in emails

Ever tried sending an email and the attachment was too large? When using images in automated emails, be sure to compress them so you don't run into deliverability issues. Unlike when you try to send too large of an email through Gmail or Outlook, you won't get a bounce back email that it failed, and this prevents the rest of your sequence from sending! If you want to use images in your sales email, first make sure you compress them using a tool like

End with a task

How does a sales sequence end? Hopefully with a reply. In HubSpot, your sales sequence will end when someone replies to one of your emails. This ensures you don't look like an idiot or reveal your automation secret. Once you're in the midst of a real conversation with a lead, you don't want them to get a stray email from you that implies you still haven't heard from them.

If you aren't successful in getting a reply (even when you swear you'll never grace their inbox again), I recommend that after the last email is sent, your last sequence action be creating a task (HubSpot CRM) or some kind of action to trigger you to review how it went.

Did they open any of your emails? If they were reading your emails and clicking on links you sent, this means they were at least somewhat interested and might not be a lost cause. Maybe try again in six months.

Did they not open in a single one? This might mean you are getting caught in their spam filter or sent to their promotions folder. More on email deliverability Or, if you were trying to engage an old lead by emailing someone you haven't talked to in a while, maybe they're no longer with that company. Do some LinkedIn research to see if they went somewhere else, who is in their old job, or who else at the company you should try to reach.

Tools YOu Need to Try These Tips 

Even if you don't have advanced automation tools yet, hopefully this sparks some great ideas for engaging your sales leads. At the absolute least, make sure you are using a CRM to keep track of your activity and keep you accountable. And you should be using email tools that give you analytics to see what's working and what's not. HubSpot's free CRM offers a task management tool, as well as tracks email opens and clicks.

You can even save up to five templates to reuse and create shortcuts for the things you find yourself typing over and over. Thanks to my snippet "#schedule," I never have to type the words: "You can use the scheduling link in my email signature to view my availability and book the time that works best for you." Serious time saver.

If you are still managing your sales follow-up using your Gmail and calendar reminders, I'm here to tell you there's a better way.

Lindsey Bowshier

Written by Lindsey Bowshier

Lindsey is the President of Tribute Media. Her degree is in English and Communication with an emphasis in Journalism, her background is in copywriting and content marketing, and she's had pretty much every job at Tribute Media since she joined the agency in 2014. Outside of work, Lindsey participates in a "super-cool-not-at-all-nerdy" writing group. Her favorite writer is Dorothy Parker.