How to automate sales follow-up emails in 3 simple steps

As salespeople we want to give ourselves the best shot at closing all our opportunities. But we don’t want to spend the majority of our day working small accounts when there are large ones to win.

My colleague Patrick calls this the problem of the big whale and the long tail. With a high volume of inbound leads, you have a long tail of small accounts that individually are worth less in ARR but collectively could mean a big pay day for your company. At the same time you have big whales — large and complex deals — you want to chase. So how do you trawl your sales-ready opportunities efficiently while also going whaling?

Here at Intercom, we’ve addressed this problem by finding scalable ways to nurture our long tail of smaller accounts. Specifically we’ve automated parts of our sales follow-up using Intercom Smart Campaigns. Doing so not only enables us to optimize for speed and response rate at the lower end of the market, but also gives our inner whaler time to focus on catching big fish.

Since implementing Smart Campaigns, we’ve been able to achieve a response rate of nearly 50% among smaller accounts that didn’t respond to our initial follow-up. We’ve added 8% more opportunities to our pipeline that would have otherwise gone dark and saved each account executive 5 hours per week manually chasing leads. I’ll walk you through how to set up a similar campaign and the best practices I’ve picked up along the way.

1. Separate the big whale from the long tail

Before you can automate your sales follow-up, you need to segment and prioritize your leads. I recommend bucketing your leads into at least two groups, but you can create as many segments as makes sense for your business. The two groups I’ve created are:

• High-value, large accounts
• High velocity, small accounts

The big whale

Leads in the first group are your big whales. They’re the large, complex accounts you’ll want to research and manually nurture from start to finish. To win these deals, optimize for thoroughness, not speed. Some general characteristics these leads share are:

• Large opportunity size
• Multiple stakeholders
• Long, complex sales cycle

The long tail

Leads in the second group make up your long tail of small accounts. Because smaller companies are far more agile and lean, they don’t take as long to make purchases. You’ll want to hit these leads across every channel to increase your odds of revving the deal into motion. Some general characteristics these leads share are:

• Smaller opportunity size
• Single or few stakeholders
• Quick, transactional sales cycle

Keep in mind, the goal of segmenting your leads is to maximize your potential pipeline by aligning reward and effort. How you group your leads should reflect that.

2. Personalize your sales follow-up

Once you’ve identified your long tail of small accounts, you should customize the first two touches. It’s important that you establish a personal connection upfront, even if you won’t manually nurture these leads the whole way. Your leads should see you as someone they want to buy from!

For the initial touches I recommend creating product-specific templates using saved replies that address the job the lead wants to get done. I use these templates as a skeleton for my message and then I add color based on what I know about the account to make it unique. Don’t be afraid to get creative with your message and remember, write something you’d want to read. Here’s how I’ve customized my messages in the past (the personalized sections are highlighted in yellow):

• Touch #1: You should send your first touch as soon as you’ve crafted your response. If you’re talking to a live chat lead, you can hop directly into the ongoing conversation.

• Touch #2: If your lead hasn’t responded yet, follow up again with another personalized note one to two days later.

3. Let sales automation do the rest

If your lead doesn’t respond to your first two messages, let automation take over. Just because your lead hasn’t gotten back to you doesn’t mean they aren’t interested, but it’s not worth trying to guess when they’ll be ready to talk. Use your messaging tool — we use Intercom’s Smart Campaigns — to nurture them over the next few months:

Here are the exact steps I follow to set up my campaigns:

1. Use tags to identify the right leads: You’ll want to define your audience by setting clear campaign rules. If you have multiple products, you should create custom campaigns for each of those and tag leads accordingly. My campaigns are organized by leads’ use cases for Intercom like capturing and converting website visitors.
2. Define a goal for the campaign: Setting a goal for your campaign makes it easy to measure its effectiveness. Because this is a sales follow-up campaign, I always set the goal to be “replied to any campaign message.”
3. Personalize the message with variables: I use variables in my messages to add the lead’s first name and company name. It’s important to greet my leads personally at the beginning of every message and specify how Intercom can help their business.
4. Set your messaging cadence: You want to be helpful, not annoying, so avoid bomboarding your leads with messages. I frontload my follow-up in the first two months when my leads are warmest and then message them every two to four months after that.
5. Find your exit points: One thing you definitely don’t want to do is message leads after they’ve taken the next step. I define exit rules to automatically remove leads from my campaigns if they’ve: received all the messages, hit the goal (replied), started a trial or become a customer.

Before you hit “send”

Even though these campaigns are automated, it’s still important to be human. If you want your leads to take action, you can’t resort to spray and pray tactics. The last thing I’ll share are the two principles I always keep in mind when crafting my automated messages:

Keep it personal

Be smart about how you communicate about your product and the value it’ll add to your leads’ business. You want your leads to have a conversation with you and sounding like a robot is a guaranteed way to be ignored. An easy way to add a human touch is by incorporating emojis and gifs. Here’s a fun gif I send prospects who’ve gone dark:

“Did I lose you? Say it ain’t so!”

Always add value

If the first rule in sales is “always be closing”, the second should be “always be adding value.” You can’t assume leads will instinctively understand why your product is the right or obvious choice. I use case studies, demo videos and blog posts to show leads how easy it is to use Intercom and the results our customers have seen. It’s common sense but if I’m talking about our live chat for sales solution, I’ll share our customer story on how Salesloft saw an 8x increase in booked demos.

Optimizing for the big whale and the long tail

By automating our sales follow-up for smaller accounts, we’ve elicited more positive responses while saving our account executives hours of time. Trawling our long tail of leads at scale has revived our stagnant pipeline, improved our day-to-day efficiency, and set us up to hit and exceed our sales targets this quarter and beyond. But perhaps most importantly, it’s given us peace of mind that our pipeline will be fed, so we can focus on high effort, high reward deals — and haul in a whale or two.