Running Multichannel Outreach

He cold outbounded Stevie at the end of last year. “He probably sent me dozens of emails,” she says, “I never gave him a response to any of them.”

But then, the rep diversified, commenting on her LinkedIn posts, talking to her as a human.

“I remember the first time one of them broke through,” says Stevie. “I had posted about my daughter getting a job at Starbucks. He posted a funny response to it. The next week, he followed up by email and asked about my daughter. Over time, he built rapport with me.”

“This poor guy was probably over 100 touches in before he found success. But he went multichannel. It was deeply thoughtful, personal engagement, more than half of which actually had no ask in it whatsoever. It was purely relationship building.”

In today’s market, a buyer’s attention is its own form of currency. Companies spend millions for less than 15 seconds of a consumer’s time. Any outbound strategy that gives even a few seconds of your prospect’s time is worth its weight in gold.

Multichannel outreach is the most effective strategy for capturing your buyer’s attention, from C-Suite prospects like Stevie to individual contributors. We have the data to prove it: in an analysis of over 100,000 outbound sales campaigns, we found that adding one diversified touchpoint, in addition to an auto-email, increases your chances of booking a meeting by up to 14%.

Add more touchpoints, and your meeting booked rate goes up by as much as 24%.

Your calendar gives you no consolation. You have:

• Prospecting tasks you need to stay on top of to fill your pipeline

• Research and preparation for upcoming client meetings

• In-progress deals that require your attention and nurturing

• And closed-won deals with lingering questions

To do all of these things, and do them well, you need a scalable system — and a half-accurate spreadsheet, whiteboard scribblings, a desk full of sticky notes is only going to get you so far.

Sales sequencing tools are your solution to scale. They allow you to build mini outreach campaigns with any number of sequential contact points and tasks that you can personalize and schedule to engage your audience wherever they are at (email, phone, LinkedIn, and beyond).

Done right, it’s a tool that generates hands-off opportunities. SafetyWing built and tested over 290 sequences, each one targeting a specific segment of their ICP with personalized, value-based messaging, and over time built an outbound motion that generated $7 million in outbound revenue.

Teams like SafetyWing that build up a library of personalized sequences see huge results for two main reasons.

When you build sequences, you pre-establish and schedule the exact touchpoints, messaging, and action items you want to deploy. This eliminates much of the guesswork that goes into engaging prospects and gives reps a clear to-do list.

“There’s no need to keep everyone guessing,” says Elanna Lalezari, Director of Corporate Sales at HubSpot. “You want to give a map to your salespeople and watch them go even further with it.”

As you build an engagement path with a sequencing tool, you have a few key channels at your disposal — some automated, some not. These touchpoints include:

• Automatic emails

• Manual emails

• Phone calls

• LinkedIn connection requests

• Linkedin messages

• Manual action items

Many salespeople see “automatic email” and think it’s a shortcut. They’ll toss their lead lists into generic three-step auto-email campaigns, spread out over a short week, then expect some kind of positive result.

54% of these “shortcut sellers” will never book a meeting.

Sequencing automation can and will save you time and effort. But, done poorly, it comes at the expense of results. Even worse, careless automation damages your domain reputation, burns through your TAM, and leaves a sour taste in the mouth of your potential buyers.

So what steps should you automate in your outreach? The philosophies outlined in this book apply here, too: automate low-value tasks, so you can focus your manual efforts on high-value tasks for high-value prospects.

See figure 6.2 for a quick cheat sheet:

The most important thing you need to understand about building sequences for your Tier 1 prospects is that automated touchpoints should be minimal (often you should use none at all!).

Think about Tier 1 sequences more for organization and consistent, strategic follow-up than for time savings. This isn’t the place to cut any corners.

An effective campaign for your highest-level decision makers and champions might look something like figure 6.3 — an eight-step, custom-tailored sequence that spans across four key channels:

People today are accustomed to digital relationships.

We’ve embraced the fact that, today, faceless interactions are how business gets done, how we connect to each other and the world around us — but there’s a lingering dissatisfaction in what screens can’t provide.

So, be the person who sends the gift.

“Everyone has an emotional bank, so to speak,” says Daniel Cmejla, Apollo’s VP of Community. “You can make deposits into that bank by sending them a gift, being a good person, or delighting them in some way.”

BuildingConnected decided to take a personalized approach by sending over 1,000 handwritten letters to their biggest opportunities.

Within days, they received over 200 call backs, a +20% positive response rate and a testament to the impact of non-digital messaging.

You don’t need a big budget to spin up a handwritten note campaign. Dedicate a few hours, grab a pack of postcards and a pen, and write a note that’s:

• Human and casual in tone
• Personalized with a first name and company name
• Short and to the point
• Includes your phone number

In-person events are another powerful form of gifting. VIP dinners, workshops, cocktail hours — these are all valuable and authentic offerings you can structure a sequence around for your Tier 1 prospects.

In figure 6.5, here’s an example of a relationship-building sequence that invites prospects to an in-person event:

For your Tier 2 prospects, you can afford to be slightly less comprehensive. As a reminder, these are prospects who are either:

1. Influential to the buying decision, but not the champion
2. A good fit for your ICP, but not the perfect fit

These prospects are valuable — and there aren’t as many of them as you might think. Tier 2 prospects, and the outbound campaigns you design for them, still deserve at least 10-15% of your time.

You might be looking at the whole of this sequence thinking, “Only three emails?” Don’t forget that emails are currency. Instead of overwhelming someone with several emails in a row, use them thoughtfully and sparingly along with other touch types to increase your likelihood of getting a reply.

A good rule of thumb here is to wait at least three days between each touch type. In this particular sequence, there are seven days between email sends. Maybe for you, you wait four or experiment with eight. The whole idea of multichannel is you’re trying a mix of different things, at different times, to increase the total surface area of your outbound.

“[We sent] VPs of marketing a generic sequence, a couple of emails, used some cold call tasks, and got a 1% meeting booked rate,’ said Gabi Sayah, Business Development Manager at Deeto. “When we sent a very personalized email and had call tasks in the Apollo dialer that used that email messaging, our reply rate and email interested rate was three to four times better.”

Gabi isn’t alone — our data shows that users who build call tasks into their outbound strategies and use the Apollo dialer book twice as many meetings as non-dialer users.

If you’re getting more comfortable on the phone and really want to capitalize on the power of a dialing tool, try building call-only sequences for your Tier 2 prospects.

This may feel slightly contradictory to the whole “multichannel is best” spiel but you may find yourself in a scenario when you don’t have an email address (or at least one that’s verified and trustworthy).

You still want to reach out to these people, so do it in a way that’s organized and strategic with a three-step call-only sequence.

Sometimes, you may even want to add even more call steps. In Michael Oelbaum’s experience, it often takes up to six calls before his team gets a meeting.

“The biggest part is persistence and making a point that you’re still there,” Michael says. He goes on to describe a recent deal he closed, all because he decided to pick up the phone a fifth time. “I almost gave up, but decided to call that fifth time. They answered and ended up asking for a quote.”

With this sequence you have a set task to call on days one, seven, and twelve. But what time of day should you be dialing?

Most salespeople make the mistake of calling during the work day. But think about the day-to-day of decision makers — from nine to five, CEOs are likely in back-to-back-to-back meetings. You’ve very unlikely to get through to them at that time — and, if you do, you’re not going to get their undivided attention.

According to Apollo data, most people pick up their phones between 6 AM–8 AM local time. If possible, dial people’s cell phone numbers to avoid the gatekeepers that come with an office or work number. Working this way, you may find that a call-focused sequence is a huge driver of pipeline and worth the manual work.

Sequences for lower priority prospects are where you can afford to automate some of your outbounding and cash in on maximum time savings. With a little upfront work, you can send fully automated sequences without sacrificing relevance or quality.

What you’re going to do is strategically group contacts to load into a sequence. So, rather than dumping a list of 1,000 Tier 3 prospects into a sequence, build ten lists of 100 prospects and create sequences with messaging that are relevant to that particular group.

Start by segmenting your prospects into highly specific lists based on common factors across industry, location, and persona.

For example:

• CEOs of marketing agencies in California

• Marketing leaders at retail startups with less than 50 employees

• 10-50 employee SaaS companies in Chicago

• VPs of RevOps at FinTech companies in NYC

The sequences you build for each one of these groups can follow a similar, multitouch structure to that of your Tier 2 leads, but instead it’s fully automated, without the effort of that first highly personalized email.

Our first email in this sequence will cover a lot of ground in a few brief sentences. It will tell prospects:

• Who you are

• What you do

• Why you’re reaching out

• Why they should care

• With a CTA to gauge interest

All in four sentences.

If this is our “marketing agencies in California” list, your email will look something like figure 6.13:

And here’s the beauty of sales sequencing tools — those snippets of personalization are automatically filled in based on contact data for each prospect. By using personalization variables, such as {{first_name}}, {{location_city}}, and {{company}}, you can send Tier 3 prospects messages that feel 1:1 but are almost entirely hands-off.

Brendan Short, Head of Product-Led Sales at Apollo, sees 100% automated, triple-touch sequences as the gold standard for Tier 3 prospects. “For these segments, don't personalize one-to-one,” he says. “You should automate everything as it relates to emails.”

But from here, don’t make the mistake of becoming stagnant, of “setting and forgetting” your sequences without a curiosity to uncover what works and what might work better.

This is where testing comes into play.

Many sales leaders think that the ability to tailor outbound messages is some sort of innate ability found only among their best salespeople. But a great outbound email strategy is as much science as it is art. With a rigorous testing strategy, anyone can learn what works and what doesn’t.

The real challenge is that there are so many different factors that go into creating a persuasive message:

• What personalization belongs in the subject line?

• Should the subject line be four words? Ten words? Two words and three exclamation points?

• Do emojis work?

• What kind of personalization should you include in the opening line?

• Are you using the right social proof?

• Should you use an interest- or action-oriented CTAs?

Without testing in place, it’s like throwing darts in a dark room.

There are fantastic sequencing tools out there that make A/B testing your outbound messaging remarkably easy and impactful. These tools have paved the way for the rapid growth of leading sales organizations, such as Glassbox, which is at the forefront of AI development largely due to their experimental and evolving outbound strategies.

A/B tests allow you to create multiple versions of an email in a sequence step. Sequence tools will test the email variations across an even distribution of prospects and automatically send the higher performer to the full list of recipients.

If you’re just starting out with building sequences and testing, here’s how to start:

1. Send out your first sequence with two to four email variants and keep an eye on opens, click throughs, email interested rates, and reply rates. If the segment is small, start with an email that has worked in the past and test engagement.

2. If you’re getting below-average engagement (anything under 20% open rate, 4% reply rate, or 1% email interested rate) add an email variation — something that’s completely different from the first email across subject line, body copy, and CTA.

3. According to Brendan Short, Apollo’s Head of Product-Led Sales, statistical significance should start to appear around 300 recipients. Turn “on” the variant that performs the best.

4. Once you get a winner, start testing more granular variables in isolation. Keep the same format, but test subject line vs. subject line, CTA vs. CTA, etc.

5. Use what you’ve learned about your specific audiences to inspire future messaging across your email copy.

6. Never stop testing and iterating.

With your new library of multichannel sequences, you’ve just placed yourself ahead of the vast majority of sales organizations still sending one-off email blasts.

But sales is highly situational and your prospects are never static. They are changing jobs, responding to your outreach mid-sequence, showing new buying signals, and researching competitor solutions. Your outbound strategies need to adapt.

Apollo’s sales copilot program was born out of this need.

Our sales team already used personalized sales sequences — plenty of them — but they were having trouble responding to new prospect actions, given the staggering volume of users across workspaces and accounts. The solution? Using our event-triggered data through workflow automation.

Growth Operations Manager Casey Krebs worked with the team to understand what account- and contact-level event triggers were most likely to signal a buyer-ready prospect, which, in turn, would tell us what sequence paths they were most fit for. These were actions like:

• Recent funding
• Webinar attended
• Email opened, clicked, or replied to
• Website visited
• Job changed or new promotion

These are similar to the “signal filters” you’re already familiar with from your prospecting efforts. But in this case, it takes it a step further, using these signals to not only tell you more about a prospect and whether or not they are the right fit, but using automation to schedule a direct action to be taken when triggered.

Casey used workflow automation to automatically add prospects to sequences based on defined rules, routing them to multichannel campaigns based on the actions that they had taken or other specific triggers.

“With Apollo's event-triggered data, we could create high-intent audiences and deliver the perfect message to our prospects precisely when it mattered most,” Casey says.

Through the sales copilot program, our sales team now generates 3x more meetings with a 23% increase in sales-qualified opportunities, securing over 350+ meetings every month — largely, hands-off.

At Apollo, we don’t have an SDR function. Nope — no SDRS.

The success of this program — paired with the outbound strategies we’ve woven through this book — have, in many ways, validated our belief that Full Cycle Selling works; that building sales processes that incentivize, equip, and facilitates selling for the full cycle rep most closely aligns with how buyers buy in 2024.

Setting up event-triggered workflow automation is an integral step in this process, and isn’t as advanced as you might think. Let’s walk through some of the most impactful sales workflows you can set up in tandem with your sales sequences.

Job changes signal a significant buying opportunity, especially if you're dealing with former champions, partners, or previous buyers. Identifying who they are and sending sequences that prompt them to consider re-starting a relationship is one of the most beneficial automations you can set up.

Reaching out to them at scale is as simple as setting up a “when-if-then” automation.

If someone visits your website, you can assume they are, at the very least, curious about your offering; at best, they are leads at the bottom of the funnel, ready to make a purchase.

This trigger-based workflow engages website visitors by sending personalized emails asking if they found what they needed on your site.

Workflow automation allows you to get hyper-specific with who should be funneled into your sequence, and under what exact conditions.

In terms of the sequence and messaging itself, here is a pre-built, 12-day campaign specifically designed to nurture prospects who recently visited your website.

The team over at Aligned has had massive success tracking website daily visitors and demo requesters and feeding them into targeted campaigns. They use a similar flow, starting with an email and a personalized video on day one to set the stage. Shortly after, reps make the call.

“By the time we call them, they recognize us and the problems we solve,” says Saad Khan, Sales Director at Aligned.

Supported by automated workflows, the Aligned team is saving 5+ hours a week.

Lots of prospects will book meetings and simply — not come.

Re-engaging them is a similar, but also completely unique, outbound motion. Your goal at this point is to send them quick, personalized emails that keep the buying conversation alive and give prospects an easy and convenient way to get back on your calendar.

One approach here is to politely and frequently ping the prospect every day over the following week. It may feel overbearing, but you have virtually no idea why a prospect missed the meeting and it’s best you strike while the iron is hot.

Experiment with this template that spans over the course of eight days. If it’s too much? Tweak it, adjust it, and make it your own.

This mini re-engagement campaign becomes a powerful sales play when you automate the funneling of these no-shows into your sequence. Within your sequencing tool, you can set triggers that instruct the software to add prospects to your "meeting no-show" sequence whenever a meeting is canceled or doesn’t occur (see figure 6.16).

Using some level of automation, you can eventually scale up to dozens of campaigns running simultaneously, firing off emails, pushing out call and LinkedIn tasks, and prompting reps to do manual action items.

As a result, you’ll get data — lots of it.

From here, you need to understand exactly how your top-of-funnel metrics — “input” metrics from your sequences like number of emails sent, calls made, and connections sent — are impacting your bottom-of-funnel outputs like net new opportunities, meetings booked, and deals closed.

It’s tempting to look at the data and draw the simple, sweeping conclusion that more input activities leads to more meetings. But after a certain growth stage, high-volume output starts to have diminishing returns and can even hurt your business (by damaging your email domain, for instance, which we’ll get to in a few pages).

To effectively measure and optimize the performance of your outbound sequences, it’s helpful to track three types of metrics:

“There are a lot of metrics that you should measure, especially top of the funnel activities,” says Florin Tatulea. “It’s important to know how many activities it’s taking you or your team to get the desired results.”

Your activity-to-revenue ratio won’t be perfectly formulaic, but measuring activity gives you a benchmark to help you set yourself or your team up for success.

For example, for my first sales job out of college, I had to make 80 dials per day and/or get 25 calls connected per day. Some days, it took 50 dials to get 25 calls connected — other days I’d make the 80 dials and get 10 calls connected.

My activity metrics fluctuated, but there were baselines set because the business knew the math played out. They deduced that of 25 connections, something like five of those would be real buying opportunities and two of those would close. Leadership built their expected activity on that in order to hit their goals.

To identify your target objective, you’ll want to start with your goal number of meetings set.

• Let’s say your target is 20 meetings booked for the month
• You look at the data and see that out of every 100 sales activities (emails + calls + LinkedIn), you land a meeting — which is about a 1% conversion rate.

That would mean you will need to get to 2,000 activities in a month to hit your goals. How you decide to disperse those activities across your outbound channels is dependent on the performance you’re seeing in your sequencing data.

What channels are seeing high returns on investment? Are your input metrics leading to positive quality metrics? Are those quality metrics leading to your desired outbound result? This analysis will also tell you where you can stand to improve.

Lars Nilsson, CEO at Sales Source and former VP of Global Sales Development at Snowflake, sees engagement metrics as the key driver behind timely, relevant outreach across the funnel.

From our dozens of interviews with some of the most successful sales leaders, we pulled together a list of the non-negotiable performance metrics to track — and suggested target benchmarks for each one.

If you’re falling short in one of more categories, try:

1. A/B testing your messaging

2. Diversifying your sequences and timing

3. Or assessing your technical setup (more on doing this for your email inboxes in the next chapter)

To borrow the words of Jensen Huang, President and CEO of Nvidia (NASDAQ: NVDA):

In this book, we’ve given you structures to build your best targeting and messaging frameworks from the ground up. If you use them over a long enough period of time and track the metrics that matter most, you’re going to find product-market fit and uncover what works and who is the most likely to say ‘yes’.

Those are your winning playbooks, and setting up automated processes across those playbooks help you and your reps focus on the manual tasks for your highest value leads — this is the end output.

We uncovered that Apollo’s top power users, the salespeople who use our product most comprehensively and most successfully, use automation to:

• Add contacts to lists based on prioritization tier and funnel them into appropriate sequences

• Send alerts to reps to manually review leads that show high buying intent

• Remove replied contacts from a sequence

• Add unresponsive contacts who finish a sequence into a new sequence three months later

• Update account and contact fields