Revenue Teams, Sales | March 23, 2024

Operationalizing Outbound Part 3: Creating Your Sequences

Read time: 8 minutes

Written by:

  • Eddie Reynolds
    Founder & CEO

Exec Summary

  • We covered outbound capacity
  • We shared how to make better lists
  • Now, let’s create better sequences
  • To dramatically improve rep efficiency
  • Plus reply rates and conversions
  • Learn how to share better messaging
  • With less time spent per message
  • This is Part 3 of our Operationalizing Outbound Series


Outbound is no longer working because the messaging isn’t relevant to prospects. Spray and Pray took over when tools like Outreach and Salesloft enabled the “Send All” button – and we’ve seen conversion rates plummet.

The remedy for Spray and Pray is to narrow focus on a very tight list of key companies in our ICP and key Personas within those companies. We covered how to build these lists, but this is of little value if we can’t dramatically improve conversion rates.

At the same time, reps can’t spend an hour writing the perfect email to every prospect. We need a system to send highly relevant and personalized messaging at scale.

Today, we’ll show you how to create this system.

Crafting Outbound Messaging the Right Way

“Tailored, Targeted, and Templated” outbound messaging is one of my favorite concepts. It was introduced to me by John Barrows, who provided the outbound training to reps at Salesforce while I worked there.

Templated Messaging

According to John, the Templated approach is the dreaded “Spray and Pray” – where you load up a generic template about your solution and blast it to everyone on a list. 

Most of the sales emails we receive (and ignore) today are Templated. The data clearly shows this doesn’t work. Even worse, it can cause your CAC to skyrocket and your email deliverability to plummet.

Don’t Spray and Pray with meaningless templates.

Tailored Messaging

The Tailored approach is on the other extreme side of the spectrum. It’s my personal messaging strategy of choice: Doing enough research on every prospect to create highly personalized and relevant messaging for each of them.

This requires more research and staying up-to-date on what’s happening in your prospect’s world. We recommend reserving this level of personalization for your Tier 1 accounts. It’s not sustainable for reps to create custom messaging for their entire list.

Targeted Messaging

Then we have the Targeted approach, which sits reasonably in the middle.

Targeted messaging is all about being relevant at scale. This is why we segment our target list. With a segmented list, we can create templates that focus on the pain points, value propositions, and opportunities relevant to each individual segment.

This way, our outreach is personalized enough to catch the interest of our prospects while spending minimal time customizing each message.

Very little research (if any) is dedicated to the individual contact or their company – rather, it’s a “tailored template”.

Enriching Your Data

Most prospecting lists have bare-bones data.

This gives reps two choices:

  • Spend far too much time hunting down meaningful information
  • Fire off an email or a quick call with generic messaging

The main reason we’re operationalizing outbound in the first place is to create a highly efficient – and more effective – process for your SDRs and AEs. This means there has to be a level of relevance or personalization in your messaging.

Bringing up the city where your prospect is from isn’t enough.

Your reps should have everything they need to create a compelling message – or populate a template – within a click or two.

This is especially important for Tier 1 accounts.

They should be able to see info such as:

  • Company firmographic data (eg; revenue, headcount, industry, sector, etc)
  • Company technographic data (eg; the software they’re using today)
  • Links to website, LinkedIn, other social accounts, Crunchbase, etc
  • Key contacts’ names, phones, emails, social links, etc.
  • Third-party intent data
  • Company news and alerts
  • Past sales/marketing data (eg; calls, webinars, content downloads, etc.)

In a perfect world, reps can look up an account and see things like: 

  • Every email that’s ever been sent to them
  • Every event and webinar they attended
  • The whitepaper they downloaded
  • The forms they filled out
  • Past sales call notes
  • Etc.

This rich level of data isn’t possible for every company, but if you can get any of it, you want it front and center for your rep.

(Not buried in 5 different disconnected systems.)

The more data your rep has at their fingertips, the better armed they are to create a compellingly targeted message that gets a response.

This is important because it will give your reps a massive leg up on the competition.

You wouldn’t believe how many companies out there are spending millions a year on SDR teams – and they haven’t even integrated their marketing data with Salesforce.

Building Out Your Sequences

Now that you have your segmented list enriched with data, you need to decide on the sequence of messaging.

This is outbound 101 – the difference is that you’re going to provide a unique sequence and messaging strategy for each segment.

You’ll also likely want a separate sequence for your Tier 1 prospects and another for Tier 2/Tier 3. In total, this will mean you’ll have 8 sequences.

RevOps and Marketing can collaborate with the sales team to create templates tailored to each sequence. They should be specific to the segments’ needs and the opportunities you want to share with them.

Your reps should have everything they need at their fingertips to deliver highly targeted messaging campaigns to a large number of contacts – without writing it all from scratch.

To go deeper, have your reps use a trigger mechanism such as Owler to monitor their best accounts.

You can include one or more blank emails early within your sequences, instructing your reps to personalize them, especially for Tier 1 prospects. That personalized messaging will come from the trigger alerts, and/or a 15 minute comb-through of the company website/LinkedIn for any recent news.

Look for triggers such as:

  • Mergers and acquisitions
  • Launching a new podcast
  • Launching a new product
  • Receiving funding

Or anything that’s current/interesting your reps can personalize a message with.

You can also build message templates for the triggers listed above, which reps insert into those blank emails. This will help your reps take a highly tailored approach without starting from a blank page.

Remember, these aren’t hard rules – you can choose to add more or less personalization if it makes sense for your situation.

Stop Asking, Start Giving

If there’s anything you take away from this entire series, let it be this:

Give value in your outbound messaging.

You can have the most efficient outbound process, but if all you do in your messaging is pitch and ask for their time, your reply rates will continue to suffer.

Don’t just tailor your message based on segment – tailor the value you provide. Whether that means sending content specific to their persona/needs or offering to connect them with a relevant subject matter expert (not a salesperson). Look for ways to add value instead of simply asking them 15 times in a row if they want to schedule a call with sales.

This level of value should be baked into the templates for each sequence. Using your trigger alerts to provide even more timely value will make you stand out from every other outbound email in their inbox.

You Don’t Have to Build This Alone

At this point, you’ve seen what it takes to operationalize your outbound process:

  • Figuring out your outbound capacity
  • Creating a list of your best contacts
  • Breaking that list into segments
  • Building sequences for each

And you know the benefits of doing it:

  • Narrowing your focus
  • Improving messaging quality
  • Increasing your conversion rates
  • Building better pipeline and more revenue

But we understand that this can be a large undertaking.

Not every RevOps team has the time or resources to create this kind of process – and have it adopted by the entire outbound team.

We see companies struggle with these things every day.

You’re not alone. It’s one thing to know you need something like this done, and another entirely to make it a reality. That’s why Union Square Consulting exists – not just to “consult”, but to get in the weeds and do the work to improve your revenue engine.

If you know your business needs to operationalize its outbound process within the next quarter, reach out to us for a quote.

We’ll make sure it gets done, done right, and adopted by your organization.

When you’re ready, here’s how we can help:

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Get one of our Senior Revenue Strategists to yourself for 1 hour and leave with a plan to increase the money-making power of your go-to-market operations.

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