Nailing Outbound Outreach: Key principles

1 Jan
7min read

Outbound sales have become much harder these last few years.

Every sales rep competes for your buyer's attention, making it harder to cut through the noise. While I'm not 100% aligned with the opinion of Mark Kosoglow, the phenomenon of being flooded by emails is real. The world is more distracted and disengaged than ever.

Apart from that, the macroeconomic situation makes finding a company with purchasing power even more complicated. The wave of layoffs & budget cuts hitting tech companies and beyond shows no signs of slowing.

People are more rigid on spending, VCs are more picky about investing, and companies want to keep their runway as long as possible.

Success in these challenging times demands that we master the art of outbound outreach. So here is a guide towards nailing outbound outreach, as per yours truly.

Multi-channel is the only option#

Email volume has risen dramatically since 2020.

In 2021, it was estimated that nearly 319.6 billion emails were sent and received daily.

As a result, nearly 40% of all emails end up in prospects' spam folders. At the same time, others go undelivered for often avoidable reasons.

Does it mean that email is dead?

Not sure. We'll probably all die before email.

Some marketers invest much time in writing, designing, and building flows. But they under-invest in making sure those emails actually land in inboxes.

This is called email deliverability.

Optimize deliverability#

Yes, the inbox is crowded, but you'll never even be seen if you don't land in it.

To optimize deliverability, you have to follow some rules:

  1. Don't use your primary domain. Use a subdomain: For example, instead of, you could use or other prefixes like "hey," "try," or "go" before your domain

  1. Do some domain warmup to establish a good reputation using tools like Warmbox (recommend warmup period: ~4-6 weeks.). It's not a set-it-and-forget-it task: always monitor your domain reputation.

  1. Get all email authentication methods set up: SPF, DKIM, at least. Adding DMARC is even better. these are ways to confirm that "you" were actually the person sending the email and it wasn't spoofed. Think of it similar to a "Made in Italy" tag for your favorite pasta 🤌

  1. Stay under the radar: Send no more than 50-150 per email address per day. Scale via multiple email addresses per campaign to do a load-balancing effect.

  1. Reduce bounce rate: Incorrect email addresses bounce (and frustrate your sales reps when they craft their best email). Instead, clean up your email lists with tools like Neverbounce, Zerobounce, and Aim < 2% for any campaign

  1. Avoid images, links & attachments for the first touch (disabling tracking open & reply is recommended by deliverability experts like Jesse Ouellette).

  1. Don't put an unsubscribe link. Ask for a reply instead: replies are considered a good signal for email reputation.

  1. Narrow your ICP and optimize for relevancy: The better your segment, the more personalized your message can be at scale. Avoid spraying & praying the same message across a broad set of segments/ICPs.

  1. Randomize copy & delay if possible: It helps not to be detected as automated & predefined behavior. {Hi|Hello|Hey} kind of syntax randomizes the message and increases deliverability. Higher variation = higher chance your email lands in the lead's inbox (possible with tools like Outreach).

On this topic, Jesse Ouellette created a great Deliverability Cheat Sheet.

OK, enough talk about deliverability because email is just one channel.

What matters most is not the performance of an individual channel but the combination of channels.

What Justin Michael / Tony Hughes call "Combo prospecting".

Each of your channels is a component of a global prospecting journey, driving the lead maturity from awareness to decision.

Combo prospecting

Think of it this way.

You call a prospect.

The prospect: Unknown number? - I don't pick up.

Then he receives a voicemail from you.

No, he won’t call you back. Less than 1% of voicemails ever get a callback. but still, that counts as a touchpoint.

Then you send an email, referencing your VM: Per my voice mail + sales pitch + LinkedIn invite.

From there, any channel is welcome (as long as it’s pattern-interrupt): Voice notes on Linkedin or WhatsApp messages and Twitter interactions are options to consider. Even Inmail may be worth it.

Beyond the mentioned channel, you can do “pre-targeting” using LinkedIn-matched audience ads to warm up targeted accounts. You can also do a pre-nurturing sequence pushing High-quality content to this audience.

Where others see boundaries, you see fresh pastures. Be the purple cow in your competitive landscape. That's the only way to be truly remarkable ( 👋 Seth Godin)

Conducting multi-channel outreach is imperative for two key reasons:

  1. It distributes the sales pressure: Getting called 14 times in one week vs. being contacted 14 times across different channels definitely doesn't feel the same. By not putting all your eggs in one basket, you increase the odds of fishing in the right place.
  2. More attempts mean more replies: Persistence often pays off in sales, it often goes with a higher meeting booked rate. 80% of sales require an average of five follow-ups to close the deal. However, 44% of sales reps follow up with a prospect only once before giving up. Same for cold calls, it takes on average 8 attempts before connecting with a lead.

The best sequence is a mix of all those touchpoints.

Most of the time, I start with something pretty similar to the SalesLoft template. Initiating multiple touches in the first 10 business days.

However, I gradually increased the wait time between each touch to not overwhelm the recipient.

Rules of thumb: the more senior your interlocutor, the longer the touchpoint interval needs to be.

One last thing.

I know I might sound like a broken record, but never forget that the ONLY evergreen best practice is “pattern interrupt.”

When things break patterns, they instantly stand out to us. When things don't break patterns, they sort of fall within the line, they become hidden" - Brian Cugelman

If everyone waits two days before following up, you should instead mimic real human behavior by sending an in-thread email with complementary information, assets, or spelling corrections just 1 or 2 hours after the first email.

Tangent over, back to the heart of the matter. What we just said for channels, the same goes for people.

Multi-threaded Outreach#

The #1 reason deals don't close is because the seller works single-threaded.

Did you know that an average B2B purchase has 11 stakeholders chiming in?

Yes, that’s right, 11! Talk about the need for harmony in the choir 😅

When you add multithreading into your deals, your chances of winning the deal go up by 42%...

John Barrows - Sales leader


I can only confirm how true it is.

The more you talk to people, the more you increase the odds of converting the account. See image below comparing the opportunity rate on single threaded vs multi-threaded.

Even the most senior people won't sign off unless they are convinced there is a consensus for the business case and change management.

You need to establish multiple bridges to span the moat into the castle.

Reaching out to multiple contacts at different levels is the only way to compete and create consensus.

Once you identify the individuals involved in making the purchase decision, it’s easy to target the buying committee as a part of your outreach strategy using a search function on B2B providers (Apollo, Clearbit, ZoomInfo, Cognism).

For instance, below is a way to retrieve all the execs from a company using Cognism API in Cargo.

Orchestrating such strategies in a scalable way requires being able to label each person based on their influence on the buying decisions like “users,” “influencers,” or “key decision makers.”

One way to achieve this is by using AI to categorize leads based on the persona the lead belongs to, team,” or seniority. If not AI-driven, you can apply the same logic using a REGEX. Both are super simple to execute inside the Cargo web app.

The output:

The goal is simply to split decision makers from the other to have different treatment based on the value of the lead.

Once categorized, leads can be routed to different sequences with tailored touchpoints based on their importance in the purchase decision process.

A key decision maker would typically be redirected to a “High touch sequence, with manual, hyper-personalized touchpoints. Meanwhile, a user would instead be routed to a fully automated sequence.

The strength of multi-threading is getting sponsored by someone in the targeted company.

Two main approaches for multi-threading:#

  • Top-down: You start by selling the high-level output of your solution to the key decision-makers and then getting sponsored down to the champions.

    • Pros: Implementation can be faster with direction from the top. It's an opportunity to pitch cross-departmental solutions and thereby increase the deal size. You also benefit from an unprecedented level of trust when you are referred to other stakeholders.

    • Cons: Sometimes, there is a considerable gap between the high-level expectations and the ground reality (lack of resources, do not fit their existing tech stack, the problem revealed by the exec is not the true root cause).

  • Bottom-up: Start targeting lower-level management or just directly potential product users and have them introduce you to those on the buying committee.

    • Pros: Easier to reach, you will have a better connecting rate, and be able to qualify the account in terms of decision process structure, tech stack, pains, and company priorities. These things will be useful to craft your best copy when targeting the key decision-makers.

    • Cons: You can waste 1 hour with different people to finally understand that there is no budget or that your solution is not the exec priority. You also rely on how well the champions understand your product pitch to the decision-maker. It's a big risk there as you are probably the best guy to do the job. So better to follow up with materials that can be used to support the champions & get the warm intro to the C level. Gartner speaking here: When buyers have high-quality information at their disposal, they're 26% more likely to purchase.

    Avoid a one-size-fits-all approach. Showcase tailored solutions for each department. Demonstrate how your solution can impact marketing, save sales time, or provide a quantifiable ROI to the C-suite.

    Whatever approach you choose, keep communication open with the different stakeholders. Don't let anyone fall through the cracks.

A/B/C/D testing in sales sequences#

The “Test & learn” motto is evergreen, and applying it to the B2B prospecting journey makes sense. We need to have a more scientific approach to selling so we can learn and identify what works from what doesn’t

Either you win, or you learn

There are three important rules to live by:

  1. Test one thing at a time: test subject lines, body email copy, CTA, or visual prospecting one step at a time.

  1. Always measure: Analyse the closest KPI to your work (open, click, reply rates) to get a clear picture of what variation works better. Positive replies are less of a vanity metric than replies alone. Fortunately, with AI, it's no longer a burden to do it, and most sales outreach tools have the feature nowadays. If you are testing more global changes (like doing pretargeting ads before the prospecting sequence), it's better to check the overall performance, like the number of opportunities created / number of accounts reached.

  1. Have a big enough audience - To gain relevant insights; we must ensure our sending volume is large enough. This requires that all your sales reps use the same sequences so that you can learn faster.
    - Statistical significance: > 90%

    • Minimal sample size: 150 leads (each variant)

    • Expected uplift on baseline conversion: > 15%

    • Run tests for a full period to eliminate seasonality (one or two months)

When it comes to sequences, you’d want to have different iterations for each metric you want to impact. You can run two different test sequences in parallel but not two things on the same one simultaneously.

Here are some components you can test for each metric.

Open rate#

The percentage of emails opened.‌

In cold outreach, the open rate measures how enticing your object or sender name is.

  • Sender Name: try different variants like {{Firstname}} from {{company}}}, {{company}}, {{full name}}

  • Subject line: For the subject line, Josh Braun already gives us some good ones that should offer a> 50% open rate. This includes {{Your_prospectname}} - {{your name}}, {{Prospected_company}} - {{your company}}, idea for {{company}}.

    • The golden rule is to keep it short (1-4 words). SalesLoft study shows "at six words in a subject line: Bad things can start to happen to the open rate & reply rate."

  • First line / Intro: As few words of your email are visible from the inbox, it's important to have something worth saying, aim for relevancy or hyper-personalization.

  • Sending Time: When you send an email is important: Morning (8h-10h) vs. Afternoon (14h-17h), Yesware made a useful tool for this.

Click Through Rate#

Click-through rate (CTR) is the percentage of emails sent where the recipient clicked an embedded link.‌

This measures how enticing your email body is, whether you've included a clear CTA, a video, or interesting content you've used as an in-thread follow-up (article, podcast, ungated ebook, webinar, industry data etc.....)

  • Content: You can send links to articles, use cases, forms, calendar scheduler link.

  • Try sharing different formats of valuable content (Video, Venn diagram, personalized assets at scale using bannerbear).

  • Test different link types (full link vs. anchor link / on different words)
    - Email Signature

Reply rate#

Response rate is the percentage of your list that responds to your emails. This measures how enticing your email body is.

The response rate is higher when targets already know who you are (e.g., the pre-targeting strategy mentioned before). As the goal of your cold outreach is to book meetings, this is the most important metric---you need to book calls to close sales. - Body email testing: Try different persuasive flows to find the most promising value proposition/ benefits copy. I recommend working with different psychological angles like "loss aversion principle," "benefits-oriented," and "pain removal," but always keep it short ('n sweet, as Salesloft would say).
- CTA: Interest-based CTA vs. Demo vs. requesting time

  • In thread follow-up vs. new thread

  • Test delay length between each step

  • Test the order of steps in the sequence

  • Add a custom video: Video brings, on average 26% uplift in reply rate). Vidyard has a great library of creative sales videos.

    It's difficult to be exhaustive of all the things you can test. Here is a good email I saw recently on a LinkedIn post (there is even a typo, missing word "a great .. to do so" = pattern interrupt, sounds human)

As you understand, experimenting goes beyond email.

It applies to cold calling, such as changing the opening (often the most important piece: Gong offers valuable insights on this), the hook, the pitch, or the call to action.

Same for your LinkedIn ads.

Same for everything when it comes to growth...

Growth is the salsa dance of revenue; it's all about mastering the steps and refining the moves!

As a closing thought, AI will probably change how we do outbound outreach in the coming years.

Tomorrow, all-bound sequences, as we know, won't exist anymore. Outreach will be fully personalized for every lead. AI will automatically give more weight to a channel based on the prospect's behavior, adapt the delay between touchpoints, and use the best copy for each persona. Sales reps will be a touchpoint within a global prospecting journey.

But today, the best way to do outbound is to think about it as a design system, providing audiences, sequences, snippets & marketing assets to your sales reps.

This will be the topic of our upcoming article covering the sales enablement part.

Read Episode 4 on Sales ops x Sales enablement

MaxMaxJan 1, 2024

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