Cold Email in 2021 — How to Automate and Scale Cold Email the Right Way

Mike Wille
26 min readApr 21, 2021

I’m just gonna come right out and say it. Most cold email advice is total 💩💩💩💩.

Too often, advice plays on the human desire for that “plug-n-play” magic bullet:

  • “30 cold email tactics you can mindlessly copy”
  • “5 cold email templates that prospects love getting all the time”
  • “11 subject lines with high open rates… because open rates magically equate to sales”
  • “be the millionth person to steal the best cold email ever written”

These “winning” templates and subject lines can be helpful as a source of inspiration but in most cases, they do more harm than good.

And before you ask, no, I’m not going to say you have to manually research and write every individual email. F#*k that, if it doesn’t automate and scale I’m not interested.

But there’s a major problem with most cold email automation advice. Those “awesome” templates and subject lines are either too generic to work for your unique company and industry…

…Or the tactic worked so well that every last ounce of novelty has been arbitraged away from it by the time you’re reading about it.

Did you know that the internet’s first-ever banner ad had a 74% click-through rate? Today banner ads are so overused and ignored that we have a term for it. Banner blindness.

The first ever banner ad from 1994

The same thing happens to “copy and paste” subject lines and cold email templates. There’s nothing intrinsically wrong with them. You’re just going to have a tough slog ahead of you trying to stand out from the crowd.

Most cold email advice falls into one of 2 camps:

  • Camp 1: “Just copy these templates and subject lines and you’ll make all the sales!”
  • Camp 2: “Automated cold email is the devil! You must research each customer and craft individual emails manually!”

Well, I’m here to tell you there is a third path. One that takes the advantages of both camps without most of the cons.

I’m going to show you a technique that almost guarantees that your cold email campaigns are:

  • High converting.
  • Difficult for others to imitate (and will therefore last a long time for you.)
  • Scalable. You will be able to send more automated emails every day without destroying your domain’s reputation and deliverability.

Keep reading to learn how…

Cold Email Can Be Your Best Growth Channel

I scaled my last startup Capshare with no marketing budget. Our 2 primary growth channels were content and cold email.

The Bucket Technique was crucial to getting traction in the beginning and to our continued growth past 2m in ARR. It’s one of the reasons we were able to get acquired by Solium within 3 years.

You absolutely can do the same thing for your company.

If you do it the right way, cold email can be better than almost every other channel from an ROI standpoint. The time it takes to see success is very short, upfront costs are moderate, and ongoing costs are low.

But if you don’t implement cold email the right way you can:

  • Permanently damage the deliverability of every email you send from your domain (including customer support replies, marketing emails, transactional emails, etc.)
  • Waste a lot of time and effort.
  • Anger your prospects and tarnish your brand.

A lot of companies do cold email the wrong way. If you’ve tried and failed, it’s probably not your fault. For some reason, there seems to be more bad advice about cold email than other topics.

What you need is a system. So I’m going to show you a system that you can use over and over again to generate cold email campaigns that crank out sales.

THEN I’ll show you amazing examples that you can steal from…

…Because once you have the framework, we can break those examples down together. You’ll be able to identify the pieces that you can use to build your own kick-ass cold email campaigns.

The 3-Steps to Use “The Bucket Technique” To Crank Out Sales

Here are the 3-steps that make up The Bucket Technique:

Step 1: Identify demographic attributes of your target customer like job title, industry, etc.

Step 2: Identify triggers that indicate when your target audience has experienced a change or event that makes them receptive to you.

Step 3: Segment your leads and messaging into little buckets based on both demographics and triggers.

I’ll get into these steps in more detail but first, let me tell you why this technique works so well:

Most people do step 1 well.

They identify the common demographic traits e.g.:

  • Title (CMO)
  • Revenue (10m — 50m)
  • Industry (SaaS)
  • Employee count (30–100)

Then they find a good template, add their unique value proposition, and sprinkle in personalization tokens like their name, title, industry, etc.

After this, they add some follow-up emails and call it good.


Let me tell you why…

Most Cold Email Campaigns Have 3 Major Problems

Problem 1: Your emails will rarely catch prospects at a time when they are open to a change. Therefore, your message will rarely be relevant.

Problem 2: Your message does not come across as a 1:1 communication from a human being. It looks like a mass email template with personalization tokens added 🙈.

Problem 3: Problems 1 and 2 create a third problem. Low relevance means fewer replies and more spam reports. It also means low sales. If you try to increase your send volume to compensate you will damage your domain’s reputation and deliverability will drop. I call this the Volume Trap…

The Volume Trap

If you do a good job with step 1 (personalize the email with demographic tokens) you’ll very likely end up with a campaign that has a lukewarm conversion rate. It’s not great but it still brings in enough sales to merit your attention.

It’s easy to think “well, it’s working decently… Let’s just send it to LOTS more people!”

Beware the Volume Trap.

An email campaign that “works” but has a low conversion rate is like a rickety old car engine. It leaks a lot and doesn’t fire on all cylinders but it’s still taking you places.

If you increase email volume to make up for unsatisfactory sales volume you will redline that rickety old engine. What’s dangerous is it works… until it implodes on itself and takes your company’s email deliverability down with it.

It’s easier for a subpar email campaign to slip under email providers’ radar when your volume is low. But with increased volume, it quickly becomes obvious that you are polluting people’s inboxes with poor-performing emails.

Why do mediocre emails work decently at low send volumes and then break at scale?

  1. Remember, a low conversion rate means that most people don’t like what you’re sending.
  2. If people don’t like what you’re sending they are going to ignore your email in the best-case scenario or they will mark it as spam in the worst-case scenario. A low reply rate is a red flag. Getting marked as spam is a huge red flag. With volume, both can seriously hurt your deliverability over time.
  3. Personal email services were meant for 1:1 or 1:few communication. It’s another red flag when email providers see hundreds of emails (that virtually look the same) going from an individual email account into their customers’ inboxes every day.
When your cold email’s conversation rate is low

What most people think will happen if they increase send volume for a subpar cold email campaign:

What people think will happen scaling a subpar cold email campaign

What actually happens when you scale a subpar cold email campaign:

What actually happens: Sales drop email deliverability deteriorates

This is why most cold email campaigns suck and why copying templates won’t get you very far.

At lower send volume you can’t get enough sales to make it worth it:

Low Conversion * High Deliverability * Low Volume = 💩

and at high send volume your deliverability goes to shit which brings your sales back down:

Low Conversion * Low Deliverability * High Volume = 💩💩💩

In the worst case, your entire company’s email deliverability ends up in the toilet

…Your support team’s emails go straight into spam and customers think your support team isn’t responding. Marketing emails go to spam as if they unsubscribed and removed themselves from your funnel. Your sales reps have a hard time finalizing sales because important emails don’t make it to their recipients.

The Bucket Technique is so powerful because it solves each of these problems by adding triggers into the timing and messaging…

The Magic of Triggers

Triggers are events that take place within a prospect’s company that indicate that they are receptive to change.

So triggers solve the timing problem. They also come across as human because they give you something immediately relevant to talk about (while still being automated).

High relevance means more replies and fewer spam reports. This is a positive signal to keep you out of would-be spam blocks.

Using triggers in combination with demographics also helps diversify the content of your outgoing emails. So you can send a MUCH larger quantity of emails without penalty because it imitates natural usage.

The combination of these 3 things makes cold email highly scalable.

High Conversion * High Deliverability * High Volume = 🔥

Example triggers:

  • New hires (Company is hiring support reps)
  • Regulatory changes (The government requires a 409A valuation to companies offering options)
  • New role (CFO took a new position)
  • Financial triggers (missed financial target)
  • Software change (Company started using new A/B testing software on their site)

Let’s look at an example.

Example Trigger

Imagine you sell cold email software. A good trigger might be when a VP of Sales from a company with 5m to 50m in ARR is hiring SDRs.

  • This is the perfect time to reach out about software that is going to help them scale their SDR team. Perfect timing? Check.
  • The trigger itself is a highly personalized and relevant topic to talk about. You can tell them you’re reaching out because you saw that they’re hiring SDRs and explain how your software helps with scaling their sales team’s performance.

The recipient KNOWS that you didn’t just copy and paste the same email and mass send it to every VP of Sales on earth because you’re talking about something that just happened in their company.

Any additional personalization you do (like talking about their industry, using their name, etc.) only adds to that perception.

Come across as a human being? Check ✔️.

“Cheat” the BANT Framework

You’re probably familiar with the lead qualification framework BANT.

BDRs often use BANT to assess the readiness of inbound leads but it’s a useful framework to apply to any lead or even entire sales channels:

  • Budget: Does the company you’re reaching out to have the budget?
  • Authority: Does the person you’re reaching out to have the authority to make a buying decision?
  • Need: Do they have a problem and need for your solution?
  • Timeline: Is their timeline for deploying a solution in the near future?

Inbound and outbound channels typically have strengths on the opposite sides of BANT.

Leads from inbound vs outbound channels tend toward opposite BANT qualification criteria

Inbound Channels

An inbound lead searching you out through your content is a signal that they might have a need and a more immediate timeline.

On the other hand, you have little control over who is searching for and finding your content. They might be an intern with no decision-making authority or a scrappy startup with no budget.

Outbound Channels

Outbound has the opposite issue.

Because of demographic data, you control who you send your cold email to. You can pick the people with titles that indicate they have decision-making authority. You can also pick companies that have revenue or funding (and therefore budget).

What plagues cold email and other outbound channels is not knowing their timeline or need for your offerings.

With the Bucket Technique you can “cheat” and target leads who are likely to qualify for all areas of BANT.

This is because triggers help you target leads that are already searching for a solution to a problem. As Newton said, an object in motion stays in motion and an object at rest stays at rest.

It’s much easier to sell a solution to a prospect who is actively looking for it.

Demographic data indicates that leads have budget and authority. Triggers indicate their need and timeline.

If you use both demographic data AND triggers, you can put your emails in front of potential customers who have Budget, Authority, Need, and a short Timeline.

Ok onto the actual process…

Step 0: Understand Your Customers

Make no mistake you have to understand your customers before you can make automated cold email work.

You need to understand who they are, their challenges, and be intimately familiar with the sales process.

Cold email is similar to marketing. In both cases, you’re writing what I call “leveraged content.” There is a 1-to-many relationship between the content and the many people it is meant to persuade.

The problem with leveraged content is that there is basically no feedback loop for the quality of your messaging. If it fails you’ll get:

  • No response
  • A courteous “no thank you”
  • A pissed off “no thank you”
  • Marked as spam
1:Many Messaging Feedback Loop

You’ll know that the email as a whole isn’t working but you won’t know which parts. Or why. You don’t get to read a prospect’s facial expressions or hear the hesitation in their voice as they are reading each line.

You need to be able to close customers 1:1 to understand their pains and nail your messaging. Marketing a message without testing it 1:1 is like giving an answer without hearing the question. It might look and sound smart but in the end, it’s just drivel.

If you’re not there yet, take some time to reach out to prospects 1:1. Don’t automate it yet.

1:1 Messaging Feedback Loop

Good growth automation reproduces a manual or analog process with minimal loss in quality. You can’t automate a growth process you don’t yet have.

If You Have Sales People

If you have salespeople in your organization who have done this then go to them first. Find the best salespeople and ask them every question you can think of about what customers are interested in and how they pitch it.

  • What questions do sales prospects have?
  • What are the concerns that must be overcome?
  • What events transpired that led them to your company?
  • How do all these things differ by job title, company stage, industry, etc.?

Role-play with the rep and have them pitch you.

Listen to phone or video recordings of sales pitches. Software like Zoom and Uberconference allows you to automatically record calls. Take advantage of that.

If You Don’t Have Sales People

Maybe you’re just starting out. That’s ok. You still need to find the answers to these questions by pitching customers 1:1. Record your calls and presentations until you have closed a few prospects.

You can use cold email too. Follow the advice in this post but write each email manually. Research each prospect, find talking points, and take note of what works.

Once you have a few wins under your belt, you’ll start to see patterns in your prospect research and in your messaging that you can automate in the future.

Bottle the Magic

Once you have a few successful sales calls recorded (whether they are your own or from your top sales reps) it’s time to bottle the magic.

Nothing is more powerful than using your customers’ own words.

When you hear the prospect give an objection, write it down. Word for word.

When the prospect is explaining what their needs are or what they like about your company’s solutions, write that shit down.

Communication is the transference of ideas. The human brain rejects over 99.9% of the ideas that are thrust upon it.

This is a survival mechanism. There is just no way your brain could function if it was persuaded to act on every ad, pitch, or request that it saw.

Even transplanted organs from donors are rejected by the body by default. In order to have a chance for success, the blood and tissue of the new organ need to be nearly identical to that of the patient. Otherwise, the patient’s body will fight the new organ off like a foreign invader, even though their body might die without it.

If you want your messaging to be accepted by your prospects then you need to feed them their own words. It’s not enough to convey the right idea. You need to convey it in their own words. Not yours.

The Sales Rep’s Words

Next, take note of the sales rep’s words. These are second in value only to the customer’s own words. Most likely they have a few deeply practiced and refined go-to lines that help to prevent or resolve objections.

These can also be worth their weight in gold. Just be sure to only learn from the best reps or you may pick up fool’s gold.

Take note of any patterns that get repeated by multiple customers or reps. Also, take note of the customers’ demographic attributes so you can further segment your messaging in the future.

Step 1: Identify Demographic & Firmographic Attributes

You need to identify demographic and firmographic attributes that describe your ideal customer (e.g. job title, industry, revenue, funding, etc..)

The best place to start is with your existing customer database if you have one. Analyze where each company and sales prospect was at the time of sale.

Prioritize attributes that you believe describe a prospect with Budget and Authority. We’ll look more at Need and Timeline in the next step.

Our goal is to end up with groups of demographic and firmographic attributes that describe distinct personas.

You can start off with broad personas and then drill down further into more specific sub-personas.

This will allow us to adjust your messaging to your prospect’s unique needs and situation. The more relevant and specific the messaging, the better received it will be.


Let’s use cold email software as an example again. Let’s say we sell cold email software to founders and VPs of sales at B2B companies with 1 to 20m in ARR.

First, we might divide out the titles. Founders and VPs of sales have meaningfully different responsibilities and incentives and would benefit from targeted messaging.

We should subdivide those further by size. A young company with just a couple of sales reps is in a very different place from one with a sales team that is scaling and hiring like crazy.

Our target customers have a wide range of revenue from 1 to 20m in ARR. Companies across this spectrum will have meaningfully different needs and could benefit from specific messaging as well. So we might consider dividing these out into 3 groups.

  • 1–3m ARR
  • 3–10m ARR
  • 10–20m ARR

If we’re selling cold email software we might want to further segment by industry.

We should pick the industries that we already have customers in. That will tell you who benefits from your software and give you something to talk about.

For example, you might mention a case study from a customer in their industry or name-drop a few similar customers they will know.

How you group together attributes will be dictated by your own customers. You need to be familiar with the sales process so you understand their problems and the messaging that resonates with them.

Deep vs Surface Personalization

Segmenting your target customers into groups by their demographic and firmographic attributes does 2 things:

  1. It clarifies who you’re going after.
  2. It allows you to personalize your message, which moves the perception of your emails from spammy to valuable.

But there are 2 types of personalization.

Deep Personalization

Deep personalization comes from a deep understanding of the customer’s problems, their dreams, the situations they find themselves, the words they use to describe each of these things, etc.

Deep personalization forms the core of all your messaging. It’s the trunk of your tree and everything else branches from it.

An example of deep personalization might be explaining to a CTO who is hiring that you understand their pain of not being able to hire enough engineers and that you can fulfill her staffing needs.

Think: “Show don’t tell.”

Surface Personalization

Surface personalization is more cosmetic in nature.

Examples of surface personalization include using the recipient’s:

  • First name
  • Company name
  • Industry
  • Title

Surface personalization is important. It helps to give your emails a more personal feel. It can also improve the clarity of your message by specifically stating who you help (e.g. “we help CTOs in early-stage startups to hire.”)

People will be glancing at your email. The use of surface personalization helps to pull their attention in long enough to read how you can help CTOs, or why you can help {{their_company_name}} specifically.

The problem comes when you use surface personalization as a substitute for deep personalization.

When an email is “personalized” with personalization tokens.

This is essentially what you get when you copy and paste a template and insert personalization tokens.

You end up with a cold email that looks unnatural and hollow upon closer inspection.

Remember the goal of surface personalization is for your email to be clear, natural, and personal. So don’t force it.

If it reads all awkward and weird they’ll either think you’re a robot or an idiot. Neither of which get people amped to buy from you.

Step 2: Identify Triggers

This is the secret sauce that allows you to automate and scale deeply personalized cold emails. It’ll make a good cold email a great one.

The goal is to identify specific events or changes that indicate that a prospect is:

  • In a state of change and therefore open to a new product offering like yours.
  • Approaching or within a window of time when a change is possible.
  • Acutely focused on challenges that you help solve.
  • In the process of evaluating a competitor

Look over the persona segments and sub-segments that we created in the previous step.

Now, look at your own customers. What events took place for the individual prior to them becoming a customer? What about at the company level?

It can be useful to not only look at the data but to speak with your sales team as well.

Let’s go through some example triggers that might apply to you:

Hiring Triggers

If your customers are CTOs you might want to monitor for when companies are hiring developers.

Let’s take Ron for example. He’s a CTO who put a job posting to hire backend developers yesterday.

Budget: You know Ron has the budget because he’s hiring and his company matches your other demographic criteria like revenue or funding.

Authority: Like your other customers, Ron is a CTO, so he’s probably the primary decision maker around hiring devs.

Need: The fact that you know Ron is expanding his dev team gives you a tremendous advantage here. If you solve problems that relate to expanding dev teams then this is not only a great prospect but you get to strike exactly when the iron is hot.

Here’s a great example of a hiring trigger email. This email also has been personalized to include a customer that the recipient is connected to on LinkedIn, but it would still be pretty epic if you drop the name of a customer that is in their space or industry.

New Position Triggers

If CFOs are your primary customers you might want to monitor for when a company hires a brand new CFO.

This is a fantastic time to reach out if you sell financial software because the financial department is going to be in a state of massive change.

Specifically, tell them you’re reaching out because of the new position, reference the problems that accompany taking that new position, and tell them how you can help.

Let’s say Sally is a new CFO at a company that would be an ideal customer for you.

The first few months are extremely important to a strategic hire like Sally. There’s a lot of pressure to wrangle in problems with the finances and get things off to a solid start.

Tell Sally how you can help her during this key transition period. Talk about the problems that CFOs experience in the first few months and how you can help her build a dashboard to get a handle on every department, or whatever it might be.

You better believe that Sally is going to be making some decisions around new products and services. You need to get into the conversation before those decisions are made.

Technographic Triggers (Technology Adoption)

Technographic triggers allow you to reach out to prospects based on their use of software or technology on their site.

For example, let’s say that you sell marketing automation software to CMOs. You might want to know when companies start trialing Hubspot.

Technographic triggers work for any technology that is actively installed on prospects’ websites (and therefore visible).

Some of these include:

  • Tracking scripts (like Google Analytics script, Hotjar script, Hubspot tracking script, Ad pixels, etc.)
  • Forms (any form that’s embedded on someone’s website like Marketo forms, Salesforce forms, etc.)
  • Hosting (the hosting provider or other technologies related to the software stack)

Understanding what technologies your prospects use or don’t use can help you to dramatically improve your messaging.

There are 3 ways you might use technographic triggers

Direct Competitors

This one is obvious. If you see a direct competitor is being trialed and used on someone’s site, NOW is the time to reach out about it.

Use this to your advantage in the messaging. Speak to the fact that they are evaluating your competitor and show them how you can help them drive to a decision during that time.

Perhaps provide a checklist of features to consider or a comparison between your platform and theirs.


If your software integrates with Salesforce, then monitoring for people who use Salesforce would be a great idea.

Salesforce can be painful to set up. Perhaps you have a tool that sits on top of Salesforce and improves usability. Or maybe you help automatically log activity so sales reps don’t get bogged down or so reporting is more accurate.

Whatever it is, you can specifically speak to how you bring added value to Salesforce and show them how other Salesforce users find value from your offering.

Getting the most out of Salesforce is going to be top of mind in the months immediately following adoption. Use that to your advantage.

Correlating Technologies

How well do you know your customers? Do you know what software they use?

Create a comprehensive list of all your customers (and your competitors’ customers if you can) and their websites.

Find out what software they use using with a tool like Datanyze or BuiltWith.

Then look for patterns. You may be surprised at what you find.

For example, if you sell website personalization software, you might find that companies who start running website A/B tests are at a stage and mindset that makes them receptive to your product.

Industry Triggers

Make sure you’re dialed into what’s happening in your prospects’ industry.

Broader industry shifts give you an opportunity to start conversations that are natural, timely and add value.

Some industry triggers might include:

  • New legislation
  • Shifts in the economy (positive or negative)
  • Political tension or uncertainty
  • Changes in spending or the economy
  • Tariffs or price increases


  • A new rule change in accounting law: You might put together a resource on how to adapt to the new rules and show how your accounting software makes it easy.
  • The announcement of Obama care created growth opportunities for HR companies to assist employers in determining their employees’ eligibility.
  • COVID-19 led to many customers freezing spending on enterprise software. This created an opportunity for lower-tier software to take their place.
  • COVID and tariffs have led to price increases across many supplies from lumber to restaurant supplies and food. The shortage led to many restaurants trying new providers, many of which completely switched over to new providers.
  • The merger or acquisition of a key player in the space creates either opportunity or challenge for competitors in the space. Use your email to show them how you can help address it while it is top of mind.

You can use Google Alerts to notify you of news and events related to specific rules, industries, or companies.

You can do the same on social media and sites like Reddit, Quora, etc.

I love to use Feedly to manage all my sources of information and news.

You can also join an association or trade group’s mailing list for a small fee.

This information can be invaluable for other forms of content and marketing as well.

You could even send a cold email inviting prospects to participate in a survey regarding how they’re handling a change in their industry. Offer to share the results with them if they participate.

Pitching them after you have positioned yourself as an authority and have created value for them will open the door to a conversation.

Ad Spend Triggers

You can track a company’s activity and approximate ad-spend on Google Adwords or Facebook.

An increase in ad-spend is a good indicator that they are focused on growing and willing to spend the money to do so.

If your product or service can help them with their growth goals, you should talk about how it can support their push into ads.

Perhaps you can help sales reps to make the most of their new leads so that their ROI on ads is better.

Or maybe you can help with lead attribution, so they can get a clearer picture of what ads are bringing in the best LTV and not just demos.

Or you might have software that can help a CFO to allocate budgets across departments and make allocating ad spend easier.

Whatever it is, you want to tie the conversation between the value you offer and the recent change that is relevant and top of mind.

Interest Triggers

If you use marketing automation software, you probably have triggers for visits to key pages of your website. For example, it might be time to reach out to a lead once they’ve visited your pricing page 3 times.

This works really well for existing leads but you can also do this for cold traffic.

You can use tools like Clearbit, Leadberry or Albatross to know who is visiting your site, even if they’re not a lead yet.

Everyone has an IP address that is visible when visiting your website. Tools like the ones mentioned above can tell you what companies are visiting your site in real-time.

With this knowledge, you can automatically email decision-makers at the company and customize the messaging based on what pages were viewed.

Vendor Dissatisfaction or Evaluation Triggers

Similar to industry triggers, you can monitor social media and question-and-answer sites for relevant keywords about your industry or competitors.

Oftentimes dissatisfied customers will declare their dissatisfaction with a vendor on Twitter.

Or customers who are looking to buy a new product or service will ask what others recommend on Twitter, LinkedIn or Quora.

You need to be tactful but these are some of the best times to get in front of potential customers who are extremely open to making a change.

It also shows potential customers that you are a part of the conversation. Not showing up to the conversation when your competitors do is not a good look.

There is also a huge inbound opportunity if you’re willing to write really thoughtful, high-quality answers to questions on Quora, Reddit, etc… but that’s a conversation for another day.

Firmographic Triggers

I think your eyes are going to bleed if I make this post any longer than it already is. So let’s keep it brief. Some ways you can use firmographic data include:

  • Headcount increase. Increased headcount leads to exciting changes but also many new problems.
  • New funding.
  • Increase or decrease in revenue.
  • Change in company structure
  • If you target public companies you can look at profitability trends, meeting or missing earning forecasts, cash flows, and many, many, others.

You would be well served to examine the firmographic data around your existing customers. Especially look at what the data was at the time they became a customer.

Are there any patterns? Is there a frequent change in any data point just prior to becoming a customer?

Lagging Attribute Triggers

Next up is something I call “Lagging Attribute Triggers.”

I coined this term. It’s a clever way of piggybacking on other triggers or attribute changes in the future.

At my previous startup, we used to sell 409A valuations as part of our product offering.

Companies that offer stock options are required to do a 409A valuation after receiving funding or within 12 months of the last valuation.

So I thought reaching out as soon as a company raised money was a great idea because I knew they were going to need a 409A valuation soon.

Genius right? Well, it kinda bombed for 2 reasons:

  • Every salesperson and their dog emails companies after funding events. If you want to F**k up your inbox go raise some money. My emails got lost in the noise.
  • The second reason it bombed is our emails arrived too late. By the time their funding round was reported (and the trigger fired) they had already done their valuation or were in the middle of it.

The ideal time to talk to them was shortly before they needed to do their next valuation.

Since companies also need valuations every 12 months, I instead used a trigger that was 10 months after their last funding date. It worked extremely well.

The barrage of emails that come after a funding event had subsided, and we were able to catch them at the perfect time.

Good messaging rides the line between relevant and creepy. I knew it was working when people responded “how on earth you know that they’re going to need a valuation in exactly 2 months?!” 🤓

Other ways to use “lagging attribute” triggers

This also works really well for software that is under contract.

Maybe your technographic trigger fired when a prospect started using a competitor and you didn’t get the sale.

Well if you know your competitor uses 12-month contracts try using a trigger to send an email 10 months after they start using that new software. Let them know the pros and cons between their software and yours.

Step 3: Segment your messaging into demographic / trigger buckets

Ok, you’re a champion if you made it this far. Seriously. When I started writing this, I had no idea it would top 6,000 words.

Let’s finish this puppy off and get you some results. The last step is to combine your persona sub-segments with your triggers. Going back to our original example, if you have 2 titles, and each title has 2 company size segments, and each of those segments has 2 industries, you end up with 8 persona subsegments (2 titles x 2 company sizes x 2 industries = 8). We have 3 triggers and those 3 triggers are applicable to all 8 subsegments, we need to have 24 unique emails.

Don’t let this scare you off! It’s actually a lot less work than it sounds. The core of your email message doesn’t change that much and they borrow a lot from each other.

In our example above, the founder and VP of sales messaging will likely be very different from each other. This will form the core of our messaging.

The 2 company size variations of the founder emails will be moderately different from each other. Same for the 2 VP of sales company size variation emails. Just cater the core message to their stage.

And then the industry variations on those will be nearly the same. You may only change the example customers you name-drop.

The way I would approach this is to figure out my core message for the founder and write an actual cold email message for the 1–3m ARR E-Com segment. Then adapt that messaging for each of your 3 triggers.

Just test out that messaging and see how it goes. If it works well, great! You’ll only need to alter it very slightly to make versions for the Founder/1–3m ARR/Tech segment. Expand laterally as you continue to find success. This is the secret to scaling cold email campaigns sustainably.

If it doesn’t work well right out the gate that’s ok too. You may need to troubleshoot your messaging. If your open rate sucks, try adjusting your subject line. If your open rate is solid but your response rate sucks, then tweak your messaging. Try a few variations.

This is where looking at examples comes into play! It can give you inspiration but it always wraps around a foundation of a relevant trigger, which gives your messaging substance.

Now It’s Your Turn

I hope you’ve enjoyed this guide to cold email.

I’d really love to hear from you. What trigger are you going to try first?

Let me know by leaving a quick comment below.

Get More

This is a brand new site and this was an absolute beast to write. If you have any questions, thoughts, critiques or found value I can’t tell you how much it would mean to me to hear your feedback. You can hit me up on Twitter or send a message right here. I’ll respond to everyone who messages me.

Also, I share my best growth tactics and insights on growth, automation, psychology and life on my weekly newsletter. It would be an honor to have you as one of my first signups.

Originally published at on April 21, 2021.



Mike Wille

Growth marketer and root beer connoisseur. Star wars nerd. Blockchain enthusiast. Growing b2b SaaS startups is my jam.