Mastering B2B Email

In January of 1975, Keith Jarrett, an acclaimed jazz pianist, was scheduled to perform at the Cologne Opera house in Germany. He’d sold out the entire venue. Everyone was really excited. He just performed in Zurich just a couple of days before that, and it wasn’t feasible for him to be hopping planes between tour dates. So it was a long car ride. He was apparently really exhausted from it. He was wearing a back brace and was in a lot of pain.

Unfortunately, his troubles didn’t end there. After his arrival and just a few hours before the performance, he finds out a pretty important detail had been missed.

He’d requested a very specific grand piano—as you do when you’re an acclaimed jazz pianist. But there’d been a mix-up. The opera house crew saw a piano with the same brand name backstage and thought it was the requested piano.

Spoiler: it was not. Unfortunately, there were some pretty serious problems with it. It was a much smaller baby grand piano. It was severely out of tune. The upper and lower registers were thin and tinny. The pedals—a pretty critical part of the piano—didn’t work.

So, you’ve got an exhausted and in-pain Keith Jarrett staring at a sold out performance starting in a matter of hours, knowing he doesn’t even have a decent piano to play. And that’s the whole concert—Keith Jarrett and this piano, that’s it. That’s what everyone was there to see. He nearly refused to play.

But famously, he decided to do something different. He decides to go ahead with the concert and will use the piano he’s got. And he proceeds to improvise the entire concert on the spot, playing around the constraints of that small, broken, out of tune piano. He focuses on the middle of the piano to avoid the upper and lower registers. He uses a technique called vamping to compensate for the lack of a sustain pedal. He was able to completely tailor the concert to this incredibly difficult and odd situation, leaving the audience with a truly once-in-a-lifetime experience.

But, incredibly, it wasn’t just a unique concert experience in light of its constraints. It was so masterfully done that the recording from that concert would go on to become the greatest selling piano album of all time. And it's still the greatest selling solo jazz album of all time. This monolithic record was made from an exhausted piano player on a broken, out-of-tune piano with practically no time to prepare. That’s mastery.

Though most of us can never expect to experience that depth of expertise and command of our bodies, the evolution of jazz greats like Keith Jarrett illuminates a path to achieving our goals and overcoming our obstacles. The way they achieved greatness is something we can emulate in connecting with other human beings emotionally to deliver a unique, personal experience, time after time.

After all, what’s successful marketing if not consistently unique, personal connection?

After nearly a decade of studying and talking to B2B marketers—and consuming countless research papers and case studies—a pattern emerges that connects high-performing marketers with exceptionally great jazz musicians like Keith Jarrett.

And you won’t just have to take my word for it. Every number and case study we discuss today has a citation and uses a source I’ve personally looked into, and I encourage you to do the same. In fact, I think you should demand this from everyone who proposed a new idea to you.

One piece of research I’ll use heavily contrasts high-performing marketers—those who are able to achieve the results they want intentionally—with those who feel less certain or successful. High performers in marketing follow a similar path to greatness as these musicians, and we’ll break that down into three sections.

Mastering the instrument, mastering comping and improvisation, and mastering mantras.

So let’s start with mastering the instrument.

The story of Keith Jarrett’s situational improvisation becoming a world-renowned recording gave us a glimpse into what this looks like. So, let’s talk about B2B email as an instrument to know deeply, flaws and all.

How do marketers get to know email as a tool? How do they learn what it’s capable of? They test. But they test in a very specific way.

Thelonious Monk once said, “All musicians are subconsciously mathematicians”. It’s been my experience great marketers are, too. They’re not overwhelmed by raw data, and they’re willing to act on the patterns they discover.

But what the High Priest of Bop is pointing out here is also a caution: your instrument isn’t a math equation. All that math is in the theory, the writing, the performance.

Similarly, we often see features like A/B testing marketed as a magical feature that helps you passively optimize your emails by taking a small measurement and then extrapolating that out across a single email send. Like when you decide on what subject line goes out to 70% of your audience based on what the first 30% did.

Instead, what we’ve seen time after time is that high performing marketers are using email tests to create benchmarks. They treat testing as a way to continually increase their own understanding of their own audience.

For instance, instead of seeing what the first 30% of your recipients do with an email, they see what 100% of their recipients do with that same email. Obviously, the more data points you have, the more safely you can draw conclusions from the patterns you see.

High-performers continually test how different segments of their audience respond to types of email, subject lines, day of the week, time of day, and everything else.

Let me show you how this works. AppVault, and HR technology company, shared in a case study that they were able to get 5 times more unique opens by personalizing subject lines with the “install tech” of the recipient, as opposed to only personalizing the subject line with their first name.

Sure, obviously, more relevant personalization tends to increase engagement. But what’s critical to note is that they first did basic testing around day of the week, time of day, and sender address. They tested enough to know how their audience usually responds to different variables.

So when they ran a test that saw unique opens go up by 5x, they avoided the false positives you often see when marketers test personalization. You can’t know what made a test successful unless you have a reliable baseline to compare it to, and that’s even assuming the test was well-designed. Otherwise, when someone tells you “personalization increased our open rate”, you have to ask: What was personalized? How tailored was it? Has the company ever sent anything personalized before?

A company who’s never sent anything but newsletter blasts is obviously going to get a boost the first time they use a first name in the subject line. That doesn’t mean it works better long term.

I’m going to give you several things to try today to make progress on these forms of mastery. So to start, try this: run at least one statistically significant test every month. You don’t need to worry about sending to the winner. You’re not doing this to get free metrics, you’re doing it to get real, reliable results.

If you’re not sure what a statistically significant email test looks like, literally google “statistically significant email a/b test” to learn more or grab a calculator. I’m not being sarcastic, there are great resources that are just a single search away. Once you know what significance looks like for your organization, starting testing: day of the week, time of day, subjects—whatever. Just make sure you only change one thing at a time.

Like AppVault, you’ll be able to test personalization more reliably and see better results.

And getting results with personalization is crucial when 90% of B2B buyers expect you to understand their business needs and expectations. That seems insurmountable.

How do you get there? The same way a musician becomes great at their instrument—practice until you want to vomit, quit music, and never look at your instrument again. Then you wake up and do it all again. As a former music student in college, I can promise you this is what progress looks like.

What does this look like when email is your instrument?

It means you find a way to send more email. That’s what high performing marketers are doing—they’re sending more email than you! They’re practicing more and more until sending great email becomes second nature, best practices are internalized, and testing benchmarks become understandings.

Critically, though, they’re not blasting their email base more. They’re segmenting their database and creating their own opportunities to send tailored emails more often. They test, learn, and repeat.

In our own internal UX research with B2B marketers, we’ve found that high-performers move from thinking about the tactics of their marketing to thinking primarily about segments. As marketers get better, they can more easily uncover segments and match messaging to them. It’s uncanny how fast a B2B marketing expert can think through potential segments in a campaign. 


One of the most common ways they segment is by behavior.

Here’s a pretty straightforward way behavior-based segments and tailored content work together. Adecco stopped blasting people who weren’t engaging with their emails and moved them into their own program in which they specifically targeted these folks. They then targeted personas and stages within that segment, considering what content would actually work for them.

Over 90,000 in their database started engaging again, and their year-over-year opportunities increased by 115%.

Not only was it a huge success, but it also freed them up to focus differently on the people who were already engaging with them. Please do this. Please reward the people who respond to your brand.

All of this builds on best practices and a clear set of key performance indicators. This is why it helps to think about B2B email like an instrument—there’s no way around the fact that you can’t do the advanced stuff unless you commit to practicing over and over. All of these emails in the case study still had to be well-designed, well-written, and well-executed.

This case study is too good not to throw in, too. It shows how internalized best practices, rapid testing, and focus on a segment can create huge payoffs.

Ramp makes t-shirts, and they decided to send cold emails about it. Honestly, that’s not the most promising start. And yet, through this campaign, they had a 25% click through rate, a 50% open rate, and 90% of their responses were positive. That’s unheard of. Here’s how it played out.

First of all, they show in their case study exactly how they structured this cold email. It shows a mastery of best practices. There’s no way around knowing how to create a good email. But even inside of this specific effort, they used rapid testing to further optimize.

In this cold email, one key part they decided to include was an image of the recipient’s company logo superimposed on a t-shirt. That’s a pretty manually process, so they made sure it was going to work before putting in the effort to scale it.

First, they manually photoshopped 50 company logos onto a model wearing a t-shirt and included those in the first batch. It worked well, so they scaled it: they started testing other stock photos and animated gifs in an automated process. After further testing, they landed on the CEO of the company wearing the shirt with the recipient’s superimposed logo. And the email was sent from the CEO’s address with a personalized subject line.

Crucially, they also tracked replies and the sentiment of those replies as a metric.

Importantly, they also tracked replies and sentiment as a metric. And it turned out that replies and sentiment were amazing.

They were getting responses to their cold email with pictures of employees at the receiving companies who had made shirts with the picture of the Ramp CEO wearing the superimposed company shirt. It was incredibly meta, but also incredibly insightful, because these replies were coming from people who didn’t even want to buy from them.

They even got a positive reply from a company that can already print their own t-shirts.

So try this: divide your biggest list (or your broadest current segment) and create three new segments based on behavior. Slice and dice it however you want, but it should be based on recent engagement (or a lack thereof). Come up with KPIs for each segment and tailor content to them based on your segment criteria and what you think will get your KPIs. Track it and see what you learn.

As an added benefit, segmenting this way will help you get clearer metrics with the audience that’s engaging with you, because they won’t be all mixed in with people who aren’t.

Make this process of segmenting, tailoring, and testing a regular habit, and you’ll see the results. Master the instrument.

Miles Dewey Davis began playing the trumpet as a youngster in St. Louis. At the age of 17, Davis was hired for his first real gig. Just a year later, Davis was able to play with two of his idols, bebop pioneers saxophonist Charlie Parker and trumpeter Dizzy Gillespie.

Later, Davis was accepted at Juilliard and moved to New York, but never really made it to the classroom, spending his time instead on 52nd Street listening to Diz and Bird.

Davis jumped at the chance to replace Dizzy Gillespie in Charlie Parker’s band, despite the fact that Parker's speed and technique were beyond Davis' reach at the time. It was both a dream come true and a nightmare of technical challenges.

You can hear in Davis’s recordings from the time that he was much more tentative and often took a major backseat to Parker’s powerful style. But the skills and sense of time space he developed during this time paid off as he went on to become one of the most well-known jazz musicians of all time.

Miles Davis jumped into the deep end of “comping” and improvising when he took the gig with Charlie Parker. Comping, in jazz, refers to accompanying others while they’re improvising.

This duality maps to how high performers work with other departments and their customers to align on goals, increasing relevance for everyone. Through mastering comping and improvising, you can improve the way you work with others to amplify email’s effect.

Oscar Peterson once said, “It’s the group sound that’s important, even when you’re playing a solo. You not only have to know your own instrument, you must know the others, and how to back them up at all times. That’s jazz”.

It’s easy for B2B marketers to get tunnel vision on the email that the marketing department is sending, or only think about marketing and sales alignment.

But it’s the group sound that’s important. It’s the collection of experiences your customers are having with all your company’s email, from anyone who sends it. It’s critical to understand this customer context whether you’re supporting others in their email campaigns or improvising something tailored for a particular segment yourself.

Let me show you how this plays out.

Gallup studied 19,000 B2B business units, and found that those with high customer engagement scores generated 50% higher revenue, 63% lower attrition, and a 33% increase in likelihood of future business. And that’s customer engagement across the entire lifecycle.

This correlation is more pronounced in B2B than B2C contexts. The reason? Likely because there’s rarely a single decision maker in B2B solutions, so engaging those individuals requires deeper relevance and personalization, and also because buyers aren’t always end users or consumers. There’s a lot of people to keep up with across the customer lifecycle, and your internal collaboration is what drives the success of personalization.

What we’ve seen in Salesforce’s research is that high performers are primarily concerned with creating a single, shared view of the customer—while others are primarily worried about budget. It’s a mindset shift that necessarily results in collaboration.

It’s not about budget. It’s not about new staff or a lack of new tools. It’s about maximizing what you have now and coordinating messages across channels and across experiences throughout the lifecycle.

When we talk about a single, shared view: the “single” part means you learn from others to get more information; the “shared” part means you support others in execution. Messaging has to be connecting from first-touch through to creating loyalty.

Like Miles Davis was, you’re going to have to be a little uncomfortable as you attempt to imitate high performers. They’re 3.7x more likely to be very satisfied with their collaboration with other departments, so this is a scenario where you can start acting as if you already feel very satisfied with your collaboration.

I’ll give you some practical tips to apply these principles of comping and improvising.

You may have approached collaboration as if marketing or sales should be coaching everyone else and controlling the entire customer experience. Instead, consider supporting before you lead to gain trust and get in more practice with your instrument. Again think of it as accompanying others as they take the lead on communication, whether that’s sales, support, renewals, partners, etc.

When departments work together, they can form a singular sound that supports one another’s efforts. This is certainly easier when all your email is coming from a singular platform that records the customer’s experience across the lifecycle. Leverage those types of tools and consider them if you don’t have them already. They’ll enable you to start tracking higher level metrics like likelihood to close or LTV. Then you can start applying those learnings earlier in the lifecycle.

Supporting others in terms of email means helping other departments get better and sending email and getting the results they need.

If you’re in marketing, try approaching sales or support or another organization that sends emails to your customers. Help them come up with new ways to achieve their goals with email. Let their goals be yours and channel your creativity.

This is a much better path to collaboration than demanding others follow your lead without an existing relationship. Plus, you can teach them to improvise—and improvisation is key when combining personalization with automation.

Improvising in jazz is all about letting the moment speak for itself. You take your knowledge of the instrument, overlay it with everything that’s been done in the song so far, and let it rip. It’s pure creativity.

With email, your biggest opportunities to create a moment come when you’re automating off behavior. Your customer is telling you in that moment that they’re listening.

High performers trigger personalized emails in real time based on behavior. Engaging with your customers in real time—when they’re ready to listen—is part of what makes it personalized.

High performers are 2.3x more likely to trigger personalized emails in real time based on user interaction.

I’ll give you an example of one of the most effective types of real-time personalized emails: the welcome email.

Clearbit used to send a general welcome email to anyone who signed up for their freemium product. This was already better than not sending a welcome email, because there are endless case studies showing you this is an effective trigger for more engagement. But, their customers had distinct roles—sales, marketing, and engineering—that weren’t represented in that welcome email.

So they used their own product—which pulls in data about companies and people—to create a system of 70 conditions that inferred job role: title on LinkedIn, social bios, or the presence of a GitHub account. Based on that, a role-specific welcome email was sent in real time that prioritized the frequently asked questions and priorities of these roles based on what they know about their own sales cycle.

How did they know what content would connect with each persona? They collaborated across departments to draw out the frequently asked questions for each persona later in the lifecycle. That’s real-time personalization.

Through this welcome email, Clearbit got an impressive paid conversion rate from the welcome email—and their products aren’t cheap!

Segmenting like this also means they can continue to optimize for the audience instead of trying to get numbers up on a one-size-fits-all welcome email.

Let me give you a couple of clear next steps, depending on where you are in your organization.

If you’re not using real-time, behavior-based triggers, get started. If you’re not sending a great welcome email, that’s a place to start—but you can try anything that’s relevant. You can use triggers like viewing more than 3 pages on your site in one session, or sending a follow-up email after a support ticket is closed. There’s always room for collaboration here. Just choose one behavioral trigger to focus on and tailor an email to that situation. Automate it, track the success, iterate, and see where it gets you.

If you’re already doing that well, then take a hint from Clearbit and start tailoring your triggered emails. Do a workshop with other departments designed to identify the different customer and user roles at each point in the journey, and then segment and tailor your existing automated emails. Clearbit’s segmentation was successful because it predicted customer needs early and gave useful information.

Through mastery of your instrument and the concepts of improvisation and accompaniment, you can make great strides towards that ideal personalized experience that creates trust between your company and your customers. But we’ve got one bit of mastery left, and it’s all about consistency and discipline.

A Love Supreme, released in early 1965, is widely considered one of—if not the—greatest jazz album of all time. It’s a four-part suite that explores the depths of John Coltrane’s spirituality and the profound gratitude he was experiencing. About 8 years prior, he’d been fired by Miles Davis for a drug habit he hadn’t kicked. It was a wake up call for him, and he got clean and channeled that energy into his music and his spirituality.

The power of A Love Supreme is in its mantra. In the opening track, right after a cymbal wash and a characteristic Coltrane chromatic intro, everything fades out and a four-note bass riff sets the stage for the entire rest of the album. These four notes become the basis for every movement and every improvisation—be it as a part of the band’s comping, or used in improvisation itself. In one instance, Coltrane plays the four-note riff in every possible key.

The mantra was simple, memorable, and repeatable. This incredible mastery of it helped to communicate the complex and nuanced concept of the record: all-encompassing love and gratitude.

Though your topics are likely a little less heavy, the concept of mantras is a helpful way to look at “staying on brand”. We know this is a concern for marketers when it comes to others in the company sending email. But acting as the bottleneck to prevent bad emails is unsustainable; instead, high performers empower others to gain confidence in how they represent the brand.

As Miles Davis reminds us, “It’s not the note you play that’s the wrong note. It’s the note you play afterwards that makes it right or wrong.”

You ought not be scared that empowering the organization to use email is going to end in a mistake. Jazz doesn’t work like that, and neither does your customer experience. You need to be aligned with one another so that “wrong notes” can be accounted for.

You want to teach others how to comp and improvise on their own to maximize the effect of email, generating that engagement across the lifecycle that produces positive metrics.

Approaching your brand as a mantra—instead of as a mandate—means your messaging can morph naturally for the recipient’s context, and every department can feel confident doing so.

High performers lead the band, leveraging the trust they’ve built with others, but also showcasing their ability to adapt to “wrong notes”. You are the email expert. You know the instrument better than anyone, but you’re constantly helping others to improve and leverage their own unique perspectives.

Your mantra acts as shared language that’s broad enough to be used in every context, but specific enough to be relevant to your brand. It reflects your company values, and should be determined as a group across departments. It’s simple, memorable, and repeatable.

Creating this shared language creates space for personalization without going off brand. Everyone practices reaching the customer at their part of the journey through the lens of the mantra.

Let me show you how this can work.

[slides] The “I Build America” campaign was the brainchild of a CEO who wanted their customers in the construction industry to be known and understood. So they built a campaign around the humanity of these folks who are often misunderstood or misrepresented.

By connecting with purpose and meaning inside the construction industry, a whole array of opportunities opened up. It was genuine. And it relied on email and social media sharing because it was necessarily grassroots—and it worked. They saw a 50% increase in revenue and 2-3x the usual engagement.

Websites, ads, merch, and more easily spawned out of this simple mantra of showing the humanity and pride of construction workers: “I build America”. This mantra reflected the value of the company while being relevant to the people they were serving.

But because the mantra was simple, memorable, and repeatable, it unlocked creativity from others on the team, and enabled community-driven content. A great mantra can be improvised upon by your customers, too.

So, try this: come together with anyone who can send email to create a simple set of brand guidelines, starting specifically with email. Keeping it simple is key if you don’t have this level of collaboration yet. Frame it for others by saying you want to maximize everyone’s KPIs by sharing what makes the company unique at every stage. Build your mantra together.

By doing it this way instead of dictating consistency, you make it valuable for others to leverage your brand—instead of making it a requirement.

For a bonus, include a customer or two in your exercise. Salesforce is a great example of a company who does mantras so well that customers use it freely. Concepts like “connect to your customers in a whole new way”, “customer success platform”, and “blaze your trail” are slight variations on the customer-focused brand. Every day, I see totally disparate departments leveraging this brand to reach the customers they’re responsible for. It creates incredible cohesion.

So, if you want to plot a course to B2B email mastery, follow the trail of the jazz greats.

Master your instrument by leveraging testing and data appropriately and finding a way to practice sending great tailored email. Segment relentlessly. Practice, practice, practice.

Master comping by supporting other departments to maximize email effectiveness and gain trust. Then, improvise with real-time triggered emails based on behavior. Create an environment where everyone can explore, learn, and grow.

Finally, master the mantra—empower everyone who sends email to leverage the company brand to get results. Bring your customers into the loop to learn from them. Build a flexible, evolving email strategy that shows you understand your customer’s needs and revel in the metrics that follow.

Mastering B2B email comes with dedication, consistency and openness to new ideas.

And even if you’re already a master, I hope I’ve at least piqued your interest in rediscovering jazz culture and music, an absolute gift that grew and spread in spite of immense oppression. Let’s honor their sacrifices with respect and admiration by giving our all to our craft.