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How to Write Sales Emails Your Prospects Will Love

Barry: First, tell me about Lavender. It’s a really cool technology. I’m just super curious about it and want you guys to know about it. From there, we’re going to talk about something we’re focusing on this month which is The Great Resignation and how companies can retain their employees. And then, stay tuned to hear some good tips for emails and sending emails.

What is Lavender Email Assistant Technology?

Will: Yeah. Lavender is a sales email assistant. We help sales reps write better emails faster. Now we approach that in three main ways, maybe four. You’re talking about the coaching dashboard, but we give you insight on who you’re talking to, we give you insight on what you’re saying and how you’re saying it and scoring it for what’s most likely to get a response. We evolve those things together within the inbox to help you do the job of writing better emails faster. And then we provide training and insight back through a dashboard for managers, for individual reps, to learn how to actually up their game.

Barry: I love that. So it’s not just correcting you one and done and maybe you’ll retain that information, so it’s teaching you, so that you actually become a better writer for sales emails. Is that correct?

Will: Exactly. Yeah. I think about everything that we’re trying to do within the product, we’re trying to help reps get better. So one of the things in particular that we just recently started to roll out is new sentence recommendations.

So say you write an overly long sentence. This will hurt the ability of someone to understand what it is that you’re trying to say. Not only will we make a recommendation on a better sentence, we’ll provide a couple options to show you different ways it could be done and explain what we’re doing behind the scenes. So it’d be like, we’re trying to break this up into two sentences to showcase the thoughts more clearly, or we’re removing a lot of unnecessary language from the sentence and then we’ll show you exactly how we did it, so you can learn from it.

Barry: Absolutely. I’m a big Hemingway app fan, which is a website, Hemingway, which does something similar, but you have to go to the Hemingway app to do that. But exactly like it, it really keeps things concise and has definitely made me a better writer as a marketer this past year, because I’ve only been using it for the past year. So I’m sure that resource, where people are already working on their emails will be super helpful.

Will: Yeah, for sure. In Hemingway, we take a ton of inspo from them. They’ve designed an elegantly simple product that really helps you cut a lot of the fluff from your writing. We’re trying to take that obviously to the next level, by providing recommendations and coaching insights and tailoring that stuff to you and who you are. But yeah, they’ve done a fantastic job with their product.

Barry: Right. And then obviously Grammarly is something that rings a bell, but they’re not just focused on sales. They’re focused on all writing. 

Will: Similar to Hemingway, it’s a broader focused product, whereas we’re much more specifically focused. I tend to have this conversation more than once in a while and so my typical response back is “Yes, those tools are fantastic. If those tools were designed to make you money, you would have Lavender.”

Barry: Right. Who’s buying this technology? Is it the sales leaders? Is it AEs? Is it SDRs? Is it the CRO?

Will: It’s a mix. So we operate our go-to-market mostly on a bottom-up model, which is when individual sales reps start using the product. They tell other sales reps about the product and then from that Slack discussion, VP or CRO finds out about us and then that’s typically how the conversation starts. We also have a secondary path of bottoms up that we see, where an individual rep will start using it, they won’t necessarily think to promote it internally, but their results in the inbox will actually speak for themselves.

And their manager will be like, “What are you doing that’s got you having five times the amount of positive responses to your peers?” And then they’ll respond back and be like, “Oh, I use Lavender.” And then they’re like, “Okay, cool. What’s Lavender?” So most of our go to market today is inbound, that said, we’ve done some outbound. We’ve tested that out and obviously we have success with it, we use our own tool, but most of our time and energy is spent on inbound. And outbound would be more focused on the traditional reaching out to a VP or CRO and then working your way in that way.

Barry: Let’s assume the SDRs, the AEs, when is it that they have such a pain that they’re reaching out to Lavender?

Will: Yeah. When is it? It’s an interesting question, because I’ve heard some stories where we started conversations with companies and then they decide to hold off and then they see some email go out the door and they’re like, “Oh my gosh, we sent that.” And then they’ll come back and have a conversation with us. So that’s happened before, but typically it’s folks who are just realizing that the status quo in email doesn’t work.

The stats that I love to look at are, and they really started in March 2020, there was something that happened there that changed the way we do business. I don’t know. But we saw the number of outbound emails skyrocket. HubSpot puts the number around 250 or no, it’s just over two times the amount of emails going out the door.

That same HubSpot research saw reply rates almost halving during that process. And so with so much outbound hitting people’s inboxes. We had to rethink, how are we approaching email? Is this actually proving the returns that we thought it would? And so that’s been a huge boon for us because folks are like, “Oh, we need to think about how we approach email. Clearly these old dry templates aren’t going to do it anymore.”

And were they doing it really before? Up for debate. But the response rates have obviously fallen off and you look at the average reply rate, it’s 1 to 5%. We look across our user base, I think the last data we published is somewhere in 30, and so we’re clearly seeing better results using our product.

Barry: 30%, that’s amazing. So yeah, definitely something to try. And then before you started Lavender, were you doing sales before then?

Will: We were actually building a marketing tech product before that. So we built a customer segmentation platform for about two years up until really May 2020. At which point we pivoted the software into what is now Lavender today. But we were having great success working with groups like Yamaha, Gravity Blankets, but ultimately we just hit this moment where we had realized we had to switch some things up. Obviously some things around us had changed and some marketing budgets were drying up. And so we took a different approach and it’s working out for us.

Barry: Great. Congrats on that.

Will: Thanks.

Make Employees Want to Stay by Investing in Them

Barry: So something that I think you can speak to since all your customers are sales reps, sales leaders, and customer success. Right now we’re going through what people are calling the great resignation. It’s happening in the software industry. And within that industry, there are many reasons why people are leaving. With your experience, working with salespeople. What is it that keeps them happy at their current employer? Are there any specific things that you’ve seen?

Will: Well, yeah. I think it’s easy to always come back to the salary discussion and say, “Are you paying your reps enough?” Inflation hit this year and you could argue that if you’re not getting a raise, you’re technically getting a pay cut. That said, the thing that really makes people happy at their job isn’t necessarily the finances. Obviously, that’s one of those staple items, you probably need to just make sure you’re checking the box on. But I think the thing that really matters is, do people feel like you’re investing in them? Do they feel like they’re growing? Do they feel like they’re learning?

Because a lot of times I run into sales reps who are just telling me, “Yeah. When it comes to email, my job is just to hit send on what I’ve been given.” Yeah. Our team had a conversation with an SDR the other day, who word for word said, “Yeah, being an SDR here sucks. I know the emails are bad and I want to fix them, but I’m not supposed to.” So there’s a level of autonomy that people are craving, there’s a level of investment that people are craving in their progression and then getting better.

And yeah, I challenge sales leaders right now to rethink how they’ve been approaching ramps, getting sales reps ready to actually get better. Because the current status quo is, “Okay, we’re too busy scaling. So let’s just give them these templates that they can go ahead and send on.” And if you actually vest in them and them getting better and them learning how to actually write an email, there’s so much good that comes from that.

The notion of good writing as clear thinking is something that I fully subscribe to. And so if you’re teaching people actually how to think, if you’re teaching people how to get better at thinking through what it is to sell, it’s going to have awesome down funnel effects for you. Not just when they’re SDRs, but as they progress in their careers, maybe they become a manager and then now they can teach other people to up their game or maybe they become an AE because they took the time to understand, think through what it is they’re actually sending out.

They’re able to be much more thoughtful about the entire sales process. So they have better success as AEs. There’s this ripple effect that comes from something as simple as investing in making sure that they know how to write. Now obviously, I like to focus on that specifically, but especially right now, most people’s “office” is their laptop screen. And so if you’re thinking about the technology you use, that’s essentially your office, whether you’re sending out emails from Gmail versus Outlook, it’s an entirely different office for your worker.

Whether it’s Salesforce or HubSpot, it’s an entirely different environment that they’re spending their day to day in. And it’s one of the things that we are obsessed with over here because every single pixel matters, because you think about how much time they spend emailing every day, it tends to be over 50% of their day.

And so we think about every single interaction, something is slightly annoying that just magnifies because it happens all the time. And so I know Rep Views put some data out about this, I can’t remember exactly what it is, but the tech stack at your company really matters. Reps seem to really care about that and they should. If they are going to be trying to grow their career and trying to build up, they should be at a place that invests in tech for them to learn on, that’s cutting edge. They should be at a place that is trying to move the ball forward, which the best tech will help you do. It enables it, doesn’t necessarily ensure it, but certainly helps.

Why You Need to Ease Technology Ramp Up for New Sales Hires

Barry: Yeah. I heard someone recently call it digital enablement because they don’t want to exactly insure it. There’s a lot to unpack there. I love that answer there. So first I want to just summarize it. So there are three main things. There’s the autonomy, investment and more in the ramp-up specifically, where companies can help keep their sales employees happy.

And then I guess the fourth one was that tech, which is really intertwined with each of them. I’ve never heard anyone talk about their office on their laptop, even though it’s obvious, but I love that comparison. I think it’s super interesting that I spend time in HubSpot and Salesforce, but the fact is that people could have different experiences, just on what their laptop is. And that’s in the office, home.

Will: Think about going from an organization that operates in G Suite and HubSpot CRM, and then you all of a sudden now have to go to Outlook and Salesforce, it’s not just a culture shift, it’s a day to day massive change that is going to impact for a decent stretch of time how you work. There’s going to be a technology ramp-up period, just as much as there’s going to be an onboarding to get to know the company period.

Teaching Sales Reps to Write Effective Sales Emails

Barry: That’s super interesting. Why do you think companies aren’t teaching people to be better writers? Yes there’s that urgency of hiring and onboarding, but could it also be that the sales leader also doesn’t know how to write the perfect sales email? Or that the sales leader doesn’t know how to teach on how to write effective sales emails?

Will: Yeah. I think part of it is the sales leader doesn’t necessarily know the best way to teach it because you think about when they came up, it was a volume-based business and now everyone has the same volume now. We can all send Gmail’s 250 limit of emails per day. And so it’s no longer a competitive differentiator. And so now the thing that’ll differentiate us has changed. We have to think through, “Well, what made our messaging work?” Yeah. I talk to sales leaders about this whole time and they typically just come back with, “Well, I just figured it out.”

They didn’t really put that extra layer of thought. So one of the big things that I’ve been promoting this year, through my newsletter as well as just content I put out, is this idea of taking the template a step further, think through the framework that it’s built on, take each sentence, break it down into what it actually is trying to accomplish.

Are you trying to build credibility with this sentence? What’s the logical progression from each idea to each idea, use that so that you can actually understand what the building blocks of the email are. You can challenge is that actually the best arrangement of building blocks or is that the best building block for this email?

Maybe you’re trying to build credibility and you’re like, “well, maybe there’s a snippier way to say that. Or maybe there’s a better way to approach that. Or maybe I need to just shorten what I talk about and what we do.” Because you probably do. But yeah, just thinking about it from a building blocks perspective, a lot of managers understand what they’re trying to accomplish, they just haven’t sat down and taken that time to build it out into the framework.

Don’t Forget to Train on “Why” When Onboarding New Salespeople

Will: And so that’s a big area of my focus and my time is just being like, “All right, just break it down for them.” Be like, “Okay, here’s exactly what we’re trying to accomplish here. Here’s why we’re doing it the way we’re doing it.” So much of onboarding skips that, “Here’s why we do it this way.” And so we just like to tell reps, “This is what you need to do.”

And it’s not like, “Here’s why and I’d love to see you challenge it and bring something new to the table.” I think it’s like an underutilized aspect of onboarding, is you have a fresh set of eyes on what you’ve been doing and you don’t ask them to come up with something new for you, because all those fresh perspectives, you’re going to brainwash them into, “Here’s exactly how we do what we do, just do it and shut up and be happy about it.”

And that’s A, not how this generation really likes to think. But B, it removes a lot of the good ideas that are potentially sitting out there that you could be testing. And so if you break it down for them and show them every reason why you’re doing what you’re doing and challenge them within their first week to be like, “Okay, this is a framework that this template’s built on. Here’s some examples of what that template looks like. Why don’t you try and build a template based on your understanding of what we’re trying to accomplish? Feel free to be creative with it.” At that level of ownership and autonomy and I saw some research, gosh, I wish I could pull exactly where it came from, but it was talking about a simple change to how you onboard a new employee.

The idea was, do you introduce them to the team. So it’s like, “Barry, join our team.” And I say, “Hey, y’all this is Barry. Barry is crushing with this podcast. We brought him in. He’s going to help us build out our brand awareness. Barry, take it from here. But here’s when our marketing meetings are.” Instead, I said, “Hey y’all, Barry’s new here. I’m going to let him just introduce himself.” Giving you, in that situation, the autonomy to introduce yourself to the team, they actually saw retention rates for those employees was dramatically better. I want to say it was 40% better.

And it’s just because of that first impression of what it was like to work there, you felt like you had autonomy, you felt like you had ownership and a stake in the game. So I think about the email ramp up process, why wouldn’t you use that exact same philosophy? Let them take some ownership of, “Here’s why we do what we do, come up with something new for us. We’re going to test it. We’re going to see if it works.”

Barry: I love that. That’s a great stat before, we definitely have to find that after this podcast.

Will: Yeah, please do.

Barry: And we’ll try to link to it when we do. Super interesting that you’re bringing back the autonomy also part of the onboarding process. Excuse me.

Will: Well, I think part of that autonomy is the process and the regimentation of all this, has been a byproduct of us searching for efficiency. It’s the whole SDR, AE model. It’s more efficient. But as technology has continued to progress, the need for that efficiency has waned.

And so depending on your price point, it might be more efficient for you to actually just go full cycle. And not enough people are actually challenging their current go-to market model to be like, “Is that the best model for us?” I’m not saying the SDR model’s dead, I’m going to be the last person to ever say that.

And do you think we need to think more about how we set up our sales teams, how we set up the actual experience for our customers in relation to how we set this up, because maybe the tech you have in place today is good enough that you really don’t need to have this segmentation of your customer experience, where they’re introduced to Barry and then they get introduced to Will, and then after Will sells, they hand it off to Steve and it moves on along this pipeline.

Instead, they get to know Barry and Barry takes them all the way through and that’s the way it goes, how sales used to be. So I think another thing to realize is this autonomy is possible now because of the advancements that we’ve made in technology where you can still capture a lot of that efficiency without having to slow down, missing out on scale.

Where is Sales Technology in the Hype Cycle?

Barry: So that’s interesting. Where do you think we are on that? Gartner puts us out a hype cycle for emerging technologies. Where are we with sales tech on that hype cycle?

Will: I’m not quite sure. I know there’s been a ton of investment and explosion of interest into this space and there’s a lot of dollars being thrown around and the question is, “Is there enough budget for those dollars?” Something we think about all the time. No, I’m not sure where we’d fall on a hype cycle. So I think the obvious thought is, if it helps you make more money, why wouldn’t you continue to invest in it? But when you’re looking at the VP of sales role and rev ops, they’re trying to all just assess all of these different things.

I think at a certain point, they get overwhelmed and there’s too much for them to evaluate. I’ve already started to see it with how folks are evaluating software, where it’s like, “Okay, let’s chunk off a piece of the sales team to go test this element and then if it works, we’ll scale it out to the rest of the org.” So very experiment-driven when it comes to new tech. So I’ve already started to see some of the processes around how we adopt tech start to change. I don’t know if that answers your question though.

Barry: The question came from the perspective that you mentioned that sales reps are already pretty efficient because of technology, but then obviously you’re starting a sales tech startup and I’m assuming you have a lot of potential and then we see all that influx of cash. So that’s where I’m trying to find that, where are we?

Will: Personally, I think there’s plenty of room to improve. There are several inefficiencies baked into the salesperson’s day. You’re like Dooly and Scratch Pad. I’m sitting here with my Dooly hat right next to my computer. Those two companies, when it comes to updating a CRM, it’s been the bane of a salesperson’s existence for a long stretch of time.

With the advent of technologies like GPT3 and the further proliferation of AI technology, it’s gotten easier to look at certain things that are happening within a sales rep’s day-to-day, just make them easier, better, more efficient, but also, looking at the true definition of efficiency and recognizing that effectiveness is part of it. So I still think there’s plenty of opportunity there.

3 Tips to Write Cold Sales Emails That Get Meetings Booked

Barry: So I promised our listeners that we were going to talk about email tips. So let’s start doing the email tips. I’m not a sales rep, so you might even have to guide me while I ask these questions, but what are the biggest mistakes sales reps are making? And you can differentiate between AEs and SDRs if necessary, but what are the three biggest mistakes sales reps are making today, when they’re writing cold sales emails?

Will: Let’s start with just the biggest misconception, because the biggest misconception that I see is this idea that a cold email is supposed to be about you, because it’s not, no one really cares. We try to be extremely comprehensive when it comes to writing email, when in reality that’s the opposite of what we should be doing. I always tell folks, they’re really showing to be like one, two sentences max about you or what you do, the rest of it should be focused around them and their problems and what’s going on with them.

Because you think about where you’re meeting them in the inbox, they’re triaging through their to-do list. You think about how you can go through your inbox, Barry. You’ve got podcasts, guests that you’re trying to coordinate, internal things that you’re trying to manage, vendors that you’re talking to. There’s a lot going on. So when you get a sales rep’s email, you’re trying to sort through this extra information. And so you don’t really give it the time of day and that extra time that it takes to translate out all the things that they do back to your problems, you’re not going to take the time to do it. Most people don’t. And so instead it’s just focusing strictly on them, their problems and then recognizing that you don’t have that much time to get your point across.

The average amount of time they’re going to spend reading your email is about 11 seconds. And so with that in mind, it’s like, “Ooh, I only have 11 seconds. I got to talk about them. And so if I’m talking about them, it doesn’t leave me a lot of time to talk about myself.” And so people can get nervous about that, but it’s actually a good thing. Yes, it’s a forced limiting factor and it’s good and it’s for a reason, just introduce what you do very concretely very quickly and then be gone, see if it’s of interest. So that’d be the top thing that I like to focus on. The other two things are the idea that personalization can’t scale. I see so many sales teams fighting the data, SalesLoft put out extensive research on the fact that personalization doesn’t matter where you’re at within the cadence. If you personalize an email, you’re going to get a more positive response 2x.

And it’s like, “Why wouldn’t you just figure out a way to systematize that and put that into what you do?” It doesn’t have to be like, “Hey, I saw you went to so and so college.” That’s never going to be relevant. It’s more about making observations about what’s likely going on within their day-to-day and integrating that into outbound. So it’s like, “Hey, I saw you’re hiring a bunch of SDRs. I imagine this is going on within your organization or is this going on within your organization.” That’s personalization, it’s just about showing the sales team what they should be looking for and then helping them build a process so that they can do it really quickly.

And then one of my favorite points is complexity. So I hit on the fact that emails are only read in about 11 seconds. That means they’re basically scanning through. We don’t read for comprehension, we read for categorization when it comes to email. And so thinking about it, if I’m only going to get a glimpse of their attention, I need to make this email as simple as possible so that they absorb as much of it as possible. So that’s why we actually see the best response rates come back from emails written at a fifth grade reading level.

That means like stupid, simple words, short, choppy sentences, really avoiding any usage of commas whatsoever. The average email, 70% of emails are written at, or beyond a 10th grade reading level. And it’s an easy place where we’re just missing opportunities to optimize, our data puts it in, if you get it from a 10th grade down to a fifth grade, you see 31% more response. So those would be my top three. I would say, recognizing that it’s not about you, it’s about them, personalizing and then clarity, being super simple with what you say.

Barry: Keep it simple, stupid. Always comes back to that. Do you see that marketers ever get involved with these sales email templates or is this a sales role?


The average time spent reading your email is 11 seconds so you’ve got to grab their attention and see if there’s interest. Your potential customers are triaging their inbox, trying to categorize their emails and move on. Write personalized emails that are easy to read and easy to categorize.

3 tips to write cold sales emails:

1. Focus on the recipient’s problems

2. Personalize the email message

3. Write for clarity in short choppy sentences at a 5th-grade reading level

Should Marketing Build Sales Email Sequences?

Will: I do see marketers get involved in building out sales sequences all the time.

Barry: Should they be writing the email campaigns for sales?

Will: It’s not my favorite thing to see. I think one of the things that marketers have to their advantage is they understand things like customer segmentation and what power that can have. I came from building a customer segmentation product and so you can actually feign a lot of these personalization insights by just running list segmentation. If I’m reaching out to a list of sales VPs that have recently gotten that VP job or SDRs before, I can build an email that probably feels like I’m reaching out to you one to one.

And that’s an easy list that I can build within LinkedIn Sales Navigator. The place where I see marketing going wrong is when they don’t do that segmentation or they Google, “What’s a good cold email?” And then you see these classic errors because they haven’t been in the weeds and they haven’t done it. Or they want to be comprehensive and treat it like a landing page and sales reps make a lot of the same mistakes. No one party is free of blame here. But I think it’s easy for us to point at some of the more comprehensive writing and say that probably came from marketing.

I think about the classic sales email subject line. So if you do a subject line that is first name, comma, some sort of whatever. It’s a classic like marketing subject line. The recent data from SalesLoft shows that if you do that, you get 18% less response in a sales email. And it’s because we got it from the marketing side of the house and we started using it and then we thought it would work because we were looking at marketing stats to say like, “Oh, it definitely works.” But have you ever forgotten an internal email where the subject line is, “Barry, increase your response rates.” No, of course not. But to flip blame on the other side. I see in a lot of cold emails, people say, “Will, I’m Barry, I work at such and such.” That introductory language is very common in cold calls and now it’s crept its way into our cold emails and that’s not necessary. You shouldn’t actually do that because the end reader immediately picks up on this. I introduce myself and they’re like, “Oh, this is a sales rep reaching out.”

Barry: So it’s that, not trickery, but it’s making the prospecting email look like an internal email.

Will: It’s not trickery. It’s not trying to pretend to be something you’re not, it’s recognizing the process that you’re actually in, which is triage, recognizing that they’re just trying to categorize and move on. And if they quickly lump you in with all the bad sales emails they’ve ever gotten, that’s not a good place to be. You’d much rather them be thinking about problems that they’re dealing with today, like their to-do list on their day-to-day, keeping that as the frame of reference.

Use Email to Keep the Conversation Going with Sales Prospects

Barry: Yeah. So that makes sense.

Will: You never really want them to feel like they figured it out. You want them to have a sense for what you do, but they have to respond to learn more.

Barry: Right, use cold outreach to start that conversation?

Will: Because if you are reaching out and you’re telling them everything about what you do and they don’t respond, what are you going to follow up with? How are you going to keep emailing them? Basically throwing the landing page at them and you’re like, “That’s too much. I don’t actually absorb any of that.” But you’re on the other side and you’re like, “Did I say something wrong? Was it the way I messaged this? This is a super helpful tool.” And it’s because they didn’t actually read anything that you actually wrote. They just saw it and they’re like, “Oh, that’s a big, long sale.” Now for the next three weeks while you put them through some monstrously long sales pitch cadence where you reach out to them a gajillion times, every time they see your name pop up in the inbox, they’ve already pre-categorized you. It’s all about categorization.

Barry: Yeah. I’m looking at emails so differently. Thank you for that. Besides using Lavender, what’s one thing that sales people can do differently tomorrow for their emails?

Will: Yeah. I think one thing that sales reps could do differently for their emails tomorrow is take the email templates that they have and break them down into their individual parts and understand why it’s actually doing what it does, because I view my job as to teach people how to write better emails.

Yes, our product makes it easier, but you can write a great email without a product. Yes, the data’s there, but people have written good emails before we existed. And so if you’re actually thoughtful, if you’ve actually put the thought behind what you’re putting out there. You’re going to be in better shape than 99% of the sales reps out there.

Barry: Love that. Will thank you so much for joining our podcast. I learned a lot about effective emails. It’s super interesting, the way sales people are using technology today to make their email processes more efficient so that they can sell more. I really appreciate your time.