The Sales Soundcheck Podcast

Personalising Outreach at Scale with Will Allred @ Lavender

In this episode of the Soundcheck we have Will Allred, Co-Founder and CEO of Lavender on the mic. Together with his team, they are helping over 30,000 people write better sales emails faster.

The Sales Soundcheck Podcast
October 12, 2023
February 16, 2024
Personalising Outreach at Scale with Will Allred @ Lavender
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In this episode of the Soundcheck we have Will Allred, Co-Founder and CEO of Lavender on the mic. Together with his team, they are helping over 30,000 people write better sales emails faster.


We'll be discussing…

  • The importance of personalised outreach especially at scale in sales
  • His top tips on how to get your emails opened
  • Why it’s so crucial to stand out in 2023
  • How you can build stronger relationships, drive more sales, and maintain customer loyalty


Where to find Will:

Linkedin

Tiktok

Twitter

Check out Lavender 💜


trumpet in the wild:

Linkedin

Twitter

Youtube

Tiktok


Episode transcript:

Rory:

Today I am so excited to be joined by Will Allred. Not only is he a top voice on LinkedIn, but he's also the co-founder and COO of Lavender.

Together with his team, they're helping over 30,000 people write better sales emails faster. In this episode together, we'll be taking a look at the importance of personalized outreach, even while reaching out to a lot of people. Also, we'll be covering why it's so crucial to stand out in 2023, how it can help sales build stronger relationships, drive more sales, and keep your customers loyal.

Awesome to have you here, Will. Thanks for agreeing to be part of The Soundcheck. I feel like this has been a long time coming.

Connected over LinkedIn many times, had the fortunate opportunity to finally meet face-to-face, which doesn't happen often in this world of SaaStr. But I’m delighted to have you on the show. And I’m not going to introduce you; I think you'll do a much better job than I would.

Will:

Yeah, and thanks for having me. It was so good to finally actually meet in person out in London. So I'm Will Allred. If you don't know, I'm one of the co-founders at a company called Lavender.

We help sales reps write better emails. We help them do it faster. And so if you are familiar with me you might know that I post a lot on LinkedIn, sharing tips, tricks, advice on what it means to write a good email. And that's all based on the data that we see at Lavender.

We see hundreds of millions of emails, bajillions of data points about what makes for a good email. And so I mix that with—a split between that and really what the buyer's perspective is on the other side to help sellers be more empathetic to the person at their end and write something that people actually want to read at the end of the day.

Rory:

From that perspective, am I right in saying there's over 30,000 people now using Lavender? So I can imagine the data points are endless?

Will:

Yeah. To say the least, it's a lot. But at the same time, it's good. It's sort of allowing us to really live up to the mission of what we were trying to accomplish.

Rory:

Love that. Cool. So we want to jump straight in with today's topic, which is scaling outreach. And even that word is a bit scary—scaling. Has anyone ever asked you to define personalization in the current world of sales?

Will:

I personally feel like it has to be defined because right now the lexicon for what equals personalization is all over the place. You've got some sellers out there who believe that it's as simple as putting something in brackets and inserting into an email.

You've got other sellers who believe that it can be pretty much anything specific to the individual that you're writing to. And then you have other people who beat this drum of relevance is the only thing that matters, and it doesn't actually even need to be personalized.

And I think at the end of the day, a personalized email is some of those things; it's none of those things. I think, what makes for a personalized email is, it creates the feel of it being one-to-one. It is actually written for the other individual on the other end. It shows up with a clear purpose for why they are reaching out to that individual.

And so that could be something as simple as a technology that the company uses, something that you see on a company's website. It could be something as simple as the fact that they are hiring for a specific role.

The challenge with doing personalization well is it has to actually serve a purpose. And that purpose is, I'm taking this information that I found in my research and I'm tying it back to a challenge that this person likely has that I can help them solve.

The problem with personalization is when you go too far down one path, it’s, hey, I see you're a fan of the Atlanta Braves, or I don't know, you're in Europe—Manchester United. And it's like, dah, dah, dah. So what? That's not personalization.

I mean, technically it is personalisation, but it's not good. Or you've got this other—as the COO and co-founder of blah, blah, blah. That just doesn't scale well at all. And so the reason people get all hot and bothered about, is it relevant, is because it really does beg the question of, why are you doing it? Now you can't use that as a pendulum swing and go straight into cheaper tactics of I'm going to build a list of people who are hiring for SDRs, because so many people can do that now that the bar of what people expect is starting to go up.

And so what I'm telling my team, what I'm telling other teams is when you're approaching an individual, it's not just—I mean, it sometimes has to be just one observation, but ideally it's a blend of things coming together that help you create a unique point of view on the person on the other end; a unique point of view on that person's situation and the problems that they're likely facing so that when you show up in their inbox, you create this feel that you understand where they're coming from with a true sense for what the problem they might face is.

And it might be something they're actively thinking about. It might be something they're not actively thinking about, but you built credibility in that moment because of the research that you showed up with.

Rory:

That resonates. It shows you did your research. How did you know I support Manchester United? I didn't think I posted that all over LinkedIn. I shouldn't even be admitting that. It's embarrassing.

Will:

They had a nice win over Arsenal last weekend though.

Rory:

They did. Yeah. Some Arsenal fans fighting in the crowd as well. We love to see it. And I guess, something you kind of keep touching on is, personalization can come in different formats.

So you're focused on me supporting Manchester United or maybe what the business is doing, and their focus, and their growth and everything. So there's different sources. So it comes down to the research as a first point, especially when it comes to outreach, prospecting. I think your friend Samantha McKenna puts it well: Show me you know me. But what do you do when you can't find anything?

Will:

Yeah. I always tell folks; you are finding things—you just don't think you're finding things. What they do, who they sell to you, what they've built, what they've built it on. All of these things are relevant pieces of information that are unique to them. So one of the classics is, they don't post anything on social media.

I bet their LinkedIn profile sits there and it looks a resume—at least looks a resume. And so if that's the case, I now have a trajectory of this person's career. I know projects they've worked on in the past, I know what they're familiar with, what they're not familiar with; I know a lot about their mindset coming into the challenges that they might be facing in their current role. And so while that might not be the thing I use to craft my outreach, it could be.

And it could be really potent, particularly if I use it in, say, PSS. Classic example would be if a sales leader is coming from a large org and they're now moving into a small org. And so if you think about that: Big orgs, more structure, more process, more procedure.

So if they're going into a small org, they're probably craving that. And so you can speak to that, you can use that, you could talk about the much more limited budget that they probably have, maybe less documented process around even how budgeting works. Those kinds of things can kind of come together to help create a narrative for where you fit into their lives.

Rory:

Definitely. I saw a good stat around the PSS as well, increasing reply rates by around 30%. Is that the one?

Will:

Yeah. I believe it was 35, it might've gone down a little bit, which we tend to see with any sort of data trend in email; they'll fluctuate as far as potency. So there's a stretch of time where really short emails were just killing it—and they still are, it's just not to the same degree. It used to be 68% more replies for an email between 25 to 50 words. Well, you beat that drum long enough, people will start to send those types of emails. And then once those types of emails start to become very commonplace, bad emails start to infiltrate those shorter emails.

And so then you see now instead of 68%, it's only 40%, it's still the optimal way to write an email, but it helps us sort of drive the narrative of what we should be focused on and talking about. So for us, the two things that I'm laser focused on right now—because I'm looking at the data and I'm seeing people aren't doing the things—is writing shorter, simpler subject lines and truncating the sentence structures within their emails. And then the third one being, personalizing their emails. So you hit on a nerve with that conversation: What does it mean to personalize an email?

Because 96% of emails that go out the door are automated, not personalized. And so sellers sit there and they think to themselves, this email's so good, I deserve a response to this. And you don't realize it's buried under all—like out of a hundred, you are one of four that actually took the time. And so people's default is just to throw it in the trash. You pair that with, most subject lines right now are five words or more. It's the stupidest thing.

Because what happens is, if you're one of those four that just personalized the email and then you write this five-word subject line, you basically buried the lead on the fact that you personalized the note. Personalized emails are getting 1200% more rep applies right now, and I bet it would be higher if more people were writing shorter subject lines.

Rory:

Do you find then that this increase in personalization and the impact it has, means that you don't need to have a seven, eight-step email sequence that's automated in the background, and forget? Do you find that the actual number of touch points reduces?

Will:

So I'm a big fan of not needing that many touch points, and people say that you're missing out on these people that respond down the line. It's backed by data and I hear that. I do. But then I also know what the data looks like from working here—what do I do here. And I'm like, most of the data is kind of trashy.

And so you have to look at it with a grain of salt. If 96% of emails are automated and then you think about most of those sequences and cadences are filled with those automated messages, of course it takes longer to get a response. Of course there's this missing tailwind of replies on the other end that you're just not seeing. And so my thought process is to approach it like a buyer and be like, I get emails, I read them, I see them, I delete them or I respond to them.

And so, it's one of those things where if you just practice the right behaviours, you don't need an 18 touch sequence. Now you can bring in other channels to extend out that cadence. You can add some phone calls. I'm a huge fan of using other channels, by the way.

People always assume that I'm Mr. Anti-cold-call, and I'm like, no. There's to a degree. I don't pick up my phone very often, particularly for numbers that I don't know. But when I was at SaaStr—I think it was probably the same day I met you—I picked up my phone at one of the events and it was somebody cold-calling me. And so you think about, people have to pick up their phone at certain points in time. And so you might get lucky and catch them in that moment, but it also just adds a sense of humanity to the process.

If I'm calling you and leaving a voicemail, I shoot you a note on LinkedIn and I'm emailing you, of course it's me on the other end. It feels harder to automate. You create more reciprocity, especially as you personalize across those different channels and those different touch points. It's like, I really did do my research; I thought about what you're going through, and I think, very validly, we can help—which I do think there does need to be a conversation in sales about, if there's no valid reason to reach out, like they're clearly not in the best possible position, is there a different way to work the account?

But the long and short of it is, you really don't need that long of a cadence to generate conversation, if you're approaching it correctly.

Rory:

I'm hearing it's because the bar is low. Too many people are doing the same thing. So actually standing out. And we’re probably both experiencing it. If a rep sends me a nice email, I'll often read them because I'm always looking for inspiration, seeing how people are mixing things up. And like you said, it does not take a lot to stand out in an inbox. Short subject.

Even that first line, you start to see it, if you use Gmail, for sure. Pulling up on LinkedIn with relevant piece of content, a voice message, I'm going to listen. I'm not going to ignore that human tone. Someone has put in the extra mile, compared to all the 20, 30 other messages that were automated with Trumpet and our emoji and you can just tell; you can smell it from a mile away. So it sounds like it's not hard.

Will:

Yeah, I was going to reference a series of emails that I've gotten from a sales rep at Vidyard. I recently did an episode… You know we produce a lot of video content and shows.

So I was recently doing one that we call Pardon the Outbound. It's an old take on the SPN Show, Pardon the Interruption. One of the episodes, I showcased this rep at Vidyard. And this rep has been personalizing emails to me for months now—and I've responded, by the way, to all of them, but just thinking about that rep, they've sent me maybe four total emails and they've gotten responses to all of them because each email is very well thought through.

Now there's copywriting things that they could be doing better to get me more excited about the opportunity. They could be thinking about, I'm not most likely to be in charge of certain things and thus I probably would've delegated that out to somebody else; which, those are easy things to fix and adjust, but the core staple of the research that rep is doing, the way that rep is thinking about it, doing the outbound, that is something that is inherently missing in most sales orgs.

Rory:

And who do you think the onus falls on? Because with a tool like Lambda, you help massively turn an average rep into a top rep and really kind of think about their communication skills, which is such a cool one and I think overlooked a lot of the time in sales. But do you feel that leadership needs to do a better job of educating their team on what actual personalization looks like, when to introduce it, how to do it? I think it's been forgotten.

Will:

Yeah. And the reason it's been forgotten is because most people in management came up in a time when volume was the competitive differentiator. And so I don't blame management. It's management's fault—and it's not management's fault. It's hard to say, do better, if you don't know how to do better. And so one of the core sort of problems right now in the marketplace is you've got leadership that's been trained in the past to just try to find the easy button.

You've got this generative AI boom that's offering a new shiny bullet. It's just like the incentives are sort of piling up to create version two of the cadence boom, which is personalized at scale; just click this button and everything's done for you. But think about if you are coming up in sales and you never take the time to research the people that you're reaching out to, you never take the time to truly get to know and understand them, you're missing out on crucial development in your path to becoming an account executive. And so on leadership, the onus is on them to actually set up these processes to help people think about it more effectively. Because yes, AI is going to speed things up, it's going to make everything better, but if you're missing the point, you are not going to develop as a rep to get better overall.

And so the thing that I like to focus on with most of the sales works that we work with is, what's the process that you've set out when X, Y, Z prospect is put in front of them for them to write an email? Because right now it's usually like, here's your template and there's a little bracket that says personalize—if they're personalizing. There's still a lot of teams out there that just hit the automation button, but usually they want to personalize emails. And so you see this flow set up where there's just brackets that say personalize the email and the reps are, what do I do right?

They have no idea what they're supposed to do with that. And so they end up just slapping random things on top of templates and it doesn't work. It creates this blah message where you get one thing and then there's this weird juxtaposition where all of a sudden you're now being pitched. And that's not really what good messaging should look like. Your research should act as discovery process of trying to seek to understand the current process of that org.

And so when I put prospect in front of you, if you're trying to maximize both the quality of content, the development of your sales reps and the volume of outbound going out the door, you should set up a workflow of you're going to go here, you're going to look there, you're going to go over this place. And with that, the idea is to understand what you're looking for, where you're looking for it, in what order you're going to go look for it, and knowing how to use all those pieces when they come together, which requires a lot of enablement, requires a lot of support.

We view what we've built in our tooling as ways to speed up the process. But that thinking, how those things come together, that still in a way needs to be on management and it needs to be on the reps in their own path to becoming better sellers. There's something good that comes out of the friction, which sounds weird for somebody who runs a tech company to say, because in reality, as a product develops, we will try to reduce friction and people's workflows, but there's something good about that struggle from learning that makes things down the line just a little bit better.

So I think about my use of generative AI versus a net new rep. For me, generative AI slows me down. I end up just having to edit the crap out of whatever it produces and it's just a waste of my time. So I'd much rather write it myself.

So I understand the value prop of, it'll generate something for you and you don't have to worry about it, but the problem is you're putting a ceiling on your development and your growth because you're never figuring out how to go past that. And so great, you found the easy button, but if management sets people up the right way, they've got such a higher trajectory that they can go to.

Rory:

Definitely. It kind of touches on what you mentioned earlier about the bar always changing as well. If you are relying more and more on AI, you're doing what everyone else is doing and you're not really thinking outside the box, taking a step back, thinking how to stand out, which is definitely important these days.

So it sounds as well, it's not just about linking up with leadership and thinking about what is actual personalization, but it is also a case of continuously iterating, trying things that are different and not just relying on one tactic. Applying all.

Will:

Yeah. This is actually in the early days of Lavender and we were picking who we wanted to have as advisors to the company. Kyle Coleman immediately comes to mind as you're talking about this because I think about Kyle's past. Kyle Coleman, he's VP of marketing now at Clari. He posts a lot on LinkedIn as well, but his brain when it comes to thinking about outbound, he was pushing his team to personalize emails well before it was the cool thing to do. It was way before.

And part of that came from his experience as a buyer, but another part of it came from him just looking at the market, being like, if everyone's going to do that, I should do the other thing so that my emails don't get trashed. It's worked out for his team. They do great. Their client is Lavender, they write fantastic emails, they've got double digit responses. And you see all these folks being, I got 5% replies. I'm like, you probably got a bunch of people saying leave me alone, but at the same time, there's a way higher ceiling that you could strive towards if you just approach the outbound the right way.

But to your point, also approached it in a different way to what's the hot new easy button? What's the thoughtful approach to being effective?

Rory:

Buyer-centric?

Will:

Yeah, it's buyer first. It's this idea of effective over efficient, because efficient is very seller-centric, but effective is very buyer-centric.

Rory:

There's me taking notes. I love that phrase. Always got a pen in hand for these because it's just so many nuggets of gold. We've touched on personalization in outreach. I know it’s something that you are quite keen on at the moment; the sales journey doesn't stop there, especially for the buyer. That's the foot in the door. You created awareness. You got my attention, let's chat. How do you treat personalization beyond that first touchpoint and once you've captured their attention?

Will:

Yeah. There's a lot to that. So if you think about most people's mindset when it comes to the initial outbound, they think of it as this conversion point, which if you've got that conversion focused mindset, you're going to be like, okay, I send them the email, they go to the meeting. But in reality, it's not always the case. I'm not always ready for a meeting. I'm not thinking about this. And the way buyers are moving—I know my schedule; I can't imagine if we were a hundred million dollars’ company and somebody was asking for 30 minutes of my time just off of a cold meet email.

And so you think about this approach that people have to it where sales reps are almost afraid to have a conversation in the inbox. And so one of the things that I think people have to get out of the mindset of is, email is about conversation, not conversion. And it's not to say, I want to sit there and chitchat with a sales rep on my inbox all day. My emails are just too busy.

But you have to start dialogue in order to move it to a conversion, which I think is fundamentally challenging to a lot of sellers, because as I mentioned—here's my template of what we do, you want to buy it? And in reality, hey, I'm seeing the following things, makes me think this is going on, but, am I off; and thinking this following thing's a priority. You're like, no, we're really focused on X, Y, Z. Oh, interesting.

Like, having that conversation via email, sets you up to get the meeting. But people are viewing the initial message as this conversion point, which gets to this larger idea that the prospecting and the discovery are one and the same. You really don't need a 15-minute discovery call if you're doing effective prospecting because you don't have to have that weird alignment phone call where you're like, here's what you do, here's what we do. And where do the things come together so that we can work together?

We've all been on that call and it's miserable because we spend 10 minutes talking about ourselves and we spend 10 minutes listening to the other person talk about themselves and then there's five minutes left to seek alignment and then next steps. And then you wonder why your sales process is getting dragged out. It's just, to me, I think of that as bonkers, as far as you could do the upfront work and save everybody a boatload of time by giving everyone a very specific direction on where you want the conversation to go once you have the conversation.

Rory:

Yeah. I think sales has become way too transactional. Everyone's trying to fit the buyer into our playbook, how we do things, we need to adapt to the buyer. The buyer journey has become far more digital as we're all seeing; the concept of collaborating, engaging asynchronously, it's blowing people's minds. But it's what we're all doing day to day. People are spending way less time on calls and quick demos and things that.

Will:

Yeah. Well it assumes that the buyer's job is to buy. It's not their job. Their job is to do whatever it is that their job is. And buying is a small fraction of what that job is. And if they spend too much time buying, they're not going to have a job very long. So this is where a lot of my notes on discovery intersect as well with multi-threading and getting into multiple conversations across the account to create that really structured unique point of view. It's this really popular topic right now of multi-threading and everyone knows it's important but nobody really talks about tactically what to do. And there's this two really core elements to what makes for good outbound in that situation.

One, it's like people have zero concept for how to message; people below the line, this invisible magical line of, people up here make decisions, people down here are just influencer—which I think is way more nebulous than people realize because the people down here have way more influence than they ever have, because nobody wants to spend on something that no one's going to use. But then the other part is, once they have conversations down here, they don't realize how important it is to keep people up here informed.

And so it's just a lot of missing pieces in the tactical tool belt for sellers right now. And so I try to talk about these things a good bit. It's like, hey, if you're talking below the line, you're not selling anymore, you are like a reporter.

You're just trying to help them and you're also trying to seek and find information so that you can have that more pointed conversation above the line. You're not going to get information without helping somebody on the other end, and helping them authentically, not this transactional version of help, like, hey, here's a blog article, can you tell me what your tech stack is? It's like, hey, I see these things going on and it makes me think this is probably a priority; are you using tools X, Y, and Z to do it?

If so, here's a really helpful blog article I found to go get that done in that situation. That's being helpful while seeking information. So you're going to have to end up personalising below the line just as much as you are above the line. Problem is people are taking above the line tactics and being, hey, have you thought about how great it would be if you have this tool belt?

You're, I don't have buying authority, leave me alone. Right? It's cold. Then everybody's just like, cold emails are terrible and I hate them.

Rory:

We noticed X in your annual report. We now drive this like, I didn't know you had that in your report.

Will:

Yeah, exactly. I haven't ever read that. Fascinating. Thank you for bringing that to my attention.

Rory:

I think as well, not enough salespeople realize that it's very difficult in outreach to land. There's always the talk of making it relevant and timely, but to actually get in front of someone and land in the midst of them exploring a project. And what I mean by that is they're currently looking to solve that problem, that pain and all of those words that we always go through.

And quite often what you'll be faced with is creating more of a conversation. So is it a project, is it a conversation? But you can nurture a conversation into a project.

But I think salespeople think that as soon as they get a reply, that company are therefore looking to buy your solution, like there's interest, they're doing this, they're excited, and happy; where a lot of the time we need to nurture that conversation and get in front of other people and understand, is there a problem to be solved?

Will:

Yeah. Which that in of itself generates challenges for sellers because now they're holding onto these accounts that are going to take longer, which means they're eating up more of their time so they just got to get better about managing reminders, managing tasks and making sure that they stay on top of reaching out to those folks over the long haul and also recognizing when an account's just not ready and being okay with letting go of it.

Rory:

Yeah. Not enough of that. Awesome. I know we're out of time. I was meant to do a quick couple of icebreaker questions at the start, but the first is your favorite musician?

Will:

My favorite musician right now, it's this guy, Zach Bryan. Very American country. It's just good stuff.

Rory:

Have to check it out. Nice. And favorite app or software or tool?

Will:

Oh man.

Rory:

Outside of Lavender.

Will:

Outside of Lavender, of course. Let's see, my favorite software application. Ooh, there's a few. There's one that I'm a big fan of: Superhuman’s mobile app. So on desktop I'm using Gmail to stick within our own product, but Superhuman’s mobile app has helped me sort of stay on top of email really well. And it's a really clean interface; big fan of how they think. The other one, got to give a shout out to LinkedIn for all it's done for me. So that's like my top favorite, even with all the bugs, all the disasters that it is; got to be number one.

Rory:

Nice. It's almost like the third and final icebreaker, which is, if you had to give a shout out to anyone else on LinkedIn, or that you'd want to see on a show, or an up and coming creator—because you're a great voice on LinkedIn—who would you be giving a call out to?

Will:

Oh man. I'd say Kyle, but I don't know if Jen Allen would ever forgive me. So I'll go with Julia Carter. She's an AE out of New York and I think she is taken a really unique approach to creating content that's fun, engaging, sassy in all the right ways.

Rory:

Nice. Awesome. Well, it's been a pleasure, and it's been long overdue, and really enjoyed having you on. Thank you.

Will:

Yeah. Hey, thank you. Appreciate it, Rory.