Episode #6. Sales Email Techniques with Ross Nibur

Episode #6. Sales Email Techniques with Ross Nibur


The guest of the day is Ross Nibur.

Director of Revenue Operation and Strategy at Toast.

Ross is recognized by many as one of the top 10 Sales Development Leads in the World and Top 100 Sales Coaches to Watch.



Toast inc, All-in-one platform for the restaurant industry.

What will you learn?

  • Why your emails are not being opened;
  • Best sales email techniques; 
  • What makes a cold email great.

Ross recommends: 

How to Win Friends and Influence People by Dale Carnegie.



Michael:    You talked about your relationship with email already. Being a Revenue Operation and Strategy, how many cold emails do you receive per day right now?

Ross:    Who counts? Dozens and dozens of cold emails a day.

Michael:    How many of them do you open?

Ross:    How many do I open? Two or three a day, probably that I actually look at.

Michael:    What catches your eye? Why are you opening those particular emails and why are they standing out among the others you are not opening?

Ross:    Look, I want to be clear about when I say I open two or three. I do open more than that. Usually, the emails that I'm even going to just click on are going to be the ones that have a compelling subject line or interesting subject line. If I can tell that it's a cold email when I look at the subject line, I'm probably not going to open it.

Michael:    Can you give an example of the latest email that you opened with this nice catchy subject line?

Ross:    Yeah. It was from a data firm that does API management and the subject line was something along the lines of can we talk about your data quality nightmares. And I was like yeah, we can talk about those, but in the email itself, they had a lot of really compelling information about what they're doing.

Generally speaking, when I'm going to open a cold email or engage with a cold email, it's going to be one of the ones that's softer.

If your email sounds like a sales pitch out of the gates and it's like, hey, do you want to buy this stuff? No man, I'm not going to open that.

Where if you think about how you guys got ahold of me, it was really soft. It was like, Hey, we just want to chat. We are interested in having you on this podcast. Are you open to a conversation? And that softness gave me the opportunity to actually be willing to engage.

It's kind of the same feeling as getting a cold call when you get a cold call, and the second that you pick up the phone, they're like, hey, this is Ross Nibur. I'm calling you from the spa. I'm totally like to have kind of a brief conversation with you today about ...you just lucked out. Dude, I have the same reaction to cold emails when they read the subject line?

Michael:    Is there any difference between the email being short or longe? Which one do you think could work better on you?

Ross:    It really depends because I think what's more important than length is a format, because ... a great example of this. I'm a child of the 21st, so forgive me for this, but do you know what TLDR is?

Michael:    No, I don't know.

Ross:    It's an abbreviation you see a lot on the internet. It means too long, didn't read. So if you're going to send me an essay, but there's like a big bold part at the very top of the email it says hey man, this is what I want. If you're interested, read more, you can get me with a longer email. But my personal preference and the thing I would encourage most prospectors to really do is to keep the email shorter.

You have a finite amount of time to capture someone's attention and if you just send them a wall of text that is not visually clear where they're supposed to focus, they're not going to. And so when you think about how do you get somebody to look at that email and know what you expect from them, using bold, using bullet points, keeping it short.

If you're only going to get them to read three lines, the most important three lines up at the top. If you're asking yourselves those kinds of questions as you're going through the emails that you're sending, you're going to just end up with a better email. Then if you just send somebody like a giant unformatted wall of text, there's no way they're going to read through all of it and they're going to miss the most important piece.

Michael:    Right. Can you approve or reject the following statement? I always like to start my cold emails if I'm sending any with a call to action. So I always want to tell people what I want from them. I mean, can we connect on the phone because there's this and this and this.

I never start with my intro or my opening is very stick to the point, like what I want from you so that if it's not something that you can give me, then you don't read that. Would you say that this is the right approach or I am too kind of straightforward there?

Ross:    As a general rule, it's the right approach. I would encourage most people to do that. 95% of the time, your starting with a really clear CTA is going to help people understand what you're gunning towards, and then to your point, they can filter in or out really fast.

The problem is that, especially if you're dealing with executives, go to market leadership, they know what you're doing and they assume that it's an email from a salesperson. And so one of the things that I would encourage, particularly if you're going after CRO is to be aware of is that they see that and in their head, they've already filed that away as a cold email. And that's sometimes breaking up format is really important to make your information stand out from the crowd.

The most important thing to do to the best of your ability is never sound like a salesperson or never sound like a marketer. And the sad reality at this point, Michael - and by the way, do you prefer Michael or Mike?

Michael:    You can do both. People call me Michael. 

Ross:    cause if you think about it, everybody sends emails that look like that now, and so slowly but surely a strategy that was very effective, becomes less effective as people start to recognize the pattern of a salesperson. And so just keeping that in mind, it's not just as simple as there's a one-size-fits-all email format for every single prospect.

Who you're emailing, are they going to be familiar with these tactics? Are they going to be getting 400 emails a day that looks just like your email with the CTA at the top? Or is that actually going to differentiate you because they're not getting those kinds of emails? Does that make sense?

Michael:    Yeah, yeah, it makes sense. You were saying this and I just remembered in 2000 or 2010, those basic sales folks like Aaron Ross and others encouraged your CTA to be strong. Your CTA should not just be, hey, are you interested, or hey, is this something you want to discuss? You need to say something like, let's have a call at 2:00 PM on Tuesday or are you available to talk?

In 2020 all of those emails are with this strong CTA, so whenever I receive an email with someone saying, hey I have a call, I was like, are you serious? I don't want to have a call with you. Tell me what you want from me, or why I need to have my time with you? Send me more information or talk to me more about what is going to be about. And I think that needs have a kind of the cycle of time. So we started with this very soft approach of emailing, more soft-hand and then we were very strong, very pushy, and that worked for some time and now we're reversing back to where people want to learn more.

Ross:    Exactly. Because humans are just really good at recognizing patterns, and when we fall into a pattern, we just react the same way to it and that's really true for how people respond to prospecting emails.

When they recognize the pattern that they're in, they're going to respond the same way every single time like clockwork. And the thing that's funny about what you bring up to me, when you think about like all of the Aaron Ross and the prospecting and how is this supposed to sound, is they always bring up that second piece, which is not just the CTA, it's the value to your prospect. What am I going to do for you? And I think that that's often what I see missing in a lot of the sales emails I'm getting right now that I just ignore flat out is there won't be any information on their company or what they're trying to do for me.

It'll just be, hey man, can we get on the phone for five minutes? I've got some questions for you. And I'm like, No! Who are you and what do you want? And it can be really challenging though to figure out the right level, that altitude, how much information should I provide? How in the weeds should I be, when you've got to learn that by braille and really figure it out for your industry specifically.

Michael:    Right, right. I think that towards this point, I think that we get to the point where email marketing is that is so exaggerated and prospecting so exaggerated just because there are a lot of providers that are offering very cheap aggregated data to everyone.

So right now, you can go to, let's say ZoomInfo and then you can buy a $2,000 database of 50,000 contacts in the US and then you can just mass-mail all of them. And even though a lot of ESP companies like Google, Microsoft, they are fighting and they are introducing new firewalls, at the end of the day you have a cheap access to leads, cheap access to all the tools and you're just mass mailing everyone without actually thinking about who and why you're selling to them, and whether they are your actual ideal customers or not.

And this is something that we've seen. For example, with Belkins, we are doing email marketing as well. We are doing all about campaigns. We are heavily into email marketing, but we always think about the customers from the database research perspective, so we never do any mass mailing.

We wanted to first do our homework like for example, when Dmitry set up this session with you Ross, what he did basically he is following some of the guys. I didn't know who is exactly but someone like an influencer on LinkedIn and leaves answers like says who should I record a podcast with and someone in the comments said hey, you should chat with Ross Nibur, and then Dmitry says let me check out Ross.

He did the homework and said well, he should be a great fit for us in terms of he's a super interesting and experienced individual. So let me see if Ross will be interested in setting up this call with Mike. That's the way it works. So do you think that let's say ... and again, my point was that we should step back from these aggregated sources that offer the cheap data, do some thinking, do some groundwork, do the research, spend more time, send let's say 10 emails, 50 emails. By the end of the day, set up those 10,15 calls that eventually build the relationships and get those few customers, rather than mass mailing those thousands of individuals by using all of these automated available tools and resources at your disposal. Do you agree with that?

Ross:    In some ways, yes and in some ways no. Let me put it like this. It's all about efficiency in your business and the number of resources that you have. If you are a niche firm dealing with a limited and addressable market and a finite number of buyers, you need to treat every single one of them like they are solid gold. If you are working with the Fortune 10 as a great example, you should not be sending a single mass email. Every single email should be tailored to your point.

If you're a one-person or two-person shop and you've got millions and millions of potential prospects and not a lot of time, these kinds of strategies can be effective. They're just not going to work as well. And I think that's the piece that I like to implore on new entrepreneurs is this is just a tradeoff. It's not a right or wrong answer.

If you sit down and you write 10 perfectly crafted emails, you're going to get a 50% response rate. You're going to hear from a lot more people and you're going to put in a lot of work, but you're going to get a good result for the work that you put in. You could also probably spend 10 minutes writing a bad email template and to your point, go spend a couple of grand, rip a list of 100,000 contacts off ZoomInfo and fire it off and you might only get a half percent conversion rate or some minuscule conversion rate, but you still get the same number of responses, right?

You still end up at the end of the day with five people who raise their hands and say, sure, I'm going to talk to you. And that trade-off is really about the nature of your business and what your resources look like, both in terms of time, money, and addressable market, and whether or not you can afford to burn that many contacts at once or put that impression in your customers' or prospects' mind. I think it just gets more complicated than just one strategy is the right choice and the other strategies, the wrong choice.

Michael:    Yeah, absolutely. In terms of actual spam, within the last two years we interacted with prospects, it's much harder to send out any prospective emails because the majority of them end up in the spam folder and we are trying to fight it, and actually developed a platform for that.

So did you notice that a lot of your emails or some of the folks that work with you go to spam, and do you know any tools or anything that helps you to fight that?

Ross:    Yeah, the number one thing to keep in mind for not hitting spam folders, and I'm sorry, I'm going to get really technical for a second. It's really trying to preserve the integrity of your main email domain. What I've seen a lot of companies forget in their early days when they're first starting up and they've got whatever their first 50 employees, they'll tie their email marketing solutions, whether they're using a HubSpot or an Outreach all of that information through Google the way they store into spam folders is all domains reputation, and they are flagging the email in the domain as potential spammer and moving it over into that bucket. And if you think about the implications of that in the long-term, it means that your individual sales reps who might be building these really customized personalized emails are going to hit that same folder because you've corrupted your domain.

And so one of the important strategies, in my opinion, is to be really thoughtful in where you generate these emails from the beginning. If you are going to use a mass cold email strategy, or you're going to use a tool like an outreach.io or a SalesLoft that could easily be mistaken for spam or hit the Google spam parameters, make sure that you've got a subdomain that you're using so that even if that one gets completely burned, your main domain isn't impacted, and you can always just shift them onto an additional subdomain if you need to, to get back out of those spam folders. But you're never going to get back at Rossnibur.com as a good domain unless you're being really smart about how you use it from the get-go.

Michael:    This is an unspoken rule in the business that you never ever need to use your main domain for outbound marketing ever. You just buy a $25 additional domain, which will be sister to your main domain, like Belkins.us or Belkins.com, or something like that or .io, and then just use it and that's it and just set up a redirect or something.

And also, we've seen that engagements are very important. If you are sending out emails and your engagement is low, it means that the chance that you're going to spam is much higher than rather that the engagement is high. So that's why the list should be clean, the message should be well-crafted as well as you should know who and how you are emailing to and then respond in a timely manner, and engage with all the responses because I've seen that a lot of folks are ignoring not interested or OOO responses.

Any responses that are not leading to an immediate sale, we just say, Hey, I don't have time to that, but when you want to work with objection or you just simply send thank you before I send off, can you tell me this or I would like to know this or I appreciate the time. It still counts as an engagement, so for the algorithm, it's a conversation and it's a plus in your box.

What is your take on follow ups? If I were to create a cadence of how many follow ups, sales follow-ups, I would have three, four or five.

Ross:    Never stop.

Michael:    Never stop to follow up?

Ross:    I think that you can have a fair debate about this, but my opinion is that any individual salesperson should never be bent on getting been so many relationships, or trying to build so many relationships that they can't be methodical about reaching back out to each one of them, and silence is not a no.

Nor is to your point, that soft rejection of saying like, I don't know if this is something I'm really interested in right now, but if somebody doesn't respond to that follow-up email, follow up on that follow up. Keep going. Really for us as salespeople, the out road should always be the yes or the no.

If the answer is later, that just means you're going to be following up again. And so either they're saying no, never contact me again for some legitimate reason, in which case you really need to understand why they will not ever be able to buy your products, or will never be interested in buying your products. That's really valuable information for you to get. Or the alternative is you get the yes and they're going to become a customer of yours.

Michael:    Or are you will receive the **** off, right, or something like this?

Ross:    Hey man, I wasn't going to curse on your podcast, but if we're going there, you're going to get the fuck off. That's a no, and hopefully, you can get some more information than just go buzz off.

But at the end of the day, I don't think that you can be a successful salesperson if you send somebody an email and be like, oh well, Michael didn't get back to me in a week, so I gave up. I hit Michael, he hit me back, I emailed him back and I'm just waiting for him to respond. Waiting for somebody to respond isn't enough action from you.

You as a salesperson should take control of the relationship. And the thing that I see people forget a lot as they're doing this kind of follow-up, is that their buyers are busy. They might not have forgotten about you or not be interested in talking to you or might be ignoring you. Something else might have come up and you might've slipped off their priority list. You have to make yourself a priority.

I find that I end up talking to people about this quite often when they're applying for new jobs, and they're there on the job hunt. This is going to sound silly, but my younger sibling is looking for a job right now and so she's been applying to all these places and I was like, well, when did you apply? She was like, oh, three weeks ago. Have you heard back? No, I'm waiting to hear from them. I'm like, call their office. Ask them if they got your application. Checking on if they filled the role, and she's like, isn't that inappropriate? Aren't I going to piss them off? No man.

They've got a thousand people applying to this job and better things to do. The hiring manager in this small university you're applying to probably has 17 other jobs and this is like the bottom of the list of things. If you make it as easy as possible for them to hire you or in the example sales, we can make it as easy as possible for them to buy your stuff, they're going to just do that because you're creating the path of least resistance.

Michael:    Yes, that's so true and actually, I agree with you that you need to follow up. You need to be more proactive.

You need to always get to the point where people hear about you from everywhere so that you can get their attention because attention is very important because of the buzz that's everywhere. At the end of the day, we've seen that you are trying to track everything like what is the bottom line in terms of the follow ups that we can keep on, and then we are hitting the spam more often or something, so we can have a more kind of patterned way to create campaigns because we are doing a lot of those.

We've seen that, let's say, five or four follow ups is the best kind of sweet spot there. But what always surprised me is the last follow up that people receive and they respond to and that actually gives some action, and every follow-up, the last follow-up is so ridiculous. We are currently, and we've been testing this follow-up with the T-ReX. Have you ever received a T-ReX email?

Ross:    Oh, what is it? Are you like being chased?

Michael:    You're chased by T-ReX so let us know if you are okay because we were getting worried or something like that.

Ross:    I think I've done that one. I've seen that one before, but the bigger thing for me is - how do I put this? 

You need to have some comedy in your emails.

If there's nothing funny in what you send to people, they're not going to really engage with it. Humor is really powerful, whether you're getting chased by dinosaurs or whatever it is you do to stand out, it's always going to help. One of my favorites - I've done it with cold calls more than I've done it with cold emails, but I sell to restaurants.

That's a hard market. They don't really like cold callers. One of my favorite talk tracks was always just like, Hey, is this Michael? Yeah, great. Are you in the mood for a cold call right now? And your giggle is exactly what I'm going for.

Of course, you're not in the mood for a cold call. No one is ever in the mood for a cold call. I know. It gets somebody to at least breakthrough and realizes, Oh, this is a human being. I'm talking to a person and they might actually have a sense of humor.

Michael:    That's a great approach for cold calling. I'm one of that generation that I don't ever, ever pick up the phone from the strange phone number. Can you just text me and say why you calling me? I am like my mother and my girlfriend are calling me if there is an emergency or something, right. You never expected a call from someone like if it's not very important. So it's super frustrating.

But yeah, I mean which channel do you personally prefer right now for prospecting - call, email or LinkedIn? Which one do you think is on top, and which one is slacking off?

Ross:    So it's important to note that when we talk about my industry with restaurants, we don't really cold calling as a tactic and that works because think about the last time you called a restaurant and no one answered the phone. I mean, we can always get somebody on the phone.

We can always get some information that will help with the cold email later. I think that what people that are reaching out to me, you really want to be using social right now, particularly channels like LinkedIn because it's really a easy way of, to your point, creating credibility and having multiple ways that you're getting in front of a person and you just can't underscore how important it is for them to be able to verify and see that you are somebody that they're connected to other people with, whether that's social selling aspect of you having that big network or Facebook that's going to let you break through to a person can be incredibly helpful.

I don't think any of them though are dead. I think that people love to exaggerate and be and take the stance of being like, Oh well cold calling is dead. You can't cold call a VP of sales and be successful. You'll never get through to them, and I just don't think that's true. I know I've had the VPs of the teams that I work with today pass people along to me that got them through a cold call, and it's really a matter of scale and differentiation.

You just need to be good at doing these things and that a lot of teams are using these tactics. And so it's always going back to how are you making yourself sound original? How are you making your content different, your emails or calls, your social media messages or text, whatever channel you're using, or are you selling intelligently or are you going through the motions and sending the same template out to a thousand people? Because that's really going to drive the level of response that you got from the prospect more than the channel itself.

Michael:    Right. And it would be a dumb question probably, but do we have a set of books, courses or channels that you would recommend for newbie salesperson to follow, or to read or look through to get to the next level of understanding the way the world works?

Ross:    There's a couple that I really like that I do recommend to people all the time. the first one, I'm just going to go completely old school here - How to Win Friends & Influence People. Have you read it?

Michael:    I didn't, no.

Ross:    Dale Carnegie is the author. God, I want to say like 1920. It's old. When was it published? Originally published, excuse me, 1936 so this is a rather old book, but it's very simple on the strategies and ways that people want to be spoken to, what people want to speak about, people's motivations and conversations.

And I think that many authors today base their ideals on what Dale was talking about. And so going back to him and just saying, hold on a second, what's the baseline of building relationships with people is going to be a really good place for new sales players to start, because it's going to give them a way of just even thinking about when they get on the phone or when they're talking to a stranger, how do you get a person to want to talk to you? And so I personally would recommend his book to add anybody out there who's looking to start a career in sales.

Michael:    We're going to put the name and the link to the book in the description below the episode. In terms of actual educating courses or something, have you interacted with any of those that could be helpful, useful with some, not scripts basically, but some kind of playbook in terms of what to use, what not to use, some terminology, some language there?

Ross:    Personally, I'm not a big fan of most of the courses that I've worked in or seen. I think that often they are a little repetitive and tend to not have the level of nuance that I personally believe people need to be thinking about when they're building their prospecting plans. If you think about a lot of my comments over the course of this conversation, 9 times out of 10 my response is it's just not that simple.

Going back to the email marketing and like, Hey, do I send 10 emails or 1000 emails? What's the right answer? It's a choice. And so what I would encourage actually for new salespeople is to break into their community, and LinkedIn is a fantastic tool for doing that. You can engage in a lot of conversations with other people who sell to similar buyers or sell to similar markets. You can find your local communities. You can find boards to post on and read content and bounce ideas off people. And in doing that, you're also practicing your sales skill because if you can figure out how to get the VP of Sales at Groupon to give you the time of day to tell you about how they think about prospecting, you're practicing prospecting.

And so I would actually more encourage people to engage in conversations with their communities than to look for a specific set of blogs or set of content that's going to hold all the answers for them.

Michael:    And then don't sell right away. I hate receiving those LinkedIn messages when someone is like, I just connected with them and they start selling. Man, stop! Give me five minutes. I think that LinkedIn is a great place for prospecting and for generating some great leads at a very low cost because you're just paying for your time and then they give all the tools for you all on LinkedIn.

At the end of the day, it's not very convenient to use the tool, especially the inbox part. Like it always slows those messages always and it's a mess there. I really hope that someone from the Microsoft team can listen to this and say, guys, stand by. We are releasing version number two when the people can actually filter out and use this LinkedIn inbox as your mailbox, or with the more convenient filters, and in tax and all of that because it's a mess.

Ross:    So LinkedIn, if you're listening please, please build a real email server for yourselves.

Michael:    All right, Ross. So, we are almost out of time, so I really appreciate you taking the time to sit and chat with me. I always think that if it's not scripted then it's very useful for people who can listen to this and pick something up for them, so thanks for sitting down with me and taking the time.

Ross:    It was really my pleasure, Michael. I had a great conversation. If you ever have follow-up questions for me, I'm happy to jump back on a call.

Michael:    Sounds good. Guys, for those who are listening, please go ahead and follow Ross on LinkedIn. I've seen you always post and tag and do some stuff on LinkedIn so you're very social there. I'm trying to follow as many people as possible and go to LinkedIn on a daily basis and read some interesting stuff, industry-related obviously, but I encourage all of you to go and check out Ross.

We hope you've enjoyed this episode of Belkin's Growth Podcast and found it useful. Be sure to subscribe and catch upcoming episodes on iTunes and Stitcher.