Advisorist Podcast – Episode 2: 6 Sales Email Hacks To Sell More Insurance Policies


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Here’s how insurance agents and financial advisors can build a personal “black box” that spits out 38 dollars for every one dollar input.

If you had a little black box you could slide a dollar into and 38 more dollars would pop out the other side, how many bills would you put into it?

Hit play to discover:

  • A 5 second mental trick to instantly boost your problem-solving capability
  • ONE easy method to get more clarity and direction when you’re stuck
  • Where to spend your digital marketing dollars for a 38x ROI
  • 3 ways to ensure your cold B2B emails are converting – COMPLIANTLY
  • The single line email with a 33% conversion rate… from a COLD list
  • How and why to humanize your emails for stronger conversions
  • A simple “squint test” you can perform in your own inbox to engineer winning subject lines
  • Examples of the EXACT emails used to generate new clients and sales that you can swipe


Note:  This Advisorist Podcast transcript was created in part by computers – Please forgive any grammatical or spelling errors…or sentences that just downright don’t seem to make sense!  Please compare to corresponding audio if clarity is needed.

Jeremiah: Hi, it’s Jeremiah DesMarais and I’m here with Devin Ambron.

Devin: Nice to see you guys today

Jeremiah: and this is episode number two of Advisorist, the most loved podcast of the insurance and financial services world. Today we’re going to share with you six sales email hacks to help you sell more insurance and financial services. As always, with every meeting we do internally at Advisorist and on podcasts, we like to ask each other, what are you grateful for today? Research shows that by putting yourself in an attitude of gratitude, before you tackle a problem or opportunity or challenge, you simply come up with more resources in your mind. So devin, let’s get started. What are you grateful for today?

Devin: My friend, I am very grateful for presence. One thing that I have been thinking about over the last couple of weeks is I made a trip a few years back to Europe and they didn’t have – at the place I was staying in Italy – It was a really nice hotel – but they didn’t have on demand hot water. They had this electric heater that was at the spigot of the water of the shower head itself.

Jeremiah: Oh yeah, yeah. I had the same thing in Dominican Republic and Ecuador. Yeah, I know exactly what you’re talking about.

Devin: Yeah. It was so strange because I thought what’s going on? Something’s wrong, but it was lukewarm water and so the reason I say that and give that as an example is because in being more present, sometimes it’s just noticing the really small things that we take for granted that keep me present. For example, cold brew coffee, which I’m drinking right now, or hot water. Just those simple things keep me more present and that’s something I’m really grateful for.

Jeremiah: Outstanding. What I’m grateful for today is my mind and you know, I’ve spent a lot of time thinking about thinking. I know that sounds very philosophical, but you know how I control my mind and as you know, one of our core values is strong mind, strong body, and I’m always trying to get better at how I think about things, particularly with my personal relationships, my relationships with my awesome team – you included – as well as people in the community that I tried to serve and I’m just grateful that I have a mind that is fully present.

Jeremiah: You know, my grandfather passed away with a severe case of Alzheimer’s and he didn’t have all of his mind into his later days and I’ve seen that with a few other people that I do volunteer work with that they just don’t have their entire mind and it’s so sad when you see somebody who’s mind is slowly wasting away because of a sickness or an illness. So I just want to be very grateful today that I have a mind that serves me well, that me to serve others. All right, well, why don’t we get started. We know we have a mind and body tip to help us keep our healthy bodies and healthy minds or even get better. So here’s the tip of the day.

Jeremiah: Got a messy desk or worse…a messy organization? Well, remember when Mary Poppins looked around the messy children’s rooms and then use her fancy powers to make it organize itself? Using creative visualization is almost like having that kind of power! Professional organizers recommend closing your eyes and visualizing a clean space and letting the vision of the clean space direct your organizational methods, constantly asking yourself what you need to do to achieve this space you envisioned. And you know what? This technique for physical spaces works just as well for mental spaces and projects you need to organize and manage. For example, visualize the best client experience. What does it look like? What’s the workflow? Who steps in? What do they receive in their hands? What’s the look on their face? Take a minute to imagine your best reality before actually starting to work on it.

Jeremiah: Awesome. Okay, Devin, we’re going to dive in to the email hacks today. Let’s start with return on investment. Now, I know in the first podcast, episode one, we talked about at a very high level the return on investment of email. Do you want to kind of remind everybody just what the ROI of email compared to other sources?

Devin: ROI of email way outperforms there. You said something like 40 times other sources and the best thing about email is that it typically doesn’t cost you a dollar to do it and the hacks that we will teach you today, the things that we’ll talk about, you can start using and sending out even while you’re listening to this podcast and that’s why, because we’ll talk about how to get the emails and who to send them to, but the biggest thing isn’t that they don’t have the email…..It’s like, what do I say? And that’s something that will start focusing on too.

Jeremiah: Awesome. Yeah. A quick fun fact for everybody is that a recent study showed that for every dollar you invest in email marketing, you get a $38 return, so imagine just having a black box on your desk and you could slide in a dollar bill and outcomes on the other side of the machine – $38. That sounds fun, right? How many dollars would you slide under there? And I know recently in our experiments with cold email, we have seen a way higher return on investment, right? Because that’s the average, right? You can. That means you can go much, much higher than that. So how do we use email in the context of insurance and financial services? Well, there’s a couple of ways.

Jeremiah: Number one is in client acquisition, right? So this would be cold email strategies which involved emailing people who don’t know you kind of like a cold call, but in this case it’s a cold email. Now you have to be very careful here. You know – Danger Will Robinson Danger – because if you do this in certain industries like Medicare and Medsup, CMS will crush you. It is not permitted to do that if people haven’t raised their hand and they haven’t asked for your email, that is considered a massive no, no. And also of course canned spam laws, right? So in the consumer side of things, we’ve learned that cold email is a risky proposition, but when it comes to a business to business setting, there’s actually seven different things that you can put inside your email to make it compliant. Now, Advisorist members, you have access to all of this in the member’s area. We have a whole program there that shows you make sure you can check the box on the seven elements to have in every email. I’ll give you a couple of them right now.

Jeremiah: Number one is don’t have a deceitful subject line, so for example, you wouldn’t put something like “Your Policy Update -Please Reply” as kind of a sneaky subject line to get them to open and they don’t even have a policy with you. So we don’t want to do any of that kind of weird, sneaky black hat kind of stuff, but what we can do in business to business, so let’s say I’m a financial advisor and I’m targeting CEOs or affluent professionals, I can absolutely email them because it is your business to their business and you can make an introduction related to helping members of their company, you know, do retirement planning and so forth. Another thing you must have if you’re going to do cold email is you must have a mailing address and a phone number that is legit, so you got to have a real working address and phone number there.

Jeremiah: The third thing you need to have is you need to have a way for people to opt out and as we all know, right Devin, whenever we see the little unsubscribe link in an email, what do we automatically know about that email?

Devin: It’s from a mailing list.

Jeremiah: It’s a mailing list, right? So a little trick we want to give you guys, and this is actually a great time for today’s marketing tip. What do you think, Devin?

Devin: Sounds like a good idea.

Jeremiah: Alright, today’s marketing tip, let’s do it. Today’s marketing tip is instead of using the word “unsubscribe”, which is a dead giveaway that you are on a mailing list. Instead you’re able to say, “if you no longer want to hear from me, please reply and let me know”. That is a nice simple conversational approach that won’t give away that that person is on a cold email prospecting lists, and Devin, I know you mentioned that a little bit earlier about conversational, so that’s a way that we can keep your unsubscribe link, very conversational, but do not use it on a newsletter.

Jeremiah: Instead use it on a cold email campaign and that is today’s marketing tip. Alright Devin, so back to when we can use, as we talked about client acquisition, let’s talk about client cross selling and this little story comes from one of our members a couple of years ago actually who sent out the one line email we talked about in episode number one and he sent it to people who already had policies and when he sent this out to people who already had policies, he reactivated. He had a very small list of 61 people on his mailing list. I’d like to give him the award for probably the smallest mailing list and the history of insurance marketing. But he wrote me this letter that was so inspiring because he wrote back and he said, Jeremiah, just want to say thank you. I sent it out to 61 people.

Jeremiah: I got 37 replies. I booked 27 appointments and I sold dozens of policies. I can’t remember the number, but it was well over 20 different policies and he was doing things like limited death benefit, critical illness, health insurance, life insurance, IUL. So on and so forth, so that was money for him to use it on his current list. So those are really the two ways you’re going to use email. You can use it for cold prospecting, you could use it for cross selling.

Jeremiah: Actually, you know what I just realized there was a third way I forgot to mention and that is to harvest interest from people who previously came into your office or went through your sales funnel or went through your newsletter or so forth, but never became a client. And that’s where really the gold is. Whenever people start with Advisorist, we really recommend they use email as the first way to get appointments on their calendar and to close some policies and that’s where we talk about the “one line email strategy”.

Jeremiah: All right? The next thing you have to be aware on how you can improve and hack the results of your email is subject lines. Man, Devin, I think you and I could probably do five podcasts on subject lines. What do you think?

Devin: Yeah, it’s art and science and one of the big things is even if you think you come up with something clever or something that’s going to work, it’s really a matter of throwing it into a campaign and seeing it work and testing it. So yeah, I think there’s so many different ways to do it all the way from the simple approach like you talked about in the “one line email” to going to things that are attention grabbing but not deceitful like you mentioned because we do want to make sure that we’re compliant.

Jeremiah: Right. One quick hack you can use in subject lines is to try your subject line, but in lowercase. And in our marketing experiments, even in the most professional and stuffy environments, if you use lower case in the subject line, it actually makes the sender seem more human.

Jeremiah: So instead of saying, “I would like to talk to you about your policy”, and you put that all in sentence case where the first letter of every word is capitalized. You could simply put, got time to talk about the policy and put it all in lower case. Even the first word right, “got time”, got g, should be minuscule and then question mark at the end and what that does is it makes people feel it comes from an actual human being and we teach a whole formula in the members area about that, about writing effective emails, but give that a try. The next time you try subject line, put it in lowercase and you know what Devin? I just realized there’s another really cool hack people can use and that’s inserting emojis. I know probably right, like I know probably what most people are thinking, oh my goodness, I would never dare to use an Emoji.

Jeremiah: Right? Or you know like Mr Monopoly man with a monocle man….(grumbling) “Does that ever work?” In fact, there’s one Emoji in particular that in our experiments has had a 72 percent open rate. I’m not going to tell you which one it is because I want you to start with the subject line techniques first, but as you get fancy, try things like the rocket ship Emoji, the smiley face with heart eyes.  Actually that one is a very high converting Emoji by the way, and actually that’s how Devin and I met is we were interacting in some online forum and I put a post out there and I put that in the subject line and then what did you think about that Devin?

Devin: What came across to me was very warm and it gave me a sense of your personality and one thing that I think of with email is if you can give someone a feeling of what it’s going to be like to do business with you and they know it’s even a little bit more personalized or a little bit different , you have the edge up on the competition. And one thing I do with email specifically is if you were to pull up your email inbox right now.

Devin: If you’re on your computer or even on your phone is do what we call a “squint test” and whether you’re writing something or creating a webpage. When you squint and look at something, what is your. I first go to and emojis anything with emojis, any subject lines that don’t look like they’re overly engineered. Your eyes can immediately go to it and give you an advantage.

Jeremiah: I love the squint test. Thanks for bringing that up. You know, we used to teach the squint test when it came to websites like where does your mind actually go when you squint, like where does your eye gravitate to. I so love, love, love that you brought that up. That’s excellent.

Devin: It works for email too.

Jeremiah: Yeah, and by the way, here’s a great link. If you guys are looking for ideas on where to get emojis, go to That is the international database of emojis. You can simply copy and paste it into a subject line and off you go. Well, Devin, I think it’s time for our joke of the podcast. We didn’t do one of the first podcast, but I know that you and I are big students of neuroscience and whenever you bring humor into a situation it instantly connects and bonds people faster, it actually is the fastest path to neuroconnections to being a friend with someone, more than anything else is humor. So I got a joke, I want to lay on you. You Ready?

Devin: Ready.

Jeremiah: A mushroom walks into the bar and he jumps on the stool and he says to the bartender, I’d like to have a beer please. The bartender just looks at him and says “I’m sorry, we don’t serve your kind here”. And the mushroom, with a sad, downtrodden face, says “why not? I’m a fun-gi.”

Devin: Man. I love it.

Jeremiah: Yes. That one comes from my dad. So by the way, if you’ve got great dad jokes, we’d love to hear them as well. You can just hit us aup at [email protected] or leave a comment socially wherever you see us and just tag us at Advisorist. Just add #dadjokes and we’d love to see it as well.

Devin: I think you also gave an embedded email hack here because one of the things is scientific research shows that laughter is the quickest way for two people to connect and so adding a little bit of humor that’s tasteful throughout your content, throughout your emails, your social media and in our case is really a great way, but we’re not going to get too deep into the content.

Jeremiah: We’re not going to get deep into content?

Devin: I’m like, wait, we are in the content. Okay, that’s a good transition!

Jeremiah: Yeah, that is a good transition!

Devin: We’re talking about email body content – Right!

Jeremiah: Alright, so let’s talk about body content of your email. Right? So a quick hack that you can use for body content is to simply make it shorter. We’ve seen in our marketing experiments that when you shorten an email, the shorter the email, the higher the likelihood to connect. So instead of the long drawn out emails, try short simple emails that get to the point. And here’s another thing that I will recommend to you is to only ever ask ONE question! And probably if you’re going to ask one question, the worst question to ask -and I used to have a client that would do this all the time…they would just write like this massive dissertation and then at the end they would put “thoughts?”. I’m like, oh, are you kidding me? Like now I have to go on a desert island, meditate on your entire email and then come up with a thoughtful reply.

Jeremiah: But in the world that we live in today, people are just snacking on information. Even information that’s relevant from important people. They’re reading it on their mobile devices. They don’t have time to swipe through this massive email, right? So instead use bullet points – that is always a more effective technique and ask short pointed questions that people can easily answer. And if you do that, you’ll find that your emails will start, your email response rates will start to soar.

Devin: And something that’s really helped me, even with personal emails that I send out, is bolding certain parts of the email and keeping in mind the formatting so whenever you’re writing something, it needs to visually look tidy because people are busy and so when they get your email, it has to be a breath of fresh air. There’s not so many things they have to think about or consider before they reply and it’s really helped a lot with our cold email campaigns as well as just interpersonal communication.

Jeremiah: I love that. In fact, I sent an email this morning to one of our members who’s going through a problem and there was a date that they needed to reply back to this email because it was dependent on something else and I highlighted that date as well as the one question I wanted them to answer. So when they go back, all they need to do is know those two pieces of information and boom, we get an answer. So…

Devin: Absolutely. Awesome insight.

Jeremiah: Love it. Okay. The next email hack we want to give you as we close out all the email hacks in this episode is “closing emails”. Typically we think of emails only to open a relationship, but really email can be used effectively to close a stagnant prospect and you know the ones we’re talking about, right? It’s people who have come through your funnel or they’ve come through your seminar or office or your process and everything seemed great, but then after a while they’ve just stopped replying to you. They don’t reply to text messages, they don’t reply to the one line email, they don’t reply to your phone calls.

Jeremiah: Here’s a great email script that you can use. We call it the closing email. The subject line is closing your file, closing your file. Now, Devin, when you see that come from somebody you have been engaged in a process with, what immediately comes to mind?

Devin: Fear of missing out, what file, what’s happened, what am I? I need to figure this out. I need to make sure that I react.

Jeremiah: Exactly, and you know it’s interesting in almost all direct marketing, there’s always an element of FOMO – Fear of missing out – right, and we know because that works! So somebody is engaged in the process and if you don’t close the loop, you can come across as what I believe is one of the insurance industry’s worst nightmares, looking like an opportunity chasing or ambulance chasing insurance agent or financial advisor, right? That you’re going, it’s going to keep following up, following up, making you look desperate. You lose control, you’ll lose credibility and you’ll lose preeminence and authority and we don’t want that to happen to anybody who’s a member of our podcasting family and especially a member of the Advisorist membership program.

Jeremiah: So a simple email you can write, you can be very friendly about this. You’d say something like “Hi John, I’ve tried to reach you a couple times. It looks as though this is not a good time, so I’m going to go ahead and close your file. If however you need some help with your financial planning or your cyber liability or your worker’s comp at sometime in the future, feel free to reach out. For now, I wish you the best”. That’s it. Very, very simple, right? You can come across professional and you can be kind and you can be nice, but really you’ve got to close the loop.

Jeremiah: Sometimes what you’ll notice is that people will respect you for that and you will even get some people that say what? What? What? What? Wait, no, no. I was just so busy. Right, and by the way, for members of Advisorist, we actually have some really great examples of alternative closing emails that use humor and graphics that we’ve seen work really, really well that are available to you in the members area. Just go under “the seven scientific methods to increase your email marketing game” inside the core section of Advisorist and you’ll see that in there. Some of them have just been unbelievable. Alright Devin? Well, I think it’s time for today’s marketing tip. What do you think?

Devin: Let’s do it.

Jeremiah: Today’s marketing hack is about getting appointments with LinkedIn with specific psychological triggers. In one marketing experiment I ran out too long ago, a version of the template that I’m about to share with, you generated 80 leads in eight appointments in 20 days from a small group of LinkedIn contacts. The reason why this email worked so well is that it had a few key elements. First, the subject line was, thanks for connecting. That relates back to the actual act of connecting on LinkedIn . Inside we started off with a sentence like “I work with presidents and CEOs in Chicago with 50 plus employees to help identify areas of overspending and risk when it comes to ______” and then insert area of expertise, right? Insurance, Cyber Liability, 401K plans. The intro of that email was so key because instantly it identified who we work with, presidents and CEOs and because we were sending it to presidents and CEOs, it instantly fired off this psycho trigger.

Jeremiah: Then “over 50 employees” really helped to narrow down the type of people we wanted to talk to. We weren’t interested in CEOs of 10 person companies or in 5,000 person companies, but really 50 and over. And then our area of specialty, so identifying areas of overspending and risk. When you have those three elements in the first sentence of any of your email introduction strategies, you will notice a marked increase in the amount of people who reply. So remember, make sure you have the three identifiers whenever you send a brand new email to somebody that doesn’t know you and watch your conversion rates soar. Thanks for checking out today’s Marketing Hack. We will see you on the next one.

Jeremiah: Awesome. So let’s do a quick recap. Devin, do you want to have the honor of doing the recap today?

Devin: Absolutely. So we went through email hacks and talked about those that you can use to sell more insurance policies. We talked about the ROI associated with that, how effective it is to essentially have a black box that you can put dollars into with digital marketing and see up to $38 or more for every dollar you put in. We talked about how to use email in regards to compliance, who to send them to you and what sorts of scenarios, how to use cold email for business to business marketing, and we also talked about when to do that and as well talking through some subject lines, giving you some tips on how to keep things short, personal and easy to respond to, and then inside of the body content we talked about making sure to keep the body content to make them not think as much so that they can respond and have a chance to actually reply to that. And then we talked about what to do with that list of folks that have come and visited you that may not have responded or haven’t bought from you and tons of hacks, tons of things that you can also learn inside of the Advisorist membership. But we hope you found this really, really useful.

Jeremiah: Wow. I have to hand it to you buddy. You really did a nice recap. Straight from memory. Good for you. Alright, so what is coming up from next episode? Episode number three, we’re going to dive into LinkedIn. So you remember in the hierarchy that we trained you on in episode number one? We talked that once you master email, the next step is to move on to LinkedIn. So in episode number three, which you can download at, you’re going to find how to get four insurance appointments a day using Linkedin. This is going to be a really eye opening training I think, and podcast for so many advisors as we reveal the step by step strategies that members are using right now and actually have been using for years. It’s almost been like a really closely guarded secret. We’re going to share it all with you in the next episode of Advisorist.

Jeremiah: If you’re someone who loves to read and you would prefer to get the transcript of this episode, you can go to Look for episode number two and you’ll be able to get the entire transcript of this episode. If you’re a member, as you know, we have a full execution sheet all around the topic of not only cold email, but also warm email, which you can access to the member’s area. And that’s it for us. My name is Jeremiah DesMarais

Devin: and I’m Devin Ambron

Jeremiah: and we’re so grateful that you listened to this podcast today. Thanks so much. If you love what you heard, do us a quick favor. Will you head on over to Itunes, give us a five star review and a little love in the comments? It really makes a difference for us. Thanks so much. Make it a great rest of the day!

Jeremiah: Hey, Advisorist Nation – are you ready to take your insurance or financial services practice to the next level and are you prepared to fill your calendar with high quality appointments and bring so many leads that you get to pick and choose with whom you’re going to work with? If yes, then be sure to check out Advisorist – a premium members only community of insurance and financial advisors who are striving to excellence inside this community. You’ll learn the strategies and tactics that most successful service providers are using and you’ll be able to implement them and see results faster than you ever thought was possible. Get all of the details here at We’ll see you inside.


For more strategies and tactics, join our exclusive community of insurance and financial advisors at

Jeremiah Desmarais

Jeremiah Desmarais

Jeremiah is the founder and CEO of Advisorist® and is a 23-time award winning financial marketer, a TED speaker and philanthropist. He’s been featured on Forbes, CNN, and Worth. His work has generated over $2 million insurance leads and helped advisors in over 51 countries generate over $300 million in sales commissions. He is the author of the best selling book, SHIFT.

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