Boost Your Email Deliverability in 2023: An Interview with Jesse Oulette

Created On
July 21, 2023
Jesse Oulette interview on email deliverability

In the ever-changing marketing landscape, one thing stood the test of time – cold emails. So much so that 80% of consumers prefer emails as their primary business communication channel. 

Gone are the days when generic templates and pitches would suffice to generate responses. Today, cold emailers/email marketing teams must blend personalization, creativity, and strategic thinking, and relevant offers to pique the interest of their target audiences.

In this blog post, Vaibhav Namburi (Founder and Director of interviewed none other than the founder and CEO of LeadMagic, Jesse Oullette. Jesse shares his secrets to staying out of spam folders and dramatically improving your email deliverability. 🚀

Let’s dive in. 

Q1: Why is email deliverability getting harder in 2023?

Jesse: “It’s pretty simple. Users want a better experience. And if you really think about it, it boils down to predictive models and training is getting a lot better. So, people who make these emails really have a deep understanding of what their users want. People want, if you kind of had to talk about a perfect world, like a superhuman, which is an email app that kind of gamifies it to get to that inbox zero. You know, when they start seeing that there's a lot of emails coming from your domain, they start to get very angry so that it's really just that people want a better user experience.”

“They've got tons of competition around, you know, Slack and Teams. Everyone said, Slack is the end of email, but we all know email's a protocol and it'll always be around. The spam filters are getting much better and sophisticated. And what you're going to have to focus on is landing outside of the folder called spam that Microsoft and Google put inside your users inboxes.” 

And we absolutely agree with Jesse. Here are some of the things you need to keep in mind to improve your email deliverability: 

  • Warm-up your IP
  • Enable SPF, DKIM, DMARC
  • Do not buy email lists from third-party providers
  • Maintain email list hygiene
  • Get in the contact list of your recipients
  • Use only double opt-in forms

Read here to learn more on how you can boost your email deliverability. 

Q2: Warming up is a big part in how people actually go ahead and ensure sender reputation. You've spoken about how GMass, amongst other players, have had their entire warmup completely disabled. So I'd love to hear what you think about the GMass block and what this means for the entire outbound community.

Jesse: “What I see first is deliverability is the end goal for everybody because it now matters way more than copy does if you're going to get the reply. So that's why deliverability is the most important. And let's just talk about warm ups. So first of all, what is it? So what you're doing with email warm up is you're joining a network of other people who send cold emails that are teaming up essentially to provide a better deliverability. It'll show higher engagement metrics for your domain and for your IP. And what that does is it looks and it can appear that you're going to be a better candidate for that person's primary inbox. So, if you're going to win against a filter that checks to see if it's high quality emails, what you're going to see if you're going to see people that have higher engagement. What's engagement? It's going to be replies. So it's a group of people that have all joined together that are kind of fighting it on a daily basis. And what those people are doing is they're sending emails around and they're doing that. And then really what's changed recently is Google has now made the first shot against cold emailers. And what that means is they went through the security protocols of Google and they've actually made it an official partner of Google's API for their Gmail product that went through the security audit.

They've told them now that they are no longer in, they're going to need to shut down any warm up services and stop marketing them that they're offering through their API. So that is a big change, right? That is a massive change because number one, it's a little bit odd because if you think about what they did, they just charged, you know, a bunch of companies, $30-40K, and then said that they can't do what you're doing anymore. And now that you've (the businesses) signed our agreements (Google’s agreements). So that's what's really happened. And GMass was probably the one that they looked at the most. 

So now you're going to need to find alternative ways to do that. It's a gray hat tactic, probably, if you really have to break it down. But it's very similar to getting good engagement on a LinkedIn post or something like that.”

On that note, read how to do email warmups despite Google ban here.  

Q3: Do you want to get into it? Let's jump into what are some other ways people can drive that. 

Jesse: “So Microsoft has a folder called junk. It's an AI model and we all know that AI has problems with transparency and how the model was built, right? And then if you also look at Google, they have a folder called Spam now that everybody's like, why are you seeing a folder called that? It is spam. Well, to some people it is, right? So what those folders are designed to do is they're designated to prevent a certain behavior which typically borders on a couple of areas. One of them's phishing. But spam is more towards people that are doing direct marketing, more like asking you for something or a sales kind of motion with maybe a group of prospectors or sales development or sort of like a full cycle.

But what, what's happened is those folders now, it is much easier to identify this type of traffic and they're getting more accurate in identifying people with a cold email patterns, which we can talk about a little bit here of like what pattern that might look like compared to the other traffic that's coming from that network.

So if you have to break down all of the different emails, you have transactional emails, which is going to be you messaging people with your product updates and are not really product updates, but more about your product and maybe ‘forgot password’, you'll use a SendGrid or something like that.

The other one you're going to have is corporate, which is your finance team emails, vendors, and all the different little ones. I guess recruiting can go a little bit towards the sales side, but let's just say it's for all intents and purposes, it might be a talent acquisition and they're sending offer letters or they're doing things like investors or emailing them.

And then the third one is the marketing in the bulk email, and those are only opt-ins. So if you think about this fourth pattern, that's the one we really want to start thinking about, right? And what that fourth pattern is it's people who send automatically generated emails to groups of people in a volume that's like 20 to 50, or maybe more per day. 

If you consider the other three options that I talked about, you have transactional email, marketing emails (newsletters and the bulk opt in), corporate emails internally, if you have all three of those and then you compare the number of complaints on one to the number of complaints on, you just found all of the sales emails. 

They're not going to come in as phishing, but as a complaint. And the number is going to be on a scale of 10X more than those other ones. Unless your marketing team is doing something really bad, which is putting people that they haven't had opted in, they would not be complaining because people don't really complain unless they haven't opted for it.

So you really just have to think about the other patterns. And what they've done is they've said that anybody who has this pattern where cold emails cause friction, and that complaint gets reported as spam in the UI, gets better and better to ask the user what they think of this email.

That's why the emails start to trend towards a spam folder now. This is one thing the gurus won't like, but you don't really know where it landed. And that's where everybody's confused right now. So what you need to do is you need to be sure through testing and warm up that you are landing inside a primary inbox. And the best way to know that is by sending in testing in groups of people to make sure that you are (landing in the primary inbox). Because if you're not, you could be in the folder called spam.

Maybe you're in the promotions, but you're typically in spam if you're sending sales emails. And what that means is the impact has been to either your IP, which is not possible because you can't really block Google or Microsoft IPs, but the domain name gets toasted and that's really where the spam filters have started to focus.”

Q4: What are five things you would do to best optimize your campaign to be successful?

Jesse: In terms of my campaign, the first thing I would do is I would find that I have the right audience. Because if you have the wrong audience, the chances of you getting reported as spam is pretty high. So audience, the next one would be the message. What I really think of when I think of messages is what would you help a company with. I'm stopping short of the next one which is the offer. This is a message like, ‘Hey, we're relevant because of this reason and here's a reward other companies have gotten by working with us. And here's a request that's in line with a cold email that they're getting thousands of emails in their inbox every single day and they want them gone, right? So if you kind of think about those three components, which would be the relevance, the reward, and the request, that's how I break down an email. Nobody wants you just to send calendar links right away. They want you to kind of like they want it. They want to feel like you're asking them a question that doesn't have to be solved with a meeting. 

And it's really about how you optimize that process. And kind of what I see a lot of people do is they say volume doesn't work, but it’s just how you handle it. So there's the automation part that'll be number four. And then number five, I would say it's sort of the process that you go through and you do all that and how you write all that copy and bring it all together.’

Q5: I want to speak on separate but individualistic topics nowadays, a lot of people are looking into spintax or A/B testing. Do you do much of that on your side? And if you do, how do you manage it? 

Jesse: “So we always like to keep at least 30-50% of the copy different on every email. We want to try to put as much spin on it. Because if two emails look the same, that's a really easy and predictive model. We do use spintax to make sure that we have different copies. I think I might disagree with a lot of personalization methods that go on. Like I'm not a huge fan of fake compliments and it lowers the value of what you're trying to do. And if you're really trying to be deliberate and you know your service is valuable and you can help them, I always caution people on things like the number of personalization.

But I think what you need to do is make sure this thing (cold emails) does not sound fake.”

Q6: So for those who are actually trying to get into personalization, what are ways they can do that at scale? Putting AI writers aside, what are other ways people can go ahead?

Jesse: “You just have to be relevant. You have to call something out. One area that I've seen work is you could talk about how long they've been at the company. And that's really interesting because you can easily pull that data. That's a little bit cleaner or maybe something they've posted about. But it's not just like, ‘Hey, I saw your cold email experts post. Are you interested in buying my cold emails for work?’ That doesn't work either.”

Q7: You briefly jumped into saying looking into their website traffic. How would I go out and get that? 

Jesse: “So there's a couple of things that are out there. There's obviously first party data which means you own the data. You might have a vendor like LeadMagic or somebody that's identifying who those people are. The good thing about that data is you own it. I stay away from third party data because I just don't know how it's scored. If I can't see the model, I don't want to actually invest any time in it.”

Q8: Walk me through some of the curtains and share a bit of your tips on configuration, how do you set up your configuration for your campaigns, for your clients? How many mailboxes per domain, how many emails per day, warmups, etc.? 

Jesse: “If we're going to run a campaign, we try to be between 250 to 1000 people on the campaign. We're usually running a 3 to 4 touch email. We want to be relevant, we want to make sure that we're going to come in with a little bit of a shorter email asking if the email is relevant.

What you're going to want to do is look for 5% of those thousand contacts that responded. So there's going to be a mixed kind of answer. You're going to have people who are out of office. You're going to have people who are interested, you're going to have people not interested. The best thing to do is just ignore the stats on it and just look at every email and read the context. There's a lot of nonverbal cues inside an email also that I think people take.

You need to keep the reply rate high. I mean all the other metrics are literally kind of wasted.” 


This interview sheds light on the increasing challenges surrounding email deliverability in 2023. Jesse highlights the evolving user expectations for a superior email experience, which again emphasizes a deep understanding of user preferences, UX, and engagement. With spam filters in action, email marketers face the risk of landing in the spam folder/junk instead of landing in the primary inbox. The interview also discusses the recent changes in warm-up services, particularly with Google cracking down on such practices, especially on GMass (and how you can still do it despite the Google ban). It emphasizes the importance of audience targeting, crafting relevant and engaging messages, and leveraging automation effectively. Furthermore, Jesse advises against excessive personalization and emphasizes the need for authenticity. By focusing on relevance, engagement, and continuous testing, email campaigns can enhance deliverability and achieve desired results in this challenging landscape.

Smartlead, get your email delivered and bring sales 

Make me an outreach pro

Ensure your emails always reach your lead's inbox by using unlimited sender accounts leveraging AI personalization, and implementing email warm-ups.This way, you can concentrate on sealing the deal without worrying about email delivery issues.

Here's how to do it

1Sign-up for

2Upload your lead list.

3Start sending emails

P.s. You can also use our pre-built templates available in the app.

What’s a Rich Text element?

The rich text element allows you to create and format headings, paragraphs, blockquotes, images, and video all in one place instead of having to add and format them individually. Just double-click and easily create content.

  • dfbvrsg
  • svsv

Static and dynamic content editing

A rich text element can be used with static or dynamic content. For static content, just drop it into any page and begin editing. For dynamic content, add a rich text field to any collection and then connect a rich text element to that field in the settings panel. Voila!

How to customize formatting for each rich text

Headings, paragraphs, blockquotes, figures, images, and figure captions can all be styled after a class is added to the rich text element using the "When inside of" nested selector system.

Author’s Details

Sattwik Das

Sattwik is a Digital Marketing professional at Smartlead. He is a dedicated content writer who focuses on juggling words to bring out meaningful content. He is experienced in well-researched and SEO-optimized content creation, content editing, and copywriting for various businesses throughout the globe. His expertise in SEO, SMM, and SMO with a touch of creativity helps businesses grow and maximize their credibility and sales.


Edited by:

Charu Mitra Dubey


Frequently asked questions

General Questions

What are active leads?

Active leads are the contacts you upload in Smartlead, similar to contacts in HubSpot; if you upload 1000 leads to a campaign, they are considered 1000 active leads. If you upload similar leads to a new campaign, they are not considered a “new active lead” as they already exist in our system.

Do you provide mailboxes, or do I need to connect my own?

We don’t offer mailboxes yet. You need to get your own dedicated list of mailboxes using popular providers like Gmail, Outlook, Zoho, and others that exist in the market. Once you get them, follow our detailed guides to connect them quickly.

Do you offer guides and articles on succeeding with cold emails?

Absolutely, one of our most popular guides can be found right here. It's been used by a large percentage of users to go from zero to cold emailing experts. Covering all topics from email infrastructure to copywriting and lead sourcing.

Is another tool needed for warmups?

No, Smartlead has over 200,000 highly reputed mailboxes connected. The advantage you get along with naturalized AI conversations is access to aged domains you will never find in any warmup tool.

What is the API commonly used for?

It is used popularly by agencies to automate their entire lead generation process as well as to connect Smartlead to external tools to push and pull data from. You can also connect to 1000s of apps using Zapier.

What type of businesses sees the most success with Smartlead?

Anyone that can close deals from demos will succeed with Smartlead. It works for Sales companies, Marketing agencies, SaaS businesses, Recruitment, and offline companies (like construction).

Do you provide me with lead sources?

We do not provide you with leads. You will need to use other data providers. These leads can be automatically added to Smartlead using our API or bulk uploaded via our CSV upload system.

Do you integrate with any CRMs?

We're building native integrations with Hubspot, Salesforce, Close, Pipedrive, and many more. The best part, due to our open API and Webhook infrastructure, you can connect to any CRM in the world without an issue.

How many team members can I add?

You can add an unlimited number of team members, as well as assign them roles and authority access.

Do you have custom plans beyond the Pro plan?

Yes, it's common for many people to move to Custom plans after a few weeks. You can view all the options for up to 10M leads on the subscription page once you sign up for free.

Powerful Automated Email Marketing that Drives Sales.

  • All Features Included
  • No Credit Card Required
  • Free Warmup Included