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Optimizing Email Deliverability

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During this Slack AMA, Camela Thompson, VP of Marketing at Calibermind, interviewed Jesse Oullette, resident B2B Email Delivery Expert and founder of LeadMagic.

For one whole hour, we asked him all about the real tactics that still work in improving email deliverability. With a wealth of experience in the field, and resources to support you, Jesse shared his insights and answered your questions on the latest best practices and tool recommendations.

In this interactive session, we asked Jesse a variety of questions around email deliverability, from navigating ever-changing advice to testing your domain health, including:

  1. What are the most important factors affecting email deliverability, and how can we measure their impact?
  2. Are there any new tools and techniques for improving deliverability that you would recommend?
  3. How can we balance the need for personalization and automation with the requirements for successful deliverability?
  4. What advice do you have for organizations that are just starting out with email marketing and want to ensure deliverability from the get-go?

Camela Thompson

HELLO @channel! I’m thrilled to introduce Jesse Ouellette  - email deliverability guru extraordinaire - and kick off this AMA session. He is the founder of LeadMagic and a trusted advisor I have consulted many times when it comes to the unexpected WOES of sales engagement automation.

Trust me. Because he is well versed in carrying a bag (AKA being IN sales) - the sales team listens. And that is a gift.

Jesse Ouellette

THANK YOU for being so generous with your time!

First question: Why is landing in the primary inbox (not SPAM) so much harder than it used to be?

Jesse Ouellette

Yes, first answer...  it's way harder now because cold emails have a certain behavior pattern.  Google and Microsoft want to compete and make their platforms better for the user.  The average user doesn't want cold emails.

Camela Thompson

So what are the factors that lead to people being "flagged" for SPAM?

I think marketers know about the old SPAM trigger words, attachments, and formatting - but are there other signals (like bounce rate)?

Jesse Ouellette

There are a lot of factors that we know about and some we don't know about... Emails have been around since the early 70s, late 60s.  They've evolved the global standard.  So there are things you need to do, like setup your DNS Records properly...  the net though is that machine learning and AI have made it much more behaviorial... so they're looking for patterns.  These are undocumented.

For marketers, sending to people who have opt'd in... you should never send to people who haven't  That's what cold e-mail is for.... you can legally do that.

Knowing the types of e-mail systems at your company is important...

1. you have corporate e-mail... your IT should setup all the settings, we see this broken a lot

2. you have your MAS - this is your marketing automation people who opt'd in never use it for cold mass blast, it's for your marketing communication and you will be banned from your ESP

3 you have your transactional e-mail which is your engineering team's forgot password etc…

4- drum roll this is the worst one, your Sales Development Team's activity... it's not wanted by users and it usually racks up complaints very important to make sure you'ree watching this

Now, the proper way to do this is to put this off on another group of domains and this is where the problem exists today...

What I see too much are 1-2-3 fine... but 4 is blasting their primary domain and breaking it

Camela Thompson

Most MAS enforce opt-in behavior - there are some ways around it, but most marketers understand their job is at risk if they violate legislative guidelines..... And I'm hearing that at minimum, DMARC and DKIM should be configured.

The other thing I'm hearing is that sales should not be cold prospecting on your main email domain. Is this a fair summary?

Jesse Ouellette

The key to it all is the domain name reputation... many think it's only the IP... it's not.

Absolutely, this is where so many businesses are taking a risk... because it's not worth it... Now, we are generating a ton of business with our Cold E-mail Programs but we run them "safely" and what i mean by that is we keep a very keen eye on our copy, we watch our reports, we watch every setting we use multiple domains and this is where companies start to go down a path that their IT Team will not usually like.,.. and the days of loading up Outreach.Salesloft and sending 250 per SDR are over... you won't get even 5% of those emails through

It's a scoring model and once you hit a threshold you go into the folder we all call "SPAM"

Which is poorly defined… and will never be defined

Camela Thompson

It seems like a pretty easy fix to put people on a new domain. Are there steps you recommend when doing this beyond DMARC/DKIM? Perhaps warming up email addresses?

Jesse Ouellette

Yes, and let me address the elephant in the room around warm up…

Camela Thompson

I saw that!

Jesse Ouellette

So - warmup IS a Grayhat Tactic... it is the act of sending around a lot of emails to people and responding


This essentially sends positive signals to the e-mail servers so you get better deliverablity

Camela Thompson

Do hacks like subscribing to well known domain newsletters like CNN / ESPN - is that worth the effort?

Jesse Ouellette

Now, it's done because even sendgrid or your ESPs do this too on fresh IPs... it's just part of it

That would not be worth the effort but the big news from Google is that ANY product that has an API warmup that was approved

Now has to remove their API connection to Google's Interface, aka their API... this means if you bought software and they told you that it would have warmup... wait for it,... it might be pulled from the product

The only way to do warmup going forward would likely not get approved by a company's IT Team.. this will be where you might look to work with agencies because you can offset the risk and not have to deal with the impact... remember E-mail is STILL the #1 attack vector

for all hackers

But google essentially got their partners to buy a security audit, then said they had to stop doing e-mail warmup... the mid-tier vendors that were doing this aree likyl going to stop talking about e-mail warm up and do the meme with homer simpson where he slides into the bushes

Google, sort of trapped them in a sense, but for good reason... they don't want people using their programmatic layer for e-mail warmup... it impacts it...

Camela Thompson


The only way to do warmup going forward would likely not get approved by a company's IT Team.. this will be where you might look to work with agencies because you can offset the risk and not have to deal with the impact... remember E-mail is STILL the #1 attack vector for all hackers But google essentially got their partners to buy a security audit, then said they had to stop doing e-mail warmup... the mid-tier vendors that were doing this aree likyl going to stop talking about e-mail warm up and do the meme with homer simpson where he slides into the bushes

Google, sort of trapped them in a sense, but for good reason... they don't want people using their programmatic layer for e-mail warmup... it impacts it…

The other elephant in the room - I have worked with a LOT of salespeople who have the volume/at bats mentality over personalization and quality. And part of me empathizes. They know marketing can't violate opt-in rules and they want to help educate the market. Are there things we can do to help them be more effective while using platforms like Outreach? Limiting total sends per day? Recommending tested sequences that are constantly optimized? Switching everyone to a LinkedIn approach?

Jesse Ouellette

so the only way to do e-mail warmup will be with "less secure" methods

The key to limiting on Outreach is to put it on another domain and let them have fun... because that's what will end up happening... the settings you want to look at are...

Send Spacing

Number of Emails Per Day Per Rep...

I know on ALL my e-mail campaigns I run no more than 50 emails per day per domain... (cold) I just know it';s trouble if you do... so when I think of orgs sending 250 - 300 it's really bad

per rep, even Salesloft has in their Best Practices to send 250 per day per rep.. if you do that now you will be blacklisted in a few weeks for sure... and very few responses…

Camela Thompson

I have seen it be a problem with even 100 per day…

Jesse Ouellette

Also - one other factor... who you e-mail is big... if you e-mail larger orgs, they have more protective e-mail servers

We recommend no more than 50 emails per day per domain wide... that are cold... because let's face it even the best cold emails are 5% response / 20% positive response... and that right there is too low to get through,.. you have to use different methods to do this at a scale... and this is where it's getting very hard now

Camela Thompson

So we're limiting output.... So let's ask the obvious question. Does cold email still work when done at low volume?

Jesse Ouellette

if you are you have more volume so you can send more and a higher reputation but eventually even that gets blacklisted

Yes, cold e-mail is actually my most effective channel right now... we've had to build plans for it...

It took a ton of planning and the way we do it is

  1. multiple domains
  2. e-mail warmup - non google way (smtp)
  3. very tight messaging to a very narrow audience
  4. validated emails
  5. light CTA
  6. constant monitoring…
  7. inbox rotation (this one helps the most it's when you use 10 domains on one campaign to offset the impact of anything that goes wrong)

Camela Thompson

And the marketer in me HAS to ask.... what kind of content works? How much personalization is "enough"?

Jesse Ouellette

As a start-up, with no VC backed funding and profitability we look at cold e-mail as an incredible way to drive business... our messages are relevant and people thank us for the emails most of the time... they convert and we are very relevant

I actually don't think any personalization works... what we find works is when you call something out like example - Hi Camela, you spent X on google ads.  Would you think bout running a cold e-mail program with us that doesn't put your company at risk?

Camela Thompson

I mean... you still have to really dial in your ICP, yes?

Jesse Ouellette

The X factor is possibly a lookup of your Google Ads over the last 90 days.,.. and that's unique to the customer, so we don't send 2 emails that everry look the same (also helps with deliverability) personalization though in a lot of ways is just annoying for someone who is technical you see it and you say, ya right buddy you're a bot


Camela Thompson

(ideal customer profile for those of you new to B2B alphabet soup)

Jesse Ouellette

But If I call out technographics + paid ad spend ... i know you could be a fit... let's say for me…

If I see someone who just installed LeadFeeder, we offer them an alternative solution... and they usually are evaluting then.. we have this real-time and it makes the emails almost never bomb.

Camela Thompson

So personalized - not necessary beyond being a match. It's more about relevance to what they're researching or other indicators. Yes?

Jesse Ouellette 

So I usually view personalization like, Hi Camela... I love what you're doing at CaliberMind... and relevance is my product does X it's relevant because of this information I researched... the relevance is where people in our experience have more success, but it's harder to actually achieve and find

Just for example... I'd think calibermind I'd want to target people who just started to install pixels on their site and increase the number of paid display ads so I'd have a big list of the right people in operations and I'd put what their moves were in {variables}} each user would get a different message with the relevant information it shows you have done your homework... but for us it doesn't take long.

The buyer is disarmed when you have your relevance and the personalization (hey we went to the same school) can just tend to be annoyingh

Camela Thompson

So I know tech companies (B2B SaaS) are more likely to buy our solution. But what's even better are people researching similar products on G2 because they likely have a greenlit product. So if I can find that subset, it's a heck of a lot more productive than just blasting B2B SaaS and ticking off my general ICP. yes?

Greenlit project

not product lol

Jesse Ouellette

Yes, and then you take that information and couple it with a few other things like...

Management changes... Hiring going on

The 2 general areas I look...

People getting hired/fired

Technology being purchased/dropped

I'd say build a program which thrives on being more relevant and you'll worry a lot less.. when you have nothing to offer people usually react that's the problem at the root of this discussion...

Camela Thompson

So.... how do I get this across to a sales manager with an "at bats" or spray &  approach? Is it okay if they still want to operate like they always have?

By the 3rd e-mail you send your buyer is super fatigued

We're seeing a lot of orgs starting to really think about this differently... I'll tell cliients... this isn't your least experienced Sales person... it's your founder, it's your CTO, it's the person who is driving the product decisions that needs to see how these messages go...

For any Sales Led Org this is an incredible chance to build efficiency... even for PLG orgs there are opportunities outside cold e-mail with cold e-mail.... Guest Blogs, PR, SEO all kinds of other use cases... and e-mail remember is a protocol it's not a social media site that changed algorithms on a weekend

Ah... so this is pretty counter-intuitive for people who've traditionally looked at the inside sales rep as someone straight out of school. What are signs people need to adjust to meet market demands?

Jesse Ouellette

it will work forever if you respect the people you send your messaging to and you craft careful campaigns with the right technologists in your company involved

Yes, and my perspective is that those orgs will continue to burn and burn until they can't anymore and they will have a tighter leash... but now efficiency wins…

I would avoid that 10 person SDR team to start your journey into SaaS Sales as a founder.. it's not what you need to drive pipeline... you need a specialized group that can get your direct reesponse feedback

Camela Thompson

REVOPS - This is your CTA! Proactively look at email rates, reply rates, and how productive your inside prospecting team is. Chances are really high you need to re-evaluate the approach! What worked in the past doesn't work well now.

Jesse Ouellette

Our biggest metrics are:

-Reply Rate (isolate the cold emails) Number of Contacts / Number of Replies on a Sequence...

-Interested Rate (number of replies to interested)

If you're below 5% you are having a deliverability problem is my guess

Camela Thompson

Or message / relevance in my experience.

Jesse Ouellette

We see 7-12% almost across the board and the other thing is we send volume too... this is why I have a hard time seeing the 7-12% on linkedin on 50 emails that were handwritten.. that certainly won't scale and you can't hire for that

Camela Thompson

I have a lot of new sales folks come in and their first instinct is to invent their own messaging. Which is problematic (to say the least) if you have a really complex product being sold to a sales-averse audience.

Jesse Ouellette  

I think of it more like Paid Ads would be thought of

Very problematic... own messaging is usually awful... cold e-mail requires a very

specialized approach <120 words

Camela Thompson

The thing that keeps coming to mind for me is that marketing learned a lot of this stuff the hard way years ago. And the sales v. marketing dynamic makes it so those learnings aren't being passed along to the people responsible for cold outbound today. Any silver linings or strategies to improve that dynamic?

Jesse Ouellette 

we like to approach it like this:


Reward (in form of story)

Request (light CTA)

3-4 sentences that's it, with shorter sentences written at a 5th grade level

Camela Thompson

there are so many great writing tools out there to help evaluate this ^^^

Jesse Ouellette

Yes, this is true on the Marketing/Sales front... Marketing obviously started to outsource to ESPs and that's the right move... cold e-mail will start to go more agency because you will need warmup etc..

There are and the only thing I caution on those tools is that... they tell you chances of % reply…

Camela Thompson

Hemingway editor is a great one and grammarly can come up with grade levels etc

Oh I didn't mean ChatGPT lol

although it def has its place

Camela Thompson

Jesse Ouellette THANK YOU so much for all the info! A lot of this contradicts the historical prospecting approach I've seen perpetuated in today's market. Where can people sign up for your newsletter, check out your company, and network with you online (other than here of course)?

Jesse Ouellette 

Just like it is paying your SDR Team all commission

commission they will do some unnatural things to get those meetings if you push them hard enough...

equal force to the reaction...

thank you it was wonderful being here sorry about the delay in teh beginning…

Camela Thompson

No problem. Internet hi-jinx happen!

Jesse Ouellette

At least I'm in Fort Lauderdale for a customer of mine's kickoff... and it's warmer than Boston... great chatting with you today and please reach out if you have any questions!

Camela Thompson

I encourage people to check out and check out Jesse on LInkedIn here:

Jesse Ouellette 

See you back in the Primary Inbo

Camela Thompson

He has really helped me out with some sticky situations - thank you again for your time!!

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