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advice Outbound mail going in Spam

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I need some guidance on outbound sales.


  1. I tried outbound, but most of my emails seem to land in spam, and I rarely get any replies. I also started using a domain-based email address instead of Gmail, but the results haven't improved much.
  2. I'm struggling to reach the right decision-makers. Most of the contact details I find belong to customer support or reception, not the owner or marketing team. On LinkedIn, I'm also unable to message top executives.
  3. When doing outbound, should I include the domain's .com link in the first email, or should I start with a simple conversation and introduce the domain later? I currently use AI tools like ChatGPT to help write my sales pitches.
 
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The views expressed on this page by users and staff are their own, not those of NamePros.
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fka is right, and I think it is worth putting the mechanism under it, because the "just fix your DNS" advice only goes so far.

Inbox placement is mostly decided by engagement, not by your auth records. The providers watch whether people open, reply, delete without reading, or mark as spam. SPF, DKIM and DMARC, which Sjpals covered, get you eligible to be judged. Relevance is what you are then judged on. So if you send 200 emails to companies with no use for the name, you fail that test, your sender reputation drops, and the next batch lands in spam even though your records are perfect. That is the loop most people never see.

Things I have not seen mentioned here is:

Sending history matters more than registration age. daholder is right that a two month old domain looks bad, but a three year old domain that has never sent an email is just as cold. What gets scored is your history as a sender, and a domain with none has to build one.

So warm up before you send. Start at a handful a day from a new sending address and build over a few weeks. Going from zero to forty in a day is the most common way people burn a sender before they have tested anything about their pitch.

I run 24 mailboxes across 8 sending domains for this and I never switch the warmup off, even on established ones.

And do not send from the domain you are selling. It has no sending history, it is the asset and if it gets flagged you have damaged the thing you are trying to sell. Same applies to your main business domain.

One very practical thing before your next batch is to send one email from your sending address to a Gmail address you control and one to an Outlook address you control, and look at where each actually lands. Most people assume spam. Often it is delivering fine and the real problem is the pitch or the recipient, which is worth knowing before you spend a week on DNS records.

On your two questions. I would put the domain in as plain text rather than a link. Fewer links reads better to both filters and humans, and the email should be short enough that the name is unmissable anyway. On the ChatGPT pitches, the problem is not AI, it is length and genericness. If the email could go to a hundred companies unchanged, it will read that way to the one who receives it. One specific sentence about their business beats three paragraphs about your domain.

The HomeDraws thing is the real lesson here, by the way. Pitching the right vertical while the lander described a different one is exactly the kind of failure that looks like deliverability and is not.
Nice write up, thanks!

Can you talk more about building up sender reputation in practical terms?

Are any of the email warm-up services legit and actually work?
 
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There's my personal opinion, my professional opinion and then what actually works.

There are endless executives at endless numbers of deep pocketed companies enamoured with new technology that just the thought of being innovative gets them all excited to spend their money. If you're a digital media service provider working with companies then executives will love to hear all about your magical mystical innovative new ways to do things, regardless of whether or not they work. For that reason, I think it's totally understandable why a consultant type would be heavily invested in pitching new technology.

My personal opinion is I hate all this LLM slop with every fiber of my being. I grew up on the internet, I became the person I am on the internet, I spent almost 2 decades absorbing every last drop of humanity I could through the internet. Real human experiences, real human words, from incoherent ramblings to beautiful prose. And even just the structure of the text mattered, I learned that French people put spaces before exclamation marks, I learned that American versions of words have z instead of s, I learned that so much is said by the words not written. LLMs have stolen the humanity from the internet.

I also viscerally hate the way LLMs speak. The LLMisms that seep through the screen. "You're absolutely right" "load-bearing" "reality check". So, so nauseating. The computer doesn't have a personality, a soul, any insight, it is just a bunch of math generating words. Why is it pretending to be human? And they stole em-dashes!

Now imagine you're a busy business person. You receive an email, the 100th of the day. And you read the first few words, instantly, you recognise it is written by an LLM. A human couldn't even be bothered to put finger to keyboard and write something they really believed in... so why are you going to waste your precious time reading whatever this email is? Skip.

The imperfect, messy, incoherent garbage that humans produce is everything that people want and need. Sales is, after all, about people. Using LLMs for sales outreach is abandoning everything we know about sales.

I don't know how long you have been using forums personally, whether you've been online since before me, or NamePros is your first, but what forums used to be, I miss it every day. Outside the box writing experiences have stolen the internet's humanity, everything that made me who I am today, and I grieve for the every future generation who has been robbed of the opportunity. I don't think it's possible to put into words just how much the internet has changed since the introduction of LLMs.

Anyway I could write about this for hours. I'll stop here.

edit: one final thought. I genuinely believe LLMs are one of the greatest dangers facing humanity. Not because of Anthropic's scaremongering about robots rising up and taking over the world, or escaping their sandboxes, none of that is of concern to me, it's fantasist junk, the real problem is LLMs have robbed people of the human experience. Speaking to an LLM is worse than brain rot, it is poison. I think they're fine to be used as a glorified search engine, but to use them for thinking, to use them for writing, it is a crime against oneself.

Allowing children to use LLMs is, I seriously believe, the biggest risk modern parents take, even worse than the brainrot of TikTok etc. LLMs are an incredible invention, the technology is beyond what I imagined possible, it is genius, it is a marvel, and used in this way it is an awful poison.
Thank you for sharing your thoughts and perspective. Please don't stop writing. I will share one thought from my own personal experience. I struggled with being able to clearly articulate myself and having these tools have helped me a lot. I have this quote in a book I co-wrote.."It's never the tech, it's who's behind the tech."

Again, I completely hear you and respect your perspective. I agree with quite a lot of it.

Have a wonderful day :xf.smile:
 
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Nice write up, thanks!

Can you talk more about building up sender reputation in practical terms?

Are any of the email warm-up services legit and actually work?
Honestly it is less exciting than people expect. It is mostly just sending history and whether people engage, so the whole game is ramp slow, stay consistent, and do not bounce.

New mailbox I start around five a day, add a couple a day, cap it at 30. If I want more volume I add mailboxes, I never push one harder. Ten at 20 a day is a much safer 200 than one at 200.

Consistency is the bit people skip. Twenty every weekday looks like a person with a job. A hundred and fifty on Monday and then nothing until Thursday looks like exactly what it is.

And verify your addresses. Bouncing two or three percent is the quickest way to wreck a domain and it is completely avoidable.

Set up Google Postmaster Tools if you have not. Free, one DNS record, and it shows you Gmail's own opinion of your domain. Most of the people you are pitching are on Workspace so that is the scoreboard that actually counts.

We use Smartlead for the warmup side and it has been good to us. 24 mailboxes across 8 domains, warmup on permanently, never turned off even while sending, and reputation sits at 99 to 100 across the fleet.

Whether the others are any good I genuinely could not tell you. Smartlead is the only one I have run properly and I am not going to repeat someone else's benchmark as if it were my own. Worth saying it only keeps the mailbox healthy though, it does not make a weak list work.
 
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Honestly it is less exciting than people expect. It is mostly just sending history and whether people engage, so the whole game is ramp slow, stay consistent, and do not bounce [...]
Thanks for taking the time to share all that info!

Previously, my emails generated clicks on the links I sent, but lately I’ve been getting zero feedback.

I ran some tests (not sure how reliable they are), and apparently my sender reputation has sunk considerably.

Now I’m trialing MailReach for warmup and letting my mailbox sit fallow in the meantime. I’ll independently retest it at a later date to see if there’s any difference.

Set up Google Postmaster Tools if you have not. Free, one DNS record, and it shows you Gmail's own opinion of your domain.
Apparently my volume doesn't meet the threshold to display data.

What is the minimum amount necessary to trigger it?

24 mailboxes across 8 domains,
Does that mean you consider different aliases (or is that referring to paid inbox accounts?) on the same domain to have distinct sender reputation profiles?

Also, do you hand-reg those domains and start from the ground up, or acquire previously used domains for this purpose?

Do you find any difference in the score depending on the content (i.e., subject line, including links, etc.)?

reputation sits at 99 to 100 across the fleet.
Is that Smartlead’s internal measurement or you independently verified it?


Thanks again for sharing your knowledge over here.
 
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