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The GTM Engineer School - Week 2 Overview

This is part 2 of a three-part series, outlining key learnings from the GTM Engineer School that took place late April through May. I’ll do one more article on this that encompasses week 3 & 4.

  • Week 1: Messaging & prospecting (with Octave & Clay)

  • Week 2: Personalized outbound (with Clay and Lemlist)

  • Week 3: Agentic automation (with Cargo)

  • Week 4: AI-led content creation (with AirOps)

This week was broken into two classes again:

  • Class 3: Messaging (continued) with Clay + Octave

  • Class 4: Automations, multi-channel campaigns, and deliverability best practices

I’ll break these down into specific learnings I’ve gained from working with startups to ensure I’m optimized for all of it.

Messaging

To ensure that emails land in the inbox, the messaging needs to be on point. Signals-based messaging is all the craze right now, future post coming in more detail there

Octave + Clay is good here, and the class focused on this. However, wanted to give a shout-out to Florin Tatulea, head of sales dev @ Common Room, who has a great class on this for email on Pclub.io.

After taking, I’ve seen an uptick in responses, which has been great, really exposed how bad I was at sending emails even a few months ago with my current copy mental mindset.

I’d also recommend better understanding how to do this in Clay, since you can use the power of Claude to help break apart emails and write them personalized at scale. See the way Clay says to do this here, which has been helpful for me.

Deliverability

Since 2024, when Apple/Google changed the rules on this, it’s super important to have knowledge on all the steps you need to take in order to make sure you are technically landing in people’s inboxes (and not in spam).

Because of these rule changes, GTM Engineers need to know the new rules of the game.

There are a few resources I have been using (along with this class) in order to catch up to speed. You can find them below, but I have also taken down some bullets that I’m doing myself.

Content:

  • Brendan Short’s article on email deliverability

  • Jasper’s article on email deliverability from Founder-Led GTM

Some tips I swear by:

  • Set up proper authentication - Configure SPF, DKIM, and DMARC. It's like your email's ID card that proves you're legit.

  • Use separate domains for cold emails - Set up lookalike domains (getyourbrand.com) for outreach. Keeps your main domain clean if things go south.

  • Warm up new accounts - Start with 10-15 emails daily for a few weeks. Email platforms get suspicious of accounts that suddenly blast hundreds of emails.

  • Keep volumes reasonable - Stick to 25-50 emails per day per inbox. Need more? Use multiple accounts (5 accounts × 30/day = 150/day).

  • Verify recipient addresses - Double-check emails with tools like ZeroBounce. High bounce rates are deliverability killers.

  • Act human - Random sending times, varied copy, and limited follow-ups. Robots send in batches; humans don't - the software you’re using for email should be able to cover this

  • Stick to plain text - Skip the fancy HTML and limit links to one per email. Less is more for deliverability.

  • Add unsubscribe options - Give people a clear way out. Prevents spam flags and keeps you compliant.

  • Monitor your metrics - Keep an eye on bounces and reputation with Google Postmaster Tools and MXToolbox. Catch issues before they become problems.

  • Skip the sales speak - Avoid "free," "limited time," and other trigger words.

Automations

Many of these tools have a bunch of automations and integrations for the common systems (like Salesforce or Hubspot for CRM).

But for when you don’t have these, this is where the following tools shine:

  • n8n (have been hearing this to be THE tool GTM Engineers are using for the glue between systems that don’t have native integrations)

  • Zapier (generally a tool a lot of people have used before, but less thought leadership on sending data to/from revenue software providers)

  • Make (another popular one among GTM Engineers)

Longer post on this coming in the future as I develop more skills as a GTME 🙂 

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