Hey, it's me, Jess. I'm Head of Marketing at Exit Five, and I'm back with another edition of The Prompt.
I sat down with three email marketing experts to figure this out. Gabby Kustner from Customer.io, Alyssa Armstrong who runs an email agency for DTC brands, and Joe Cunningham, an email copywriter who's written hundreds of newsletter ads. We talked about why cold email is SO much harder now, how to actually stand out when every message sounds the same, when to use email vs. SMS vs. in-app messaging, and what makes people open, read, and reply.
What I realized from that conversation:
AI didn’t hurt email.
We did.
The moment anyone could blast 10,000 “AI personalized” cold emails with one click, something shifted.
Now the bar for earning attention is way higher than it used to be. Cold email is 10,000x harder than it used to be, too.
Are you feeling that?
So how do you stand out when every inbox is packed with copy that sounds like it was written in five seconds by a tool?
Will email shift completely away from being a cold outbound channel and instead be used as a nurture-only channel? Cold outbound works for some, and for others, it never makes sense. Either way. It's even harder now.
We broke down what's actually working right now: the right (and wrong) ways to personalize, real campaigns that worked, and how top teams are using AI without sounding like AI.
Here’s your roadmap to cut through the noise and actually earn attention.
An AI answer engine for your website that sounds like you and knows your product.
Most B2B websites look fine. Good design, good copy, but buyers still bounce. Not because your product is weak, but because their real question never gets answered.
Buyers will not dig through pages, PDFs, or chatbots that link them to more pages. If they cannot get clarity instantly, they leave.
Concierge.ai fixes that. It brings your site into the LLM era and answers buyer questions on the spot using your product knowledge and your voice.
And when Concierge determines a visitor is qualified to speak with sales, it will book a demo for them with your sales team.
Write Like You Were Invited Into Someone's Personal Space
The inbox is a personal space. Treat every email like someone invited you into their home.
You wouldn't walk into someone's house and immediately pitch them. You wouldn't talk in corporate speak. You wouldn't blast them with nine different CTAs.
You'd be respectful. Relevant. Most importantly: Human.
And yet, most marketing emails feel like someone kicked down the door and started selfishly yelling about a product feature.
What this looks like in practice:
Send emails from real people on your team, not generic company addresses (been a best practice for some time now)
If you hit reply, it should go to that person's actual inbox
Add a photo to your sender profile in your CRM settings
Stop writing emails that sound like press releases
Use your audience's actual language (steal phrases from sales calls, support tickets, LinkedIn comments)
One email = one clear purpose. Not three product updates crammed together.
Small shifts can make a big difference. People can feel when an email was written for them versus at them.
Stop Overthinking Your Subject Lines
Start paying attention to what makes YOU open emails.
As marketers, we forget that an actual human is sitting on the receiving end of that email. Scroll through your inbox with complete awareness over the next few days. What did you open? What did you read? What did you immediately delete? Why?
Is it the subject line? The sender? Is it just the time of day when you're clearing out your inbox anyway?
Most of the time, it's a mix. But here's what consistently works:
Short and punchy (under 50 characters)
Curiosity-driven without being clickbait ("The lab experiment every marketer should know")
Brand-aligned (a short cryptic subject line works for some brands, feels gimmicky for others)
VALUE - This one usually gets skipped, probably because it takes the most time, and it's the most important.
A real example: Lenny's Newsletter (which is typically focused on product, growth, and career advice) sent an email recently with the subject line "My Christmas tech recommendations."
Gabby had been ignoring all his other emails about AI and unicorn stories, but clicked that one immediately.
Why? Because it was different. Personal. Human. And actually valuable. Helpful. Relevant. Timely.
Tactical takeaway: Mix up your content. Your ICP isn't one-dimensional. They care about their work, but they also have hobbies, interests, side projects. Tap into that occasionally and watch your open rates spike.
Email vs. SMS vs. In-App: What to Use When
This came up a lot. When should you use SMS and when should you stick to email?
The consensus:
Email = Best for content, nurture, storytelling, anything that requires thought or multiple clicks
SMS = Best for time-sensitive, transactional, or event-based updates (e.g., "Your event is tomorrow, here's the address")
In-app = Best for behavior-triggered nudges when someone is actively using your product
For B2B SaaS, SMS is tricky. Most people don't want work-related texts on their personal phone. But for events, reminders, or urgent updates? It works.
Helpful rule of thumb: Think about where your audience is when you want them to take action. If they need to be on their phone, use SMS or push. If they need to be at their desk clicking through something, use email.
Measuring Success Beyond Opens and Clicks
Opens and clicks are good. But they're supporting metrics, not leading KPIs.
For some campaigns, success is replies. For others, it's who's reading (tracking engaged accounts, not just individuals). For nurture emails, it could be whether people engaged over time, were nurtured to a demo, etc.
One Exit Five member stopped sending a monthly customer email. Usage dropped. When they dug in, customers said, "Oh yeah, I used that email as a reminder to log in."
Sometimes the best marketing is just reminding people you exist.
Tactical takeaway: Define what success looks like for each email before you send it. Not every email needs to drive a demo. Some emails are there to build trust, stay top of mind, or provide value.
🛠️ The Tools We're Really Using
Let's be clear: these aren't tools to automate generic outreach at scale. They're tools to help you think sharper, personalize better, and send fewer, smarter emails.
✏️ AI Writing Assistants (For Strategy, Not Spam)
ChatGPT / Claude
Use these for brainstorming, not blasting. They're great for workshopping subject lines, crafting hooks, or thinking through how to position value for specific segments or accounts.
The goal? Write messaging that sounds like you, just faster.
Best for: Developing your strategy and drafting thoughtful emails.
🎯 AI Personalization: Two Tiers That Actually Matter
Here's the thing about AI email personalization: most tools just generate opening lines. A few actually help you personalize based on real data. There's a big difference.
Basic Tier: AI Line Generators
These tools pull public info to create personalized icebreakers. They work, but they're surface-level.
Lyne.ai — Analyzes LinkedIn and other sources to generate personalized opening lines based on company news, bios, or recent events.
Warmer.ai — Goes a bit deeper with competitive context and recent activity to create relevant intros.
SmartWriter.ai — Creates tailored opening lines using public data from across the web.
The reality: These save time, but you'll need to review and edit the output. They sometimes pull irrelevant details or generate awkward phrasing. Think of them as assistants, not replacements for your judgment.
Advanced Tier: Data Enrichment + AI Personalization
This is where things get interesting. Instead of just generating lines, these platforms help you build entire personalization systems based on enriched data.
Clay — I know you’ve heard of it by now. Clay combines 75+ data enrichment tools and uses AI to analyze webpages, PDFs, tech stacks, LinkedIn activity, and more to create genuinely personalized messaging at scale.
It's not just adding a custom line. It's helping you understand who someone is, what they care about, and what's actually relevant before you write to them.
Real example: Rippling used Clay to 2x their cold email performance by creating 12 targeted variants with deep personalization at a scale they said wouldn't have been possible manually.
Instantly.ai — Uses AI to generate context-specific personalization variables and first lines at scale, with bulk sequencing for hundreds of accounts. Starts at $30/month.
Saleshandy — Features an AI Sequence CoPilot that builds entire multi-step sequences with trigger-based follow-ups that auto-personalize based on engagement.
The honest truth: Personalization without good data is just fancy merge tags. Clay solves the data problem first, then layers AI on top. That's why it works better.
🎠Behavioral Email Platforms (Send Based on Actions, Not Lists)
Customer.io — Sends emails triggered by what someone actually does — not because they're in a database. You're responding to intent signals, not guessing.
HubSpot + Klaviyo (with AI features) — The AI helps with copy, but the real power is in segmentation and automation logic. Build triggers like "visited pricing page 3x" or "downloaded this guide" instead of sending generic blasts.
You're not flooding inboxes. You're responding to real engagement.
🔍 Insight Tools (Understand Before You Send)
Instead of automating more emails, these help you understand what actually works.
Internal Analytics + AI — Turn CRM notes, feedback, and purchase behavior into patterns you can use to craft better messaging. You're finding insights, not just sending noise.
Gong / Chorus (AI Call Analysis) — Analyze real sales conversations to find what messaging actually resonates. Then use those patterns to write better emails with less guesswork.
🧠How to Actually Use These Tools Without Adding to the Noise: Intent Signals
Start with intent signals: website activity, content downloads, event attendance. Email people when they show real interest, not just because they're in your database.
Make personalization mean something
Skip the "Hey [firstName]" templates. Open with one real insight:
Recent funding round?
Tech stack they just implemented?
Article or post they wrote?
AI can help you surface and phrase that insight. But you still need to decide if it's worth sending.
Segment tightly
Group people by industry, role, or actual behavior. Create micro-segments and tailor messages based on what's relevant, not what's easy to automate.
Scale quality, not quantity
Set daily caps on outreach. Review AI-generated content before you use it. Treat suggestions as starting points, not defaults.
The goal isn't to send more emails. It's to send emails that people actually want to read.
So Where Does This Leave Us?
AI is supposed to make our jobs easier. Instead, it makes standing out harder.
Every marketer I talk to is dealing with this tension. You're expected to send more emails, test more campaigns, personalize at scale. But you're also watching open rates drop because everyone else got the same memo.
You're automating workflows while also trying to sound less automated.
You're using AI tools while also defending why you still need writers, strategists, people who actually know your audience.
And you're stuck wondering: Am I using these tools well enough? Should I be doing more? Am I falling behind?
Here's the truth: The best email marketers right now aren't the ones using the most AI. They're the ones who figured out where AI helps and where humans matter.
AI can research your audience. It can draft subject lines. It can personalize at scale.
But it can't tell you what will make someone actually care. It can't build trust. It can't turn a cold email into a relationship.
That's still on you.
So yeah, use the tools. Test the workflows. Automate what makes sense.
But don't lose the thing that made you good at this in the first place: knowing how to talk to people like they're people.
A quick question for you: What's your biggest struggle with email right now? Reply and let me know. I read every response.
-Jess
P.S. Shoot me a reply so I know you’re out there reading this. I read every response and try to reply to all of them. Let me know how email is working for you as a channel. I may feature your use case in a future newsletter.
đź«– Spilling the AI Tea (Recent News)
🚀 1. Anthropic Launches Cowork (The Desktop Agent is Here) Anthropic officially released Cowork, a Claude-powered desktop AI agent designed to live alongside your local files. Unlike standard browser-based AI, Cowork can navigate your folders and work with information directly on your computer (all without you needing to write a single line of code).
Why it matters for marketers: Think of this as a digital chief of staff for your hard drive. It’s a game-changer for document triage, deep-dive research across messy project folders, and internal knowledge work. Instead of uploading files one by one to a chat box, you can point Cowork at a campaign folder and ask it to synthesize a strategy in seconds.
🔍 2. AI is Officially Reshaping How B2B Buyers Discover Vendors New research confirms a massive shift in the B2B buyer journey: Generative AI now ranks alongside traditional web search and peer referrals as a primary discovery channel. Buyers are increasingly asking LLMs for vendor recommendations and "best-of" lists before they ever hit a landing page.
Why it matters for marketers: Your "AI visibility" is the new SEO. If your brand, founder insights, and case studies aren't being ingested and cited by these models, you’re missing the discovery phase entirely. Content strategy now requires a "double-down" on brand authority to ensure your name pops up when a buyer asks an AI for the best solution in your category.
[JANUARY 21] AEO for CMOs: Lessons Learned and Where Search Might Be Going In 2026
Over the last year, AEO has fundamentally changed the buyer's journey, with potential customers turning to ChatGPT, Gemini, and Perplexity for product recommendations before they ever land on your website.
But for a CMO, the challenge is separating the signal from the noise. How do you evolve the traditional SEO playbook without chasing the hype?
Join Marcy Comer (CMO, Eagleview), Dave Steer (CMO, Webflow), Clare Schmitt (VP, Marketing & Comm, Piedmont Global), and Dave Gerhardt (Founder, Exit Five) for a breakdown of the lessons learned from a year of navigating AEO.
What you’ll learn:
How to think about AEO at the leadership level
What to focus on in the next 90 days
The risks of ignoring AI-driven discovery
How to gauge AEO maturity, from basic visibility to real authority
Bring your questions. This will be an open, live conversation about where discovery is going in 2026 and how to build authority while the rest of the market is still catching up.
Join us in Scottsdale, AZ (March 18–20) for an exclusive gathering of 100 B2B Marketing Executives. This is two days out of the office at a beautiful resort, specifically designed to connect top B2B marketing leaders IRL.
The lineup Includes:
Dave Kellogg (EIR, Balderton Capital) on becoming a top‑tier CMO.
Hillary Carpio (VP Growth, Snowflake) on building high‑performing teams.
Kim Storin (CMO, Zoom) on her leadership playbook.
Emily Kramer (Founder, MKT1) on Ecosystem Marketing.
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