This is the banner I’m referring to below… notice anything?
Hi there! Hope everyone had a fun and safe holiday weekend!
In the world of weekly newsletters, one of the first milestones we can look forward to is our 26th issue… which of course is the half-way point in a year, so its "officially” official that Selling with AI has hit its half-aversary. Yea, its not a word. I know. Kinda wish it was though.
Anyway, welcome to the halfway point, and hello and welcome to so many new subscribers! The growth over the past 6 months has been so fun to watch, and thank you so much for continuing to read and follow!
One more thing, did you see the banner at the top of this week’s issue? Did you notice anything? Every Tuesday… Starting with S01E27 (the next issue), Selling /AI will be delivered to your inbox every Tuesday at lunchtime… well, at my lunchtime (EST). A very wise man (you know who you are) told me :
“bro, literally ANY day of the week is better suited for a #sales newsletter than Sunday!!”
BTW, thats literally a copy/paste too. like, I’m not trying to make a big deal out of this… but I love you bro. Thank you for being you.
With that being said, we’re all in sales here. And we all know what a persona is. When I began writing, I did so from the positioning of an account executive. Today I write to you as a solopreneur. And starting today, my topics are going to be expanded a bit to cover more founder-led sales tips and tricks… essentially, I am going to write to you weekly about what is working… and maybe even what’s not working.
And that begins with today’s issue, this FINAL Sunday issue, ever, of Selling with AI.
Your next 100 customers are already in Apollo
Find, reach, and close your perfect deals — without juggling five tools or hiring more reps.
Apollo gives you everything you need to build real pipeline, fast. From inbound to outbound, first touch to close.
All in Apollo.
Outbound isn't dead. It's just all the same now.
Everyone opens with "congrats on the round." Everyone references the same hiring post. Everyone "noticed" the same thing on LinkedIn, or in the news recently. Buyers noticed this new age of hyper-personalization happening very quickly… and outbound changed.
The problem was never personalization. It's that personalization stopped being proof you did the work. AI made it free. And free proves nothing.
I get the same automated emails you do. I can name the sequence tool in the first line. Your buyers can too. The personalized opener that used to signal "this person actually researched me" now signals the opposite: a machine filled in a variable and hit send.
This issue is for anyone whose reply rates quietly fell off a cliff this year. SDRs and BDRs running outbound all day. Founders doing their own prospecting. AEs building their own pipeline. The fix is the same for all of you, and it isn't more volume.
Why Outbound Stopped Working
Walk through what actually changed.
Three years ago, a personalized first line took effort. You read their LinkedIn. You found a hook. You wrote something specific. The effort was the message. When a buyer got a genuinely tailored email, the tailoring told them someone chose them on purpose.
Then everyone got the same tools. The same data providers. The same AI writing the same "personalized" opener at a thousand accounts an hour. The tailoring got automated, which means it stopped being a signal of effort. It became a format.
And buyers can read the format.
"I noticed you're hiring for an SDR."
“Congrats on the new role!”
"Loved your LinkedIn post about..."
"Congrats on the Series B."
These lines don’t say "I researched you" anymore. They say "you got added to a sequence." The exact thing that used to earn a reply now earns a delete.
Here is the trap most teams are in. They feel the reply rates dropping, so they reach for the obvious lever: send more. More accounts, more touches, better-sounding AI. That pours more water into a flood. It burns your domain, it trains buyers to ignore you faster, and it makes the core problem worse.
The volume game is over. Not because outbound stopped working. Because everyone is playing it with the same machine.
Prospect on Signals, Not Titles
The edge AI gives you was never the writing. Writing is the part everyone now has for free.
The edge is research at a scale a human can't match. One person cannot monitor four hundred accounts for the moment each one develops a real reason to buy. A model can. That is the job to hand the AI: not "write me a clever opener," but "tell me which of these accounts just gave me a reason to call."
That reason has a name. It's a signal.
A signal is a dated change inside an account that creates a reason to act now. A funding round. A new VP who owns your problem. A job posting for the exact pain you solve. A product launch. A tech-stack change. A reorg. A public statement from a leader about a priority.
Title-based prospecting starts with "who matches my ICP." That gives you a list. Signal-based prospecting starts with "who just changed." That gives you a reason. The list is what everyone has. The reason is what almost nobody brings.
Here is the four-step workflow that I built into my day to day. Find the trigger. Build the angle. Write from the signal. Sequence to its shelf life. Ten minutes per account, and most of that is the AI working while you do something else. (By the way, I use Perplexity for this).
See what enterprise-ready AI support looks like
How are leading teams getting AI support to work? We're breaking down the playbook, live July 9.
Step 1: Hunt Triggers, Not Titles
Start with a list of target accounts and ask the AI to find the one real reason to reach out to each. No reason, no outreach this cycle.
Use this prompt:
You are a B2B prospecting researcher.
Here is who I sell to and the problem I solve, in one sentence:
[WHO I SELL TO / THE PROBLEM MY PRODUCT SOLVES]
Here are my target accounts:
[PASTE COMPANY NAMES, OR A SINGLE COMPANY]
For each account, find the single strongest buying signal from the last 90 days.
Look for: funding, leadership changes, job postings tied to my problem area, product launches, M&A, expansion, public statements, or tech-stack changes.
For each account, return:
1. The signal (what happened, and the date if you can find it)
2. Why it creates a reason to act now, tied to the problem I solve
3. A confidence level: Strong / Weak / None, and flag where you are guessing
If an account has no real signal in the last 90 days, say "No signal" and tell me to deprioritize it. Do not invent a signal to fill the gap.
One thing that matters more than the prompt: run this in a model with live web access, or paste in what your sales intelligence tool already surfaced. A model working from training data alone will confidently hallucinate a funding round that never happened. The "flag where you are guessing" line is your safety net. Read it every time.
What comes back is a filtered list. Half your accounts will have no real signal. That is the point. Those accounts are not bad, they are just not now. You stop spending your best messages on people who have no reason to answer.
Step 2: Build the Angle
A signal is not a message. "They raised a Series B" is not a reason for them to talk to you. It's a reason for you to think.
This step turns the raw signal into a point of view: what the change means for their priorities, who inside the company now owns that problem, and the one observation a generic rep would never make.
Use this prompt:
For this account, I found this signal:
[PASTE THE SIGNAL FROM STEP 1]
Here is the problem my product solves:
[ONE SENTENCE]
Build me a short prospecting brief:
1. What this signal likely means for their priorities over the next two quarters
2. The role most likely to own the problem this signal creates (a title, not a name)
3. One specific, non-obvious observation about their situation that a generic rep would miss
4. A single sentence I could say that proves I understand their moment, without mentioning my product
Keep it under 150 words. Be concrete. If you are inferring, say so.The fourth output is the one to study. If that sentence could be sent to any company in their industry, the angle is too generic and you keep working. If it could only be true for this account this quarter, you found the reason.
This is the part of the work AI can speed up but can't fake for you. Read the brief and decide if it's actually specific. Your judgment is the filter the model doesn't have.
Step 3: Write From the Signal (2 minutes)
Now the message writes itself, because you finally have something true to say.
The opener leads with their situation. The signal is the reason for the timing. Your product shows up late, if at all. And every automated tell gets banned at the door.
Use this prompt:
Write a cold outreach message (email or LinkedIn) to [ROLE] at [COMPANY]
The reason I am reaching out:
[THE SIGNAL + THE ONE-SENTENCE OBSERVATION FROM STEP 2]
What my product helps with:
[ONE SENTENCE]
Rules:
- Open with the specific situation they are in, not their title or my product
- Use the signal as the reason for the timing
- Make one clear, low-friction ask
- Under 75 words
- Banned: "I noticed," "I saw you're hiring," "congrats on," "hope this finds you well," flattery, and three-part sentence fragments
- It should read like a peer who did the work, not a sequence step
Then write one alternate version that is shorter and more direct.The banned list is doing real work here, by ensuring those phrases that are quite literally the fingerprints of automated outbound are stripped and the message has to stand on the strength of the reason. If the reason is weak, you'll feel it here, because there's nothing left to hide behind. That's a feature, and its there by design.
Step 4: Sequence to the Signal's Shelf Life (2 minutes)
Triggers decay. A funding round is a hot reason for about a month, then it's old news everyone else already mentioned. A new executive is most reachable in their first 90 days, while they're still forming opinions. A job posting is live until it's filled.
A fixed seven-touch drip ignores all of that. It sends touch four three weeks after the reason went stale. Time the sequence to the signal instead.
Use this prompt:
Build a 3-touch outreach sequence for [ROLE] at [COMPANY] based on this signal:
[THE SIGNAL]
For each touch:
1. Space it according to how time-sensitive this signal is, and tell me the gap in days
2. Give it a distinct angle: a new observation or resource, never "just following up"
3. Keep each touch under 60 words
This signal has a shelf life. If it goes stale in 30 days, compress the sequence and tell me when to stop and move on.The instruction to name when to stop is the part most reps need. Outbound discipline isn't sending more. It's knowing when a reason has expired and moving your attention to an account where a new one just appeared.
Why This Works
Four reasons.
Relevance is the only scarce thing left. AI made writing, formatting, and surface personalization free. The one thing it can't manufacture is a genuine reason to reach out today. When you lead with that reason, you're trading in the only currency that still has value.
A signal is permission. You're not interrupting someone at random. You're responding to something real that just happened in their world. That changes how the message reads, from a stranger selling to a peer paying attention.
Fewer, better touches protect what volume destroys. Every irrelevant blast trains the buyer to ignore your name and trains the mailbox provider to bury your domain. Signal-based outreach sends less and lands more, which keeps both your reputation and your deliverability intact.
You get there first. The rep who shows up the week of the trigger, while the priority is fresh and the budget conversation is just starting, beats the rep who shows up in next quarter's list pull. Timing was always the edge. Signals are how you find it.
Rep Action this week
Pull 10 target accounts. Not 100. Ten.
Run the Trigger Scan on all of them. Delete every account that comes back "No signal," even if it hurts. You're probably cutting half.
For the survivors, run the angle and message prompts. Send 5 messages built on real signals this week instead of 50 built on a template.
Then watch your reply rate, not your send count. The whole point is to make the smaller number win.
Jay
PS: See you on Tuesday… and for the paid subscribers, the playbooks being dropped over these next few weeks…. wow. You’re welcome in advance… haha, jk. But… no really… its good stuff.
I frequently get asked which tools I use/recommend.
You just read the motion. Now run it.
The prompts, checklists, and templates that turn this into a 10-minute execution are in the Vault.
Get Vault AccessVault access includes::
- Copy and paste execution prompt packs
- Deal, outbound, and follow-up playbooks
- Operating checklists for every motion
- Members Vault access