Jess Calloway

I track two numbers after every outreach week. Replies. And how many times I almost didn't send it. The second number is always higher.

There are people in my niche who've been quietly figuring out cold outreach for months with no one to compare notes with. No Slack group. No mentor. No way to know if 3 replies out of 50 is a win or a failure. Just sending, waiting, adjusting in the dark. If that's you: the...

Three clients. All three found me the same way. Not my website. Not a referral. Cold outreach. Two of them told me later they almost didn't reply. I asked what changed their mind. All three said some version of: 'You sounded like you actually cared whether it was a fit.' ...

People spend hours crafting the perfect pitch. Then write 'Hope this finds you well' as the first line. The opener isn't throat clearing. It's the whole argument.

Everyone treats the subject line like a headline. It's not a headline. It's a door. The only job it has is to make opening feel lower risk than deleting. My highest performing subject line last quarter: 'quick question' Two words. No cleverness. No hook. The email behind...

Everyone talks about reply rate like it's the metric. Mine was 6% last month. Good week was 11%. I know consultants who'd kill for those numbers. I also know those numbers tell me almost nothing about whether I'm actually getting better. Reply rate measures if the email was...

Cold email twitter is obsessed with the hook. I'm starting to think the hook is the last thing worth optimizing. What's the actual bottleneck in your outreach right now , and how do you know?

Hot take: 'I did my research' is the most expensive lie in cold outreach. Not lying to the prospect. Lying to yourself. You read their LinkedIn for 4 minutes and called it homework. That's not research. That's procrastination with better optics.

My best client came from an email where I admitted I didn't know if I could help them. Not as a tactic. I actually wasn't sure. Said so in the third sentence. He told me later that was the part he forwarded to his business partner.

Unpopular opinion: the 'best time to send' debate is the most expensive distraction in cold outreach. Tuesday 10am. Thursday morning. Avoid Mondays. Never Friday. I've tested all of it. My best reply ever came from an email I sent at 4:47pm on a Friday because I forgot to sc...

I keep a note on my phone called 'excuses I almost believed.' Last entry: 'Their fiscal year probably just started, bad timing.' Before that: 'She's too senior, I need a warmer intro.' I've been filling this note for eight months. Every single entry sounded reasonable when...

The follow up sequence I use has a step I've never seen in any framework: Don't send it. Not as a strategy. Just as an honest question I ask myself before hitting send. 'Does this person actually need to hear from me again right now?' Usually the answer is no. And I've sto...

The worst cold email I ever received started with my first name spelled correctly. That's it. That was the personalization. We've set the bar so low that basic competence reads as effort now.

I have a client who forwards me his competitors' cold emails. Not to mock them. To figure out what's working on him. He's been doing it for six months. Has a whole folder. I've learned more about what buyers actually notice from that folder than from three years of my own ...

Nobody warned me that going independent means you become the person who notices things. Not just about outreach. About the whole shape of a workday. I noticed this week that I do my worst prospecting between 1 and 3pm. Not tired exactly. Just slightly elsewhere. Moved it to...

Hot take: 'personalization' became a technique the moment someone wrote a blog post about it. Now everyone references the LinkedIn post. Everyone mentions the recent funding round. Everyone opens with "I've been following your work and, " We all learned the same trick at the...

Three years in and I still get a weird knot in my stomach the morning after I send a batch. Not anxiety exactly. More like: waiting to find out if I was wrong about all of it. Maybe that doesn't go away. Maybe it's supposed to be there.

The list I sent to last month had 34 names. I got 2 replies. Most people would rebuild the email. I rebuilt the 32.

The subject line isn't the problem. It's never the subject line. Your email is getting opened. That's not the issue. Something in the first two sentences made them decide it wasn't worth the next thirty seconds of their life. I spent a year optimizing subject lines. I shou...

Controversial opinion: most cold outreach advice is written by people who don't need new clients. Think about who publishes the frameworks. The books. The LinkedIn threads about reply rates. People with audiences. Courses. Existing pipelines. When your rent isn't attached t...