These are the facts: 

Most companies have a TON of prospects that visit their website, have genuine interest, but never go through the hassle to book a demo themselves. 

If ONLY there was a way to have more conversations with THESE prospects...

DM me to learn how  ;)

Salespeople… It’s friday. Who’s up for a debate? 


If a prospect is totally ICP - should SDRs be comped for a meeting held, even if no next steps are scheduled? 

My take?

Absolutely. 100%. 

Even if the prospect isn’t ready right now, it’s still EXTREMELY valuable to get in front of the right people, build a relationship, create awareness, and make sure that when the timing is right… you’re already top of mind.

PLUS - it’s not the SDRs fault if the AE bombs a demo, doesn’t clearly ask for next steps, etc. 

Jasper, Krish, Adia, Marc, Jake, 🔥 Tom,  what do you guys think?

Oliver Johnson

GTM & Community Lead at Rep.ai || Founder of Tech Sales Tutors

Salespeople… I want to know… Do you HATE this cold email I received, or love it? 


My take? 

The first line stood out enough for me to click on it, read it all the way through, and think about it hard enough to write this post. 

I think this email could be pretty polarizing which is better than a BORING email any day of the week. 

I’m not the buyer, but I replied and told him who to reach out to. That’s better than most people get from me. 


Ace, 🐜 mike, Ryan, 🔥 Tom, Dariia, What do you guys think? Hate it or love it?

Salespeople… this has nothing to do with sales, but I’m proud of how these pictures turned out, and I want to brag for a sec hahaha. 


A little over a year ago - my wife and I bought our first home. 

The house was built in 1917, and was pretty much a DISASTER (as you can see by that INSANE green carpet lol). 

BUT, we saw the vision and fell in love with the area/bones of the house. 

Soo, after months of hard work (Mostly by my father. Thanks dad lol!) - it’s all finally coming together. 

Super proud of how it’s turned out, and how these pictures look!


PS: if you’re thinking about renovating an old home. Here’s just a few things we had to do to get it in the current spot. 

- Remove carpet. 
- Refinish hardwood floors.
- Get new electrical. 
- Peel off wallpaper.
- Repaint walls. 
- Scrape off linoleum flooring.
- Put in new flooring. 
- Repaint kitchen cabinets. 

… you get the point.

Salespeople… I ran an experiment last week. The results will SHOCK you (or actually maybe they won’t at all). 


While cold calling lawyers, I tried 2 openers that are almost IDENTICAL…

Opener 1: “Hey Jim, it’s Oliver with Rep. Did I catch you with a quick second?”

Opener 2: “Hey Jim, it’s Oliver with Rep ai. Did I catch you with a quick second?”

I had 36 connects total last week with lawyers. 

19 connects with opener 1. 

17 connects with opener 2. 

One opener led to 15 conversations and 4 premature hang ups. 

The other opener led to 9 conversations and 8 premature hang ups. 

Which one do you think led to more conversations?

You probably guessed it. Opener 1. 

I said the SAME thing after each opener, but it seemed like anytime I said AI to start the cold call - people IMMEDIATELY checked out. 

This is far from scientific, but something to think about if you sell something AI related… 

AI can help in a LOT of ways, but be VERY careful on how you package it to your prospects... and maybee don’t lead with it from the jump. 

Elijah, Marc, Roy J., Adia, Harry, 🔥 Tom, Evan does this surprise you at all or would you expect this? Do you think people are already getting sick of hearing "AI" haha.

Salespeople… here’s how I turned this email reply into a meeting booked. 


Just kidding. I didn’t. 

Happy Thursday everyone. Hope your day is starting off better than mine. 🤣 


Sneha, YuChin, Travis, Adia, Kieran, ☁️Justin What’s the most unhinged email reply you’ve ever gotten LOL.

Salespeople... It's Friday. Who's up for a debate? 


What's the hardest persona to outbound into?

I've cold called a WIDE variety of persona's including: 

- CTOs 
- HR Leaders
- Warehouse/Construction managers
- Hospital Administrators
- Chief Lending Officers
- CEOs 
- Product Leaders
- CISOs
- Chief Data Officers
- Marketing Leaders
- Sales Leaders 
- Law firm owners/lead attorneys 

Without a DOUBT the hardest personas to cold call IMO are... 

CISOs and Lawyers

CISOs are scared of you and lawyers think they're BETTER than you 🤣 

PS: We're trying a new vertical with lawyers, so if anyone has any tips - I'm all ears lol. 

🔥 Tom, Ronen R., Abe, Martin, Kevin, Kellen, Elijah, John What do you guys think is the hardest persona to reach via outbound/cold calling?

Salespeople… I hit 100% of my meeting held quota in November. Here’s the breakdown of where each meeting came from. 


20% from cold calls. 
30% from linkedin. 
40% from cold email. 
10% from proactively video calling someone on our pricing page (using Rep.ai). 

Not horrible considering I took off a full week this month, was on the road for another half week, tested a new ICP/set up brand new cold email infra (that's why cold call volume was much lower than usual), AND got hit with, “follow up in Jan” about 1M times LOL. 

Also cool to note that 7 of these meetings were with C level decision makers. 

Travis, Kade, Nate, Martin, Sneha, Carla, How about you guys? How was November? Did you hit?

Salespeople… Watch me book a meeting with the owner of a law firm on a LIVE cold call below. 


Key takeaway from this call? 

For many personas - the best thing you can do is start the call by immediately telling them the purpose of your call (to book time to chat later). 

That sounds something like, “Reason for my call is simple… I know I’m calling you out of the blue right now. I wanted to get just 15 or so minutes on your calendar next Tuesday to properly introduce myself and company when I’m not a total interruption. Do you have a few minutes that day?”

I stole this line from Shawn and Aubrey - and it’s worked like a CHARM. 

Such an easy way to get the prospect to relax right off the bat, and then ask YOU - what your company does. 

If you're selling to any persona besides GTM leaders (they don’t like this in my experience lol)  - give that line a shot. 


PS: Got this prospects number from upcell (they’ve had a good amount of lawyer personal cells in my experience), and dialing with Minari's power dialer (inexpensive, month to month, and no delay). 

Marc, Ronen R., 🔥 Tom, Jasper, Roy J., Adia What do you guys think of this call? Anything you'd change?

Salespeople… Watch me book a meeting with a VP of Sales on a LIVE cold call below. 


Key takeaway from this call? 

If the prospect doesn't give you a firm time to meet - suggest a date for them, get it on their calendar, and say that they can propose a different time later if they need. 

The WORST thing you can do when a prospect shows interest - is email them times that you have available. 

I did this a few times early on and I don't think I ever got a reply back. 

The BEST thing you can do for yourself is get it on the calendar, and confirm they got it in their inbox WHILE you have them on the phone. 

Your likelihood of getting them to attend literally SKYROCKETS. 

PS: found this one's number with upcell. if you need good mobile data - check them out. 

Jamis, Ronen R., Juan, Eric ☎, Marc, Aubrey What’d you guys think of this call? What do you do if a prospect gives you a “wishy washy” time to meet?

Salespeople… In the last 2 weeks I’ve booked 6 meetings with founders via mass cold email campaigns. Here’s 3 things I recommend if you want to do the same. 


1. Aim for replies, not meetings. 

The chances of a founder agreeing to a 30 minute demo with little context is VERY slim. 

The chances of a founder saying, “sure” when you ask if you can send a video… Much better. 

EVERY single one of these meetings booked came in the following way:

- Send email with CTA of, “Mind if I send over a 30 second video?”
- Founder replies, “sure.” (always 1 word replies lol)
- I reply with video and ask if they have time to dive deeper. 


2. Reply ASAP when you get a response. 

It is CRUCIAL that you stay on top of your replies when you set up a mass email campaign. 

I aim to reply in <5 minutes. 

Pro Tip: Make sure you use a good email sending platform that has a clean inbox  where you can check for replies quickly across all domains/channels. lemlist is a good example of this. Great sending platform + great inbox management.


3. Follow up with cold calls. 

For this campaign we’ve been targeting the founder at various kinds of law firms. 

At least 3 of these meetings booked came from following up with a call to their office saying, “John expressed some interest via email. Wanted to call to get some time on his calendar.”

If you aren’t doing something similar - you’re 100% leaving money on the table. 


🔥 Tom, Sam Ackerman, Martin, Sheriff, Christopher, What else do you guys recommend to crush via cold email?

Salespeople… I took on one of my first fractional clients recently to cold call for them. Here’s what happened. 


9 meetings booked in the last week and a half. 

The secret? 

(No, it’s not because I’m the greatest cold caller ever (although I am pretty good 😉 ).

It’s because they had 3 things NAILED down:

1. They knew their ICP EXACTLY

They are targeting hospital administrators at skilled care facilities that work under ONE giant healthcare holding company. 

Getting THIS niched down was huge. Anytime I had a prospect pickup, I knew they’d have at least SOME interest. 


2. They had a good script. 

This script was short, conversational, and started IMMEDIATELY with references that the prospects knew. 

It’s SO important to start your calls off with something that builds trust ASAP. 


3. They had good data. 

The list wasn't filled with a bunch of wrong numbers. They invested in a good system to ensure they had accurate phone numbers. 

I always recommend upcell for this. 


So, if you’re planning on working with an outbound agency, or ramping up an SDR to start dialing for you. 

PLEASE. Get these things right FIRST. 

Your calendar/pipeline will thank me later. 

PS: If you want someone to cold call for you that genuinely LOVES dialing, and is pretty decent at it. DM me. I’d be happy to help ;)

Elijah, Hunter, 🔥 Tom, Ronen R., Abe, Martin, what’s the ONE thing you wish every client had ready before you ever dial for them? 

What do you think is most important out of the 3 of these?

Salespeople… Watch me book a meeting with a VP of sales/marketing on a LIVE cold call below. 


Key takeaway from this call?

If it sounds like your prospect is busy (you hear them driving, kids are crying, they’re obviously in a meeting, etc.) CALL IT OUT IMMEDIATELY. 

The WORST thing you can do in a scenario like that is just pitch them as quickly as possible and hope your message resonates. 

This literally never works and just makes you sound desperate/inexperienced. 

So, show some restraint and DETACH like Josh Braun says. 

Say something like I did in the call below, “Hey Matt, it sounds like you’re driving. Did I catch you at a bad time or do you have a quick second?”

Either the prospect will tell you a better time to call them, OR they’ll correct you and say, “No, I can talk. What’s up?”

That’s what happened in this call here and it earned me the meeting at the end. 

PS: Using Minari to make dials for those that have asked. 

Aaron, Kieran, Martin, Jamis, ☎️James What do you guys think of this call? Do you ask if the prospect has a minute, or do you go straight to pitching?

Salespeople… Rate this DM (1-10) that got me a meeting booked with a VP of Marketing. 


I’ll start with what I think is GOOD about it: 

1. Shares exact/believable metrics. 

I think what makes this message work is that I show an actual screenshot from our dashboard that shows how many website visitor conversations + meetings booked in a 7 day period. 

Also - I honestly think prospects listen MORE when you share a metric like “3 meetings booked in a week” compared to, “want to know how I booked 40 meetings in 2 days?” 

Most prospects KNOW that if you’re booking that many meetings, something’s off or you’re lying lol. 


2. It’s short. 

No linkedin DM should be more than 3 paragraphs. EVER. 


What could be IMPROVED?: 

1. CTA could be stronger IMO. 


Dylan, Sam, Dylan, Tommy, Devanshu, Colton R, Edin What do you guys think? Is this a good message? How would you improve it?

Salespeople… Rate this email 1-10 that got me a meeting booked.


Here’s what I think is good AND what could be improved about the email…

The GOOD: 

1. It highlights a problem. 

A big problem law firms have is that by time they reach out to a potential client’s inquiry - that person has already signed up with another attorney. 

The first line immediately speaks to this problem and gets them to stop and think for a second. 


2. It doesn’t immediately ask for a meeting. 

Low ask CTAs CONSISTENTLY get way more replies than asking for the meeting immediately. 

I think this email does a good job of getting them intrigued enough to say, “Sure. I’d like to see a video.”


3. Most important: it actually LANDED in the inbox. 

People forget this. Your copy doesn’t matter AT ALL if your email never reaches the prospect. 

We’ve seen a massive spike in meetings lately - not just because the messaging is good, but because the sending infra is actually working. 

If you’re doing any sort of volume you NEED: 

- High-quality infrastructure (inboxes and domains) 
- Proper warmup 
- Perfect DNS setup (SPF, DKIM, DMARC) 
- And a tool that won’t tank deliverability 

(Mailpool is what I recommend for this. Again, If you aren’t hitting the inbox, none of the messaging even matters.)


The BAD:

- Could definitely use some more personalization. 
- I think MOST people are jaded with the word AI and I avoid saying it on cold calls. BUT, for this cold email campaign - I think it's caught lawyers that are looking to be more tech forward. 

Lauren, Andy, Kevin, Julia, Elmer, Ivan, What do you guys think of this one?

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