Rook ♜

Most AI-generated outbound ends up deleted before it ever gets read.
 So I’ve spent all year building a Claude workflow trained around how I actually prospect.
 …and it gets my emails ~95% done in seconds.
 I dropped the full prompt/workflow in today’s newsletter here:

The whole goal of outbound sales is really just figuring out when the accounts you’re prospecting into are going to evaluate vendors. That’s basically it. You should start with the signals in your book & ideally you reach out while they’re actively evaluating. But most of the time, the real goal is doing enough outbound to figure out if they’re going to evaluate, when that might happen, and who you need to stay in touch with. Then over time, you build relationships with those people and come back around when the timing actually makes sense. It might feel slow at first, but if you think about outbound from a long-term perspective, eventually you become a known contact within your book of business. At that point, finding buyers in a buying window should require a lot less outreach... because you already had the conversation months ago & just nurtured since then.

Knowing your prospect’s pain is one thing. But understanding the downstream impact of that pain is what actually makes your messaging work. Anyone can repeat the problem back to them. The better reps understand what that problem is actually costing, slowing down, or creating internally.

With cold emails, every line has to earn the next one. If the reason for reaching out sucks, they’re not reading about the problem. If the problem doesn’t feel relevant, they don’t care how you solve it. If the solution is too long, they never make it to the CTA. Make every line earn the next one.

People underestimate how important the three words: “I appreciate you”are. It can take you so far just being good to people, being likable, bringing good energy, not complaining, and actually getting to know the people around you.
 The bar is honestly pretty low in those areas.
 Take care of the people around you and, more often than not, they’ll take care of you back.

How to break into tech sales simplified: -Find companies that are worth joining -Understand the business & product (just enough) -Apply directly -Find the right people internally & create referrals -Prepare & crush the interview process -Stack commission checks

A lot of people are making fun of this (and I get it)... but I like to look at the bigger picture. You truly don't understand something if you can't explain it to a 10 year old &/OR you can't relate it back to something simple. In sales, one of the best ways to explain a complicated topic is to use analogies that your prospects will understand... that is the real litmus test to see if you actually understand what is going on & who is impacted. This example with Tyreek is honestly no different... not ideal use case (for sure), but look at the bigger picture of it / the lessson.

What’s the best way to get past a call screener? I never have any luck & haven’t found a successful solution. Need recs.

Reminder that this is the game plan:

As a tech sales rep - when do you know it’s time to start looking at other companies to sell at?

In all honesty, a lot of cold calling is just playing dumb to get more information out of the prospect. If you know too much then it’s creepy & they will hold back. Start playing more dumb.

How to become a top sales performer: -do the simple things really damn well -follow-up quickly & effectively -ask better questions -talk less -never stop prospecting -understand your ICP really well -network internally -don’t stop perfecting you craft Anything else I’m missing?

As an SDR you should really be focusing on your stage conversion rate. This is your internal brand. I promise you management notices this. Are you booking a lot of meetings? Great. -whats the show rate? -what % of meetings have followups? -what is your conversion rate from S0 to S1 to S2? Always focus on quality of opportunity. Qualify more. Run the discovery meetings yourself. Send the extra email to find out more context. It can be done.

I’m all for handling objections. It’s a critical skill in sales. But I’ve never believed in forcing a meeting - just like anything in life. Some reps try to handle every objection: “No time” “Too busy” “Not a priority” There’s always another rebuttal + some trick up the reps sleeve to handle the objection. Eventually the prospect says: “Fine… put something on the calendar.” But they never actually wanted the meeting. So what happens? -they no-show -they cancel -they show up disengaged And now you’ve left a bad impression / poor experience. Sometimes the better move is to find them at their timing: “I’ll send some resources - we can reconnect when this is more relevant. When might that be?” Keep the relationship positive. Leave the door open. Good sales isn’t about trapping people into meetings. It’s about meeting them when the timing is right. It benefits everyone.

Sales ultimately comes down to being able to help take a company from where they are today to where they want to be. The earlier you can attach yourself to that initiative the better chance you have.

You can tell who’s gonna make it in tech sales by how they approach their first 30 days: NGMI: - Wait to be told what to do - Don’t prospect until ramp is over - No curiosity / replicating what is working GMI: - Figure out ICP early - Learn what customers actually care about (not just the product) - Book time with top SDRs/AEs to steal their playbook