Rook ♜

Documenting the climb in tech sales & sharing lessons along the way | DMs Are Open 📩

[Rook ♜ @RooktoRep]

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:

[Rook ♜ @RooktoRep]

@dingraps yes

[Rook ♜ @RooktoRep]

Spend enough time in sales and you will realize…

a lot of the best reps can’t even fully explain why they’re good.

It becomes all feel + instinct.

Sales is way more art than people give it credit.

[Rook ♜ @RooktoRep]

@RagnarDrees it’s a fine line tbh

[Rook ♜ @RooktoRep]

@RandyCristero that’s actually good point lol

[Rook ♜ @RooktoRep]

@RandyCristero I agree… it really isn’t that hard

[Rook ♜ @RooktoRep]

How long should it take to land your first tech sales role?

Depends on how many people you actually talk to.

Applying = slow (potentially never)
Cold outreach = fast

[Rook ♜ @RooktoRep]

Curious on how the interview process works? I wrote an article here:

https://t.co/LPJjB16tY2

[Rook ♜ @RooktoRep]

@samharborne understanding who & what team is key

[Rook ♜ @RooktoRep]

Most people think a call without a follow-up meeting is a failed call.

I disagree.

Any intel gathered + touch point is a win.

Whether that is:
- tooling
- pains
- team structure
- priorities
- who actually owns the problem

Info on an account compounds over time.

[Rook ♜ @RooktoRep]

@emptyguitar53 yep… inside intel is soooo key

[Rook ♜ @RooktoRep]

@RagnarDrees @tylercosgrove indeed

[Rook ♜ @RooktoRep]

The SDR who just got a shoutout from their AE for booking at a tier 1 account

[Rook ♜ @RooktoRep]

@Mountain_Focus committed

[Rook ♜ @RooktoRep]

Being at a tech startup, you learn quickly that the only constant is change.

The product is always evolving and changing. People come and go. The sales cycle, territories, and rules of engagement change.

Everything is constantly changing, and that is the only constant.

[Rook ♜ @RooktoRep]

@itsajinkyaraj yep… very true

[Rook ♜ @RooktoRep]

@mikutechsales being likable is key… some just have it & others don’t

[Rook ♜ @RooktoRep]

One thing I've noticed in tech sales:

The people who get promoted aren't always the top performers.

A lot of times they're the people who have built a really strong internal brand.

They're good at showing what they've done for the business, being able to put their finger directly on it, and telling their story in a compelling way…

Usually some of the most well-networked people internally too.

Performance matters, but visibility is key.

[Rook ♜ @RooktoRep]

There have been over 130,000 tech layoffs and we're not even halfway through 2026.

But I think there's another metric that's much harder to track:

All the positions that aren't being backfilled

I can promise you a lot of companies have quietly frozen hiring.

Teams are being asked to do more with less.

Sales reps are covering more accounts. Territories are getting bigger (& smaller at the same time ifykyk)

Efficiency expectations keep increasing.
A lot of this is being enabled by AI.

So yes, the layoffs matter.

But I think the lack of backfills & trying to be leaner tells an equally important story.

[Rook ♜ @RooktoRep]

@Pipeline_papi and stop being so uptight w them when you are working together.

reminder you work with them… not for them.

if an account is shit.. just tell them. don’t be a pushover & be straight up

[Rook ♜ @RooktoRep]

@getcinderai yep

[Rook ♜ @RooktoRep]

🧵Most objections aren't objections. They're signals.

They tell you about:
-timing + budget
-tech stack
-priorities
-buying process

The reps who handle objections the best are the ones who learn the most from them.

A few examples:

[Rook ♜ @RooktoRep]

@kyledstyle @repvue exactly… why it’s so key

[Rook ♜ @RooktoRep]

PMF is arguably the most important aspect in sales when it comes to being successful.

Nothing else matters if there is no fit.