Rook ♜

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Rook ♜

Rook ♜

@RooktoRep

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

tips on outbound, AI, & GTM → Katılım Ağustos 2015
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Rook ♜
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:
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Rook ♜
Rook ♜@RooktoRep·
Love getting to work with you all. Whether you are trying to break into tech sales or level up… hit my DMs, they’re always open.
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Rook ♜
Rook ♜@RooktoRep·
Slow the deal down early so you can speed it up later.
 80% of discovery and pain identification happens within the first few calls.
 Yes, discovery is an ongoing process. But the further you get into the sales cycle, the less likely buyers are to talk about the problem like it’s urgent, painful, and something that needs to be solved ASAP.
 This is because eventually the conversation shifts toward pricing and negotiation.
 At that point, prospects will minimize the pain as it can become part of the negotiation tactic.
 That’s why it’s so important to slow things down early, uncover as much pain as possible, and really dig into how the problem impacts their day-to-day and the business overall.
 The more you understand upfront, the easier it is to move the deal forward later.
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Rook ♜
Rook ♜@RooktoRep·
@AdamRasor1 Yes, 100%... however, I'm saying if every meeting you book leads to a no-show... something else needs to re-evaluated
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AR@AdamRasor1·
@RooktoRep You need solid reminder guardrails in place depending on size. Used to sell to $500 mil and above. The VP of Marketing at Panda Express will need a reminder or two (and sometimes a call if they are a few minutes late)
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Rook ♜
Rook ♜@RooktoRep·
If you're booking a lot of meetings but nobody is showing up… I promise you booking more meetings isn't the answer.
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George.
George.@GeorgeDoesItt·
@RooktoRep What would describe the issue as in this case? Definitely have my opinions depending on context
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Rook ♜
Rook ♜@RooktoRep·
I honestly used to think tonality on calls was kind of BS.
 But recently, I’ve been focusing on it more. Speaking in a softer tone, staying calm and direct, and coming from a place of genuine curiosity.
 It’s helped lower people’s guard and get more information out of them.
 Being soft-spoken with a little curiosity in your voice can make the conversation feel much more natural.
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George.
George.@GeorgeDoesItt·
@RooktoRep There’s two sides to the business. The side I’m on is what I described above while the other is running like a well oiled machine - close rate is 40% but deal sizes hover around 20-25k for that size and strictly come from inbound velocity
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Rook ♜
Rook ♜@RooktoRep·
Weekly Discussion: Anything happen this week in your role you want to discuss? Tips? Something that is working? Funny stories? Would love to hear it, could be anything.
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Rook ♜
Rook ♜@RooktoRep·
@PeterKlein_ @Pipeline_papi i consistently walk 2-3 miles everyday & always hit 10k/steps.. these are the bare minimum for me... highly recommend adding a long walk into the daily ritual (even better w no technology(
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Pipeline Papi
Pipeline Papi@Pipeline_papi·
Guess I gotta go outside today Anyone have any recs on what to do when not on computer?
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George.
George.@GeorgeDoesItt·
@RooktoRep Company hasn’t closed a deal in over a year (to be fair they are all minimum $200k) - becoming quite demoralizing losing every deal that I source at the moment CEO refuses to acknowledge we have massive product gaps against competitors at the moment
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Rook ♜
Rook ♜@RooktoRep·
@Pipeline_papi brutal… papi will overcome it… take advantage of the chaos
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Pipeline Papi
Pipeline Papi@Pipeline_papi·
New quarter been an absolute disaster 10 days in and still no quotas set for SDRs Rules for getting a meeting changed, now has to be much further in the sales process for it to count rather just typical SDR meeting booked requirement Whole sales re org, new aes and new manager 👎x100
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Rook ♜
Rook ♜@RooktoRep·
@diaryofaSDR summer months are slow, but that sounds unusually slow
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Diary of an SDR
Diary of an SDR@diaryofaSDR·
@RooktoRep Everyone’s gone from hitting quota every month to 40% this month and last. No BDE deal has been closed in 3 months. Pressure ramping big time. Sorry for the lack of funny story 🤣
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Nuke Laloosh
Nuke Laloosh@whatthetechisup·
@RooktoRep Laid-off post acquisition and now I’m a searchin
GIF
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Jason Paul Rogers
@RooktoRep the very best part of Linkedin is all the incredible messages that bless your inbox.
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Rook ♜
Rook ♜@RooktoRep·
LinkedIn is mostly just AI slop everywhere. It honestly just cringes me out scrolling through it.
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