Cris Cafiero

VP Sales @sequoiatpi // notes on early stage startups, gtm and sales

[Cris Cafiero @criscafiero]

Cold email isn’t dead but it shouldn't be your first outbound move in 2026

everyone's ai writer is blasting everyone's ai spam filter. Nobody wins

What‘s working for my team:

[Cris Cafiero @criscafiero]

@TheSignalclub @_dan_lee_ @jeffignacio The show is cooking, this is great content

[Cris Cafiero @criscafiero]

@natolisnuggets I agree with this. I coach every seller to learn how to adapt on the fly and think on their feet. New reps need to learn how to:
- think in frame works instead of talk tracks
- ask questions that follow the convo’s thread
- get rid of robotic scripts & be themselves

[Cris Cafiero @criscafiero]

I’ve been selling HCM tools my whole career, I get the same 3 questions nearly every deal:

ceo: will the implementation distract us?
cfo: what's it cost per employee, all in?
head of people: what’s the impact to me, my employees & their families?

I’ve learned that first meeting has to address all 3 BEFORE they ask, and the proposal has to validate your answers

[Cris Cafiero @criscafiero]

@saastr Definitely implementing this. I spend most of my time watching individual call recordings these days, but this way better long term

[Cris Cafiero @criscafiero]

@thedealdirector I think the pre meeting gifting approach is gimmicky… the product has to be s-tier for it to even remotely work, and even then I can’t imagine sorting through all the wasteful meetings that only wanted the gift. Tough use of time for the AEs if they’re not valid opps

[Cris Cafiero @criscafiero]

@natolisnuggets Definitely a recruiting tool, always seems super exaggerated

[Cris Cafiero @criscafiero]

@NickAbraham12 Any rep reading this: tape #8 to your monitor!!

[Cris Cafiero @criscafiero]

@Motiva8ore A mug is the goal

[Cris Cafiero @criscafiero]

My most overused phrase in sales coaching:

“Earn the right”

My team is probably sick of me saying it but it’s a major pillar in our approach:

Earn the right to discovery
Earn the right to booking next steps
Earn the right to ask for referrals
Earn the right to ask to be a reference
Earn the right to ask for the business

To be an effective, trusted seller, you gotta earn the right, which means doing the work to show you know their business, know their industry, and how you can solve their problems

It also means being a good, decent person

[Cris Cafiero @criscafiero]

what reps say vs what the buyer hears:

what else?

[Cris Cafiero @criscafiero]

@BenyaminHolley So much for taste being a moat

[Cris Cafiero @criscafiero]

@mistamor I would argue cold calling is actually easier than LI/email. The biggest grind is actually getting good phone numbers & data. In my experience that’s the biggest blocker from people actually doing the dials

[Cris Cafiero @criscafiero]

@brendanjshort @jeffignacio @noahadelstein From the sales side I'd ask: at an ai-native startup with say 1 or 2 AEs, which role do they hire next? and what should the sales leader STOP doing once that person starts?

[Cris Cafiero @criscafiero]

@KyleAsay_ Great alpha, video is a great differentiator. That said, hard to do at scale (at the individual level, maybe there are better tools now) so it’s important for the rep to target top quality accounts with these vs spray & pray

[Cris Cafiero @criscafiero]

@Chris_Orlob Share please!

[Cris Cafiero @criscafiero]

An easy tell that a seller is getting better:

They can recap what the buyer actually said easily (not what they think the buyer meant), and pattern match to similar challenges we’ve solved before

the more reps a seller gets, the faster this skill improves

[Cris Cafiero @criscafiero]

“Closing the loop on this in case things have changed. Mind letting me know if that’s the case? Totally fine if so, would rather know either way"

One is easy to ignore, while the other asks them to correct you or gives the buyer an out

[Cris Cafiero @criscafiero]

Two versions of last chance follow-up:

Bad: "just bumping this"

Good:

[Cris Cafiero @criscafiero]

@Kazanjy I’d add agreed timeline (including kickoff call) in writing

[Cris Cafiero @criscafiero]

I get a 90% response rate on this one:

“I know things change and you’re probably working on a million other things. I’d hate be a bother following up if evaluating [product] isn’t a priority right now.

Mind letting me know if this is the case?

Totally fine if the answer is no. Would rather know either way!”