Caleb Winston

Builder. Dad. Jiu Jitsu. Agentic GTM.

[Caleb Winston @CalebWinston]

Curiosity is the spark of imagination.

[Caleb Winston @CalebWinston]

Don’t just show them how to play the game.

Teach them how to question the rules.

[Caleb Winston @CalebWinston]

@Luv_Xcuses being optimistic

[Caleb Winston @CalebWinston]

Optimism is one of America’s most valuable commodities.

[Caleb Winston @CalebWinston]

@EricSimons @pronounced_kyle this is even more effective when you start with eye shrugs and add a strong exhale

[Caleb Winston @CalebWinston]

I have personally developed a method that is even more effective than than the highly acclaimed 'military method.'

While similar, it involves several key upgrades to this method that I've not seen anywhere else.

👇🧵

[Caleb Winston @CalebWinston]

@elonmusk Elon, wen @grok cli?

[Caleb Winston @CalebWinston]

@Mkpareek19_ @businessbarista @tenex_labs or sales people that deeply understand engineering and AI solutions

[Caleb Winston @CalebWinston]

vibes are the ultimate differentiator

[ₕₐₘₚₜₒₙ @hamptonism]

people with good vibes will be highly highly valuable in the near future.

[Caleb Winston @CalebWinston]

@Seannywilson script

[Caleb Winston @CalebWinston]

@levelsio @steipete https://t.co/XuWLuWQG05

[Caleb Winston @CalebWinston]

Optimism is one of America’s most valuable commodities.

[Caleb Winston @CalebWinston]

@shiftj i have this built w/custom audio notes so the bdr agents actually reach out in the founders voice with a personalized message

it’s open for beta if anyone’s interested

[Caleb Winston @CalebWinston]

@luwie211 @shiftj here ya go:

https://t.co/bOvGbZEU1H

[Caleb Winston @CalebWinston]

this but land the $100k deal right away so they’re already comfortable signing when you follow it up quickly with the $1M deal

[Harry Stebbings @HarryStebbings]

I always get in trouble for these types of posts, but age or arrogance, I do not care anymore.

I have interviewed 100 of the best sales leaders over the past 5 years. None has impressed me as much as @Carles_Reina @elevenlabs . He scaled their GTM from $0 to $330M in ARR in just 3 years.

This weekend I released our episode with him and have gone over it to condense my biggest lessons from the discussion.

🚀 8 Lessons on Building a $330M+ Revenue Machine

1. The "20x" Quota Rule
Forget the standard SaaS 6x–8x multiple. At ElevenLabs, the rule is simple: you must bring in 20 times your base salary in revenue. If your base is $100k, your quota is $2M. It sounds aggressive, but it sets a high-performance bar where over 80% of the team hits their targets.

2. Hire "Hunters," Not Just Product Experts
A common mistake is hiring for product knowledge and hoping to "train" the sales muscle. Carles learned the hard way: you need people with a natural "hunter" mentality who are hungry, driven, and passionate. You can teach the tech, but you can’t teach the hustle.

3. Be "Ruthless" with Pipeline Reviews
Carles holds monthly pipeline reviews where he drills into every detail in front of the entire team. If you aren’t doing your job, you get called out publicly. This transparency ensures everyone learns from each other's mistakes and keeps the team on their toes.

4. Salespeople Belong on the Road
If the sales team is in the office for multiple days, Carles starts getting worried. A remote culture works if it’s a "road" culture. Sellers need to be out talking to customers face-to-face, not just hiding behind virtual meetings.

5. Land Small, Expand Fast
Don't get bogged down waiting months for a six-figure enterprise deal. Land with a $12k contract to bypass layers of approval. Once the MSA is signed, the "land" is over, and the "outbound" mission begins to capture every other team in the organization.

6. Forecast with Brutal Negativity
Optimism kills sales organizations. Carles advises being as negative as possible when forecasting. If a deal is worth $500k, forecast it at $24k. This prevents "inflated" pipelines and forces the team to work twice as hard to ensure the real targets are hit.

7. The 72-Hour "First Contract" Goal
Onboarding at ElevenLabs isn't about weeks of reading manuals. New hires join calls immediately. The target? Sign your first contract within your first two weeks. Some have even closed enterprise deals within 72 hours of joining.

8. Treat Customers as a Community
Transactional selling leads to churn. Building a community—where you give customers your WhatsApp, interact constantly, and do what's right for them even if it costs you money—is how you retain them forever.

Huge thanks to @matiii and @lukeharries for helping to make this one happen.

(link in comments)

[Caleb Winston @CalebWinston]

@HarryStebbings @Carles_Reina @elevenlabs super solid list

especially 2 and 7

you can’t train hunter mentality.

have to be born with it

if you have that then you can be trusted to be in the room from day dot

[Caleb Winston @CalebWinston]

@Chris_Orlob is there an upper bound?

at some point multi threading more people starts to complicate the deal and compound objections.

[Caleb Winston @CalebWinston]

@jackhnels it’s from model API costs

you can select from a variety of models and it works best when you add an Exa key for web search.

the cli is bring your own keys but I’m building a web app version which more user friendly

[Caleb Winston @CalebWinston]

Literally never using google or Apollo for gtm again.

I rebuilt this for sales teams and the results are insane 🤯

Recon is a full stack gtm research agent in the cli — company background, funding rounds, contacts, tech stack insights and personalized outbound all from your terminal.

Run recon on any company.

In 90 seconds you have full company intel, buying signals, ICP targets identified, tech stack, cold email variants with personalization notes, all for about $0.15

Oh and it's also open source.

Drop a comment and I'll send it over.

[Virat Singh @virattt]

Another big week for Dexter.

Our goal: a personal financial assistant that’s fully open source, like OpenClaw.

Shipped this week:
1 • SEC filing reader
2 • OpenRouter support
3 • Smart caching

Dexter now reads the actual 10-K, 10-Q, or 8-K, so you never have to dig through EDGAR.

OpenRouter support means you can plug in whatever LLM you prefer.

We also added @findatasets data caching and LLM prompt caching, so each research session costs less.

Finally: Dexter is growing quickly.

If you want to help shape the future of personal financial assistants, we’re looking for maintainers - DM me.

[Caleb Winston @CalebWinston]

@signulll @illscience “just be right a lot”

[Caleb Winston @CalebWinston]

@mfishbein solid stack

[Caleb Winston @CalebWinston]

@Jacobsklug building a platform for fractional AE’s

think design joy but for revops

[Caleb Winston @CalebWinston]

@ryancarson I definitely see a future where AEs become multi-agent operators — overseeing agentic BDRs, reps and marketers but for now you still need a person in the loop to close larger deals.

[Caleb Winston @CalebWinston]

@itsjoaki this is really cool.

I’ve been putting in a lot of late night hours on something similar.

thanks for sharing. definitely inspiring

[Caleb Winston @CalebWinston]

@draprints https://t.co/40t10ReiAN

[Caleb Winston @CalebWinston]

no one stacks signals.

everyone treats them independently.

someone visits pricing page → sales gets pinged

someone downloads whitepaper → marketing sends nurture

someone's ceo posts about the problem you solve... nobody notices

and when all three happen in the same week?

that's not a lead. that's urgency.

we started flagging accounts with 3+ signals in 7 days. piped them to a separate queue. our bdr agents sends a personalized voice note within 4 hours instead of 4 days.

result: 31% connect rate on stacked signals vs 2-8% on single triggers.

the stack: hubspot + linkedin sales nav + our tool.

one unified view. takes 15 min to set up.

your signals are in 35 tabs.

ours are in one.