Sudhee Chilappagari

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Sudhee Chilappagari

Sudhee Chilappagari

@webaficionado

Software & AI VC @BatteryVentures. Formerly Product Guy @Segment @Twilio, Founder @BelongCo. Views are my own, and no investment advice.

San Francisco, CA Katılım Aralık 2009
4.8K Takip Edilen7.6K Takipçiler
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Sudhee Chilappagari
Sudhee Chilappagari@webaficionado·
Battery XV is here — $3.25B to back the next generation of iconic Software and AI companies, from seed to IPO. 43 years. 530 investments. 70+ IPOs. And we’re ready to do it all over again. battery.com/blog/attacking…
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Sudhee Chilappagari
Sudhee Chilappagari@webaficionado·
Although this one seems more than just a name change, "Working closely with Anthropic, we have integrated the technology behind Claude Cowork into Microsoft 365 Copilot".
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Jared Sleeper
Jared Sleeper@JaredSleeper·
For the love of God, why do big companies always do the thing where they slap the same tired, failed branding everywhere? "Copilot Cowork" "XBox Music" "Watson Health" "Agentforce Tableau" Make it stop
Satya Nadella@satyanadella

Announcing Copilot Cowork, a new way to complete tasks and get work done in M365. When you hand off a task to Cowork, it turns your request into a plan and executes it across your apps and files, grounded in your work data and operating within M365’s security and governance boundaries.

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Cailen D'Sa
Cailen D'Sa@cailen·
@webaficionado If you were buying the bottom with some of these companies trading at 1.5-2x NTM, it was a gift.
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Endowment Eddie
Endowment Eddie@endowment_eddie·
If Intercom is at $400m ARR with $100M of true AI revenue, why not be the first agentic application to hit the public markets? The public markets don’t want SaaS 2.0. If they don’t want Intercom, I’m not sure what B2B they do want.
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Sudhee Chilappagari
Sudhee Chilappagari@webaficionado·
"Don't Be Afraid to Give Up the Good To Go For the Great." - John D. Rockefeller
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Sudhee Chilappagari
Sudhee Chilappagari@webaficionado·
Traditional SaaS companies have two choices - either disrupt themselves or get disrupted. Who are some notable ones that have successfully transitioned to an AI-native architecture or rolled out Agentic capabilities? Intercom (Fin) comes to my mind, but looking for more examples.
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Sudhee Chilappagari
Sudhee Chilappagari@webaficionado·
@jack 💯 here’s a better chart. As you said this isn’t about right sizing headcount, rather an “AI-native” restructuring. GPE (gross profit per employee) will become the defining measure of how AI-native a company really is. Block is setting the example.
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Sanjay Nath
Sanjay Nath@sanjaynath·
Beauty and the Bay 💙🙌
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jack
jack@jack·
yes we over-hired during covid because i incorrectly built 2 separate company structures (square & cash app) rather than 1, which we corrected mid 2024. but this misses all the complexity we took on through lending, banking, and BNPL. and that we’re now targeting $2M+ gross profit per person, 4x our pre-covid efficiency, which stayed flat at ~$500k from 2019 until 2024. we have and do run an efficient company... better than most.
Will Slaughter@BamaBonds

In 3 years from December 2019 to December 2022, Block $XYZ more than tripled its headcount from 3,900 to 12,500. Unwinding less than half an insane COVID overhiring binge has much more to do with Jack Dorsey's managerial incompetence than whether AI is going to take your job.

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Sudhee Chilappagari
Sudhee Chilappagari@webaficionado·
Block (formerly Square) grew headcount from ~5,500 to ~12,500 FTEs during the ZIRP era. With the 40% reduction in headcount, their Gross Profit per Employee (GPE) will nearly double — from $1M (2025) to ~$2M (2026e). As AI absorbs low-level knowledge work, GPE will become the defining productivity metric for tech companies. Block might be Exhibit A.
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Sudhee Chilappagari
Sudhee Chilappagari@webaficionado·
I’ve been a loyal ChatGPT Pro user for almost two years. I recently tried out Claude and noticed a significant improvement in the quality of reasoning and responses. 30 days into it, I haven’t logged into ChatGPT even once!
Stephanie Palazzolo@steph_palazzolo

New: Anthropic says daily signups to its Claude chatbot have tripled since November. Meanwhile, paid users of the chatbot have 2x+ since Oct while free users have grown by 60% since Jan. The news comes as Anthropic looks to boost its consumer business. theinformation.com/briefings/excl…

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