Gavin Winchell

18 posts

Gavin Winchell

Gavin Winchell

@GavinWinchell

GTM Leadership @UseCorgi | @Penn alum

San Francisco Se unió Mayıs 2023
47 Siguiendo40 Seguidores
Garrett Martel
Garrett Martel@GarrettMart7·
2 Corgi employees spotted touching grass
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Chanhee
Chanhee@hiddnest·
.@UseCorgi is he a real gtm leadership or it is a fake account? @GavinWinchell i got a dm from him, but not sure it is real or not
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Gavin Winchell retuiteado
Connor White
Connor White@connor_trycorgi·
Corgi is disrupting a $1T industry from the ground up! It has been incredible to see the velocity with which we have been growing after our $266M series B a few weeks ago. Always welcome to connect, email me: Connor.White@trycorgi.com
Connor White tweet media
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Gavin Winchell
Gavin Winchell@GavinWinchell·
the deal doesn't die in the demo. it dies in procurement. your champion loves you. legal has questions. security has a questionnaire. finance wants 20% off. the AE job in 2026 is less 'convince the user' and more 'keep five departments from quietly killing the thing they all already said yes to.'
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Gavin Winchell
Gavin Winchell@GavinWinchell·
self-serve will close the deal a buyer already understands. it will not multithread. it will not build the mutual action plan. it will not get procurement unstuck at the 11th hour when legal goes quiet. 54% of new logos closing with no rep doesn't kill the AE. it deletes the easy half of the job and leaves the part that actually needs a human in the room.
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Gavin Winchell
Gavin Winchell@GavinWinchell·
@DanielSmidstrup same curve is hitting discovery. week 1 AI writes the recap. week 6 it writes the MAP. week 9 you're on a forecast call and can't answer 'why now' because you outsourced the thinking, not just the typing. the draft is fine. not knowing your own deal is the problem.
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Daniel Smidstrup
Daniel Smidstrup@DanielSmidstrup·
Your founder friends using AI: week 1: "just helping with small tasks" week 3: "it writes the rough draft" week 6: "it handles half the workflow" week 9: "it writes all your code" The shift is always gradual until it isn't. Where are you on that curve?
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Gavin Winchell
Gavin Winchell@GavinWinchell·
self-serve eating 54% of new logos doesn't shrink the AE role. it filters it. the deals that still need a rep are the $200k+ ones with seven stakeholders, a security review, and a procurement gauntlet. that's not fewer AEs, that's a harder AE. did Eleanor say what happened to quota and OTE for the reps who now only touch the complex deals?
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Jason ✨👾SaaStr.Ai✨ Lemkin
10 learnings from Anthropic's Eleanor Dorfman at SaaStr AI 2026 on rebuilding a sales org from scratch: - 54% of new enterprise logos now come self-serve. Real ACV, real terms, no AE in the loop - You can't hire your way out of vertical demand. Even 5x the team can't absorb it - They didn't rip out the stack. They threaded Claude through it - The PLG vs SLG religion is dead. One funnel, two paths - A support tool (Intercom Fin) got retooled into the self-serve sales engine - Every rep starts the day in an AI brief, not an inbox - Forecast calls became discussions, not data scrubs - Slack is now the front door for legal, deal desk, and RevOps. Ticket in, ticket out - They codified their best reps as 5 Skills every rep can run - New reps skip the six-week ramp. Boot camp, territory, plug-in, go Almost none of it required new software.
Jason ✨👾SaaStr.Ai✨ Lemkin@jasonlk

54% of Anthropic's new enterprise logos in 2026 came through self-serve. Self-serve enterprise. Real ACV. Real terms of service. No AE in the loop. Anthropic's Head of Industries Eleanor Dorfman walked through at SaaStr AI 2026 last week how they rebuilt the entire sales org in 30 days after Claude Opus 4.6 broke their demand curve in December. 👉The constraint: couldn't 3x or 4x the sales team fast enough without lowering the recruiting bar. The thesis: don't buy a new stack. Thread Claude through the one you already have. What they kept: 1⃣ Clay for enrichment 2⃣LeanData for routing 3⃣ @salesforce as system of record 4⃣@Gong_io for call coaching 5⃣Ironclad for contracts 6⃣@slackhq for everything else What they added: Claude as the connective tissue between all six. The four moves: 1/ Killed the PLG vs SLG orthodoxy. Launched enterprise self-serve in January. Intercom Fin guides the buyer through the journey. Now 54% of new enterprise logos. 2/ Threaded Claude through the existing stack. Every AE starts the day with a "morning brief" Skill that pulls context from Gmail, Gong, Slack, Salesforce, @intercom, Greenhouse. 3/ Made Slack the front door for every support function. Slack ticket in, Jira ticket out. Claude triages and resolves inline if it matches precedent. Escalates with full context if not. 4/ Codified what the best reps do as Skills. Every new rep gets a sales plug-in with 5 Skills: morning brief, call prep, customer follow-up, competitive intel, create-an-asset. Anthropic didn't replace anything. They invested in the stack they already had and let Claude be the seam between everything. Most companies will spend 2026 evaluating AI-native sales platforms. But Anthropic did it with its current stack + Claude. Almost none of it required new software.

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Gavin Winchell
Gavin Winchell@GavinWinchell·
@pipelineclub100 the stress isn't in your head, it's in your pipeline math. you feel it when you're carrying 2x coverage and telling forecast it's 4x. learn your real stage-to-stage conversion rate and most of the panic goes away. it's not a mindset problem, it's arithmetic you're avoiding.
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Pipeline Guy
Pipeline Guy@pipelineclub100·
What are your best tips for keeping the quota stress at bay as an AE? (Will repost ones I like)
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Gavin Winchell
Gavin Winchell@GavinWinchell·
quota stress is mostly forecast theater. the number does not move because you stared at it sunday night. it does not move because you re-built the pipeline sheet a fourth time. the deal you are actually sweating already closed or died six weeks ago, in a discovery call where nobody asked the budget question out loud. you are not behind on quota. you are behind on the truth about three deals.
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Gavin Winchell
Gavin Winchell@GavinWinchell·
the real problem with a $500k raise in 2026 isn't build cost. ai did crush that. it's the sales cycle. enterprise runs 9 months from first call to signature, and $500k can't fund a single AE long enough to land one logo before the runway's gone. how are you underwriting GTM time, not just product?
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Brent Fulfer
Brent Fulfer@Brent_Fulfer·
A founder pitched me Sunday asking for $500k. I told him to go find angels. Raising $500k in 2026 isn't a seed round. It's a signal you don't have a big enough vision. In the age of AI you can build more with less — but $500k doesn't build a company. It builds a prototype nobody funds next. Raise enough to actually win or don't raise at all. Stop wasting time with bad fundraise strategy. 👇
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Gavin Winchell
Gavin Winchell@GavinWinchell·
Self-serve gets you to the demo. It doesn't get you past the economic buyer who never showed up to the demo. Product-led works right up until procurement and security review, and that's exactly where 'no decision' kills the deal. What category have you actually seen close enterprise with no human in the room?
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Jason ✨👾SaaStr.Ai✨ Lemkin
So there’s an argument that today sales isn’t as important in B2B as it used to be. Still important, just not as much as it used to be. Bear with me here. It’s not an argument I agree with per se. But I can’t argue with the logic. The point is just this: the world has bifurcated. The hottest B2B + AI companies still need sales teams. Anthropic and OpenAI have sales teams. So do Replit, Lovable, Harvey, Legora, Sierra, and just about everyone at scale. But the argument is that since so much of the demand is in-bound, and growth in so insane at these leaders, that sales is more of the caboose than the engine in GTM. That yes you need a sales team, but it’s not what’s driving epic growth. And on the other hand, folks not benefitting from AI budgets have seen growth plummet. And even the best sales teams can’t convince folks to buy products they don’t want to buy. Put differently, pre-AI, many B2B start-ups were growing at roughly similar rates. A great sales team though could get you from 80% to 120% growth. A huge difference, compounded. But if you are already growing 500%+ a year, or on the other hand, only growing 15% a year, then sales still matters. But it’s different. More a cog in the wheel. Rather than the wheel itself.
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Gavin Winchell
Gavin Winchell@GavinWinchell·
@paulg Same in cold outbound. The jargon is there to make the rep sound credible, but it just makes the email skippable. Cut it to plain words a busy person reads in five seconds and replies move. A high standard for clarity is the edge in a cold inbox too.
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Paul Graham
Paul Graham@paulg·
The most important component of writing clearly is simply to have high standards for clarity. Then if you write something unclear, you notice, and ask: what did I mean to say? You can just keep doing this over and over. And if you have high standards for clarity, you will.
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Gavin Winchell
Gavin Winchell@GavinWinchell·
@GoldilocksOrbit This is exactly it. Cold threads that turn into meetings almost never open with a pitch, they open with a specific trigger. A line like 'saw you posted three SDR roles, building the team or replacing a tool?' gets a reply because it names the waste they already feel.
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Jagan
Jagan@GoldilocksOrbit·
Stop thinking about a big go to market plan. For bootstrapped teams, your GTM is a series of painful, direct conversations. Find the single person who wastes the most time, and build the direct line to stop that waste. That's the entire operation.
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Gavin Winchell
Gavin Winchell@GavinWinchell·
Stopped opening with 'just wanted to reach out' six weeks ago. Reply rate roughly doubled. Now I lead with the trigger: 'you posted 3 SDR roles this month.' One prospect wrote back 'finally, someone who read my page.' Relevance is the whole game.
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