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bret taylor

T2 · manager / operator

Bret Taylor is the CEO and co-founder of Sierra, an AI agent platform for customer experience. He previously served as co-CEO of Salesforce, CTO of Facebook, and co-creator of Google Maps. He currently sits on the board of OpenAI.

19 calls·13 names·79% bull·last heard 4 months ago·Stripe+3
track record

no scored calls yet — needs a stated position or a categorical verdict, with a matured window vs SPY

top calls

highest conviction · one per company
1sthigh conviction
$SIERRASierraposition

Sierra CEO: $200M ARR, FedRAMP certification opens government market, outcomes-based pricing

Sierra has crossed $200M ARR, achieved FedRAMP certification to serve federal agencies, and pioneers outcomes-based pricing where payment only occurs on successful resolution, aligning incentives and accelerating deployment in government and enterprise.

TBPN2026-06episode →
2ndhigh conviction
$OPENAIOpenAIposition

OpenAI revenue scale unprecedented; labs racing to build self-improving AI researchers

OpenAI's revenue scale is unprecedented and all major labs are specifically investing in automated AI researchers as a prerequisite for AGI self-improvement, with OpenAI openly discussing using models to build the next generation of models.

Kleiner Perkins2026-03episode →
3rdhigh conviction
$HARVEYHarvey

Harvey admired for expanding legal tech TAM from productivity tools to AI agents doing actual legal work

Harvey transforms legal tech from a small productivity-enhancement market into a massive labor-replacement market by having AI agents perform antitrust reviews and legal work directly, dramatically expanding addressable market.

The Logan Bartlett Show2025-09episode →

most discussed · click a bar to filter

  • $SIERRA
  • $MSFT
  • $OPENAI
  • $HARVEY
  • $RDFN

recurring themes

  • AI Agents5
  • AI Economics & Business Models4
  • AI Infrastructure3
  • Enterprise Software2
  • AI Coding Agents2
19 total
$SIERRA
Sierra
HIGHbret taylor·Stripe·7 months ago·Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board· position
Sierra hits $165M ARR in 8 quarters with outcomes-based AI agent pricing
Sierra's AI agents for customer experience are scaling rapidly with outcomes-based pricing that aligns incentives; the company believes AI agents will become the primary digital interface for most businesses across voice, chat, and phone channels.
"We reached $100 million in ARR in seven quarters, $150 in eight quarters. We're, I think, around $165 now, one month into our next quarter. So growing really rapidly and really pr…"
21:00
$RDFN
···
Redfin
MEDbret taylor·Stripe·7 months ago·Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Redfin and Rocket Mortgage executing AI-native transformation of home ownership
Rocket Mortgage (owner of Redfin) is using Sierra to build an end-to-end AI agent experience across home search, mortgage origination, and servicing — a rare example of a traditional industry incumbent reimagining its core product with AI agents.
"If you go to Redfin, you can search for a home using an AI agent. If you go to Rocket.com, you can originate a mortgage with an AI agent, and you can service that mortgage. It bec…"
23:20
$MSFT
···
Microsoft
MEDbret taylor·Stripe·7 months ago·Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Microsoft cited as model for SaaS incumbents navigating AI platform shift
Microsoft's successful pivot to Azure and partnership with OpenAI demonstrates that large software incumbents can adapt to AI disruption; Taylor believes any major SaaS company could execute a similar turnaround.
"When we first met, I doubt either of us had an extremely positive view of the future of Microsoft. At the time, it felt a previous generation company. Now you look at Azure, their…"
60:30
$SOFI
···
SoFi Technologies
LOWbret taylor·Stripe·7 months ago·Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
SoFi raises NPS 33 points with Sierra AI agents for customer service
SoFi's deployment of Sierra's AI agents improved net promoter score by 33 points, demonstrating measurable customer experience gains from generative AI in financial services.
"We just did a great case study with SoFi, and I'm really proud that we raised their net promoter score by 33 points just because it's just so delightful."
21:00
$SONO
···
Sonos
LOWbret taylor·Stripe·7 months ago·Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Sonos AI agent leverages LLM's broad Wi-Fi knowledge for effective troubleshooting
Sonos uses Sierra to power an AI agent that combines product-specific data with the LLM's pre-trained knowledge of Wi-Fi issues, illustrating how general world knowledge augments domain-specific agents.
"Sonos is one of our clients... If a Sonos speaker ever breaks, it's never the speaker. It's always Wi-Fi... Why does the Sonos AI work so effectively? Well, it knows a lot about W…"
41:20
$OPENAI
OpenAI
MEDbret taylor·Stripe·7 months ago·Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
OpenAI board's non-profit fiduciary duty to humanity clarifies AGI governance
As chairman, Taylor finds the non-profit board structure — with a fiduciary duty to ensure AGI benefits humanity — uniquely clarifying for decision-making; the board was rebuilt post-crisis to balance safety, economic impact, and infrastructure expertise.
"The other thing is it's the first not-for-profit board I've been affiliated with. That's really interesting as well just because... when you're making decisions and you realize yo…"
97:00
$SIERRA
Sierra
HIGHbret taylor·Kleiner Perkins·7 months ago·How Sierra Is Pulling Ahead in the AI Race | Co-founder Bret Taylor· position
Sierra targets $400B contact center market with AI agents, hits 150M ARR in 8 quarters
Sierra is executing a land-and-expand strategy targeting Fortune 100 companies with AI agents that replace IVR systems, achieving rare 100M ARR in 7 quarters by combining senior enterprise sales credibility with AI-native junior talent, and using outcomes-based pricing plus forward-deployed engineers to ensure customer success.
"We started the company with the thesis that a lot of the impact we can have on the economy and the world is through some of the largest companies in the world. So, we said, 'Hey,…"
4:52
$OPENAI
OpenAI
HIGHbret taylor·Kleiner Perkins·7 months ago·How Sierra Is Pulling Ahead in the AI Race | Co-founder Bret Taylor· position
OpenAI revenue scale unprecedented; labs racing to build self-improving AI researchers
OpenAI's revenue scale is unprecedented and all major labs are specifically investing in automated AI researchers as a prerequisite for AGI self-improvement, with OpenAI openly discussing using models to build the next generation of models.
"OpenAI's revenue scale is truly unprecedented. There's no way to AB test what you would have needed, you know, preceding it. ... software engineering is both getting the most atte…"
39:40
$RIPPLING
Rippling
MEDbret taylor·Kleiner Perkins·7 months ago·How Sierra Is Pulling Ahead in the AI Race | Co-founder Bret Taylor
Rippling's pace-of-innovation philosophy admired as key to winning in AI era
Rippling's emphasis on pace of innovation over current product features is the right strategy for AI companies where roadmaps become archaic in 12 months, and Sierra is emulating this approach.
"I always admire sort of what the Ripple guys talk about this, but like your pace of innovation is it's is actually almost important than your product, right? Because in a world wh…"
47:20
$HARVEY
Harvey
MEDbret taylor·Kleiner Perkins·7 months ago·How Sierra Is Pulling Ahead in the AI Race | Co-founder Bret Taylor
Harvey leading credible legal AI agent market with growing competition
Harvey is a credible entrant in the maturing legal AI agent market with decent competition emerging, validating the category as a major applied AI opportunity alongside coding and customer service.
"We're really close to Harvey, one of the entrants, but there's a couple other decent players. They have competition now as well. And, um, and just like you said, they're credible…"
20:50
9
AI Agentstailwind
AI agents shift software valuation from productivity seats to outcome-based pricing tied to business results
Agents perform work (sales, support, legal review) rather than enhance productivity, enabling pricing based on business outcomes (commission-equivalent, cost-per-contact savings) rather than seat counts; this expands TAMs dramatically (e.g., Harvey in legal) and shifts customer engagement from cost center to revenue driver.
9
AI Agentstailwind
AI agents for contact centers unlocking $400B+ TAM with expanding demand
The $400B contact center/BPO market will expand as AI lowers unit costs, generating more demand (Jevons paradox), and Sierra's early traction with Fortune 20 customers proves enterprise readiness for AI agents replacing IVR systems.
9
AI Agentstailwind
AI agents will become the primary digital interface for most businesses
Conversational AI agents operating across voice, chat, WhatsApp, and phone will replace websites and apps as the main customer touchpoint; this shift expands addressable interactions by making support affordable for low-margin customers and enables new revenue-generating use cases.
9
AI Economics & Business Modelstailwind
Outcomes-based pricing disrupts SaaS seat/usage models by aligning vendor-customer incentives
Charging for resolved cases or sales commissions — not tokens or seats — creates vertical alignment where the vendor's revenue grows only when the customer succeeds; this mirrors the shift from impression to CPC advertising and forces continuous product improvement.
9
Applied AItailwind
Trillions in economic value remain unrealized from current model capabilities; applied AI market immaturity is the main adoption barrier
Even if model development paused today, trillions of dollars of value could be unlocked by building purpose-built agents for boring but critical business processes (procurement, compliance, contracting); the bottleneck is not model intelligence but the lack of applied AI companies solving specific workflows.
8
AI Infrastructuretailwind
Agent harnesses (skills, docs, guardrails) will replace APIs as the primary integration layer for AI agents
APIs expose only discrete actions; agents need rich context — documentation, rules, skills, evals — to operate autonomously. The winning SaaS model provides an 'agent harness' that teaches agents how to extract maximum value, not just an API spec.
8
Enterprise Softwareheadwind
SaaS incumbents face innovator's dilemma as business model shift to outcome-based agents threatens seat-based revenue
Transitioning from ARR/seat model to outcome-based pricing creates a 'messy middle' where revenue drops before scaling; incumbents are addicted to current product/business model and few (like Microsoft under Satya) successfully navigate such shifts, making disruption the default outcome for most.
8
AI Applicationstailwind
Applied AI companies solving business processes will outpace AI tooling plays
There are not enough applied AI companies working on high-value business processes (legal, finance, back office, marketing) versus tooling around AI itself; these vertical agent markets will go through competitive waves like coding and customer service before consolidating.