1 Sierra raises $950M at a $15.8B valuation — AI customer service is the new platform layer
Bret Taylor's Sierra closed a $950M round led by Tiger Global and Google's GV at a $15.8B post-money valuation, up from $10B last fall. Existing investors Benchmark, Sequoia, and Greenoaks all rolled in. The startup hit $150M ARR in eight quarters — unprecedented for traditional software — with customers including Prudential, Cigna, Blue Cross Blue Shield, Rocket Mortgage, one in three of the world's largest banks, and 40%+ of the Fortune 50.
Customer service was the soft underbelly of every B2C brand — outsourced, off-shored, and silently broken. Sierra is making it the front door to the brand. If your AI agent is the first conversation customers have with you, it's also the first place your brand voice, pricing, and offer logic live. That's no longer a contact center decision — it's a marketing decision, and the buyer is now the CMO.
2 OpenAI launches "The Deployment Company" — a $10B JV with TPG to embed engineers inside enterprises
OpenAI finalized a $10B joint venture anchored by TPG with 19 investors including Brookfield, Advent, and Bain Capital. OpenAI's contribution: a $500M equity check at close with an option for another $1B later. The structure embeds OpenAI engineers inside client orgs Palantir-style. Healthcare, logistics, manufacturing, and financial services are the priority sectors. Investors get a 17.5% guaranteed annual return over five years.
Anthropic announced a parallel $1.5B venture last week with Blackstone, Hellman & Friedman, and Goldman. Two of the top labs just stopped pretending they're SaaS companies and started building consultancies — at consulting margins, but with engineering inside the deal. For brand and marketing teams, the practical effect is the same: the people deploying generative AI inside your enterprise are now investor-backed, scale-trained, and looking for marketing use cases where the ROI is clean.
3 Pinterest Q1: $1B revenue, +18% — Performance+ now drives 30% of lower-funnel revenue
Pinterest reported Q1 revenue of $1.008B (+18% YoY, +15% constant currency), MAUs of 631M (+11%), and a 20% adjusted EBITDA margin. Performance+ — Pinterest's AI-powered performance ad suite — now accounts for ~30% of lower-funnel revenue. Ad pricing dropped 5%, but impressions grew 24%. Q2 guide of $1.13–$1.15B beat the Street's $1.11B and the stock popped 15%.
Pinterest finally has a story marketers can underwrite: AI is generating more impressions cheaper than humans can, and conversion is following. The 5% price drop matters — it's deflation in the ad market, not just at Meta and Google. If you've been parking budget on Pinterest for "test and learn," this is the quarter the test ended. The platform's own numbers say Performance+ is the only place to put new dollars.
4 Roku Q1: $1.25B (+22%), DSP ad spend +40%, 100M households
Roku posted Q1 revenue of $1.25B (+22% YoY), with platform revenue up 28% to $1.13B, advertising up 27%, and subscriptions up 30%. Programmatic DSP ad spend jumped 40%+. Roku raised full-year guide to ~$5B in platform revenue and crossed 100M streaming households globally. At least five Wall Street firms raised price targets between $140–$160 on May 1.
Three years of "is CTV ever going to scale?" just answered itself. The DSP number is the one to circle: programmatic buying inside Roku grew 40%+ while linear TV continued its slow contraction. CTV is no longer a growth narrative — it's the load-bearing wall of TV ad spend. Which makes next week's upfronts the most important pricing moment of the year.
5 Spotify reboots Sponsored Playlists + tests Carousel Ads — Priceline, eBay, GNC are the betas
Spotify revamped Sponsored Playlists to give brands 100% share of voice on flagship lists like RapCaviar, New Music Friday, and Today's Top Hits with much more visually prominent placements. Carousel Ads — a new swipeable display format in Now Playing showing up to six cards with images, descriptions, and unique links — launched in beta with Priceline, eBay, and GNC. Companion research, "The Sound-On Era," dropped from 5,000 consumers, 105 advertisers, and 30 experts.
Audio platforms are finally treating display real estate like display real estate. Spotify spent years selling host-read podcast spots and audio creative. The honest version is that most audio impressions are wasted — listeners aren't looking. Carousel Ads concede that and put a small visual unit where attention actually lives (the Now Playing screen). The brands that figure out how to write a swipeable card-based story for an ear-first user will own the format.
6 Perplexity drops the Comet paywall — free worldwide, ad-targeting baked in
Perplexity moved its AI browser Comet from $200/month to free across iOS, Android, Windows, and Mac. The pitch: a personal AI that browses with you. The company has publicly stated that Comet is "partly designed to collect customer data for ad targeting" — full browsing and search history flow back into Perplexity to build profiles, with no current opt-out in the app. (Earlier this year Perplexity formally dropped ads inside its core answer product, calling it a trust decision.)
This is the textbook "give the razor away" move — except the razor is your browser and the blades are your behavioral data. Don't expect the absence of ads inside Perplexity to last. The economics make it inevitable that ad targeting comes back, this time grounded in a richer signal than search history alone. If you sell to Comet's likely audience (paid Perplexity users and AI early adopters), the targeting they're building will probably be among the cleanest available next year.
7 Microsoft AI Max for Search hits open pilot — across Bing, Copilot Search, Copilot Answers
Microsoft Advertising opened the AI Max for Search pilot in May, extending AI-assisted campaign tools across Bing, Copilot Search, and Copilot Answers. Features include expanded query matching, URL routing, brand inclusions/exclusions, term exclusions, and audience generation in closed pilot in the US and Canada — describe your audience in a prompt, AI translates it into targeting settings. Search term and asset reporting ship immediately.
The under-discussed story of 2026 is that Microsoft Ads quietly went from "Bing search ads" to "the only major ad platform with paid distribution inside an AI assistant most people actually use." Copilot's user base now matters to advertisers in a way it never did to consumers. AI Max is the lever Microsoft pulls to convert Copilot interactions into bid logic — and if it works, the Bing/Copilot stack becomes the cheapest entry point into AI search inventory.
8 YouTube Brandcast set for May 13 at Lincoln Center — Trevor Noah hosts, $100B paid to creators
YouTube's annual upfront pitch lands May 13 at Lincoln Center with Trevor Noah hosting and Chappell Roan performing. CEO Neal Mohan, CBO Mary Ellen Coe, and Google President Sean Downey will pitch advertisers on YouTube as "the future of media." The creator lineup includes Adam W (21M), Alex Cooper (2M), Dude Perfect (61.8M), and Jesser (38.5M). The headline number: YouTube has now paid $100B+ to creators.
YouTube's argument is simple: the linear TV upfront is selling reach inside a shrinking pie; YouTube is selling reach inside the platform that already won. That $100B paid-to-creators number is the unanswerable one — there's no equivalent on broadcast. For brands choosing how to allocate their next upfront commitment, YouTube increasingly treats the question as already settled.
9 Upfront week May 11–13 stacks up tight — NBCU + Amazon Monday, Disney Tuesday, Discovery Global solo at MSG Wednesday
The Big Week stacks up tight: NBCUniversal at Radio City and Amazon Ads at the Beacon both kick off Monday May 11. Disney is at the North Javits Center on Tuesday May 12 with ESPN's standalone streamer as the headline pitch. Discovery Global runs its first solo upfront — post-WBD restructuring — at Madison Square Garden on Wednesday May 13. The previous NBCU upfront saw Peacock streaming volume hit ~1/3 of the company's total commitments. Disney closed last year with sports advertising near $4B and streaming volume above 40% of total upfront commitments.
For the first time in a decade, the upfronts feel like a competitive market again — not a polite ritual. Streaming is now 40%+ of upfront commitments at the big networks. Sports continues to be the only inventory advertisers won't move off. Watch Discovery Global's solo debut closely: it's the first time post-merger that linear-cable inventory has to defend itself without a Warner Bros. studio slate to justify pricing. This is the week budgets get committed for the next 12 months.
10 Cannes Lions 2026 honors Oprah Winfrey with the LionHeart — and adds a "Deconstructed" track
Cannes Lions revealed the 2026 programme — June 22–26 in Cannes — and named Oprah Winfrey as the LionHeart honoree, recognizing those who use their platform to drive lasting positive change. The new "Cannes Lions Deconstructed" stream will spotlight emerging voices reshaping the industry across innovation, technology, culture, talent, and impact. Six total content streams plus a new two-day "business of competition" programme on June 24–25.
For the second year running, Cannes Lions is positioning itself less as a creative trade show and more as a transformation summit. "Deconstructed" is the festival's quiet acknowledgment that the agency model the festival was built around is itself being deconstructed. If you're building a brand without a holdco at the center of it, this year's Cannes is the most relevant it has been in 20 years.
The throughline
The week split cleanly into two markets that, until now, mostly operated in different time zones. AI infrastructure is locking in: Sierra's $15.8B says agents are a permanent platform layer, OpenAI's $10B Deployment Company says the AI labs are now consultancies, and Microsoft AI Max says the only place AI ad inventory exists at scale is also a place advertisers can already buy.
At the same time, Madison Avenue's biggest week of the year is about to begin. Pinterest and Roku just gave that week a tailwind: AI-powered performance is actually working at meaningful scale, and CTV is now load-bearing. Next week's upfronts will price the next 12 months of TV money on the assumption that AI keeps improving conversion. That bet just got more credible.