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May 4, 2026 - Deals

Sierra Raises $950 Million In Series E Round Led By Tiger Global And Google’s GV

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Sierra, the AI startup cofounded by OpenAI chair Bret Taylor and Clay Bavor, raised $950 million in a Series E round led by Tiger Global and Google’s GV, with participation from Benchmark, Sequoia, Greenoaks and others, pushing its post-money valuation to $15.8 billion from $10 billion last fall. The company, which builds AI customer service agents for enterprise clients, says the new capital will help it scale amid intensifying competition in the fast-growing AI agents market and deepen its lead as demand from large enterprises accelerates. FOUNDERS: Bret Taylor & Clay Bavor INVESTORS: Tiger Global, Google’s GV, Benchmark, Sequoia & Greenoaks ROUND: Series E AMOUNT: $950,000,000 HQ: San Francisco, California #VentureCapital #Sierra #BretTaylor #ClayBavor #TradedVC

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Puppy Sphere Secures Seed Round Of $24 Million From Strategic Investors Including The School Of Hard KnocksPuppy Sphere (@ThePuppySphere), a New York-based wellness brand centered on the human-animal bond, has raised a Seed round from a group of strategic investors including The School of Hard Knocks, Tobi Oluwole, Jake Fleshner, Torch Collective, former Massage Envy CEO David Humphrey, and other founders and operators. Founded by Francesca Albo and Lea Burbidge Izquierdo, Puppy Sphere has scaled its puppy yoga concept into a broader experiential wellness platform with 13 studios, corporate wellness programs, brand partnerships, and live activations, serving more than 450,000 customers and partnering with companies including Google, Amazon, Netflix, TikTok, and the NBA. FUN FACT: Puppy Sphere was born from two Canadian founders’ own mental health journeys and has since grown into 13 studios across North America, $14M+ in cumulative revenue, and 450,000+ customers, all without outside capital. Along the way, the brand has welcomed names like Sabrina Carpenter, Simu Liu, Trevor Noah and Alessia Cara, while building a broader wellness platform around the gentle power of puppy therapy. Now Puppy Sphere is opening its cap table for the first time through a strategic angel round, bringing together leaders across media, consumer growth and wellness, including The School of Hard Knocks, former Massage Envy CEO David Humphrey, growth entrepreneur Tobi Oluwole, and Nucleus Network co-founder Jake Fleshner, alongside a broader group of strategic founders and operators. The vision: bring the gentle power of puppy therapy across the globe. FOUNDERS: Francesca Albo (@FrancescaaAlbo), Lea Burbidge Izquierdo (@LeaburbIz) INVESTORS: The School of Hard Knocks (@TheSchoolofHardKnockz), Tobi Oluwole (@TheTobiOluwole), Jake Fleshner (@JakeFleshner) Torch Collective, Heather Stark, Will Bodewes, Craig Zingerline & more ROUND: Seed VALUATION CAP: $24,000,000 HQ: New York, New York #VentureCapital #PuppySphere #TradedPartner #FrancescaAlbo #TradedVC