Bret Taylor, co-CEO of Salesforce, speaks at the Viva Technology Conference in Paris on June 15, 2022.
Nathan Laine | Bloomberg | Getty Images
Artificial intelligence startup Sierra, co-founded by ex-Salesforce co-CEO Bret Taylor, is more than quadrupling its valuation to $4.5 billion in a fresh funding round.
The San Francisco-based company, which was valued at $1 billion in January, raised $175 million in a funding round led by Greenoaks Capital. The Information reported earlier this month that Sierra was in the midst of raising capital.
Taylor is chairman of OpenAI’s board and previously ran Salesforce, alongside Marc Benioff. He was also chairman of Twitter when Elon Musk was negotiating to buy the social media company. Taylor is a longtime entrepreneur, widely credited with helping to create Google Maps. At Google, he met his Sierra co-founder Clay Bavor, who spent nearly two decades at the tech giant, leading virtual reality efforts and Google Labs.
Sierra is focused on helping enterprises like home security company ADT, Sonos, Weight Watchers and Casper personalize and implement AI agents for customer service. Taylor and Bavor unveiled the startup earlier this year.
“We think every company in the world, whether it’s a technology company or a 150-year-old company like ADT, can benefit from AI, and the technology is ready right now,” Taylor told CNBC in an interview. “We want to enable Sierra to address that market, and that means expanding internationally and to other industries.”
ICONIQ and Josh Kushner’s Thrive Capital contributed to the new funding round.
Taylor describes Sierra as “conversational AI,” and bristles at the word “chatbot,” even banning the phrase in the company’s downtown San Francisco office. Sierra is looking to create a more conversational style of interaction, Taylor said. He pointed to the ease of OpenAI’s ChatGPT and compared it to the frustrating experience of talking on the phone with an airline bot.
“When you think of chatbots, you think of those annoying, robotic things — you can feel the difference,” Taylor said, adding that Sierra is making their agents more “empathetic and conversational.”
Sierra’s team lets each client customize the agent’s personality to its corporate brand. Clothing company Chubbies, for example, took a more sarcastic route with a younger sounding agent named Duncan Smothers. Taylor said some luxury brands are opting for a British accent with a more serious tone.
“We really think that your conversational AI agent should be not only transactional, but a brand ambassador,” Taylor said. “It’s actually something that is a statement of your values. So do you want to be sarcastic? Do you want to use emoji? Do you want it to sound like text messaging, or do you want it to sound like a lawyer?”
Sierra uses what Bavor and Taylor describe as a “constellation” of models, with a “supervisor.” The technology uses one model to do the heavy lifting, with the expectation that it won’t be 100% reliable, but use a second model as a backup, to “check” the others and help with accuracy. The company currently relies on large language models from OpenAI, Anthropic and Meta, among others.
There’s competition in the space. Taylor’s former company, Salesforce, as well as Microsoft, in partnership with OpenAI, are exploring the AI agent space. Taylor compared Sierra to the companies that built cloud software on top of Amazon Web Services and other cloud infrastructure.
“In the cloud era, you had Shopify, Salesforce, ServiceNow and Adobe — I think the same thing will play out in AI with Sierra,” Taylor said. “We’re helping their branded customer facing agent.”
He mentioned startups like Cursor, which makes coding agents, and Harvey, which makes legal agents.
Sierra’s funding follows a flurry of major AI announcements in Silicon Valley. OpenAI raised billions of dollars at a $157 billion valuation. Perplexity is in the midst of raising a round that values the company at $9 billion, a source confirmed to CNBC. One in three venture dollars this year has gone to an AI startup, according to CB Insights.
“When a technology wave like this happens, I think a lot of people are trying to place their bets,” Taylor said. “I don’t know which company will win, but it’s a smart investment, categorically. Clearly customer experience and customer service is a huge opportunity, and I think we are the leader in this space, and seeing a lot of demands because of that.”
Fixed-income markets recorded significant re-pricing during the week ending July 25, 2026, as a convergence of strong labor market metrics and surging energy costs drove U.S. Treasury yields higher across all maturities. The benchmark 10-year Treasury yield climbed toward 4.70%, reaching its highest point in several months. Institutional bond investors rapidly adjusted portfolio durations as expectations for near-term interest rate cuts by the Federal Reserve faded in response to inflation concerns.
The upward shift in sovereign yields reflects a broader fundamental reassessment of global monetary policy. Earlier in the quarter, money markets had priced in a series of rate reductions designed to support economic activity. However, with initial jobless claims falling to 187,000 and crude oil breaching $100 per barrel, fixed-income traders are pricing in a ‘higher-for-longer’ interest rate environment. The inversion between short-term Treasury bills and long-term bonds narrowed, indicating a shift toward term premium expansion.
Rising Treasury yields present both challenges and opportunities for institutional wealth managers. While commercial lenders and mortgage origination volumes face headwinds from elevated borrowing costs, fixed-income investors are locking in attractive real yields on high-quality sovereign and investment-grade corporate bonds. Institutional debt issuers, conversely, are recalibrating their capital structures, opting for shorter-term refinancing instruments or private credit facilities to avoid committing to elevated long-term coupon rates.
Navigating the current bond market landscape demands strict duration management and credit selection. Wealth advisors recommend maintaining flexible fixed-income allocations, combining short-duration Treasuries with inflation-protected securities (TIPS) to shield capital against potential energy-driven inflation spikes while earning dependable nominal income.
Private credit markets reached a pivotal milestone during the week ending July 25, 2026, as non-bank direct lending consortiums captured a record share of middle-market corporate debt originations. With commercial banks maintaining conservative credit standards and public bond yields remaining elevated, corporate borrowers are increasingly turning to private fund managers for customized capital solutions. This expansion marks a permanent structural shift in enterprise finance, establishing private credit as a primary pillar of institutional corporate liquidity.
The acceleration of private credit deals is driven by speed, deal certainty, and flexible terms. Unlike traditional syndicated bank loans that require lengthy underwriting, credit rating approvals, and public roadshows, private direct lenders can structure tailored financing packages within days. Middle-market firms facing upcoming debt maturities are utilizing private debt facilities to execute recapitalizations, strategic acquisitions, and growth capital deployments without risking execution delay in public markets.
However, financial regulators and central bank supervisors are scrutinizing the sector’s rapid growth. Supervisory agencies are evaluating potential systemic risks associated with non-bank leverage, valuation transparency, and liquidity mismatches during economic downturns. Despite regulatory interest, major pension funds, insurance firms, and sovereign wealth entities continue to expand capital allocations to private credit funds, attracted by reliable floating-rate yields that outperform public fixed-income benchmarks.
As private credit matures into a dominant asset class, corporate chief financial officers must evaluate non-bank lenders alongside traditional banking relationships. Direct lending partnerships provide valuable balance sheet resilience, enabling companies to secure flexible financing terms even during periods of public market turbulence.
The landscape of institutional debt markets is undergoing a profound structural shift on July 21, 2026, as major corporate issuers and commercial banks rapidly accelerate the deployment of tokenized debt instruments. Data published by leading capital market consortiums indicates that primary issuances of digital commercial paper and tokenized corporate bonds have reached record volumes this month. By moving legacy debt origination, underwriting, and secondary distribution onto permissioned distributed ledgers, corporate treasurers are unlocking unprecedented operational flexibility and instantaneous cross-border liquidity.
The adoption of tokenized debt is fundamentally altering how enterprise balance sheets manage short-term liquidity needs. Traditional corporate bond settlement cycles historically required multi-day clearing processes involving numerous intermediaries, custodial entities, and clearinghouses. Through programmable smart contracts on distributed ledgers, issuers can now execute atomic settlement—enabling continuous, 24/7 access to institutional capital pools. This instantaneous clearing mechanism drastically reduces counterparty risk, eliminates costly settlement friction, and allows treasury teams to dynamically optimize working capital in real time.
A major catalyst driving this institutional migration is the establishment of comprehensive digital asset regulatory frameworks across major financial hubs. Clear legal guidelines regarding ledger-based securities ownership have provided institutional compliance officers with the regulatory confidence necessary to transition multi-billion-dollar liquidity facilities onto digital platforms. Furthermore, the integration of automated regulatory reporting directly into token smart contracts simplifies ongoing compliance audits, ensuring that secondary market trades automatically enforce investor accreditation limits and tax withholding requirements.
For chief financial officers and institutional portfolio managers, tokenized debt represents a fundamental evolution in fixed-income strategy. Companies that embrace ledger-based debt structures gain direct access to a broader, global base of digital-native institutional investors while substantially reducing borrowing overhead. As ledger interoperability continues to improve across global exchanges, tokenized debt is poised to become the standard infrastructure for global corporate finance.