S

Sierra

AI agents for real-time customer support

Software Engineer Intern - Agent

Summer 2027
No salary listed
Internship
Bachelor's, Master's
San Francisco, CA, USA+1 moreMore locations: New York, NY, USA
In Person

About the job

Requirements
  • Pursuing a bachelor's or master's degree in computer science or a related field.
  • Demonstrated technical problem-solving skills, especially in fast-changing and ambiguous environments.
  • Ability to find creative ways to overcome obstacles and ship work.
  • Ability to communicate clearly, directly, and persuasively with technical and non-technical audiences.
Responsibilities
  • Work directly on production artificial intelligence agents for customers.
  • Contribute to the design and development of artificial intelligence agents.
  • Ship features and learn from real-world use cases at scale.
Desired Qualifications
  • Experience building or deploying artificial intelligence or large language model systems in production.
  • Familiarity with evaluation frameworks, agent tooling, retrieval-augmented generation pipelines, and prompt engineering.
  • Prior experience with React, TypeScript, or Go.

About the company

Sierra.ai builds and deploys conversational AI agents for customer service that handle real-time interactions and take actionable steps within a client’s systems (e.g., CRM, order management) to resolve issues. The agents are always-on, empathetic, and aligned with a client’s brand voice, following strict policies and security procedures. They operate deterministically, with built-in quality assurance that reveals the reasoning behind each interaction, ensuring transparency. The platform is subscription-based and scales to large client ecosystems, serving brands like Sonos, SiriusXM, and WeightWatchers, with a reported CSAT of 4.6/5 and a 70% resolution rate. Sierra.ai emphasizes data governance, using client data only to train models and securing it with industry-standard practices. Its goal is to improve customer experience by delivering real-time, automated support that can understand, resolve, and learn from interactions while remaining controllable and auditable.

Company Size

1,001-5,000

Company Stage

Series E

Total Funding

$1.6B

Headquarters

San Francisco, California

Founded

2023

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Simplify Jobs

Simplify's Take

What believers are saying

  • Liberty Global signed a three-year Sierra rollout on September 23, 2026.
  • Sierra announced AIUC-1 certification on September 17, 2026, strengthening regulated-enterprise sales.
  • Sierra said September 28, 2026 it exceeded $150 million ARR and joined OpenAI Marketplace.

What critics are saying

  • Salesforce and OpenAI can bundle Sierra-like agents, crushing pricing by 2027.
  • Outcome-based revenue flattens after support automation saturates, forcing constant new-logo growth.
  • Liberty Global's 80-million-connection rollout starts phased; slow implementation would expose Sierra's concentration risk.

What makes Sierra unique

  • Bret Taylor and Clay Bavor give Sierra unmatched enterprise credibility with Fortune 50 buyers.
  • Sierra sells outcome-based agents, charging for resolved work instead of seats or tokens.
  • Horizon agents handle long-horizon workflows across chat, voice, text, and Slack.

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Benefits

Unlimited Paid Time Off

Medical, Dental, and Vision benefits for you and your family

Life Insurance

Disability Insurance

401(k) Company Match

Parental Leave

Fertility Treatment Support

Discretionary Benefit Stipend

Growth & Insights and Company News

Headcount

6 month growth

↑ 0%

1 year growth

↓ -17%

2 year growth

↓ -3%
Value Add VC
Sep 27th, 2026
Sierra AI valuation 2026: $15.8B, $950M Series E, and ~$200M ARR.

Sierra AI valuation 2026: $15.8B, $950M Series E, and ~$200M ARR. Bret Taylor and Clay Bavor's enterprise AI agent startup went from a $1B valuation at launch to $15.8B in 27 months, on roughly $200M in annualized revenue and outcome-based pricing. Founder, Value Add Holdings LLC · 3x founder (BrandYourself, Launch.it, SPOT) · 65+ investments · Based in Boca Raton, FL 65+Investments 3xFounder $200M+Funds Tracked Quick Answer $15.8B is Sierra AI's valuation after a $950M Series E in May 2026, led by Tiger Global and GV, up from $1B when it launched in February 2024. Revenue was near $200M in annualized run-rate by that point, after crossing $100M ARR in November 2025 - about 21 months after launch. Sierra AI is valued at $15.8B after a $950M Series E in May 2026 - up from a $1B valuation at launch just 27 months earlier - on roughly $200M in annualized revenue from enterprises paying per resolved customer-service interaction rather than per seat. Bret Taylor left the OpenAI board chairmanship - he still holds it alongside running Sierra - and his own company just became one of the fastest-compounding valuations in enterprise software history. The pace matters more than the headline number: four rounds, four step-changes in valuation, in barely over two years, on a bet that AI agents replace the seat-based software model entirely. Sierra AI valuation 2026: from $1B to $15.8B in 27 months. Sierra's valuation is $15.8B as of May 2026, set by a $950M Series E led by Tiger Global and GV, with Benchmark, Sequoia Capital, and Greenoaks Capital also participating. That is up from $10B eight months earlier and from $1B when Bret Taylor and Clay Bavor launched the company in February 2024. up from $10B in Sep 2025 Valuation (May 2026) led by Tiger Global, GV Series E raised up from $100M in Nov 2025 ARR (~May 2026) since Feb 2024 launch Time to $15.8B The step-change pattern is the story. Fortune reported the February 2024 launch: a $110M round from Sequoia and Benchmark at close to a $1B valuation, before Sierra had a paying customer. By October 2024, CNBC reported a $175M round led by Greenoaks Capital at $4.5B. Less than a year after that, in September 2025, the valuation reached $10B on a $350M round. Compare Sierra against every other AI company repricing this fast on the AI Valuations dashboard. The revenue behind the number: ~$200M ARR on outcome-based pricing. Sierra crossed $100M in annualized recurring revenue in November 2025, about 21 months after launch - a pace TechCrunch called out as among the fastest for enterprise software. By the May 2026 raise, reporting around the round put run-rate near $200M, though Sierra has not disclosed a newer figure since. At $15.8B on roughly $200M ARR, that's close to 79x revenue - a multiple that only holds up if growth keeps compounding at 2025's pace. The mechanism behind that revenue is unusual: Sierra doesn't sell seats or API credits. It charges roughly $1.50 for every customer interaction its AI agent actually resolves, an outcome-based model Taylor has argued repeatedly is the correct pricing unit once software does the work itself rather than assisting a human who does. Value Add VC break down the full mechanics - pricing tiers, margin structure, and what "resolved" means contractually - in how Sierra AI makes money. Disclosed customers span ADT, Sonos, WeightWatchers, and Casper - physical-product and subscription businesses with high support-ticket volume, which is exactly where outcome-based pricing has the clearest ROI story to sell into a procurement committee. Sierra vs decagon, Agentforce, and Intercom Fin on price. Every credible competitor in enterprise AI customer agents has converged on some version of outcome- or resolution-based pricing, which makes the per-interaction rate one of the few apples-to-apples numbers across the category. Decagon and Salesforce Agentforce price custom enterprise contracts rather than publish a flat per-resolution rate, so they are not shown on this chart. Decagon is the closest AI-native challenger by growth trajectory, and Salesforce Agentforce and Zendesk AI are the incumbent-platform answers - Sierra's pitch against both is that it's vendor-neutral rather than bundled into a CRM or helpdesk you may not already run. Salesforce closed its acquisition of Intercom's Fin on September 10, 2026, folding a direct competitor into the same incumbent camp Sierra is positioned against. The bull case: pricing software like labor, not seats. If Sierra is right that AI agents should be priced on completed work rather than logins, it has built the pricing model the rest of the category will eventually copy - and being first with the enterprise logos and the renewal data to prove the model works is a real moat. Outcome-based pricing also aligns Sierra's revenue directly with the value it delivers: as its agents resolve a larger share of a customer's support volume, revenue scales with them, without a separate sales motion to expand seats. Where I could be wrong. A 79x-revenue multiple prices in years of continued hypergrowth, and outcome-based pricing has a structural ceiling problem: once an enterprise's AI agent resolves nearly all of its support volume, that customer's spend flattens - there's no more "seats to add." That's the opposite of traditional SaaS expansion revenue, and it means Sierra needs a constant stream of new logo growth rather than compounding existing accounts as heavily. The other risk is competitive: Salesforce folding Fin into Agentforce and Zendesk running its own resolution-priced agent both show the incumbents can copy the pricing model without needing Sierra's valuation multiple to make the economics work for them. Explore related dashboards. Interactive tools with live data on this topic Track Sierra and the rest of the enterprise AI agent category on the AI Valuations Dashboard at Value Add VC. Latest from the pulse. Get VC data most people never see - 100% free Weekly benchmarks, valuations, and fund data. Join 5,000+ investors. No spam. Frequently asked questions. What is Sierra AI's valuation in 2026? How much revenue does Sierra AI have? How does Sierra AI make money? Who are Sierra AI's investors? What companies use Sierra AI? Is Sierra AI going to IPO? Related tools & dashboards. Explore 45+ free VC tools, dashboards, and recommended startup software.

TelecomTV
Sep 24th, 2026
Liberty Global signs strategic partnership with Sierra to rollout AI-powered customer experiences.

Liberty Global signs strategic partnership with Sierra to rollout AI-powered customer experiences. Sep 24, 2026 * Framework agreement underpins phased deployment across Liberty Global operating companies * AI-powered customer interactions will create simpler, faster and more effective customer journeys allowing care teams to focus on more complex tasks DENVER and LONDON: Liberty Global today announced a three-year strategic partnership with Sierra, a conversational AI platform that is redefining how businesses interact with their customers, to support the rollout of its technology across Liberty Global operating companies. Liberty Global is accelerating the use of AI across its businesses to make customer interactions easier, more intuitive and more effective. The framework partnership agreement provides Liberty Global's businesses with a common approach to deploy AI agents capable of engaging customers in natural language, across chat, voice and text. By enabling AI agents to handle routine and increasingly complex interactions, the partnership will also allow customer-care teams to focus more of their time on situations requiring human judgement and deep expertise. Liberty Global will deploy Sierra across its approximately 80m fixed and mobile connections in Europe through a phased programme, with implementation already started and the use cases and channel mix tailored to the requirements of individual markets, brands and customers. Founded by Bret Taylor, former Co-CEO of Salesforce and Chairman of OpenAI, and Clay Bavor, former Google executive, Sierra has emerged as the leading company in the customer experience AI space. The company was valued at $15bn in its latest funding round in May 2026 and its platform is already used by more than 40% of the top 50 companies in the Fortune 500 and one in three of the leading banks, powering billions of customer interactions in industries such as financial services, retail, telecommunications, healthcare and more. Mike Fries, Liberty Global Chairman and CEO, said: "Sierra has built a game-changing platform that we are excited to deploy across our footprint. By combining Sierra's technology and deployment expertise with the deep knowledge of our local teams, we will deliver better customer experience across our group by making customer journeys simpler, faster and more effective." Bret Taylor, Sierra CEO and Co-Founder, said: "We're excited to partner with Liberty Global - a pioneer in applied AI and a telecommunications leader with significant scale, expertise and a deep understanding of European customers. This partnership is a strong vote of confidence in Sierra's ability to improve customer experiences, reduce the burden on support teams and grow revenue. We look forward to working with Mike and the team as we roll out agents across Liberty Global's companies." ABOUT LIBERTY GLOBAL Liberty Global Ltd. (Nasdaq: LBTYA, LBTYB, LBTYK) delivers long-term shareholder value through the strategic management of two complementary platforms: Liberty Telecom and Liberty Growth. Liberty Telecom is a world leader in converged broadband, video and mobile communications, providing approximately 80 million fixed and mobile connections across Europe through advanced fiber and 5G networks that empower customers and strengthen national economies. The business generates aggregate revenue of $22 billion, including approximately $18 billion from nonconsolidated joint ventures and $4 billion from consolidated operations. Liberty Growth invests in scalable businesses across the technology, media, sports and infrastructure sectors, with a portfolio of roughly 70 companies and funds valued at $3.4 billion.* Together, these platforms reflect Liberty Global's focus on operating, enabling and investing in businesses with strong strategic fit and the potential to deliver sustainable long-term returns. *As independently valued as of December 31, 2025.

Sierra
Sep 17th, 2026
Sierra achieves AIUC-1 certification.

Sierra achieves AIUC-1 certification. I'm excited to share that Sierra is now AIUC-1 certified, following an independent audit by Schellman and extensive testing by the Artificial Intelligence Underwriting Company (AIUC). AIUC-1 is a new standard designed specifically for AI agents, that tests how agents actually behave - including what happens when someone tries to manipulate them, access protected information, or push beyond what they're authorized to do. This matters because agents built on Sierra do more than answer questions: they coordinate patient care, troubleshoot technical issues, resolve insurance claims, and even refinance mortgages. Some of the most highly regulated companies - over 40% of the Fortune 50, one in three of the leading banks, and five out of 10 of the largest healthcare companies in the world - work with Sierra because Sierra deliver measurable results. And they can trust its platform to act safely and reliably under pressure. Putting Sierra's safeguards to the test. As part of the certification, AIUC tested Sierra chat and voice agents across everyday interactions and adversarial scenarios. The testing included attempts to manipulate agents or expose protected information, plus a range of real-world voice conditions. Separately, Schellman reviewed Sierra's technical, legal, operational, and governance controls and found that Sierra met all applicable AIUC-1 requirements. These technical evaluations recur at least quarterly, with a full audit every year so the certification continues to reflect changes in both Sierra's platform and the broader AI risk landscape. Trust throughout the agent lifecycle. At Sierra, security, safety and reliability is built into how agents are created, tested, released, and improved. Trust extends across the full agent lifecycle. Sierra applies a defense-in-depth approach, combining multiple safeguards rather than relying on any one control. Grounded content and customer-defined policies guide the agent's behavior. Once the agent is live, Supervisors evaluate conversations in real time and can correct, block, or escalate responses. Deterministic guards enforce the absolutes that cannot be left to model judgment, such as authentication and access requirements. Together, these layers help enterprises build and deploy agents they can trust. Building for what's next. Businesses still decide how their agents behave: what they know, which systems they can access, what actions they can take, and how they represent their brand. AIUC-1 provides independent validation of the platform underneath those agents. For security, risk, compliance, and AI governance teams, it means Sierra's controls have been tested against situations AI agents encounter in the real world. This certification complements Sierra's existing SOC 2 Type II attestation, and ISO 27001 and ISO 42001 certifications. Those standards validate its security and AI management systems, while AIUC-1 adds recurring technical testing designed specifically for AI agents. As agents move from answering questions to taking meaningful actions on behalf of customers, this kind of independent testing is becoming more important. Sierra'll continue investing in independent evaluation, alongside its own testing, monitoring, and product development.

Associated Press
Sep 10th, 2026
Figure partners with Sierra to cut home equity loan abandonment with AI agents that boost conversion by 143%

Figure Technology Solutions has partnered with Sierra to deploy AI agents that help recover abandoned home equity loan applications. The collaboration uses Sierra's Horizon platform to tackle a significant industry problem: only 49% of home equity applications reach closing, according to the Mortgage Bankers Association. The AI agent autonomously contacts stalled applicants via voice and SMS over several days, helping them navigate friction points like credit checks and ID verification before transferring them to human loan officers. Early results show borrowers who engaged with the agent funded 67% more loan volume. When combined with loan officers, the system achieved a 143% lift in funded loan conversion compared to loan officers working alone. This marks the first US deployment of Sierra's Horizon platform, which enables agents to handle complex, revenue-generating tasks. Figure plans to roll out the integration to network partners in coming months.

GlobeNewswire
Sep 10th, 2026
Figure partners with Sierra to supercharge Loan Officers with AI Agents that turn abandoned Home Equity applications into funded loans.

Figure partners with Sierra to supercharge Loan Officers with AI Agents that turn abandoned Home Equity applications into funded loans. * Integration with Takeoff, newly acquired by Sierra, tackles a major bottleneck in the $2 trillion mortgage industry, where less than half (49%) of home equity applications reach closing * Combining Agent with Loan Officers yields a 143% lift in funded loan conversion * First US integration for Sierra's Horizon Platform that tackles revenue-generating, long-horizon tasks NEW YORK and SAN FRANCISCO, Sept. 10, 2026 (GLOBE NEWSWIRE) - Figure Technology Solutions, Inc. ("Figure," Nasdaq: FIGR; OPEN: FGRS), the blockchain-native capital marketplace for the origination, funding, sale, and trading of tokenized assets, today announced a partnership with Sierra, the conversational AI platform co-founded by Bret Taylor and Clay Bavor. The collaboration marks the first U.S. use of Sierra's newly-established Horizon platform. Horizon enables businesses to build agents that expand beyond customer support functions to revenue-generating workflows through the ability to work for longer periods of time on complex tasks. U.S. homeowners currently hold $35 trillion in home equity, yet complex documentation requirements often lead to excessive friction and application abandonment. According to the Mortgage Bankers Association's 2025 Home Equity Lending Study, average closing pull-through for Home Equity Lines of Credit (HELOC) was just 49% in 2024, with nationwide HELOC volume at $271 billion in 2025. Taking into account fees, interest and marketing costs, abandoned applications represent a major bottleneck for originators in the $2 trillion mortgage industry. The Figure Agent is powered by Sierra's Horizon platform and was trained by Figure to work natively in its Loan Origination System. The agent reaches out to stalled applicants via voice and SMS, operating autonomously over days. It progresses stagnated applicants and brings them closer to conversion by assisting borrowers through routine friction points such as credit check permissions, ID verification, and bank account linking, and then seamlessly transfers them to an Loan Officer (LO) to finalize the loan. "Enterprise AI is increasingly moving beyond reactive, cost saving use cases to complex, revenue-generating opportunities that can deliver additional growth and help innovative companies differentiate themselves in highly competitive industries," said Bret Taylor, Co-Founder of Sierra. "Accessing home equity is a complex, high-friction workflow that presents a perfect use case. Figure is a likeminded leader, bringing transformational technology and data transparency to capital markets, and we're so proud to partner with them." Early results[1] demonstrate significant conversion gains: * Stalled applicants who interacted with the Figure Agent progressed through individual friction stages at a 30-52% higher rate than those who didn't. * Borrowers who engaged with the Figure Agent, whether with or without Loan Officer assistance, funded 67% more loan volume. * Combining the Figure Agent with Loan Officers yields a 143% lift in funded loan conversion when compared to Loan Officers operating alone. Following success with its pilot, Figure plans to make the integration available to partners in its network over the coming months. "The future of mortgage is human-agent synergy, and Sierra was the natural partner for Figure to harness that future to improve our partners' revenue outcomes. The results we have seen, in particular the reduction in the industry scourge of abandonment, is a testament to the simplicity and automation of our marketplace. There is no other capital market that could offer the simple, deterministic training ground to an AI agent and get these incredible results," added Michael Tannenbaum, Chief Executive Officer at Figure. "We founded Takeoff in the belief that building deeply integrated solutions directly tied to business results is the future of enterprise software," said Aakash Thumaty, Founder of Takeoff and GM of Horizon. "By bringing our long-horizon agent architecture with infinite patience to Sierra, and integrating natively into Figure, AI co-pilots are executing complex, multi-day financial tasks alongside human loan officers with unprecedented efficiency." About Figure Figure Technology Solutions, Inc. (Nasdaq: FIGR; OPEN: FGRS) is the leading blockchain-native capital marketplace for the origination, funding, sale and trading of tokenized assets. More than 480 partners use its loan origination system and capital marketplace. Collectively, Figure and its partners have originated over $30 billion of loans to date, among other products. The fastest growing components are Figure Connect, its credit marketplace, and Democratized Prime, Figure's on-chain lend-borrow marketplace. Figure's ecosystem also includes DART (Digital Asset Registry Technology) for asset custody and lien perfection, and $YLDS. Figure is the market leader in real-world asset (RWA) tokenization. The company has received AAA ratings ratings from S&P and Moody's on multiple loan securitizations, the first of its kind for blockchain finance. For more information, visit https://figure.com or follow Figure on LinkedIn. *Terms and conditions apply. Figure Lending LLC dba Figure. NMLS #1717824. Equal Opportunity Lender. Visit figure.com for details. About Sierra Sierra is the leading conversational AI platform, helping businesses build better customer experiences with AI. Agents built on Sierra resolve customer service issues and drive key business workflows, from account set up and troubleshooting, to originating mortgages, scheduling appointments, and saving subscribers from churning. Sierra works with over 40% of the Fortune 50, one in three of the world's leading banks, and five out of 10 of the largest healthcare companies. Leading brands like The GAP, Rocket Mortgage, SoFi, Sutter Health, and Wayfair partner with Sierra to improve customer satisfaction and drive better business outcomes. [1] Figure Performance Data Analysis Conducted July 2026