Full-Time
Updated on 8/13/2026
AI agents for real-time customer support
$170k - $200k/yr
San Francisco, CA, USA
In Person
Travel up to 30% for on-site execution.
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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
501-1,000
Company Stage
Series E
Total Funding
$1.6B
Headquarters
San Francisco, California
Founded
2023
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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
CarMax has partnered with Sierra to improve its inbound call experience using AI voice-enabled agents. Deployed in May, Sierra's technology helps customers reach the right destination or associate faster by asking conversational questions to understand their needs. The system provides quick answers to common queries about store hours and vehicle availability. Since launch, CarMax has seen increased call resolution and fewer unresolved calls. The company plans to expand capabilities to include appointment management for appraisals and test drives. The partnership demonstrates CarMax's ongoing commitment to leveraging AI technology. The retailer already operates Skye, its 24/7 virtual assistant, and was the first US auto retailer with a ChatGPT app supporting car shopping.
Sierra and Plaid have announced a partnership to enable AI agents to make payments on behalf of customers. The collaboration aims to ensure secure transactions amid rising cybersecurity threats. Plaid CEO Zachary Perret and Sierra co-founder Clay Bavor discussed the partnership, which focuses on integrating payment capabilities into AI-driven financial services whilst maintaining robust security measures. The companies are working to address safety concerns as AI agents take on more financial responsibilities in consumer transactions.
Plaid gives Sierra's AI agents live access to bank accounts. New Plaid and Sierra integration allows AI agents to access real-time banking data to streamline consumer financing and loan applications. Curated by Financing Your Way from original reporting by PYMNTS. Summary is AI-assisted and editorially reviewed - see its editorial standards. This partnership between Plaid and Sierra is a major step forward for automated consumer financing. It allows AI customer service agents to access real-time banking data during a live chat. For retailers and service providers, this means the 'wall' between a customer asking about financing and actually qualifying for it is disappearing. Instead of an agent telling a customer to go fill out a separate application, the AI can now request account access mid-conversation to verify income or account balances. This technology effectively turns an AI chatbot into a loan officer or financial advisor. When a customer expresses interest in a high-ticket purchase, the AI can pull the necessary data to provide personalized financing offers immediately. This reduces friction in the sales process and prevents customers from dropping off during the transition from your website to a third-party lender portal. By integrating Plaid's secure data fetching with Sierra's conversational AI, businesses can offer instant loan refinancing, credit limit increases, or personalized payment plans without human intervention. For operators, this translates to higher conversion rates on financed purchases and a more seamless digital storefront. Who else is covering this
Sierra buys Takeoff, launches Horizon agent platform. JUL 24, 2026 The deal pairs Sierra's enterprise reach with Takeoff's long-horizon agent runtime under a new joint platform aimed at outcome-based AI. The gist. * Acquisition announcement. Sierra acquired Takeoff to build long-horizon AI agents. * Joint platform launch. The combined teams will develop a new platform called Horizon. * Enterprise impact. Leaders gain access to scalable, outcome-driven AI agents across industries. Sierra has acquired AI agent startup Takeoff and unveiled Horizon, a joint platform for long-running, outcome-driven enterprise agents. Sierra made the announcement on July 23. Takeoff according to its team grew from $0 to nearly eight figures in annual recurring revenue (ARR) in about seven months with a three-person team. Takeoff built what it describes as a "long-horizon agent runtime" designed to let AI agents handle end-to-end tasks across industries including lending and healthcare. Aakash Thumaty of Takeoff said the company secured several seven-figure contracts across five industries by focusing on revenue-aligned outcomes rather than inference APIs alone. The acquisition aligns with Sierra's broader strategy of scaling industry-specific AI agents globally. Thumaty said both companies share the conviction that the largest AI businesses will be built around measurable outcomes, not model inference. "We've spent the last 14 months building Takeoff into a long-horizon agent runtime that enables agents to operate like humans but scale like software," Thumaty said in a statement. Sierra-Takeoff Horizon platform capabilities. The combined Sierra-Takeoff effort centers on the Horizon platform. Below are the stated capabilities, according to company officials. | Capability | Description | | Horizon platform | Joint platform for long-running, outcome-driven AI agents | | Long-horizon agent runtime | Agents designed to execute multi-step tasks over days or weeks | | Industry-specific deployment | End-to-end solutions tailored to lending, healthcare and other verticals | | Outcome-based model | Revenue tied to results produced, not inference volume | | Global scale | Extends agent deployment worldwide via Sierra's partnerships | Sierra's recent moves. Sierra has emerged as one of enterprise AI's most valuable players, closing a $950 million Series E in May 2026 led by Tiger Global and GV at a $15 billion valuation - its third major funding milestone in roughly 18 months, up from $4.5 billion in late 2024. The company crossed $150 million in ARR seven quarters after its February 2024 launch, with more than 40% of the Fortune 50 now counted as customers. New capital is earmarked for European and Asian expansion and for extending agents into sales and customer lifetime value optimization. Notable news & distinguished data for tomorrow's c-suite. Sierra's platform has expanded beyond customer support into Agent OS 2.0, an Agent Data Platform and enterprise change management tooling. Notable deployments include Nordstrom's voice agent "Nora" (live in five weeks), Singtel (10 weeks, resolution rates above 70%) and Cigna (eight weeks, cutting patient authentication time by 80%). The company also achieved FedRAMP High authorization in June, unlocking access to federal agencies. This month, it named SoftBank Corp. as its exclusive Japan sales partner, building on a LINEMO deployment that delivered 97% inquiry resolution and 93% customer satisfaction. Agentic AI platforms: ROI & architecture. Autonomous agent platforms are moving past pilots into production, with vendors tying architecture decisions directly to revenue outcomes and compliance requirements. Grounding agents in systems of record. Effective autonomous agents depend on systems of record. Agents resolve up to 40% of inquiries across chat, email, voice and WhatsApp when integrated with CRM knowledge bases and workflow APIs. Learning Opportunities ServiceNow's Autonomous CRM platform, launched May 5, illustrates the architecture. Prepackaged actions span service, sales and field operations across government, finance, telco, healthcare and retail. The company said the platform resolves more than 100 million customer cases monthly. Omnichannel deployment patterns. Autonomous agents now operate across voice, web, chat, email and messaging in what amounts to a modern omnichannel contact center architecture. The model replaces handoff-heavy processes with multi-step autonomous execution. Governed agents - those constrained by business logic and human-in-the-loop oversight - deliver deterministic outcomes in regulated environments. Clear escalation paths remain important in sectors governed by HIPAA, SOC 2 and the EU AI Act. Sierra background. Sierra was founded in 2023 by Bret Taylor and Clay Bavor. The company offers Agent OS, a conversational AI platform for designing, deploying and managing autonomous agents across chat, SMS, WhatsApp, email and voice. Sierra serves financial services, healthcare, telecommunications and retail. Have a tip to share with its editorial team? Drop Gingertec a line: [email protected] Main image: Dom Nicastro is editor-in-chief of CMSWire and an award-winning journalist with a passion for technology, customer experience and marketing. With more than 20 years of experience, he has written for various publications, like the Gloucester Daily Times and Boston Magazine. He has a proven track record of delivering high-quality, informative, and engaging content to his readers. Dom works tirelessly to stay up-to-date with the latest trends in the industry to provide readers with accurate, trustworthy information to help them make informed decisions. Featured Research
I’m incredibly excited to share that Sierra is acquiring TakeOff, the leader in long-horizon AI agents. @claybavor and I couldn't be more excited to welcome @letsleverup and the entire TakeOff team.In less than a year, they've built something truly special: an agent platform…— Bret Taylor (@btaylor) July 23, 2026