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Location: Toronto Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce. - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way. - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency. - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product. EXAMPLE PROJECTS These are some examples of projects that engineers on our team have worked on recently: - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services! - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers WHAT YOU'LL BRING - Experience building and scaling end-to-end production systems - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship - Comfort working directly with customers to understand their needs and solve real-world problems - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences EVEN BETTER... - Experience building or deploying AI/LLM systems in production - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering - Prior experience with React, TypeScript, and/or Go - Previous roles where you interfaced with customers or led technical projects with external stakeholders OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: Riyadh, Saudi Arabia; Dammam, Saudi Arabia; Al Khobar, Saudi Arabia Eram Talent is seeking a proficient Master Data Management (MDM) Business Analyst - Informatica to join our dynamic team. In this role, you will serve as a key liaison between business stakeholders and technical teams to ensure that Informatica-based MDM solutions effectively meet organizational data management needs. You will be responsible for gathering and documenting business requirements, analyzing existing data processes, and collaborating with technical teams on solution design and implementation. You will also help in identifying data quality issues, facilitate data governance activities, and support ongoing MDM initiatives to improve data accuracy, consistency, and compliance. If selected, the work location would be onsite at Al Khobar. Key Responsibilities Collaborate with business stakeholders to understand their master data requirements, document data definitions, and analyze data structures for optimal data management. Plan and execute data migration activities, including data mapping, data extraction, transformation, and loading (ETL) processes, during system upgrades or platform transitions. Ensure compliance with data security and privacy regulations, implement access controls, and monitor data usage to protect sensitive master data. Conduct thorough analysis of existing master data sets to identify discrepancies, anomalies, and opportunities for improvement, providing actionable insights to stakeholders. Develop and generate reports, dashboards, and data visualizations to provide insights into master data quality, trends, and performance, supporting decision-making processes. Facilitate change management activities related to master data management initiatives, including communication, training, and stakeholder Develop and enforce master data governance policies, standards, and processes to ensure data quality, consistency, and compliance with regulatory requirements. Collaborate with business users and IT teams to map data sources, define data hierarchies, and create data models that support effective master data management. Define and implement data standardization rules and processes to harmonize master data elements across disparate systems and business units. Coordinate the integration of master data management solutions with existing enterprise systems, ensuring seamless data flow and interoperability. Requirements Bachelor’s degree in Information Technology, or equivalent from a recognized and accredited university is required 5+ Years of Work Experience as a Master Data Management (MDM) Business Analyst or similar role is required. Certified Data Privacy Solutions Engineer (CDPSE) preferred Certifications in MDM or Informatica is highly preferred. Experience in Information Technology / Data Solutions / Networking / Cybersecurity preferred Proven experience as a Business Analyst, specifically in Master Data Management (MDM). Strong understanding of MDM principles, data governance, and data quality management. Experience with MDM tools (e.g., Informatica, SAP MDG, Oracle) is a plus. Excellent analytical and problem-solving skills. Strong communication and interpersonal skills to effectively engage with stakeholders.

Location: Al Khobar, Saudi Arabia; Dammam, Saudi Arabia Eram Talent is in search of a dedicated Data Quality Development Analyst to enhance our commitment to delivering exceptional staffing solutions. In this pivotal role, you will ensure that our data quality standards are met and continuously developed, contributing to our data-driven decision-making capabilities across the organization. The role holder is responsible for designing data quality assurance policies and standards, developing an enterprise data quality solution, defining metadata repositories and master data management to enable leverage enterprise data for business intelligence. The role holder is also responsible for installing and maintaining business intelligence tools and fine-tuning their performance. Key Responsibilities Responsible for designing, testing, deploying and documenting the data quality procedures and their outputs Design processes and technology to enable the client to leverage the enterprise data for business intelligence purposes. Define the data policy, standards and guidelines and ensure consistency. Coordinate with Master Data Quality Manager and define metadata repository for digitally and physically storing and cataloguing data. Design master data management to provide processes, governance, policies, standards and tools to define and manage master data. Define quality assurance policies and standards to ensure consistency in business intelligence reports. Identify and highlight issues related to data quality in order to improve accuracy of reports leading to proper decision making. Liaise with Master Data Quality Manager to provide support in development, operations and maintenance of dashboards and reports in the Technology environment. Install business intelligence tools and configures hardware and software components. Perform users’ administrator setup and provides continuous support for maintenance. Perform business intelligence performance tuning to ensure optimal performance. Recommend training and development interventions for team members to build their capabilities. Contribute to the identification of opportunities for the continuous improvement of systems, processes and practices to increase productivity and operational efficiency. Implement all relevant Department’s policies, processes, procedures and instructions so that work is carried out in a controlled and consistent manner. Contribute to the preparation of timely and accurate reports to meet departmental requirements, policies and standards. Requirements Bachelor’s degree in information technology, or equivalent from a recognized and accredited university is required. 5+ years of experience in data analysis, data quality, or a similar role. Knowledge of Data Quality principles, policies and procedures. Knowledge of Data Quality tools. Strong understanding of data governance, data quality metrics, and data management principles. Experience with data profiling tools and techniques. Proficiency in SQL and experience with data visualization tools (e.g., Tableau, Power BI). Strong analytical and problem-solving skills. Excellent communication skills and ability to work collaboratively with diverse teams. Detail-oriented with a strong focus on data accuracy and reliability.

Location: Al Khobar, Saudi Arabia; Dammam, Saudi Arabia Eram Talent is seeking a dedicated Data Quality Business Analyst to join our growing team. In this role, you will be responsible for ensuring the integrity, accuracy, and reliability of data across our business systems. You will collaborate with cross-functional teams and stakeholders to define data quality standards, develop metrics, and implement processes that enhance data management practices. Your responsibilities will include performing data analysis, identifying data quality issues, and recommending solutions to improve data governance. You will also work on data quality initiatives and may be involved in data profiling, cleansing, and monitoring to ensure adherence to organizational data quality standards. Responsibilities Consolidate guidelines, processes and parameters for conducting business analysis in order to follow a consistent approach in the process followed for collating data and carrying out analytics. Support in coordinating with Technology departments through periodic meetings to understand the specific business requirements related to business analytics. Coordinate with different internal departments to identify the most suitable data resources to ensure effective data collection and analysis based on the requirements. Support in identifying potential external vendors/market research agencies etc. and coordinate with them to establish the data collection and reporting needs in order to ensure efficiency in the data collection process. Coordinate with external consultants/forums to keep updated with the latest developments in the Technology landscape. Perform data cleaning and standardisation for conducting the relevant analysis and ensures adherence to data quality standards while developing reports on procurement and logistics updates. Stay up to date on the latest business intelligence tools, databases, systems or methods etc. and shares insights with Master Data Quality Manager on leveraging the same for business requirements. Develop the requisite reports (weekly/monthly/ad-hoc) and ensures timely submission of the same to facilitate decision making. Requirements Bachelor’s degree in Information Technology, or equivalent from a recognized and accredited university is required. 5+ years of experience as a Data Quality Analyst or in a related field. Certified Data Privacy Solutions Engineer (CDPSE) preferred. Experience in Information Technology / Data Solutions / Networking / Cybersecurity preferred. Strong understanding of data management principles, data governance, and data quality best practices. Proficient in data profiling and analysis tools (e.g., SQL, Python, or ETL tools) to assess data quality. Experience with data visualization tools such as Tableau, Power BI, or similar is a plus. Strong analytical and problem-solving skills to identify data quality issues and develop actionable solutions. Excellent communication skills, with the ability to work collaboratively with diverse teams and stakeholders. Detail-oriented with a focus on delivering high-quality results. Familiarity with data privacy and regulatory compliance standards is a plus.

Location: Global (Remote) Workplace: Remote COMMUNITY GROWTH MANAGER Team: Community Location: Flexible / Remote Reporting to: VP of Community ROLE OVERVIEW Rwazi’s Community function represents the human layer of the company — contributors, mappers, and platform participants across global markets. The Community Growth Manager owns measurable network expansion. This role scales user acquisition, accelerates activation, and increases network density across priority geographies. Community growth is treated as infrastructure — not marketing. The Community Growth Manager builds a predictable, compounding human network. CORE MANDATE The Community Growth Manager is accountable for: - Scaling contributor and user acquisition - Increasing activation velocity (sign-up → first participation) - Expanding network density in key markets - Improving referral-driven growth loops - Strengthening repeat participation This role owns the growth mechanics of the human network. KEY RESPONSIBILITIES USER ACQUISITION & EXPANSION - Design and execute multi-channel contributor acquisition strategies - Identify high-density geographic clusters - Optimize cost-per-active-user - Test and scale growth channels systematically ACTIVATION VELOCITY - Reduce time-to-first-submission - Optimize onboarding flows - Improve conversion from interest → active participation - Identify and remove friction in early journey stages NETWORK DENSITY & COVERAGE - Increase active contributors per city - Balance growth across underserved regions - Maintain supply resilience across markets REFERRAL & ORGANIC GROWTH SYSTEMS - Design referral programs tied to measurable expansion - Track referral conversion rates - Strengthen peer-driven network growth GROWTH ANALYTICS & OPTIMIZATION - Track acquisition, activation, and retention metrics - Run experiments to improve conversion rates - Provide structured reporting to VP of Community ROLE IMPACT Strong performance results in: - Faster log fulfillment due to stronger network density - Lower acquisition cost per active user - Higher activation conversion rates - Stronger organic growth - Increased supply resilience This role directly influences execution speed and ecosystem strength. WHAT THIS ROLE IS NOT - Not community moderation - Not delivery operations - Not reactive messaging - Not event management This role requires structured growth discipline. QUALIFICATIONS AND PROFILE We are looking for individuals who demonstrate: - 4–8+ years in growth, marketplace scaling, or community expansion - Experience building distributed user networks - Strong analytical ability with funnel metrics - Comfort running structured experiments - Bias toward action and iteration - Experience operating in multi-geography environments Candidates may come from gig platforms, marketplace startups, creator ecosystems, or growth-driven SaaS environments. CULTURAL FIT We value operators who: - Think in funnels and density, not vanity metrics - Care about measurable outcomes - Move quickly and iterate - Build systems that compound - Operate with ownership and accountability HOW CANDIDATES ARE EVALUATED Candidates are evaluated based on: - Growth metrics achieved in prior roles - Activation and retention improvements driven - Ability to design scalable acquisition systems - Analytical rigor behind growth decisions - Structured experimentation discipline SUMMARY The Community Growth Manager scales Rwazi’s human network by driving acquisition, activation, and expansion across markets. This role ensures the Community layer grows predictably, efficiently, and sustainably as the company scales.

Location: Global (Remote) Workplace: Remote EXECUTIVE ASSISTANT Team: CEO Office Location: Flexible / Remote Reporting to: CEO ROLE OVERVIEW Rwazi operates in a high-velocity, AI-native environment where clarity, follow-through, and structured thinking are essential. The Executive Assistant supports the CEO in day-to-day executive operations — documentation, planning cadence, structured follow-ups, and internal coordination. This is a foundational role inside the CEO’s office. While the title is traditional, the expectation is not. We are looking for someone with former founder instincts or strong analytical pedigree — who understands strategy, but is comfortable operating in a support capacity without ego. This role requires intelligence, discipline, and humility. CORE MANDATE The Executive Assistant is accountable for: - Maintaining executive documentation rigor - Structuring meetings into clear outputs and actions - Tracking cross-functional commitments - Supporting board and planning cycles - Reducing cognitive load on the CEO This role strengthens executive execution hygiene. KEY RESPONSIBILITIES EXECUTIVE DOCUMENTATION & STRUCTURING - Capture high-quality, structured notes in executive and board meetings - Translate discussions into clear action items with owners and deadlines - Maintain organized, searchable documentation systems - Draft memos, summaries, and internal briefs PLANNING & CADENCE MANAGEMENT - Support quarterly and annual planning processes - Assist in preparing board decks and executive materials - Maintain visibility over key company-wide priorities - Ensure follow-through across functional leaders CROSS-FUNCTIONAL COORDINATION - Track execution commitments across teams - Follow up on deadlines and deliverables - Escalate slippage early and objectively - Maintain structured dashboards of ongoing initiatives OPERATIONAL & ADMINISTRATIVE SUPPORT - Manage executive scheduling and prioritization - Coordinate internal and external communications - Maintain high professional standards in all outputs ROLE IMPACT Strong performance results in: - Clear executive decision trails - Fewer dropped commitments - Tighter cross-functional alignment - Faster execution cycles - Increased CEO focus on strategic priorities WHAT THIS ROLE IS NOT - This is not a strategic leadership role - This is not independent product or revenue ownership - This is not a stepping stone to immediate executive authority This role requires comfort operating in a support function — regardless of prior seniority. QUALIFICATIONS AND PROFILE We are looking for individuals who demonstrate: - Former founder, operator, or builder experience OR strong analytical background (consulting, finance, research, technical environments) - Exceptional structured writing ability - Strong analytical reasoning and pattern recognition - Comfort synthesizing complex discussions into clarity - High attention to detail - Ability to operate without ego in a support capacity - Strong discretion and professionalism Former founders are welcome — provided they are motivated by discipline and execution, not status. CULTURAL FIT We value individuals who: - Think sharply but act humbly - Prefer execution over visibility - Take pride in structured output - Care about precision - Follow through consistently HOW CANDIDATES ARE EVALUATED Candidates are evaluated based on: - Clarity and structure of written work - Analytical depth in summarizing complex discussions - Discipline in tracking commitments - Comfort supporting executive workflows - Absence of ego in operational contexts SUMMARY The Executive Assistant strengthens the CEO’s office by applying founder-level thinking and analytical rigor to executive documentation, planning, and follow-through. This role is foundational to maintaining speed, clarity, and execution discipline as Rwazi scales.

Location: Global (Remote) Workplace: Remote SALES DIRECTOR, EU Team: Monetization Location: LATAM Reporting to: Head of Monetization ROLE OVERVIEW Rwazi sells enterprise AI-powered decision intelligence subscriptions. The Sales Director, LATAM owns new revenue execution across the LATAM market. This role lands new enterprise accounts and expands existing subscriptions through structured pipeline discipline, executive engagement, and value-based selling. This is revenue ownership, not relationship management. CORE MANDATE The Sales Director, LATAM is accountable for: - Closing new enterprise subscription revenue - Expanding ARR within existing accounts - Driving pipeline-to-close efficiency - Maintaining structured deal discipline - Representing Rwazi at executive buyer level KEY RESPONSIBILITIES - Own full-cycle enterprise sales (land and expand) - Maintain predictable forecast accuracy - Navigate complex buying committees - Align product capabilities with enterprise pain points - Close multi-year subscription contracts - Drive expansion within multi-department enterprise accounts ROLE IMPACT - Increased ARR - Higher win rates - Larger deal sizes - Stronger LATAM market penetration

Location: Global (Remote) Workplace: Remote SALES DIRECTOR, MIDDLE EAST Team: Monetization Location: Middle East Reporting to: Head of Monetization ROLE OVERVIEW Rwazi sells enterprise AI-powered decision intelligence subscriptions. The Sales Director, Middle East owns new revenue execution across the Middle East market. This role lands new enterprise accounts and expands existing subscriptions through structured pipeline discipline, executive engagement, and value-based selling. This is revenue ownership, not relationship management. CORE MANDATE The Sales Director, Middle East is accountable for: - Closing new enterprise subscription revenue - Expanding ARR within existing accounts - Driving pipeline-to-close efficiency - Maintaining structured deal discipline - Representing Rwazi at executive buyer level KEY RESPONSIBILITIES - Own full-cycle enterprise sales (land and expand) - Maintain predictable forecast accuracy - Navigate complex buying committees - Align product capabilities with enterprise pain points - Close multi-year subscription contracts - Drive expansion within multi-department enterprise accounts ROLE IMPACT - Increased ARR - Higher win rates - Larger deal sizes - Stronger Middle East market penetration

Location: Global (Remote) Workplace: Remote SALES DIRECTOR, EU Team: Monetization Location: European Union Reporting to: Head of Monetization ROLE OVERVIEW Rwazi sells enterprise AI-powered decision intelligence subscriptions. The Sales Director, EU owns new revenue execution across the European Union market. This role lands new enterprise accounts and expands existing subscriptions through structured pipeline discipline, executive engagement, and value-based selling. This is revenue ownership, not relationship management. CORE MANDATE The Sales Director, EU is accountable for: - Closing new enterprise subscription revenue - Expanding ARR within existing accounts - Driving pipeline-to-close efficiency - Maintaining structured deal discipline - Representing Rwazi at executive buyer level KEY RESPONSIBILITIES - Own full-cycle enterprise sales (land and expand) - Maintain predictable forecast accuracy - Navigate complex buying committees - Align product capabilities with enterprise pain points - Close multi-year subscription contracts - Drive expansion within multi-department enterprise accounts ROLE IMPACT - Increased ARR - Higher win rates - Larger deal sizes - Stronger EU market penetration

Location: Global (Remote) Workplace: Remote SALES DIRECTOR, UK Team: Monetization Location: United Kingdom Reporting to: Head of Monetization ROLE OVERVIEW Rwazi sells enterprise AI-powered decision intelligence subscriptions. The Sales Director, UK owns new revenue execution across the United Kingdom market. This role lands new enterprise accounts and expands existing subscriptions through structured pipeline discipline, executive engagement, and value-based selling. This is revenue ownership, not relationship management. CORE MANDATE The Sales Director, UK is accountable for: - Closing new enterprise subscription revenue - Expanding ARR within existing accounts - Driving pipeline-to-close efficiency - Maintaining structured deal discipline - Representing Rwazi at executive buyer level KEY RESPONSIBILITIES - Own full-cycle enterprise sales (land and expand) - Maintain predictable forecast accuracy - Navigate complex buying committees - Align product capabilities with enterprise pain points - Close multi-year subscription contracts - Drive expansion within multi-department enterprise accounts ROLE IMPACT - Increased ARR - Higher win rates - Larger deal sizes - Stronger UK market penetration

Location: Global (Remote) Workplace: Remote SALES DIRECTOR, US Team: Monetization Location: United States Reporting to: Head of Monetization ROLE OVERVIEW Rwazi sells enterprise AI-powered decision intelligence subscriptions. The Sales Director, US owns new revenue execution across the United States market. This role lands new enterprise accounts and expands existing subscriptions through structured pipeline discipline, executive engagement, and value-based selling. This is revenue ownership, not relationship management. CORE MANDATE The Sales Director, US is accountable for: - Closing new enterprise subscription revenue - Expanding ARR within existing accounts - Driving pipeline-to-close efficiency - Maintaining structured deal discipline - Representing Rwazi at executive buyer level KEY RESPONSIBILITIES - Own full-cycle enterprise sales (land and expand) - Maintain predictable forecast accuracy - Navigate complex buying committees - Align product capabilities with enterprise pain points - Close multi-year subscription contracts - Drive expansion within multi-department enterprise accounts ROLE IMPACT - Increased ARR - Higher win rates - Larger deal sizes - Stronger US market penetration

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE HEALTHCARE TEAM - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system. - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms. - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone. WHAT YOU'LL DO - Build enterprise-grade AI agents for healthcare: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day. These agents help people understand their coverage, find providers, schedule appointments, navigate billing, and more—all while maintaining strict HIPAA compliance and the trust that healthcare demands. - Discover where agents will make an impact: Ground-up discovery is a critical part of the role. Work closely with providers, payers, RCMs and pharmaceutical companies to identify new use cases and opportunities for AI Agents to deliver impact for their business. You should be our customer’s trusted advisor, and be able drive strategic decisions for our customers. - Engage with customers: In the role, you will engage with all levels of our customers’ businesses: - Discover and assess their requirements. - Prepare and present demonstrations of Sierra’s agent. - Address and overcome technical challenges in the business process by working with technical counterparts. - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes. - Become trusted advisors and drive strategic technical strategies for our customers. - Shape the platform and healthcare roadmap: Your direct work with healthcare customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development in healthcare. EXAMPLE PROJECTS These are examples of projects our healthcare team has worked on: - Develop net new agentic healthcare products that can cut costs and drive revenue in the healthcare ecosystem. - Build AI agents for major health insurance networks that handle detailed questions like "what's my co-pay for a primary care visit?" and "how many physical therapy sessions do I have left?" - Develop voice and chat agents for nonprofit healthcare providers that help members find in-network specialists, check availability, and locate providers based on specialty or location - Create AI agents for multi-site primary and urgent care providers that manage appointments and answer common questions across 30+ clinics - Build agents that replace lengthy paper intake forms with conversational experiences, boosting pre-visit intake conversion rates - Develop AI agents for healthcare financial platforms that help patients understand billing, payment status, explanations of benefits, and financial assistance eligibility. - Experiment with the latest voice models and integrate them at scale for healthcare enterprises requiring secure, compliant phone interactions WHAT YOU'LL BRING - 5-7+ years experience in product development of highly technical products. - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager. - Experience crafting and tailoring a message for potential customers, including executives. - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments. - Degree in a technical or related field, or equivalent professional experience. - Genuine interest in healthcare and improving patient/member experiences EVEN BETTER... - Experience in healthcare technology, health IT or working with healthcare organizations - Understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy) - AI-related experience (experience with product development for AI agents a plus). - Some coding experience with React, Typescript, and Go. - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles). - Past roles that interface with end customers to influence software development. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: Global (Remote) Workplace: Remote RESEARCH ENGINEER Team: Research & Development Location: Flexible / Remote Reporting to: Head of R&D ROLE OVERVIEW Rwazi’s research initiatives require rapid experimentation, prototyping, and system validation. The Research Engineer enables applied research through technical system construction. This role builds prototypes, experimental pipelines, evaluation tooling, and research infrastructure that allow decision concepts to be tested under real-world constraints. The Research Engineer operationalizes research velocity. CORE MANDATE The Research Engineer is accountable for: - Building research prototypes and sandbox environments - Developing evaluation tooling for decision systems - Implementing experimental system architectures - Enabling fast iteration between theory and validation - Maintaining technical research infrastructure This role bridges conceptual research and system reality. KEY RESPONSIBILITIES PROTOTYPE DEVELOPMENT - Implement experimental decision pipelines - Build modular, testable research architectures - Translate conceptual models into runnable systems RESEARCH TOOLING & INFRASTRUCTURE - Create evaluation frameworks for reasoning outputs - Build simulation environments for controlled testing - Develop benchmarking systems for decision performance EXPERIMENT ENABLEMENT - Implement A/B logic and structured experiment tracking - Optimize iteration cycles for research testing - Ensure reproducibility of experimental results SYSTEM INTEGRATION SUPPORT - Collaborate with Decision Research Scientists to encode models - Provide technical validation of research concepts - Identify engineering constraints early ROLE IMPACT Strong performance in this role results in: - Faster research iteration cycles - More reliable prototype validation - Reduced gap between research and production - Higher experimental rigor This role accelerates Rwazi’s long-term capability development. WHAT THIS ROLE IS NOT - This is not product feature engineering - This is not maintenance development - This is not short-term optimization This role builds experimental systems. QUALIFICATIONS AND PROFILE We are looking for individuals who demonstrate: - Strong software engineering fundamentals - Experience building experimental or prototype systems - Comfort working in ambiguous research environments - Ability to balance speed and technical rigor - Familiarity with AI pipelines or decision architectures Candidates may come from research labs, AI startups, advanced analytics teams, or system architecture roles. HOW CANDIDATES ARE EVALUATED Candidates are evaluated based on: - Their ability to rapidly implement experimental systems - Technical clarity and modularity of their code - Comfort working with incomplete specifications - Understanding of evaluation logic and system validation - Ability to collaborate with research-oriented thinkers SUMMARY The Research Engineer enables Rwazi’s applied decision research by building the technical infrastructure required to explore, validate, and evolve next-generation decision systems. If you'd like, we can next define: - Decision Systems Fellow (elite individual contributor track) - AI Evaluation & Alignment Lead - Advanced Simulation Architect - Future Platforms Lab

Location: Global (Remote) Workplace: Remote Product Analyst Location: Global (Remote) Reports to: VP of Product Employment Type: Full-time MISSION AT RWAZI Rwazi’s AI-powered SaaS platform serves enterprise clients who rely on decision-grade data and actionable intelligence. The Product Analyst owns the quantitative visibility layer of the product. This role analyzes user behavior, product performance metrics, feature adoption, and retention signals to inform product strategy and roadmap decisions. The Product Analyst ensures product decisions are grounded in evidence, not intuition. CORE MANDATE The Product Analyst is accountable for: - Measuring and interpreting user behavior across the SaaS platform - Tracking feature adoption, engagement, and retention metrics - Identifying friction points and drop-offs - Translating behavioral data into actionable product insights - Providing structured recommendations to VP of Product This is a product intelligence role embedded inside product execution. KEY RESPONSIBILITIES USER BEHAVIOR ANALYSIS - Track user journeys across dashboards, workflows, and modules - Identify usage frequency patterns across accounts - Analyze session depth, repeat usage, and expansion signals - Detect behavioral differences across verticals and enterprise segments FEATURE PERFORMANCE & ADOPTION - Monitor new feature launch performance - Track adoption velocity and engagement rates - Identify underutilized features and diagnose causes - Support A/B testing and experiment analysis RETENTION & EXPANSION METRICS - Measure account-level retention and churn indicators - Identify signals predictive of expansion or contraction - Build cohort analyses across industries and client tiers PRODUCT KPI GOVERNANCE - Define and maintain core product metrics - Ensure data accuracy and consistency across dashboards - Maintain product performance reporting cadence (weekly/monthly) INSIGHT GENERATION & STRATEGIC INPUT - Translate data into clear, structured insights - Provide recommendations to VP of Product and cross-functional teams - Surface early warning signals affecting product health ROLE IMPACT Strong performance in this role results in: - Data-driven roadmap decisions - Faster detection of product friction - Improved feature adoption rates - Higher retention and expansion metrics - Reduced reliance on anecdotal product feedback This role strengthens the intelligence behind product evolution. WHAT THIS ROLE IS NOT - This is not a passive reporting role - This is not general business analytics disconnected from product - This is not ad-hoc dashboard building only This role requires structured reasoning, proactive insight generation, and product fluency. QUALIFICATIONS AND PROFILE We are looking for individuals who demonstrate: - 3–6+ years in product analytics or SaaS analytics roles - Strong fluency in SQL, data modeling, and analytics tooling - Experience working closely with Product teams - Ability to conduct cohort analysis, funnel analysis, and retention modeling - Strong quantitative reasoning and pattern recognition - Comfort translating data into executive-level insights Candidates may come from high-growth B2B SaaS, marketplace platforms, or data-intensive environments. CULTURAL FIT We value analysts who: - Think in systems and causal relationships - Question assumptions and validate with data - Prefer clarity over complexity - Move quickly and iterate - Are comfortable operating with executive visibility This role is suited for individuals who enjoy turning behavioral data into product advantage. HOW CANDIDATES ARE EVALUATED Candidates are evaluated based on: - Their ability to interpret behavioral product data - Clarity and rigor of their analytical reasoning - Experience building actionable product insights - Comfort working with ambiguity and incomplete signals - Their ability to influence product decisions through evidence We prioritize demonstrated analytical capability and product impact over resumes alone. SUMMARY The Product Analyst ensures Rwazi’s product evolves based on measurable user behavior and performance signals. This role strengthens the product intelligence layer and enables disciplined, data-driven product growth.

Location: Global (Remote) Workplace: Remote Head of Research & Development (R&D) Location: Global (Remote) Reports to: CEO Employment Type: Full-time MISSION AT RWAZI Rwazi’s long-term advantage depends on expanding the frontier of what decision systems can reason about. The Head of R&D owns long-horizon capability development — exploring, prototyping, and formalizing the next generation of decision intelligence that will power future versions of Rwazi’s platform. This role operates beyond immediate roadmap pressures. It identifies structural opportunities in reasoning systems, signal modeling, AI-assisted judgment, and decision automation — and transforms them into foundational capabilities. The Head of R&D defines what Rwazi becomes 3–5 years from now. CORE MANDATE The Head of R&D is accountable for: - Advancing future decision system architectures - Formalizing higher-order reasoning capabilities - Exploring new signal classes and evaluation logic - Identifying structural AI leverage points - Converting research into reusable system primitives This is a capability-building role, not a feature-delivery function. KEY RESPONSIBILITIES LONG-HORIZON CAPABILITY EXPLORATION - Identify unsolved reasoning challenges within Rwazi’s domain - Explore advanced decision frameworks beyond current product constraints - Develop conceptual models for higher-order AI reasoning systems - Investigate new signal environments and structured judgment methods PROTOTYPE & FORMALIZATION - Build experimental prototypes to test new system architectures - Formalize reasoning patterns into structured logic frameworks - Create reusable primitives that Product and Engineering can adopt - Document system logic in technically rigorous formats AI & DECISION SYSTEMS ADVANCEMENT - Push beyond current signal-to-output pipelines - Explore multi-layer reasoning and tradeoff modeling - Design evaluation criteria for increasingly complex decisions - Anticipate future enterprise use cases and model their structural requirements STRATEGIC INTERFACE WITH EXECUTIVE LEADERSHIP - Advise CEO on long-term technical differentiation strategy - Translate research insights into strategic investment decisions - Identify potential defensibility moats RESEARCH GOVERNANCE - Define standards for experimentation rigor - Establish evaluation frameworks for prototype validation - Maintain clarity between exploratory work and production systems ROLE IMPACT Strong performance in this role results in: - Structural differentiation in decision intelligence - New classes of solvable enterprise questions - Expansion of AI-assisted reasoning depth - Long-term defensibility against competitors - Research-driven product evolution This role ensures Rwazi does not stagnate at feature-level innovation. WHAT THIS ROLE IS NOT - This is not roadmap feature delivery - This is not short-term optimization - This is not pure academic research detached from application - This is not reactive problem-solving This role requires frontier thinking and disciplined formalization. QUALIFICATIONS AND PROFILE We are looking for individuals who demonstrate: - Deep systems thinking and formal reasoning ability - Experience designing structured decision frameworks - Strong understanding of AI systems, modeling logic, or computational reasoning - Ability to translate abstract research into usable system components - Comfort operating autonomously at high strategic altitude - Demonstrated work on complex, ambiguous problems Candidates may come from applied research, AI system design, computational modeling, advanced analytics, or technically rigorous environments. CULTURAL FIT We value leaders who: - Think in decades, not quarters - Formalize ideas with intellectual rigor - Challenge existing system boundaries - Operate independently without constant direction - Care about structural innovation over incremental gain This role is suited for builders who want to shape the long-term intelligence core of an AI-native company. How Candidates Are Evaluated Candidates are evaluated based on: - Their ability to formalize complex reasoning into structured systems - Evidence of pushing technical or decision boundaries - Clarity of thought in ambiguous domains - Ability to design experiments with rigor - Strategic alignment with long-term capability building We prioritize demonstrated intellectual depth and system-building ability over conventional titles. SUMMARY The Head of R&D defines the next generation of Rwazi’s decision intelligence. This role ensures that as the market evolves, Rwazi advances beyond incremental product iteration — and continues to expand the frontier of what enterprise decision systems can reason about.

Location: London, England Our mission at Duolingo is to develop the best education in the world and make it universally available. It’s a big mission, and that’s where you come in! At Duolingo, you’ll join a team that cares about educating our users, experimenting with big ideas, making fact-based decisions, and finding innovative solutions to complex problems. You’ll have limitless learning opportunities and daily collaborations with world-class minds — while doing work that’s both meaningful and fun. Join our life-changing mission to develop education for our half a billion (and growing!) learners around the world. Read our blog to learn more. About the role... We’re looking for a Senior Creative Director to set the creative vision for Duolingo’s brand building and marketing efforts and lead a team that delivers culturally resonant, high‑impact work across campaigns, social, partnerships, and user acquisition. You will raise the creative bar, turn bold ideas into clear concepts, and guide execution from brief through launch—collaborating closely with Brand Marketing and Growth, International Marketing, Product, Design, BD, and global agency partners to build an iconic brand with measurable business impact. Reporting to the Head of Brand Marketing, this role will lead other creative leaders in the Marketing function. 🧠  You will... Drive all creative work in the Marketing function, ensuring it consistently ladders up to the company strategy and moves key brand and business metrics. Lead, mentor, and grow a team of creatives; set a high bar for craft, narrative, and taste while creating space for diverse voices and experimentation. Turn great ideas into end‑to‑end campaign concepts; guide direction across channels (social, video, experiential, partnerships), from insight to execution. Partner with Brand Marketing to shape briefs, make strategic trade‑offs, and deliver work that’s part of culture and drives brand love and growth. Partner with Growth Marketing to build a performance marketing creative studio enabling our user acquisition efforts across the globe. Partner with our Country Marketing team to lead and evolve our global agency roster; ensure scopes, standards, and handoffs produce A+ creative worldwide. Oversee creative feedback and quality across all project stages; provide clear, timely decisions that keep momentum without sacrificing excellence. Inspire the organization with industry trends, creative references, and new platforms; codify what’s “on‑brand” and how we measure brand success. ✅  You have... Experience in brand/creative roles with significant time leading other creative leaders; proven success shipping integrated campaigns across a wide range of budgets at a high bar. Demonstrated ability to set vision, influence senior stakeholders, and connect creative decisions to strategy, KPIs, and ROI. A track record of turning insights into iconic, culture‑driving ideas and guiding multi‑disciplinary teams from concept to launch. Excellent communication and feedback skills; you simplify complex topics, make fast, sound calls, and bring others along. Experience managing agencies and external partners across markets, with a reputation for raising quality and speed. The ability to work from or relocate to New York City or London, UK ⭐  Exceptional candidates will have... Experience working with IP-led brands Global brand experience, including creative leadership across multiple regions and cultures. A portfolio demonstrating world‑class craft and storytelling— work that drives buzz and earned media attention instead of relying on paid channels for distribution. Deep familiarity with social media and creator ecosystems, and how to translate cultural signals into breakthrough brand ideas. Experience establishing clear creative operating mechanisms with marketing, product, and design partners. The offered salary is dependent upon several factors, including work experience, skills, and internal peer comparisons. The posted range is subject to change in the future. For this role, base salary is supplemented by equity compensation. We encourage you to talk with your recruiter for more information related to compensation for this role! Salary Range: £150,300 — £225,400 GBP Benefits: Take a peek at how we care for our employees' holistic well-being with our benefits here . Job Alerts: Sign up for job alerts here . Accommodations: We will do everything we can within reason to make sure that your interview takes place in an environment that fairly and accurately assesses your skills. If you need assistance or accommodation, please contact accommodations@duolingo.com . Equal Employment Opportunity: Duolingo is proud to be an Equal Employment Opportunity employer. We do not discriminate based upon race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. Fraud Warning: Unfortunately, there is a rise in scammers pretending to be real Duolingo employees. Duolingo and our employees will never ask for your Social Security number, bank details, or passport info, and we’ll never ask you to deposit a check, purchase equipment, or exchange money during the interview process. Real Duolingo employees always use an email that ends in @duolingo.com or @recruiting.duolingo.com. Stay alert and double-check these details before sharing any information. By applying for this position your data will be processed as per the Duolingo Applicant Privacy Notice .

Location: New York, NY Our mission at Duolingo is to develop the best education in the world and make it universally available. It’s a big mission, and that’s where you come in! At Duolingo, you’ll join a team that cares about educating our users, experimenting with big ideas, making fact-based decisions, and finding innovative solutions to complex problems. You’ll have limitless learning opportunities and daily collaborations with world-class minds — while doing work that’s both meaningful and fun. Join our life-changing mission to develop education for our half a billion (and growing!) learners around the world. Read our blog to learn more. About the role... We’re looking for a Senior Creative Director to set the creative vision for Duolingo’s brand building and marketing efforts and lead a team that delivers culturally resonant, high‑impact work across campaigns, social, partnerships, and user acquisition. You will raise the creative bar, turn bold ideas into clear concepts, and guide execution from brief through launch—collaborating closely with Brand Marketing and Growth, International Marketing, Product, Design, BD, and global agency partners to build an iconic brand with measurable business impact. Reporting to the Head of Brand Marketing, this role will lead other creative leaders in the Marketing function. 🧠  You will... Drive all creative work in the Marketing function, ensuring it consistently ladders up to the company strategy and moves key brand and business metrics. Lead, mentor, and grow a team of creatives; set a high bar for craft, narrative, and taste while creating space for diverse voices and experimentation. Turn great ideas into end‑to‑end campaign concepts; guide direction across channels (social, video, experiential, partnerships), from insight to execution. Partner with Brand Marketing to shape briefs, make strategic trade‑offs, and deliver work that’s part of culture and drives brand love and growth. Partner with Growth Marketing to build a performance marketing creative studio enabling our user acquisition efforts across the globe. Partner with our Country Marketing team to lead and evolve our global agency roster; ensure scopes, standards, and handoffs produce A+ creative worldwide. Oversee creative feedback and quality across all project stages; provide clear, timely decisions that keep momentum without sacrificing excellence. Inspire the organization with industry trends, creative references, and new platforms; codify what’s “on‑brand” and how we measure brand success. ✅  You have... Experience in brand/creative roles with significant time leading other creative leaders; proven success shipping integrated campaigns across a wide range of budgets at a high bar. Demonstrated ability to set vision, influence senior stakeholders, and connect creative decisions to strategy, KPIs, and ROI. A track record of turning insights into iconic, culture‑driving ideas and guiding multi‑disciplinary teams from concept to launch. Excellent communication and feedback skills; you simplify complex topics, make fast, sound calls, and bring others along. Experience managing agencies and external partners across markets, with a reputation for raising quality and speed. The ability to work from or relocate to New York City or London, UK ⭐  Exceptional candidates will have... Experience working with IP-led brands Global brand experience, including creative leadership across multiple regions and cultures. A portfolio demonstrating world‑class craft and storytelling— work that drives buzz and earned media attention instead of relying on paid channels for distribution. Deep familiarity with social media and creator ecosystems, and how to translate cultural signals into breakthrough brand ideas. Experience establishing clear creative operating mechanisms with marketing, product, and design partners. The offered salary is dependent upon several factors, including work experience, skills, and internal peer comparisons. The posted range is subject to change in the future. For this role, base salary is supplemented by equity compensation. We encourage you to talk with your recruiter for more information related to compensation for this role! Salary Range: $236,800 — $355,200 USD Benefits: Take a peek at how we care for our employees' holistic well-being with our benefits here . Job Alerts: Sign up for job alerts here . Accommodations: We will do everything we can within reason to make sure that your interview takes place in an environment that fairly and accurately assesses your skills. If you need assistance or accommodation, please contact accommodations@duolingo.com . Equal Employment Opportunity: Duolingo is proud to be an Equal Employment Opportunity employer. We do not discriminate based upon race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. Fraud Warning: Unfortunately, there is a rise in scammers pretending to be real Duolingo employees. Duolingo and our employees will never ask for your Social Security number, bank details, or passport info, and we’ll never ask you to deposit a check, purchase equipment, or exchange money during the interview process. Real Duolingo employees always use an email that ends in @duolingo.com or @recruiting.duolingo.com. Stay alert and double-check these details before sharing any information. By applying for this position your data will be processed as per the Duolingo Applicant Privacy Notice .

Location: United States & Canada Workplace: Remote About WorkOS 🚀 WorkOS builds modern developer tools and APIs that make it easy for companies to become Enterprise Ready. Our platform powers authentication, identity, authorization, and other critical infrastructure that developers need to securely scale their products to large organizations. We recently raised a $100M Series C, valuing the company at $2B, led by Meritech and Sapphire with participation from Greenoaks, Craft, Abstract, and Audacious. WorkOS powers enterprise features for many of the fastest-growing AI companies, including OpenAI, Cursor, and Perplexity, Sierra, and Plaid. As AI reshapes software, WorkOS is at the frontier of Human and Agent Authentication, Identity, and Access Control helping companies answer a new critical question: who are your agents, and what are they allowed to do? Our fast-growing customer base includes hundreds of modern software companies building the next generation of enterprise-ready products. ABOUT THE ROLE We're growing our Applied AI team to dramatically increase productivity across Engineering, Sales, Support, and Operations, and to ship AI-powered products that customers rely on directly. As an Applied AI Engineer, you'll design and ship production AI systems that change how WorkOS builds, sells, supports, and scales. You’ll also be building things that WorkOS customers use, and systems that the entire company depends on daily. You'll work on a small, high-ownership team that: - Chooses problems based on measurable impact - Moves from idea → prototype → production in days or weeks - Ships at both layers: internal leverage and customer-facing product - Adapts quickly as models, tools, and best practices evolve This is a 0→1 role with company-wide visibility. What you'll do - Design and ship customer-facing AI products like ask.workos.com http://ask.workos.com, AI support bots embedded in customer Slack channels, and new surfaces we haven't built yet - Build internal tools that become part of people's daily work: agents, automations, and workflows that are stable, observable, and easy to maintain - Work on big bets: a unified bot framework, a sandboxed coding harness agent, and infrastructure that lets the entire company ship - Use LLMs, embeddings, retrieval, and tool-calling to plug into docs, Slack, GitHub, CRM, analytics, support systems, and internal services - Replace repetitive, multi-step manual processes with orchestrated, AI-driven flows that span multiple apps and data sources - Stay current on new models and tooling, run focused experiments, and help the team converge on patterns, libraries, and infrastructure that compound over time Example problems you might work on - A sandboxed coding harness that can safely take a bug report or feature spec all the way to a deployed change - A unified bot framework that powers every AI touchpoint, internal and customer-facing from a single, observable backbone - A GTM intelligence layer that gives reps live account context, meeting prep, and follow-up from CRM, product usage, and conversation history - Turning noisy, cross-tool workflows (tickets, Slack threads, docs) into a single agent that handles triage, routing, and suggested actions - Infrastructure that lets any WorkOS team ship a reliable internal AI app without reinventing the stack What we're looking for - You've taken AI-powered systems from idea to production and through at least one iteration cycle with real users - Strong engineering fundamentals. You're comfortable owning services, data flows, and integrations end-to-end - Experience building with LLM APIs - You think about failure modes, observability, and ownership, not just whether the demo works - Bias toward action. You care less about the model and more about removing real bottlenecks, saving hours, or unlocking workflows the company couldn't do before - Comfort with ambiguity and fast change. The problem, the tools, and the "right" patterns are all evolving, you're excited to help define them Nice to have - Prior work on customer-facing AI products - Experience with embeddings, retrieval/RAG architectures, and structured tool-calling or agents - Exposure to MCP or similar protocols for connecting AI agents to real systems Benefits and Perks (US Only) 💖 At WorkOS, we offer resources that emphasize personal and familial well-being. We offer healthcare coverage for you and your family, including medical, dental, and vision. We offer parental leave, paid-time off and fully remote working arrangements.   - 401k matching - Competitive Equity - Healthcare, dental and vision coverage - FSA, ST/LT Disability, Voluntary Life - Carrot fertility benefits - 20 days paid vacation + 10 holidays + unlimited sick leave - 12 weeks fully paid parental leave - Fitness: Monthly stipend for gyms, yoga classes, race registrations or whatever keeps you active - Wellness: Monthly stipend for a massage, meditations class, therapy, or activities that enhance your well-being - Commuter benefits for hybrid employees in SF/NYC - Unlimited token usage! Please inquire directly with our recruiting team for benefits available to those working outside the US.   Equal Opportunity Employer WorkOS is an equal opportunity employer, committed to diversity and inclusiveness. We will consider all qualified applicants without regard to race, color, nationality, gender, gender identity or expression, sexual orientation, religion, disability or age. We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.