[All remote jobs](https://jobicy.com/jobs.md)Open role[![Sierra logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/08/9877fe33-221.jpeg)](https://jobicy.com/company/sierra.md)Remote opportunity at[Sierra](https://jobicy.com/company/sierra.md) # Strategist, Agent Development Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/sierra.md)Share26 Aug 2026Published34Listing views1Application actions25 Sep 2026Apply before Opportunity details ## About this role. AI SummarySierra is hiring an Agent Strategist to lead enterprise AI-agent engagements from initial scoping through production launch and ongoing optimization. The role combines customer strategy, conversation and workflow design, technical collaboration, evaluation design, and delivery ownership. The Strategist will work directly with executive and operational customer stakeholders while translating business objectives into measurable agent outcomes. Success requires strong communication, comfort with APIs and system architecture, and the ability to manage several ambiguous, high-visibility implementations at once. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a demanding cross-functional role that requires ownership of production AI-agent outcomes, technical fluency, and executive-level customer advisory work. The stated culture of intensity, rapid iteration, and handling high-stakes enterprise use cases indicates a fast, high-accountability environment. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job medianMarket rate$160,000US market range$130k–$210k0$231k AI insightNo actual salary was disclosed, so these are estimated US-market annual base-salary figures in USD for a senior customer-facing AI implementation and product-strategy role. The estimate reflects the role's enterprise scope, production LLM-agent expertise, technical requirements, and high autonomy; equity or other variable compensation may be additional. ## Core skills Skills and capabilities most closely associated with this opportunity. [AI agent development](https://jobicy.com/jobs?search_keywords=AI%20agent%20development.md)[LLM agents](https://jobicy.com/jobs?search_keywords=LLM%20agents.md)[Enterprise customer strategy](https://jobicy.com/jobs?search_keywords=Enterprise%20customer%20strategy.md)[Conversation design](https://jobicy.com/jobs?search_keywords=Conversation%20design.md)[Prompt engineering](https://jobicy.com/jobs?search_keywords=Prompt%20engineering.md)[RAG](https://jobicy.com/jobs?search_keywords=RAG.md)[Agent evaluation frameworks](https://jobicy.com/jobs?search_keywords=Agent%20evaluation%20frameworks.md)[API documentation](https://jobicy.com/jobs?search_keywords=API%20documentation.md)[Systems architecture](https://jobicy.com/jobs?search_keywords=Systems%20architecture.md)[Program delivery](https://jobicy.com/jobs?search_keywords=Program%20delivery.md) Sample interview questionsHow would you take an enterprise AI agent from an initial pilot to a successful production deployment?I would begin by aligning on the highest-value customer outcome, defining the target users, constraints, escalation paths, and measurable success metrics. I would map priority conversations, required data and integrations, safety requirements, and evaluation cases before launching a controlled pilot. After launch, I would use production feedback and quality metrics to prioritize iterative improvements, while maintaining clear stakeholder communication and a documented decision process. Describe how you would evaluate whether an agent is outperforming a human-led process. I would establish a baseline using historical human performance and compare like-for-like outcomes such as resolution rate, retention, conversion, accuracy, compliance, customer satisfaction, handling time, and escalation rate. The evaluation set would include representative, edge-case, and regulated scenarios, with qualitative review for failures that metrics may miss. I would report results transparently, distinguish agent limitations from process issues, and use findings to drive targeted improvements. How do you communicate technical tradeoffs to an executive customer stakeholder? I frame the tradeoff in terms of business impact, risk, timeline, cost, and customer experience rather than implementation detail alone. I provide a clear recommendation, explain the viable alternatives and their consequences, and identify the decision needed from the stakeholder. For example, I might explain that a narrower initial scope can launch sooner with higher reliability, while a broader scope requires additional integration and evaluation work. What would you do if a customer reports that a production agent is giving inconsistent answers? I would first triage severity, affected users, and potential safety or compliance impact, adding guardrails or routing to human support if needed. I would then inspect conversation logs, prompts, retrieval quality, tool behavior, data freshness, and evaluation coverage to isolate the failure mode. Once a fix is validated against regression tests and representative live cases, I would deploy it carefully and communicate the root cause, remediation, and prevention plan to the customer. How do you manage multiple high-priority customer implementations with competing timelines? I prioritize based on customer impact, launch risk, contractual or operational commitments, dependencies, and the reversibility of decisions. I make work visible through a structured delivery plan with owners, milestones, risks, and regular stakeholder updates. When capacity conflicts arise, I surface them early, propose tradeoffs, and secure alignment rather than allowing critical decisions or customer communication to drift. ### About us At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such as SoftBank, Uber, Rivian, CLEAR, and Sutter Health. 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 Family. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are [Bret Taylor](https://www.linkedin.com/in/brettaylor/) and [Clay Bavor](https://www.linkedin.com/in/claybavor/). Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google’s earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ### What you’ll do As an [Agent Strategist](https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai), you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business. * Own the [Agent Development Life Cycle](https://sierra.ai/blog/agent-development-life-cycle). Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome. * Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there. * Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. * Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. ### Example projects These are the kinds of projects that strategists on our team have worked on recently: * Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers. * Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation. * Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our [financial services blog](https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services) for examples. * Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner. * Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in [outcome](https://sierra.ai/blog/outcome-based-pricing-for-ai-agents) week over week. ### What you’ll bring * Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. * Communication. Clear, direct, and persuasive across technical and non-technical audiences. * Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. * Technical aptitude. Comfortable engaging directly with technical concepts – reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. * Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. ### Even better… * Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. * You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. * A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. ### 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 through Carrot * Lunch, as well as delicious snacks and coffee to keep you energized * 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 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 even if your experience doesn’t precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class. Show more [Apply now >](https://jobicy.com/jobs/151673-strategist-agent-development.md) > Annual salary information is not provided for this position. Explore salary ranges for similar roles in our [Salary Directory ›](https://jobicy.com/salaries.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. Next step ## Apply now. Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information. Keep exploring ## Related remote jobs. Matched by job category10 related opportunities[Product & Operations](https://jobicy.com/categories/management.md) [Browse all jobs](https://jobicy.com/jobs.md) * ![Upwork logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2020/10/upwork.png) Upwork Aug 26 ### [Chief of Staff to GM & Chief Operating Officer](https://jobicy.com/jobs/151729-chief-of-staff-to-gm-chief-operating-officer.md) Upwork Inc.’s (Nasdaq: UPWK) family of companies connects businesses with global, AI-enabled talent across every contingent work type including freelance, fractional, and payrolled. This portfolio includes the Upwork Marketplace, which… * ![Spreedly logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/10/c7ecd47f20eec380edf63d11c0dad38d.png) Spreedly Aug 26 ### [Business AI Operations Specialist](https://jobicy.com/jobs/151722-business-ai-operations-specialist.md) About Us: Spreedly is the world’s leading Open Payments Platform. Founded in 2007 and headquartered in Durham, NC, the company gives mid-market and enterprise businesses the infrastructure to connect to… * ![Future PLC logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/2da60a56-221.jpg) Future PLC Aug 26 ### [Staff Product Manager](https://jobicy.com/jobs/151710-staff-product-manager.md) About Us: Future is building a personalized guidance system for lifelong health. We help people understand what to do next for their body, goals, and stage of life — then… * ![Mural logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2022/01/9b6f1383-221.jpeg) Mural Aug 26 ### [Senior Product Manager, Growth & Engagement](https://jobicy.com/jobs/151698-senior-product-manager-growth-engagement-2.md) ABOUT THE TEAM At Mural, we’re changing how teams collaborate, think, and make decisions together. The Growth & Engagement team owns the experiences that turn a single-player tool into a… * ![FastSpring logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2024/04/76c6c41f-221.jpeg) FastSpring Aug 26 ### [Senior Data Product Manager](https://jobicy.com/jobs/151696-senior-data-product-manager.md) About FastSpring: FastSpring is how AI, SaaS, gaming, software, and digital product companies sell online in more places around the world. We handle all payment needs from checkout to taxes… * ![Obsidian Security logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/3c84d813-221.jpeg) Obsidian Security Aug 26 ### [Head of GTM Enablement](https://jobicy.com/jobs/151670-head-of-gtm-enablement.md) Obsidian Security is the leading SaaS security platform, trusted by global enterprises like Snowflake, T-Mobile, and Algolia. We protect 200+ organizations across North America, Europe, the Middle East, Southeast Asia,… * ![Sierra logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/08/9877fe33-221.jpeg) Sierra Aug 26 ### [Strategist, Agent Development (French speaking)](https://jobicy.com/jobs/151668-strategist-agent-development-french-speaking.md) About us At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such… * ![Binance logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/bc822f38-221.jpg) Binance Aug 26 ### [Core Experience & AI Product Manager](https://jobicy.com/jobs/151651-core-experience-ai-product-manager.md) Binance is a leading global blockchain ecosystem behind the world’s largest cryptocurrency exchange by trading volume and registered users. We are trusted by 300+ million people in 100+ countries for… * ![Alimentiv logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/d11f5845-221.png) Alimentiv Aug 26 ### [Director, Project Management](https://jobicy.com/jobs/144411-director-project-management.md) ABOUT ALIMENTIVAlimentiv is a global CRO with a singular focus: advancing therapies for patients with gastrointestinal diseases. GI is our WHY and for more than 30 years that purpose has… * ![Fortive logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2026/06/08ee6cc3-221.webp) Fortive Aug 26 ### [ASC Regional Director – West](https://jobicy.com/jobs/147553-asc-regional-director-west.md) Job Description Business Title: Account/Direct Sales – Software P16Job Title: Regional DirectorJob Summary: The ASC Regional Director plays a critical role in driving revenue growth by identifying, engaging, and closing new business…