Sierra Jobs & Hiring Trends

Sierra is seeking an Agent Strategist for its Travel, Transportation, and Hospitality team to own the AI agent development life cycle from pilot to production. In this role, you will sit at the intersection of product, customer strategy, and agent building to solve complex problems for enterprise clients. You will serve as a trusted advisor to customer executives while directly impacting Sierra's core platform capabilities.

Sierra is seeking an Agent Strategist for its healthcare team to own the complete lifecycle of customer-facing AI agents from pilot to production. In this role, you will advise enterprise healthcare leaders, design and iterate on AI agents, and collaborate with internal technical teams to shape Sierra's platform. The position sits at the intersection of product, customer engagement, and technical execution to improve patient and member experiences.

As a Software Engineer on Sierra's Travel, Transportation, and Hospitality team, you will design, build, and deploy mission-critical, production-grade AI agents for major industry brands. You will own the full Agent Development Life Cycle from pilot to deployment, collaborate directly with enterprise customers, and help shape Sierra's core platform.

Sierra is seeking a Software Engineer to design, build, and deploy production-grade AI agents for high-profile financial services customers and enterprise partners. In this role, you will drive the full Agent Development Life Cycle (ADLC) from pilot through deployment while partnering directly with leaders at major financial institutions. You will also collaborate with core platform teams to translate customer needs into new AI agent capabilities and features.

As an Agent Strategist on the Tech, Media & Telecom team at Sierra, you will own the end-to-end development life cycle of AI agents from initial scoping to production deployment. You will serve as a trusted strategic advisor to enterprise leaders, shaping AI strategy and translating business goals into high-performing agents. Additionally, you will partner closely with customer working teams and surface unmet needs to internal research and platform teams.

Sierra is seeking a Software Engineer for its Healthcare team to design, deliver, and scale production-grade AI agents for health plans, providers, and healthcare platforms. The role involves taking complete ownership of the Agent Development Life Cycle, partnering directly with healthcare leaders, and navigating complex healthcare workflows while maintaining HIPAA compliance.

Sierra is seeking a Software Engineer to join its founding Public Sector team to design and build production-grade AI agents for federal and state government institutions. In this role, you will work directly with public servants to understand their workflows and prototype new tools that guide the evolution of Sierra's core platform.

Sierra is hiring a Software Engineer for its Retail Agent Engineering team to design, build, and scale production-grade AI agents for enterprise consumer brands. In this role, you will take ownership of the full Agent Development Life Cycle from pilot through deployment, working directly with customers and shaping Sierra's core platform. Projects involve modernizing complex commerce systems and enabling full discovery-to-checkout shopping experiences.

As an Agent Strategist on the Retail team at Sierra, you will own the Agent Development Life Cycle, guiding AI agents from initial scope and conversation design to launch and continuous iteration. You will serve as a strategic advisor to enterprise retail leaders while working closely with technical and product teams to translate customer needs into effective AI solutions.

Sierra is seeking a Software Engineer to join the Tech, Media & Telecom team to build and scale production-grade AI agents for major enterprise clients. The role involves managing the complete Agent Development Life Cycle, partnering directly with customers, and using real-world deployment insights to evolve Sierra's core platform. Candidates should have experience building end-to-end production systems and working in ambiguous environments.

Sierra is seeking a Business Value Strategy and Operations professional to join its pricing team. In this role, you will partner with sales teams and enterprise customers to build ROI models, investment cases, and customer-specific value frameworks. You will also establish Sierra's business value framework from the ground up to demonstrate measurable business impact.

Sierra is seeking a Senior Accountant to manage the end-to-end global accounting close, reconciliations, payroll reviews, and audit readiness. The role involves driving finance transformation initiatives to build an AI-native accounting function and scale operational efficiency. Candidates should have a mix of public and private accounting experience.

Sierra is seeking a Brazilian Portuguese-speaking Agent Strategist to guide AI agents from initial scoping and conversation design to full production deployment. In this role, you will act as a strategic advisor to enterprise leaders, partner closely with customer working teams, and feed insights back to product and research teams.

Sierra is looking for a Web Developer to own the frontend across product and marketing surfaces. The role involves developing content infrastructure using Sanity CMS, driving site performance and accessibility, and partnering across teams to enable analytics, localization, and growth experimentation.

Sierra is seeking an Office Coordinator in San Francisco for a 6-month fully on-site contract position to oversee daily office operations and workplace hospitality. In this role, you will greet visitors, manage office inventory and facilities requests, support meeting logistics, and assist with new hire onboarding. The position requires 2–4 years of experience in office coordination or administrative roles.

Sierra is seeking a Partnerships Manager to lead and expand its Government and Public Sector partner ecosystem across the US, Canada, and the UK. In this role, you will build scalable partner enablement engines, structure joint GTM strategies, and manage executive relationships with resellers and systems integrators. You will work closely with internal teams to accelerate growth and expand Sierra's public-sector reach.

Sierra is seeking a Technical Accounting Lead to own technical accounting policies, review monthly financials, and lead audit and IPO preparedness. The role involves advising on strategic investments and leveraging AI tooling to scale and automate the finance function. Candidates must be CPAs with experience at a Big Four firm and in-house at a high-growth enterprise software company.

Sierra is looking for an Area Vice President to lead, mentor, and grow an enterprise sales team within the Consumer Business Services vertical. The role involves owning regional performance and forecast accuracy while remaining deeply involved in complex, high-value customer deals. Candidates must bring extensive enterprise sales and people leadership experience.

Sierra is seeking a Software Engineer Intern to work directly on production AI agents for customer-facing applications. In this role, you will gain hands-on experience designing, developing, and shipping AI agent features for major global brands. The position is open to students pursuing a computer science or related degree with an expected graduation between December 2027 and June 2028.

Sierra is seeking an Enterprise Sales Director to independently drive complex 6- and 7-figure AI deals end-to-end within the healthcare sector. The role involves building trusted C-suite relationships, managing deal risks, and leveraging AI tools to optimize the sales process. Candidates should have 8-10 years of enterprise sales experience managing a $1M+ quota.

Sierra is seeking a Software Engineer to design, deploy, and iterate on production-grade AI agents across enterprise clients and cutting-edge startups. In this role, you will own the full Agent Development Life Cycle and partner directly with customers to solve complex real-world challenges. Your hands-on work with enterprise systems will directly guide the evolution of Sierra's core AI platform.

Sierra is seeking a Commercial Counsel to join its legal team and handle a broad scope of commercial contracts, operational workflows, IP, and regulatory privacy matters. The role involves structuring and negotiating SaaS agreements, technology licenses, and NDAs, as well as advising on AI legal issues. Candidates should bring 2-6 years of legal experience across both top law firm and tech in-house environments.

Sierra is expanding its Solutions Product Marketing team to drive industry-first go-to-market strategies for its AI customer experience platform. In this role, you will translate product capabilities into industry-relevant positioning, sales enablement playbooks, and tailored product launches. You will also establish repeatable operational processes and assets to scale messaging across diverse industry verticals and buyer personas.

Sierra is seeking an Enterprise Sales Director to join its Healthcare team and drive revenue growth across major health plans, providers, and platforms. The role involves prospecting enterprise accounts, building relationships with key stakeholders, and negotiating complex 6- and 7-figure ACV deal cycles using AI-native selling practices.

Sierra is hiring a Commercial Counsel to serve as a core member of its legal team. The role focuses on structuring, negotiating, and advising on commercial contracts, including SaaS subscription agreements and technology licenses. You will also help build scalable legal workflows while advising across IP, privacy, and evolving AI frameworks.

Sierra is hiring a Software Engineer to design and build foundational systems for its Identity & Enterprise Platform. In this role, you will develop enterprise platform capabilities, including identity, access management, and integrations to support large-scale enterprise clients. The position requires a focus on security, reliability, and scaling systems across complex environments.

Sierra is looking for a GTM Engineer to design and build automated workflows, data pipelines, and AI-powered internal tools for marketing and sales teams. The role owns end-to-end lead enrichment infrastructure, fit scoring pipelines, and modern GTM data architecture. Candidates should have technical experience building software, working with LLMs, and managing modern GTM stacks.

Sierra is seeking a Site Reliability Engineer to define and build the foundation of reliability, observability, and scalability across its AI-driven infrastructure. In this role, you will own the observability stack, design AWS cloud infrastructure using Terraform, and optimize LLM deployments. You will collaborate closely with core engineering and product teams to establish standard SRE practices and improve CI/CD pipelines.

Sierra is seeking an Enterprise Sales Engineer to own the end-to-end technical pre-sales process, from scoping customer use cases to designing platform demos and architecture reviews. In this role, you will partner cross-functionally with Sales, Product, and Agent Engineering to support enterprise clients and drive GTM operations. Candidates must have experience in technical sales, demo presentation, and leveraging AI tools efficiently.

Sierra is looking for a Platform Software Engineer to build the primitives, runtime systems, and internal developer tooling that power customer-facing AI agents. In this role, you will design scalable, reliable infrastructure and workflows that enable engineers to build, orchestrate, and deploy agents efficiently. The position requires 4+ years of hands-on experience building production systems.