Jobs at Sierra

Build frontend features across Sierra’s product and marketing sites. Develop Sanity CMS infrastructure, structured content models, preview workflows, analytics, experimentation, localization, and accessibility-focused components. Own Core Web Vitals, asset optimization, and performance improvements while collaborating with marketing, sales, operations, designers, and content teams.

Own the end-to-end technical pre-sales process for federal and state government customers. Scope use cases, communicate business value, build and deliver demos, lead architecture reviews, and serve as a trusted technical advisor. Partner with Sales, Product, and Engineering to improve the AI platform, support capture and market strategy, and help establish the public sector team. Apply AI tools to discovery, solution design, prototypes, demos, and technical proposals while maintaining accuracy and customer trust.

Coordinate daily office operations at Sierra’s San Francisco headquarters, including reception, guest experience, mail and packages, inventory, meeting logistics, facilities requests, safety supplies, and onboarding support. Partner with Operations, IT, HR, Executive Assistants, and property management to maintain welcoming, organized, well-functioning workplace environments. This is a fully onsite, six-month contract role with potential extension or conversion.

Own Sierra’s public-sector partnership strategy across the US, Canada, and UK. Recruit and manage systems integrators, resellers, distributors, and strategic alliances; develop joint go-to-market plans, partner enablement, commercial frameworks, and governance programs; and drive pipeline and growth. The role requires strong government procurement knowledge, executive relationship-building, AI fluency, and collaboration across Sales, Marketing, Product, and Legal.

Build scalable data foundations and personalization systems for AI agents. Responsibilities include real-time event infrastructure, streaming and batch ETL, Iceberg-based lakehouses, OLAP querying, data orchestration, governance, analytics products, long-term agent memory, customer data platform primitives, and ML-powered personalization. The role may emphasize platform or full-stack product engineering and requires strong distributed systems, data modeling, product development, and software engineering expertise.

Leads technical accounting policy documentation, advises on investments, acquisitions, and partnerships, reviews monthly financials, and coordinates external audits. Oversees financial statement presentation and disclosure compliance while driving IPO preparedness. Leads finance transformation initiatives by improving accounting technology, automating processes, and applying AI to scale the function. The role requires CPA certification, Big Four and high-growth enterprise software experience, US GAAP expertise, and strong process-building skills.

Provides strategic and administrative support to the co-founder, including calendar, travel, inbox, correspondence, meeting preparation, action-item follow-up, stakeholder communication, and confidential information management. The role also establishes and improves administrative systems while working primarily in person at the San Francisco office and traveling as needed.

Own Sierra’s public-sector enterprise sales business across federal, state, and local government accounts. Build pipeline, manage strategic relationships, lead complex six- and seven-figure sales cycles, develop capture and acquisition strategies, coordinate bids and proposals, and establish partner and teaming ecosystems. The role also helps build repeatable public-sector go-to-market processes, forecasts, contract-vehicle strategies, and sales playbooks while engaging agency executives, procurement officials, technical teams, and systems integrators.

Rotational APX participants will build and ship AI agents for enterprise customers, contribute code and product designs to Sierra’s platform, learn scalable agent development, and collaborate with engineering, product, and operations teams. The program includes rotations across Agent Development and Core Product teams, internal reviews, and product discussions. Candidates should be pursuing a bachelor’s or master’s degree, have software engineering or product management experience, demonstrate expertise in modern programming technologies, and show interest in AI applications.

Build and scale Sierra’s internal IT infrastructure as the first internal IT team hire. Responsibilities include migrating identity management to Okta, implementing device compliance, identity analytics, DLP, automated onboarding and offboarding, compliance integrations, SaaS lifecycle management, and internal tools using APIs and automation. The role requires operating independently in a fast-paced enterprise environment while improving security, reliability, documentation, and operational efficiency.

Lead and develop a regional enterprise sales team, own sales performance and forecast accuracy, and support complex $1M+ deals through negotiation and close. Hire, coach, and develop account executives; inspect pipeline quality; partner with Revenue Operations; and build a culture of accountability and collaboration. The role also contributes to go-to-market strategy and requires extensive enterprise sales and people leadership experience.

Own the enterprise technical pre-sales process, including customer discovery, solution scoping, business-value articulation, architecture reviews, platform demonstrations, prototypes, and technical proposals. Partner with Sales, Product, and Agent Engineering teams to improve Sierra’s AI solutions. Build executive and technical relationships, lead customer sales cycles, translate business problems into solutions, and communicate effectively with technical and non-technical audiences while using AI tools responsibly.

Build systems to analyze, visualize, and monitor conversational agent performance, enable A/B testing for agents, and create an AI-powered exploratory interface for conversational data (clustering and search). Deliver full-stack production features supporting developer workflows and proactive defect detection.

The Product Manager for Voice will craft real-time AI conversation experiences, building reliable systems, defining interaction models, and enhancing performance based on user feedback.

Design, build, and operate scalable, secure infrastructure and self-serve platform for LLM inference and services. Own cloud IaC (Terraform), CI/CD, observability, incident response, authentication, and integrations with enterprise environments to ensure reliability and performance.

The Product Designer will solve user problems by designing innovative AI tools, collaborating across teams, and building design systems to enhance customer experience.

As a Frontend Software Engineer, you'll own the frontend experience, lead design systems, collaborate with design teams, maintain UI components, and ensure high performance, accessibility, and code quality, while also integrating with backend services.

Build AI-driven product features and platforms for conversational agents: agent architecture, retrieval, evaluation, voice/telephony, simulation/benchmarking, content management, and agent development lifecycle. Collaborate cross-functionally to design, ship full‑stack production systems and tooling that improve agent quality and customer experience.

The Business Systems Engineer will design and implement billing systems, integrate Salesforce with financial systems, and ensure data accuracy for revenue operations.

The Commercial Counsel will handle commercial contracts, drive operational excellence, advise on legal issues, and collaborate across teams to support business initiatives.