Jobs at Sierra

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.

Own revenue close activities, including revenue policy, contract review, consumption analysis, and ASC 606 journal entries. Lead customer onboarding, purchase-order collection, invoicing, tax coordination, and collections processes. Build scalable dashboards, systems, and procedures while driving finance transformation through AI, automation, and technology improvements. Partner cross-functionally with Sales, Tax, and customers to improve accuracy, timeliness, and operational efficiency.

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.

Lead enterprise sales across Japan as a player-coach, initially prospecting, building pipeline, managing customers, and closing complex deals. Hire, onboard, coach, and develop account executives; own regional quota and forecast accuracy; inspect pipeline quality; improve sales execution; and support strategic negotiations. Partner with Revenue Operations on data quality and insights while helping shape go-to-market strategies and sales motions for an AI platform.

Design and demonstrate Sierra’s AI Agent product, develop technical solutions for enterprise customers, answer technical questions, and support the sales process. Collaborate with Sales, Product, and Agent Engineering teams to improve products based on customer needs. Build customer relationships with executives and technical leaders, translate business problems into solutions, and use AI tools for discovery, solution design, demos, prototypes, and technical proposals.

Lead enterprise sales by prospecting, building executive relationships, managing complex deal cycles, negotiating contracts, and closing large accounts. Develop sales strategies, meet revenue targets, shape the company’s early go-to-market motion, and collaborate with marketing, product, technical, operations, legal, and finance teams. The role requires strong English and Korean communication, enterprise sales experience, and the ability to manage $1M+ quotas.

Own end-to-end territory strategy and operations: design and carve territories, manage bi-weekly account allocation, analyze territory performance, prioritize accounts, partner with Sales/RevOps/leadership, communicate changes sensitively, and improve territory planning processes while executing strategic initiatives.

Lead EMEA brand presence as the region's first dedicated brand designer. Localise global campaigns, design GTM presentations, support regional events, build brand systems, collaborate with cross-functional teams, and maintain high design craftsmanship across markets.

Serve as the GTM technical expert: design and demo Sierra Agents, answer technical questions, lead early enterprise sales conversations, work cross-functionally with Sales, Product, and Engineering to drive customer-driven product improvements and translate technical needs into solutions.

Partner with sales to develop pricing proposals and ROI case studies, and collaborate with product, marketing, and ops to define pricing and packaging strategy. Support complex negotiations and data-driven GTM operations to optimize customer deals and commercial outcomes.

Lead and scale recruiting across Japan for technical and non-technical roles. Build and develop a high-performing recruiting team, partner with senior leaders on hiring strategy, advise on Japan talent market and compensation, design sourcing strategies, personally close senior hires, improve recruiting operations and candidate experience, and collaborate cross-functionally with People, Compensation, Immigration, and Recruiting Operations.

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.

Provides hands-on IT support for the New York office, including macOS troubleshooting, global helpdesk queue management, hardware lifecycle, conference room AV, office networking, onboarding, SaaS administration, vendor coordination, and IT logistics. The role also supports office build-outs and moves, executes endpoint and workplace technology projects, improves processes, and documents solutions. Requires strong troubleshooting, organization, communication, and experience supporting technical users.

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.

Full-cycle recruiter owning end-to-end hiring: partner with hiring managers, source active and passive technical and business candidates, track recruiting metrics, and deliver an excellent candidate and interviewer experience.

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.