Sierra

Web Designer

• Designing websites and brands
• Working on early-stage naming to full-scale brand rollouts
• Ideating with engineers on implementation
• Staying sharp on trends
• Exploring new tooling and workflows

Brand/Web Designer

Backend Engineer

• Design, build, and ship full-stack features in their customer web app and growth surfaces.
• Collaborate with product and revenue leadership to ideate, run, and analyze experiments (funnels, pricing/packaging, referral loops, lifecycle nudges, onboarding, and conversion optimizations).
• Build and refine product flows that help families make confident, informed decisions.
• Instrument analytics and event tracking to ensure clear, causal measurement of impact.
• Contribute to a fast feedback loop: quick prototypes → data-informed iteration → polished releases.
• Uphold reliability, accessibility, performance, and security across the stack.

Senior Software Engineer, React, TypeScript, Node.js

Sales Engineer

• Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.
• You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
• As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.

Full-stack Engineer

• Design and deliver production-grade AI agents central to Sierra’s growth and revenue
• Drive the Agent Development Life Cycle (ADLC) with ownership from pilot through deployment and continuous iteration
• Build, tune, and evolve AI agents in production environments across industries like finance, healthcare, and commerce
• Partner with large enterprises and startups to understand business challenges and implement AI agent solutions
• Surface unmet customer needs, prototype new tools and features, and guide platform evolution
• Build industry-specific agent frameworks, integrate voice models at scale, and facilitate design partnerships for new product initiatives
• Collaborate with research, product, and platform teams to define ADLC best practices

Software Engineer, Agent – New Grad

Product Manager

• Build enterprise-grade AI agents: partner directly with engineers and customers to build and ship AI agents handling thousands of conversations per day
• Engage with customers at all levels: discover and assess requirements, prepare and present demonstrations, address technical challenges with technical counterparts
• Develop and improve Sierra virtual agents to fit and anticipate customers’ needs and business processes
• Become trusted advisors and drive strategic technical strategies for customers
• Shape the product roadmap: work with engineering and product teams to scope and implement new features essential to customer success

Product Manager, Agent Development

Security Engineer

• Lead security initiatives for Sierra’s Conversational AI Platform spanning data protection, identity and access management, infrastructure hardening, change management, operational resilience, and vulnerability management.
• Bring structure, visibility, and accountability to critical security programs, aligning them with company growth and customer trust goals.
• Shape compliance readiness by aligning with frameworks such as ISO 42001, ISO 27001, PCI DSS, SOC 2, HIPAA, and the EU AI Act and translating these into actionable controls and scalable processes.
• Build a security-first culture by designing awareness programs that empower every team member.
• Embed trust by design, partnering with Product, Platform, and Agent Engineering to integrate security, privacy, and responsible AI practices into the stack.
• Collaborate across Product, Platform Engineering, Agent Development, Legal, Operations, Sales, and GTM to embed security and compliance across the tech stack.

Technical Program Manager, Security

Human Resources

• Employee Relations: Serve as a key resource for employees and managers, providing guidance on HR policies, addressing and resolving employee conflicts, and fostering a positive and productive work environment.
• HR Administration: Manage HR systems, maintain accurate employee records, benefits enrollment, and generating HR reports.
• Employee Onboarding: Ensure a seamless experience from candidate offer approval to new hire start date.
• HR Policy Implementation: Develop and ensure the effective implementation of HR policies and procedures across Sierra, ensuring alignment with legal requirements and company values.
• Employee Engagement: Design and implement employee engagement programs to enhance employee satisfaction and foster transparent and effective communication.
• Organizational design: Structure teams for efficiency and scalability, define roles and responsibilities, align talent with business strategy; provide strategic thinking, coaching, and business acumen.
• Partner with engineering, product, and other technical teams to align people strategies with business needs.

HR Business Partner, Tech

Project Manager

• Manage the full lifecycle of commercial construction projects from initial design through occupancy
• Serve as primary point of contact for facilities support and work with local office managers
• Execute multiple projects simultaneously, including complex retrofits and large-scale buildouts
• Lead project management initiatives and specialty programs (e.g., EBCs)
• Collaborate cross-functionally with Operations, IT, Finance, Recruiting, contractors, and architects
• Support capital and facilities budget planning, variance tracking, and financial reporting
• Conduct detailed project estimating, budgeting, and financial analysis
• Support office management to maintain uniform operations across offices
• Lead vendor management and contract administration
• Evaluate and improve facilities operations processes and engage external vendors to deliver high-quality work

Project Manager, Real Estate Operations

Technical Writer

• Work closely with Product Management, Engineering, and Agent Development to craft documentation, guides, videos, and educational content that help people succeed with the platform.
• Own and maintain high-quality documentation across different personas: Developers (API references, SDK guides, tutorials, code samples, reference agents); No-code builders (step-by-step product walkthroughs, task-based guides, video explainers); CX leaders (conceptual overviews, operations guides, success playbooks).
• Translate technical details into clear, approachable explanations without losing precision.
• Collaborate with Engineering and Product teams to understand new features and ship documentation in sync with product releases.
• Collaborate with Product Marketing and Product Management to curate and maintain the changelog, ensuring product updates are communicated clearly and consistently.
• Maintain the documentation product and its surrounding UX and features, ensuring docs are discoverable, usable, and integrated into the overall platform experience.
• Create educational resources such as quickstarts, blog posts, best-practice guides, and video tutorials tailored to different audiences.
• Establish documentation standards, style guides, and templates to ensure consistency and scalability across technical and non-technical content.
• Proactively identify content gaps and improve discoverability, usability, and overall customer experience.
• Engage with the community of builders and operators to learn from real-world usage and incorporate feedback into docs.

People Operations

• Manage all aspects of the employee lifecycle including pre-boarding, onboarding, Sierra 101 & 102 programs, offboarding, and employee changes focused on creating a seamless employee experience
• Define and refine People processes and best practices; build the People playbook and continuously optimize operations as Sierra scales
• Create and operationalize performance review processes and develop frameworks for evaluating and growing talent
• Lead employee engagement initiatives such as surveys, knowledge wikis, learning & development programs, and other people-focused programs
• Manage HR systems (currently Rippling) and build/maintain operational dashboards to track key People metrics; support future systems and tool implementations
• Ensure HR policies and practices comply with federal, state, and local regulations; maintain accurate employee records and support audits and reporting requirements; develop training and communications to align organization

People Operations Manager

• Build enterprise-grade AI agents: partner directly with engineers and customers to build and ship AI agents that handle thousands of customer conversations a day
• Engage with customers at all levels: discover and assess requirements; prepare and present demonstrations; address and overcome technical challenges with technical counterparts; develop and improve Sierra virtual agents to fit and anticipate customers’ needs and business processes; become trusted advisors and drive strategic technical strategies
• Shape the product roadmap: work with engineering and product development teams to scope and implement new features essential to the success of customers
• Collaborate cross-functionally to prioritize features, resolve technical challenges, and deliver production-ready agent solutions

Engineering Manager

• Lead the design and delivery of production-grade AI agents, managing and growing a team of engineers building highly performant, reliable, and intuitive AI agents
• Ensure technical excellence, operational reliability, and high customer impact for production systems across industries like finance, healthcare, and commerce
• Own the Agent Development Life Cycle (ADLC): guide team from initial pilot through deployment and continuous iteration, coaching engineers on ADLC best practices
• Ensure projects are delivered on time, meet customer needs, and scale effectively in production environments
• Partner with large enterprises and startups to understand business challenges and guide the team in building AI agents that transform operations at scale
• Shape the future of Sierra’s platform by surfacing unmet needs, prioritizing initiatives, and collaborating with research, product, and platform teams

Agent Engineering Manager

Administrative Assistant

• Greet visitors and oversee the day-to-day functioning of the office
• Ensure the office environment is welcoming, clean, and organized by managing office supplies, equipment, and kitchen inventory
• Coordinate with building management for office maintenance and repairs
• Help the admin team organize company happy hours, in-office trainings, team lunches and celebratory events
• Hand out and track company merch for new hires and send merch packages/gifts when necessary; execute new inventory orders
• Address any office-related issues promptly and effectively to foster a positive work environment
• Partner with facilities and real estate team on office improvements
• Maintain a high level of confidentiality and discretion with all materials and information
• Note: This is a 6-month contract position and is ineligible for full-time benefits

Office Manager

Revenue Operations

• Support the execution of revenue forecasting by leveraging data insights to drive strategic planning and financial projections
• Design and refine compensation structures to incentivize performance, align with company goals, and maintain competitiveness
• Develop models to assess staffing needs, optimize team structures, and support efficient resource allocation as the organization scales; optimize sales territory planning
• Build and refine data-driven models to analyze customer behavior, predict demand, and identify revenue opportunities
• Own and evolve business reporting frameworks; develop and manage dashboards and KPIs to track performance and ensure data integrity
• Establish and enforce standardized processes across GTM functions to ensure clarity, efficiency, and scalability
• Partner with customer-facing teams to drive alignment between Sales and Agent Development and maintain operational cadence

Revenue Operations Lead

Data Engineer

• Design and operate scalable batch and real-time data systems
• Create and maintain trusted data models to power analytics, experimentation, and AI agent development
• Build and operate pipelines that deliver high-quality, reliable data to all areas of the business
• Ensure business teams have access to reliable data to drive insight and innovation
• Influence how data is captured, governed, and leveraged across Sierra to enable decision-making at scale
• Partner with engineering, product, ML, analytics, and GTM teams to shape data strategy and infrastructure
• Establish foundations of Sierra’s data ecosystem and drive standards for reliability and trust
• Directly power next-generation AI-driven customer experiences through data engineering work

Data Scientist

• Play a foundational role in driving data strategy and shaping Sierra’s data future
• Conduct deep-dive analyses of customer data to identify trends, patterns, and actionable insights
• Develop and deploy machine learning models to analyze customer engagement and optimize experiences across chat, agent interactions, and product usage
• Build experimentation capabilities and evaluate models for experimentation and causal inference (A/B testing)
• Partner with product, engineering, and research teams to inform product strategy and execution and experiment rapidly
• Partner with the data platform team to ensure robust data pipelines and a scalable infrastructure for advanced analytics

Sales

• Help define the sales motion as a founding member of the team
• Prospecting and lead generation: identify and target potential customers through research, networking, and cold calling
• Lead qualification via discovery calls to ensure alignment and increase engagement
• Craft and deliver tailored sales presentations to enterprise customers
• Manage relationships and serve as primary point of contact until hand-off to Enterprise AEs
• Collaborate closely with Sales team and Account Executives to align strategies, campaigns, and ensure seamless transitions of qualified leads

Enterprise Sales Associate

Account Executive

• Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling; build new relationships with our commercial customers and prospects to drive revenue, pipeline, and deployment capacity
• Manage relationships: Build and maintain strong relationships with customers' key decision-makers and stakeholders; serve as their primary point of contact and exceed their expectations
• Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, address objections and close deals; navigate contracts and agreements quickly and effectively, working closely with legal and finance
• Sales strategy & planning: Develop and execute sales strategies to exceed sales targets; craft tailored sales presentations and proposals; collaborate with marketing to implement effective sales campaigns
• Help define our sales motion: Contribute to shaping GTM function and how it operates and succeeds
• Collaborate cross-functionally: Work closely with GTM, product, technical and operations orgs to deliver the product

Commercial Account Executive

• Design and deliver production-grade AI agents: build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue
• Drive the Agent Development Life Cycle (ADLC): ownership from initial pilot through deployment and continuous iteration; build, tune, and evolve AI agents in production
• Partner with large enterprises and cutting-edge startups: work directly with leaders to understand business challenges and embed AI agents across customer stacks
• Build the future of the platform: surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform teams
• Example projects: design agents to manage subscription churn for telecom/media; develop agents for complex customer interactions and personalized recommendations; create generalizable AI agent frameworks; facilitate design partnerships for new product initiatives; experiment with and integrate voice models at enterprise scale

• Bring Enterprise-grade AI Agents to the World: empower every business to build a world-class AI agent that represents its identity and brand
• Solve for the Customer: serve multiple stakeholders (end users, CX managers, and developers) and address their unique needs
• Innovate: discover new tools and processes for building AI Agents and lead 0–1 product work
• Collaborate: partner closely with engineering, design, leadership, and the entire company to define and build cohesive experiences
• Advise: become a trusted and strategic advisor to customers alongside sales, go-to-market, and forward-deployed teams
• End-to-End Ownership: lead the product through all stages from concept to execution in close collaboration with cross-functional partners

Brand/Web Designer

Senior Software Engineer, React, TypeScript, Node.js

Sales Engineer

Software Engineer, Agent – New Grad

Product Manager, Agent Development

Technical Program Manager, Security

HR Business Partner, Tech

Project Manager, Real Estate Operations

Technical Writer

People Operations Manager

Product Manager, Agent Development

Agent Engineering Manager

Office Manager

Revenue Operations Lead

Data Engineer

Data Scientist

Enterprise Sales Associate

Commercial Account Executive

Software Engineer, Agent – New Grad

Product Manager, Core