How to Apply to Sierra AI

8 min read Last updated March 8, 2026 138 open positions
Blake Crosley
Blake Crosley Researched using publicly available information, hiring data, and ATS analysis.

Key Takeaways

  • Sierra AI is led by Bret Taylor (ex-Salesforce CEO) and Clay Bavor (ex-Google VP), bringing unmatched enterprise technology leadership to the conversational AI space
  • The company uses Ashby for recruiting — format your resume with standard sections and submit as PDF for optimal parsing
  • With 138+ open positions and a $4.5B valuation, Sierra is in a rapid growth phase offering significant career opportunities across all functions
  • Interviews focus on practical problem-solving and customer empathy rather than abstract puzzles — prepare with real-world examples from your experience
  • Sierra values intellectual humility and operational excellence — demonstrate how you handle ambiguity and make decisions with incomplete information
  • Enterprise customer experience is central to everything Sierra does — highlight any relevant CX, B2B, or conversational AI experience prominently

About Sierra AI

Sierra AI is building the next generation of conversational AI, creating intelligent AI agents that transform how enterprises interact with their customers. Founded by Bret Taylor, former CEO of Salesforce and former CTO of Facebook, and Clay Bavor, former VP at Google who led AR/VR and Labs initiatives, Sierra brings together two of Silicon Valley's most accomplished technology leaders. The company has raised over $500 million in funding and achieved a valuation of $4.5 billion, making it one of the most well-capitalized AI startups in the world. Based in San Francisco, Sierra employs approximately 300 people and is growing rapidly with 138+ open positions across engineering, operations, legal, and go-to-market functions. The company's AI agents are deployed by major enterprises to handle customer interactions with a level of sophistication and empathy that traditional chatbots cannot match. Sierra's technology goes beyond scripted responses, enabling AI agents that can reason about customer problems, take actions across enterprise systems, and maintain natural, contextual conversations. Sierra's founding team brings extraordinary depth in both consumer and enterprise technology. Bret Taylor co-created Google Maps, served as CTO of Facebook, and led Salesforce through its largest growth period. Clay Bavor spent nearly two decades at Google building products used by billions. Together, they are applying their combined expertise to the massive opportunity in enterprise customer experience, where companies spend billions annually on customer service infrastructure that often frustrates both customers and agents alike.

Application Process

  1. 1
    Browse Open Positions on Sierra's Career Page

    Visit sierra.ai/careers to explore current openings at Sierra. The company lists positions across Engineering, Product, Design, Go-to-Market, Operations, Legal, and People teams. Each listing provides detailed role descriptions, required qualifications, and team context. Sierra is transparent about which roles are based in San Francisco versus open to other arrangements. Take time to read the company's mission statement and values on the careers page to understand what Sierra prioritizes in candidates.

  2. 2
    Submit Your Application Through Ashby

    Sierra uses Ashby as its applicant tracking system. Click 'Apply' on your chosen role to access the application form. Provide your resume, contact information, and responses to any screening questions. Engineering roles may ask about your experience with specific technologies, LLMs, or distributed systems. Non-technical roles often include open-ended questions about your interest in AI and customer experience. Take the screening questions seriously — they are read by humans and heavily influence whether you advance.

  3. 3
    Recruiter Conversation

    Qualified candidates are contacted by a Sierra recruiter for an introductory call, typically lasting 30-45 minutes. The recruiter will discuss your background, motivations for joining Sierra, and understanding of the conversational AI space. Be prepared to articulate why you are interested in Sierra specifically rather than other AI companies. Recruiters also cover practical details including compensation expectations, location requirements, and timeline.

  4. 4
    Hiring Manager Interview

    The hiring manager interview dives deeper into your relevant experience and how it maps to the specific role. For engineering positions, this conversation explores your technical background, system design thinking, and approach to building production AI systems. For go-to-market roles, expect discussion of your sales methodology, customer success philosophy, or partnership strategy. The hiring manager is evaluating both your capabilities and your potential fit within their team's dynamics.

  5. 5
    Technical or Functional Deep Dive

    Sierra's assessment varies by role. Software engineers typically complete a coding exercise followed by a system design session focused on building conversational AI infrastructure at enterprise scale. Product and design candidates may present a portfolio or work through a product case study. Operations and business roles often involve a practical exercise or presentation relevant to their function. Sierra designs its assessments to mirror the actual challenges you would face in the role.

  6. 6
    Onsite or Virtual Interview Day

    The final round consists of 4-6 interview sessions over a half-day or full day. You will meet cross-functional team members, senior leaders, and potential collaborators. Sessions cover technical depth, behavioral competencies, collaboration style, and values alignment. Sierra looks for candidates who are not only skilled but also genuinely excited about the mission of making AI agents that customers actually enjoy interacting with. Expect at least one session focused explicitly on how you handle ambiguity and make decisions with incomplete information.

  7. 7
    Offer and Onboarding

    Sierra moves efficiently from final interviews to offers, typically within one week. Compensation packages include competitive base salary, substantial equity grants, and comprehensive benefits. During onboarding, new hires are immersed in Sierra's technology, customer use cases, and team processes. The company emphasizes a strong first-90-days experience, pairing new team members with onboarding buddies and ensuring early exposure to customer deployments.

Resume Tips for Sierra AI

critical

Lead With Customer Experience or Enterprise AI Experience

Sierra's entire mission revolves around transforming customer experience through AI. If you have worked on customer-facing products, CRM systems, contact center technology, conversational AI, or enterprise SaaS platforms, make this experience the centerpiece of your resume. Even tangential experience with customer journey optimization, NPS improvement, or support automation is relevant and should be highlighted.

critical

Quantify Your Contributions to AI or Product Systems

Sierra values measurable impact. For engineering roles, include metrics such as latency improvements, model performance gains, system uptime improvements, or scale metrics (requests per second, concurrent users). For business roles, reference revenue growth, customer retention rates, deal sizes, or operational efficiency gains. Concrete numbers differentiate your resume from candidates who only describe responsibilities.

critical

Demonstrate Experience at High-Growth Companies

Sierra is scaling rapidly from 300 employees with significant funding behind it. Experience at companies during similar growth phases is highly relevant. Highlight roles where you helped build processes, scale systems, or establish teams. Show that you understand the unique challenges and opportunities of a company that is growing quickly while maintaining quality and culture.

critical

Highlight Large Language Model or Conversational AI Work

Sierra builds sophisticated AI agents powered by large language models. Any experience with LLMs, prompt engineering, fine-tuning, retrieval-augmented generation, dialogue systems, or conversational AI should be prominently featured. Include specific models, frameworks, or techniques you have worked with. Even experience evaluating or deploying third-party LLM APIs demonstrates relevant technical context.

recommended

Show Cross-Functional Impact

Sierra's product requires tight collaboration between engineering, product, design, and go-to-market teams. Describe specific instances where you worked across functions to deliver outcomes. Did you partner with sales to build customer-requested features? Did you collaborate with design on user experience improvements? Cross-functional effectiveness is a core competency at Sierra.

recommended

Use Clean, ATS-Compatible Formatting

Sierra uses Ashby, which handles most resume formats well, but clean formatting ensures nothing is lost in parsing. Use standard section headers (Summary, Experience, Education, Skills), a single-column layout, and consistent date formatting. Submit as PDF. Avoid headers, footers, text boxes, or images that may not parse correctly.

nice_to_have

Reference the Founders' Vision in Your Summary

Sierra was founded by two of the most prominent leaders in technology. If you have experience with products or platforms they built (Salesforce, Google Workspace, Facebook), or if their vision for conversational AI resonates with your career goals, mention this in your professional summary. It demonstrates you have done your research and understand the company's direction.

recommended

Include Enterprise or B2B Sales Cycle Experience

For go-to-market roles, Sierra's customers are large enterprises with complex procurement processes. Highlight experience navigating multi-stakeholder deals, working with C-suite buyers, managing enterprise pilot programs, or building relationships with Fortune 500 companies. Include deal sizes and sales cycle lengths to demonstrate your enterprise sales maturity.

ATS System: Ashby

Sierra uses Ashby, a modern applicant tracking system built for fast-growing technology companies. Ashby provides candidates with a streamlined application experience, automated status updates, and structured interview scheduling. The platform is designed to handle high application volumes efficiently while maintaining a positive candidate experience.

  • Submit your resume as a PDF to ensure consistent formatting across all reviewers
  • Ashby parses resumes well, but standard section headers (Experience, Education, Skills) ensure the best results
  • Complete all screening questions thoroughly — these are reviewed by the hiring team and significantly impact advancement decisions
  • Ashby sends automated status updates via email, so add sierra.ai to your contacts to avoid spam filtering
  • If applying to multiple roles at Sierra, Ashby tracks all applications under one candidate profile — be strategic about which roles you apply to
  • LinkedIn profile imports are supported but always verify the parsed information for accuracy before submitting

Complete Ashby Resume Guide →

Interview Culture

Sierra's interview culture is shaped by its founders' experience building world-class teams at Salesforce, Facebook, and Google.

The company conducts structured interviews with clear rubrics, designed to evaluate candidates fairly and consistently while identifying people who can thrive in a high-growth AI company. Engineering interviews at Sierra focus on practical problem-solving with an emphasis on building production systems. Rather than abstract algorithmic challenges, you can expect questions about designing conversational AI systems, handling real-time inference at scale, managing state across multi-turn conversations, or building reliable integrations with enterprise systems. Sierra values engineers who think about the complete system — from model performance to user experience to operational reliability. For product, design, and go-to-market roles, interviews emphasize strategic thinking and customer empathy. Product managers might be asked to design an AI agent for a specific industry vertical. Designers could work through improving a conversation flow that is confusing customers. Sales candidates may walk through how they would approach a Fortune 500 prospect. Sierra wants to see that you understand the unique challenges of selling and deploying AI in enterprise environments. Culturally, Sierra values intellectual humility, customer obsession, and operational excellence. The company was built by leaders who scaled some of the world's most important technology platforms, and that experience shapes an expectation of both ambition and rigor. Interviewers assess not just what you have accomplished but how you think, how you collaborate, and how you handle situations where the right answer is not obvious. Sierra provides timely feedback throughout the process and communicates decisions clearly. The company respects candidates' time and aims to make the interview experience itself a reflection of the kind of company Sierra is building — thoughtful, respectful, and focused on quality.

What Sierra AI Looks For

  • Passion for transforming customer experience through AI, with genuine interest in how conversational agents can solve real business problems
  • Experience building or working with production AI systems, particularly conversational AI, dialogue systems, or LLM-powered applications
  • Proven ability to operate effectively at a high-growth startup where processes are still being built and priorities shift quickly
  • Strong communication skills and the ability to translate complex AI concepts into business value for enterprise customers
  • Customer-centric mindset — Sierra builds for end users and expects everyone in the company to deeply understand customer needs
  • Track record of measurable impact with specific metrics and outcomes, not just responsibilities or titles
  • Comfort with ambiguity and the ability to make progress on loosely defined problems with limited guidance
  • Collaborative approach to work, with demonstrated ability to partner effectively across engineering, product, design, and business functions

Frequently Asked Questions

What is the hiring process like at Sierra AI?
Sierra AI's hiring process typically consists of a recruiter conversation, a hiring manager interview, a technical or functional deep dive assessment, and a final onsite or virtual interview day with 4-6 sessions. The process is structured with clear rubrics for evaluation. From initial application to offer, the timeline generally runs 3-5 weeks. Sierra communicates clearly throughout the process and provides timely feedback at each stage.
What ATS does Sierra AI use for applications?
Sierra AI uses Ashby as its applicant tracking system. Ashby is a modern ATS built for high-growth tech companies that offers a clean, efficient application experience. To optimize your application, use standard resume formatting with clear section headers, submit as PDF, and provide thoughtful answers to all screening questions. Ashby sends automated status updates, so ensure sierra.ai emails are not filtered as spam.
Who founded Sierra AI and what is their background?
Sierra AI was co-founded by Bret Taylor and Clay Bavor. Bret Taylor previously served as CEO of Salesforce and CTO of Facebook, and co-created Google Maps. Clay Bavor spent nearly two decades at Google, where he led AR/VR efforts and Google Labs. Together, they bring deep expertise in building consumer and enterprise technology products at massive scale, which they are now applying to transform enterprise customer experience through AI.
What kind of engineering roles are available at Sierra AI?
Sierra AI hires across multiple engineering disciplines including Software Engineering, Machine Learning, Infrastructure, Data Engineering, and Agent Platform Development. The engineering team builds the core AI agent platform, handles real-time conversational inference, develops enterprise integrations, and ensures system reliability at scale. Roles range from early-career to senior and staff levels, with particular emphasis on candidates who have experience with LLMs, distributed systems, or conversational AI.
What is the company culture like at Sierra AI?
Sierra AI's culture emphasizes intellectual humility, customer obsession, and operational excellence. The company was built by leaders who scaled some of the world's most important technology platforms, creating an environment that combines startup agility with enterprise rigor. Sierra values collaboration across functions, transparent communication, and a bias toward action. The company is headquartered in San Francisco and emphasizes in-person collaboration.
What does Sierra AI's product do?
Sierra AI builds conversational AI agents for enterprise customer experience. Unlike traditional chatbots that follow rigid scripts, Sierra's AI agents can reason about customer problems, take actions across enterprise systems, maintain context across multi-turn conversations, and communicate with natural, empathetic language. The company's agents are deployed by major enterprises to handle customer service, sales support, and other customer-facing interactions at scale.
What compensation and benefits does Sierra AI offer?
Sierra AI offers competitive compensation packages including base salary, meaningful equity grants in a company valued at $4.5 billion, and comprehensive benefits. Benefits typically include health, dental, and vision insurance, 401(k), generous paid time off, and professional development support. The company's strong funding position and high valuation mean equity grants carry significant potential upside. Specific compensation details are discussed during the recruiter conversation.
How can I stand out when applying to Sierra AI?
To stand out at Sierra AI, emphasize any experience with customer experience technology, conversational AI, enterprise SaaS, or LLM-powered systems. Quantify your impact with specific metrics. Complete screening questions with thoughtful, detailed answers rather than generic responses. Research Sierra's products and be able to articulate why you are excited about the specific opportunity in enterprise conversational AI. Demonstrating customer empathy and understanding of enterprise buyer needs is a significant differentiator.
Is Sierra AI remote-friendly or does it require in-office work?
Sierra AI is headquartered in San Francisco and emphasizes in-person collaboration for most roles. The company believes that the tight collaboration required to build cutting-edge AI products benefits from co-located teams. However, some roles may have flexibility, and specific location requirements are listed in each job posting. Check the individual listing for the most accurate information about work location expectations.

Open Positions

Sierra AI currently has 138 open positions.

View 138 Open Positions at Sierra AI →

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Sources

  1. Sierra AI Careers — Sierra AI
  2. Sierra AI About — Sierra AI