Benefits:

• Competitive Compensation + Equity

• 401k Plan

• Medical, Dental, Vision Insurance

• Gear Stipend

• Professional Development Stipend

Benefits:

• Competitive Salaries

• Flexible Work Arrangements

• Health & Wellness

• Continuous Learning

Benefits:

• Comprehensive health plans (100% premium coverage)

• Mental health programs

• Family planning allowance

• Home office stipend

• Education reimbursement ($3,000 annually)

Benefits:

• Comprehensive health plans (100% premium coverage)

• Mental health programs

• Family planning allowance

• Home office stipend

• Education reimbursement ($3,000 annually)

Benefits:

• Comprehensive health plans (100% premium coverage)

• Mental health programs

• Family planning allowance

• Home office stipend

• Education reimbursement ($3,000 annually)

Benefits:

• Health benefits

• 401K plan

• Company equity

• Remote-first

• Flexible PTO

Benefits:

• Health benefits

• 401K plan

• Company equity

• Remote-first

• Flexible PTO

Benefits:

• Health benefits

• 401K plan

• Company equity

• Remote-first

• Flexible PTO

Benefits:

• Health benefits

• 401K plan

• Company equity

• Remote-first

• Flexible PTO

Benefits:

• Flexible (Unlimited) Paid Time Off

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• 401(k) Plan with Sierra match

• Parental Leave Fertility and Family Building Benefits through Carrot Lunch, as well as delicious snacks and coffee to keep you energized Discretionary Benefit Stipend giving people the ability to spend where it matters most Free alphorn lessons

Education Requirements:

• Degree in Computer Science or related field, or equivalent professional experience

Experience Requirements:

• 3+ years experience in hands-on software development of highly technical products

• Past experience in Software Development or other similar hands-on development roles at or above the level of Senior Software Engineer

• Experience crafting and tailoring a message for potential customers, including executives

Responsibilities:

• Build enterprise-grade AI agents

• Engage with customers

• Shape the product roadmap

Benefits:

• Flexible (Unlimited) Paid Time Off

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• 401(k) Plan with Sierra match

• Parental Leave Fertility and Family Building Benefits through Carrot Lunch, as well as delicious snacks and coffee to keep you energized Discretionary Benefit Stipend giving people the ability to spend where it matters most Free alphorn lessons

Education Requirements:

• Degree in a technical or related field, or equivalent professional experience

Experience Requirements:

• 5-7+ years experience in product development of highly technical products

• Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager

• Experience crafting and tailoring a message for potential customers, including executives

• Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments

Responsibilities:

• Build enterprise-grade AI agents

• Engage with customers

• Shape the product roadmap

Benefits:

• Flexible (Unlimited) Paid Time Off

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• 401(k) Plan with Sierra match

• Parental Leave Fertility and Family Building Benefits through Carrot Lunch, as well as delicious snacks and coffee to keep you energized Discretionary Benefit Stipend giving people the ability to spend where it matters most Free alphorn lessons

Education Requirements:

• Pursuing a bachelor’s or master’s degree (or comparable program) in computer science or a related field

Experience Requirements:

• Professional experience in software engineering or product management, especially with customer-facing responsibilities

• Expertise in React, TypeScript, Python, Go, and other modern programming languages

• Demonstrated curiosity and interest in AI applications (e.g., research, jobs, side projects)

Responsibilities:

• Agent Engineering

• Agent Product Management

Benefits:

• Flexible (Unlimited) Paid Time Off

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• 401(k) Plan with Sierra match

• Parental Leave Fertility and Family Building Benefits through Carrot Lunch, as well as delicious snacks and coffee to keep you energized Discretionary Benefit Stipend giving people the ability to spend where it matters most Free alphorn lessons

Education Requirements:

• Degree in Computer Science or related field, or equivalent professional experience

Experience Requirements:

• A passion for being on the frontier of AI products

• Pride in building reliable, maintainable, and secure systems that scale

• Motivation and high-agency to drive outcomes - we have a high-autonomy culture and each team member has lots of agency to overcome obstacles and achieve customer impact

• Alignment to our company values throughout your work, notably finding a balance between Craftsmanship, Customer Obsession, and Competitive Intensity

• 4+ years hands-on experience building production products and systems

Responsibilities:

• Build Sierra’s platform

• Scale with growth

• Form the foundation of trust

Benefits:

• Flexible (Unlimited) Paid Time Off

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• 401(k) Plan with Sierra match

• Parental Leave Fertility and Family Building Benefits through Carrot Lunch, as well as delicious snacks and coffee to keep you energized Discretionary Benefit Stipend giving people the ability to spend where it matters most Free alphorn lessons

Education Requirements:

• Degree in Computer Science or related field, or equivalent professional experience

Experience Requirements:

• A passion for being on the frontier of AI products

• Motivation and high-agency to drive outcomes - we have a high-autonomy culture and each team member has lots of agency to overcome obstacles and achieve customer impact

• Alignment to our company values throughout your work, notably finding a balance between Craftsmanship, Customer Obsession, and Competitive Intensity

• 4+ years hands-on experience building production products and systems

• Experience and comfort to build and ship full-stack solutions

Responsibilities:

• Build Sierra’s products

• Discover & invent

• Iterate & refine

Benefits:

• Flexible (Unlimited) Paid Time Off

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• 401(k) Plan with Sierra match

• Parental Leave Fertility and Family Building Benefits through Carrot Lunch, as well as delicious snacks and coffee to keep you energized Discretionary Benefit Stipend giving people the ability to spend where it matters most Free alphorn lessons

Experience Requirements:

• 5+ years of B2B marketing experience

• Expertise in content marketing, including blog, social, digital content development, and more

• World-class writing skills, capable of drafting and editing content in the tone and voice of Sierra. Comfortable with highly technical content development.

• Exceptional program management skills

• A strong background in traditional content creation, including written editorials and art direction A strong editorial sensibility and the ability to balance AI-enabled insights with human creativity and judgment Expertise in building beautiful presentations using Google Slides and Keynote

Responsibilities:

• Content strategy

• Blog

• Social

• Webinars and other digital events

• Customer stories Cutting-edge content development Measurement and optimization

Benefits:

• Flexible (Unlimited) Paid Time Off

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• 401(k) Plan with Sierra match

• Parental Leave Fertility and Family Building Benefits through Carrot Lunch, as well as delicious snacks and coffee to keep you energized Discretionary Benefit Stipend giving people the ability to spend where it matters most Free alphorn lessons

Experience Requirements:

• 10+ years of B2B marketing experience, preferably with a focus on event marketing

• Expertise marketing to an executive audience, delivering strong event oversight and leadership

• A solid understanding of the enterprise B2B third party event scene A proven track record of creating and executing owned events The ability to develop and deliver outstanding field events within a very high-velocity, shifting environment Exceptional program management skills with the ability to work independently against timelines within a fast-paced, changing environment while keeping a sharp eye on detail and accuracy A deep understanding of our customers, their needs, and the context in which they work A curiosity for data and an understanding of basic analytical and statistical techniques The ability to work across functional teams and with multiple collaborators, engaging with the broader team of marketers Strong communication and presentation skills, with an excellent ability to connect through writing, presentations, and storytelling Deep experience working with external vendors and marketing agencies

Responsibilities:

• Event strategy & alignment

• Event execution & operations

• Analytical mindset

• Sales partnership

• Marketing generalist & cross-functional leader

Benefits:

• Flexible (Unlimited) Paid Time Off

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• 401(k) Plan with Sierra match

• Parental Leave Fertility and Family Building Benefits through Carrot Lunch, as well as delicious snacks and coffee to keep you energized Discretionary Benefit Stipend giving people the ability to spend where it matters most Free alphorn lessons

Experience Requirements:

• 5+ years of experience in web content management or digital production

• Deep expertise with enterprise-grade content management systems

• Strong technical understanding of web technologies and digital content best practices

• Experience with international content deployment and localization workflows

• Excellent project management skills and ability to coordinate multiple stakeholders Understanding of SEO, web accessibility standards, and digital brand governance

Responsibilities:

• Lead end-to-end content publishing workflows

• Manage and optimize our content management system (CMS)

• Oversee quality assurance for all published content

• Maintain the integrity and timeliness of our blog, news section, and resource center

• Drive continuous improvement in our content operations

Benefits:

• Flexible (Unlimited) Paid Time Off

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• 401(k) Plan with Sierra match

• Parental Leave Fertility and Family Building Benefits through Carrot Lunch, as well as delicious snacks and coffee to keep you energized Discretionary Benefit Stipend giving people the ability to spend where it matters most Free alphorn lessons

Experience Requirements:

• 8+ years of B2B marketing experience

• Past experience in building marketing demos, from scripting and storyboarding to creating the demo orgs and capturing the footage

• Strong writing and content creation skills

• Expertise in building beautiful presentations using Google Slides and Keynote

• Experience using screen capture and video editing software like with Camtasia, Adobe Creative Cloud, or Apple Final Cut Pro Passion for understanding enterprise customers, their needs, and the context in which they work Passion for helping Sales succeed by creating beautiful and differentiated assets for them, while also creating and delivering the enablement programs to help them leverage those assets

Responsibilities:

• Demo strategy & execution

• Technical sales content & enablement

• Cross-functional partnership

Benefits:

• Flexible (Unlimited) Paid Time Off

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• 401(k) Plan with Sierra match

• Parental Leave Fertility and Family Building Benefits through Carrot Lunch, as well as delicious snacks and coffee to keep you energized Discretionary Benefit Stipend giving people the ability to spend where it matters most Free alphorn lessons

Experience Requirements:

• 7+ years of experience as an Executive Assistant or similar

• Ability to build relationships, partnering effectively with cross-functional teams and external partners

• Excellent time management skills, willingness to quickly shift tasks and priorities, and anticipate the needs of others before they arise

• Ability to organize, analyze, and prioritize executive workflows, often using and interpreting data

• Willingness and ability to travel as needed (est. 2x per quarter) Advanced proficiency with Google Suite & Slack

Responsibilities:

• Proactively manage the co-founder’s calendar

• Draft correspondence and responses on behalf of the co-founder

• Liaise with internal staff and other stakeholders on behalf of the co-founder

• Maintain a high level of confidentiality and discretion with all materials and information

• Establish new—and improve existing—administrative systems and processes

Benefits:

• Flexible (Unlimited) Paid Time Off

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• 401(k) Plan with Sierra match

• Parental Leave Fertility and Family Building Benefits through Carrot Lunch, as well as delicious snacks and coffee to keep you energized Discretionary Benefit Stipend giving people the ability to spend where it matters most Free alphorn lessons

Education Requirements:

• Degree in Business Administration, Finance, or related field, or equivalent professional experience

Experience Requirements:

• 5-7+ years of experience in GTM operations, specifically executive business operations at a scaled tech organization or consulting firm

• Experience negotiating complex customer partnerships

• Familiarity with navigating sales cycles

• Strong understanding of developing GTM operations using data-driven decision-making

Responsibilities:

• Serve as a liaison between all of our executive touchpoints

• Work with account executives to standardize how our executives engage with customers

• Work with Sierra’s network of investors and advisors to facilitate customer introductions