Canada · Remote OK
$305k–$370k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Enterprise sales, Lead generation, Relationship management, Negotiation, Sales strategy
San Francisco, California, United States · On-site
$160k–$270k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Sales Engineering, Solutions Engineering, Technical Sales, Demo Building, Presentation Skills
United States · Remote OK
$315k–$370k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Enterprise sales, Strategic sales, Deal structuring, C-suite relationship management, AI landscape knowledge
Canada · Remote OK
$305k–$330k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Enterprise sales, Lead generation, Prospecting, Cold calling, Relationship management
San Francisco, California, United States · On-site
$220k–$250k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Pricing strategy, SaaS pricing, GTM operations, Sales operations, Marketing operations
United States · Remote OK
$300k–$345k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Enterprise sales, Strategic sales, Deal structuring, C-suite relationship management, Pipeline forecasting
Canada · Remote OK
$375k–$430k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Enterprise sales, Strategic sales, Deal structuring, C-suite relationship management, AI landscape knowledge
United States · Remote OK
$295k–$340k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Sales, Enterprise sales, Lead generation, Prospecting, Cold calling
San Francisco, California, United States · On-site
$180k–$390k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Software engineering, Healthcare interoperability, FHIR, HL7, EHR integration
San Francisco, California, United States · On-site
$170k–$200k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Videography, Video editing, Social media content creation, Adobe Premiere, Final Cut Pro
San Francisco, California, United States · On-site
$130k–$200k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Full-cycle recruiting, Stakeholder management, Sourcing strategies, Candidate pipeline management, Data-driven recruiting
Sydney, New South Wales, Australia · On-site
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Full-cycle recruiting, Outbound sourcing, Candidate closing, Strategic partnership, Hiring manager collaboration
San Francisco, California, United States · On-site
$200k–$290k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: AI strategy, Customer relationship management, Strategic problem-solving, Technical aptitude, API documentation
Singapore, Singapore · On-site
$200k–$270k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Pricing strategy, SaaS pricing, GTM operations, Sales operations, Marketing operations
Japan · On-site
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Recruiting, Team leadership, Talent acquisition, Strategic planning, Market analysis
San Francisco, California, United States · On-site
$370k–$400k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Sales leadership, Enterprise sales, Deal strategy, Pipeline management, Accountability
Singapore, Singapore · On-site
$230k–$445k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Product Management, AI Agent Development, Customer Engagement, Product Roadmap Strategy, Technical Communication
Japan · On-site
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Investment Banking, Management Consulting, Private Equity, Corporate Strategy, Business Operations
London, England, United Kingdom · On-site
$135k–$185k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Full-cycle Recruiting, Sourcing, Stakeholder Management, Candidate Experience, Pipeline Management
San Francisco, California, United States · On-site
$180k–$390k/yr
About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New Y…
Skills: Product Management, AI Agent Development, Spanish Fluency, English Fluency, Technical Communication
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The Enterprise Sales Director will identify and target potential healthcare enterprise customers while managing complex, high-value deal cycles. They will also collaborate cross-functionally to deliver AI-driven solutions and maintain strong relationships with key decision-makers.
Candidates must have 6-8 years of experience in an enterprise customer-facing sales role with a proven track record of managing $1M+ quotas. Exceptional communication skills and an analytical mindset are required to navigate complex 6- and 7-figure deals effectively.
At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
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
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
Sierra helps businesses build better, more human customer experiences with AI.
Offices: San Francisco, California, US
Sierra helps businesses build better, more human customer experiences with AI.
Offices: San Francisco, California, US
