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: Enterprise Sales, Prospecting, Lead Generation, Relationship Management, Contract Negotiation
United States · Remote OK
$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: Enterprise Sales, People Leadership, Deal Strategy, Pipeline Management, Forecasting
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: Enterprise Sales, Prospecting, Lead Generation, Relationship Management, Contract Negotiation
United States · Remote OK
$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: Enterprise Sales, People Leadership, Deal Strategy, Pipeline Management, Forecasting
San Francisco, California, United States · On-site
$140k–$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: Event Marketing, Strategic Planning, Content Development, Sales Enablement, Campaign Management
Singapore, Singapore · On-site
$210k–$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: Brand Development, Creative Design, Localization, Presentation Design, Visual Storytelling
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: Enterprise Technology Sales, Channel Partnerships, Pipeline Generation, Partner Enablement, Go-To-Market Execution
San Francisco, California, United States · On-site
$180k–$210k/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: End-to-end accounting close, Balance sheet reconciliations, US GAAP, ASC606, Revenue recognition
London, England, United Kingdom · On-site
$210k–$295k/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, Prospecting, Lead Generation, Relationship Management, Complex Deal Negotiation
Paris, Ile-de-France, France · On-site
$210k–$295k/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, Prospecting, Lead Generation, Relationship Management, Complex Deal Negotiation
San Francisco, California, United States · On-site
$180k–$210k/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: Accounts Payable, Global Multi-entity Accounting, Multi-currency Management, Vendor Onboarding, Bank Verification
London, England, United Kingdom · On-site
$135k–$165k/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: Brand Development, Creative Design, Localization, Presentation Design, Visual Storytelling
Singapore, Singapore · On-site
$295k–$495k/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 Agent Development, Production System Scaling, Technical Problem Solving, Customer Interaction, Communication
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: AI Agent Development, Production System Scaling, Technical Problem Solving, Customer Relationship Management, Communication
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: AI Agent Development, Production Systems Scaling, Technical Problem Solving, Customer Interaction, React
New York, New York, 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: Commercial Contracting, SaaS Agreements, Technology Licensing, Professional Services Agreements, Channel Partner Agreements
San Francisco, California, United States · On-site
$190k–$225k/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: Global Payroll Operations, Payroll Compliance, Tax Regulations, Multi-state Payroll, International Payroll
San Francisco, California, United States · On-site
$175k–$225k/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: Financial Planning And Analysis, Financial Modeling, Budgeting And Forecasting, KPI Tracking, Stakeholder Management
San Francisco, California, United States · On-site
$175k–$225k/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: Financial Modeling, Strategic Finance, FP&A, SaaS Metrics, ARR Analysis
Munich, Bavaria, Germany · On-site
$290k–$335k/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, People Leadership, Deal Strategy, Pipeline Management, Forecasting
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Lead the identification and acquisition of large enterprise healthcare accounts to drive revenue and pipeline growth. Develop sales strategies and collaborate cross-functionally to define the GTM motion for AI agents in the healthcare sector.
Requires 8-12+ years of experience in enterprise customer-facing sales with a proven track record of managing $1M+ quotas and closing 6- and 7-figure ACV deals. Strong communication skills and an analytical mindset are essential, with a preference for AI industry knowledge.
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.
Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.
Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.
Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
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.
8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Proven ability to multi-thread and build trusted relationships across customer C-suites.
Exceptional verbal and written communication.
Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.
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
