[All remote jobs](https://jobicy.com/jobs.md)[![Sierra logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/08/9877fe33-221.jpeg)](https://jobicy.com/company/sierra.md)[Sierra](https://jobicy.com/company/sierra.md) # Enterprise Sales Director, Healthcare AI Summary Sierra is hiring an Enterprise Sales Director to grow strategic healthcare accounts for its customer-facing AI agent platform. The role owns enterprise prospecting, executive relationship management, sales strategy, negotiations, and closing complex six- and seven-figure ACV opportunities. The successful candidate will bring 6–8 years of enterprise sales experience, a record of managing a $1M+ quota, and strong healthcare or AI-market familiarity. This is a high-impact, customer-facing position that partners closely with GTM, product, technical, operations, legal, and finance teams. The role is remotely available within the United States.[Apply for this job](#job-application)[View company](https://jobicy.com/company/sierra.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md)SalaryUSD 280k–315k / yrDepartment[Sales](https://jobicy.com/categories/seller.md)EmploymentFull TimeExperienceDirectorPublished13 Nov 2026Apply before13 Dec 2026Listing views36Application actions2Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. Opportunity details ## About this role. ### About us [Sierra](https://jobicy.com/company/sierra.md) is the leading platform for customer-facing AI agents, working with many of the world’s biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. 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 a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by [Bret Taylor](https://www.linkedin.com/in/brettaylor/) and [Clay Bavor](https://www.linkedin.com/in/claybavor/) who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ### About the Healthcare team * 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. ### What you’ll do * 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. ### What you’ll bring * 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. ### Even better… * Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends. ### Our values * 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. ### What we offer 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 * Lunch, as well as delicious snacks and coffee to keep you energized when working onsite * 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 employment type, 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. ### Be you, with us 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 through the link on this page even if your experience doesn’t precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws. Show more [Apply now >](https://jobicy.com/jobs/161768-enterprise-sales-director-healthcare-2.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a senior enterprise sales role involving complex, high-value healthcare transactions, executive stakeholders, and ambitious revenue expectations. Success requires independent pipeline creation, strategic account execution, and coordination across multiple internal teams. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$297,500US market range (per year)$250k–$350k0$385.00k AI insightThe employer discloses a yearly base-pay range of $280,000–$315,000 USD, with a midpoint of $297,500. This is a credible range for a senior US enterprise sales leadership role focused on strategic healthcare accounts; incentive compensation or equity may be separate from the stated base pay. Estimated US market compensation for comparable base-pay roles is $250,000–$350,000 per year. ## Core skills Skills and capabilities most closely associated with this opportunity. [Enterprise Sales](https://jobicy.com/jobs?search_keywords=Enterprise%20Sales.md)[Healthcare Technology](https://jobicy.com/jobs?search_keywords=Healthcare%20Technology.md)[Strategic Account Management](https://jobicy.com/jobs?search_keywords=Strategic%20Account%20Management.md)[Complex Deal Negotiation](https://jobicy.com/jobs?search_keywords=Complex%20Deal%20Negotiation.md)[Sales Strategy](https://jobicy.com/jobs?search_keywords=Sales%20Strategy.md)[Pipeline Management](https://jobicy.com/jobs?search_keywords=Pipeline%20Management.md)[Lead Generation](https://jobicy.com/jobs?search_keywords=Lead%20Generation.md)[Executive Stakeholder Management](https://jobicy.com/jobs?search_keywords=Executive%20Stakeholder%20Management.md)[Consultative Selling](https://jobicy.com/jobs?search_keywords=Consultative%20Selling.md)[Revenue Forecasting](https://jobicy.com/jobs?search_keywords=Revenue%20Forecasting.md)[AI Solutions](https://jobicy.com/jobs?search_keywords=AI%20Solutions.md)[Cross-functional Collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20Collaboration.md)[Cold Calling](https://jobicy.com/jobs?search_keywords=Cold%20Calling.md)[Market Analysis](https://jobicy.com/jobs?search_keywords=Market%20Analysis.md) Sample interview questionsDescribe a complex enterprise healthcare deal you closed and the strategy you used to win it.I would explain the customer problem, stakeholder map, buying process, competitive landscape, and measurable business case. I would highlight how I aligned executive sponsors, technical evaluators, procurement, and legal teams, then describe the actions that moved the opportunity to close. How do you build pipeline for a new enterprise territory or vertical? I segment the market by ideal customer profile, urgency, strategic fit, and expansion potential. I combine account research, executive networking, partner channels, targeted outreach, and value-led messaging, then track conversion metrics to refine the approach. How would you position customer-facing AI agents to a cautious healthcare executive? I would begin with the executive's operational and patient-experience priorities, then connect the solution to practical use cases such as benefits guidance, billing support, and service resolution. I would address safety, trust, implementation, measurable outcomes, and change management with a clear, phased business case. How do you manage six- or seven-figure opportunities with long sales cycles? I use a documented mutual action plan, multi-threaded stakeholder engagement, qualification checkpoints, and a clear understanding of decision criteria and procurement requirements. I maintain forecast discipline while creating executive alignment around value, timing, and implementation readiness. How do you use AI tools to improve your sales execution? I use AI for account research, personalization, call summaries, next-step tracking, and forecasting support. I validate outputs, protect customer-sensitive information, and reinvest the saved time into high-value discovery, stakeholder engagement, and deal strategy. Next step ## Apply now. Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information. 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