[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 Leader, Healthcare Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [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 450k–470k / yrDepartment[Sales](https://jobicy.com/categories/seller.md)EmploymentFull TimeExperienceOpen levelPublished26 Oct 2026Apply before25 Nov 2026Listing views44Application actions1Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Sierra is seeking an Enterprise Sales Leader to lead and scale a healthcare-focused enterprise sales organization in the United States. The leader will hire, coach, and develop account executives while owning regional quota attainment, forecasting, pipeline quality, and execution discipline. This role remains directly involved in strategic customer conversations, complex buying committees, pricing, negotiation, and late-stage deal closure. Candidates need 10–15+ years of enterprise sales experience, at least five years of people leadership, and a record of leading complex $1M+ deals. Success requires healthcare-market credibility, strong GTM judgment, data-driven management, and fluency with AI products and workflows. ## 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 revenue leadership role with responsibility for regional performance, hiring, forecast accuracy, and high-value enterprise transactions. It requires navigating long healthcare buying cycles and influencing executive stakeholders while building a scalable sales motion. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Highly competitive$460,000US market range (per year)$350k–$550k0$605k AI insightThe employer discloses annual compensation of $450,000–$470,000 USD, with a midpoint of $460,000. This is a credible range for a senior US enterprise sales leadership role in AI and healthcare, likely reflecting a senior total compensation or on-target earnings structure; the posting does not specify its component mix. The estimated US market range is $350,000–$550,000 per year. ## Core skills Skills and capabilities most closely associated with this opportunity. [Enterprise sales leadership](https://jobicy.com/jobs?search_keywords=Enterprise%20sales%20leadership.md)[Healthcare technology sales](https://jobicy.com/jobs?search_keywords=Healthcare%20technology%20sales.md)[Sales team coaching](https://jobicy.com/jobs?search_keywords=Sales%20team%20coaching.md)[Strategic account management](https://jobicy.com/jobs?search_keywords=Strategic%20account%20management.md)[Pipeline management](https://jobicy.com/jobs?search_keywords=Pipeline%20management.md)[Sales forecasting](https://jobicy.com/jobs?search_keywords=Sales%20forecasting.md)[Complex deal negotiation](https://jobicy.com/jobs?search_keywords=Complex%20deal%20negotiation.md)[Go-to-market strategy](https://jobicy.com/jobs?search_keywords=Go-to-market%20strategy.md)[Revenue operations](https://jobicy.com/jobs?search_keywords=Revenue%20operations.md)[Executive stakeholder management](https://jobicy.com/jobs?search_keywords=Executive%20stakeholder%20management.md)[AI solutions sales](https://jobicy.com/jobs?search_keywords=AI%20solutions%20sales.md)[Sales hiring](https://jobicy.com/jobs?search_keywords=Sales%20hiring.md)[Data-driven decision-making](https://jobicy.com/jobs?search_keywords=Data-driven%20decision-making.md) Sample interview questionsHow have you improved forecast accuracy for an enterprise sales organization?I establish consistent stage definitions, require evidence-based deal reviews, inspect pipeline coverage and aging weekly, and compare rep forecasts with objective customer milestones. I use the resulting trends to coach early, remove obstacles, and make forecast calls transparent. Describe how you would coach an AE through a complex $1M+ healthcare deal. I would map the buying committee, clarify the customer’s clinical and business outcomes, identify security, legal, procurement, and executive approval paths, and create a mutual action plan. I would join pivotal meetings where executive sponsorship, pricing, or risk resolution is needed while ensuring the AE retains deal ownership. What approach would you take to hiring and developing a high-performing enterprise sales team? I hire for enterprise rigor, customer curiosity, resilience, and collaboration, not only past quota attainment. After onboarding, I provide clear operating expectations, structured call and deal coaching, measurable development plans, and opportunities for high performers to lead strategic initiatives. How would you build a healthcare go-to-market motion for an AI-agent platform? I would segment the market by payer, provider, and healthcare-platform use cases, then prioritize customers with high-volume service interactions and clear value opportunities. I would align messaging to measurable outcomes such as improved access, service efficiency, billing resolution, and patient experience, while partnering closely with product, security, and customer teams. How do you balance aggressive revenue goals with customer trust in a sensitive industry? I treat trust as a core qualification criterion rather than an afterthought. I ensure teams set accurate expectations, surface security and implementation risks early, involve the right experts, and sell outcomes that can be delivered responsibly over the long term. Opportunity details ## About this role. ### About us Sierra 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. Our co-founders are [Bret Taylor](https://www.linkedin.com/in/brettaylor/) and [Clay Bavor](https://www.linkedin.com/in/claybavor/). 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. ### 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 * Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team. * Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights. * Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy. ### What you’ll bring * 10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts. * People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team. * Enterprise experience: You’ve run and managed end-to-end complex deals ($1M+). * Strong communication skills: Exceptional verbal and written communication abilities. * Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions. ### Even better… * Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows. * Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth. ### 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 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. ### 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 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. Show more [Apply now >](https://jobicy.com/jobs/157239-enterprise-sales-leader-healthcare.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. 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