# Sales Director – Healthcare Remote from[Canada](https://jobicy.com/job-region/canada.md)Salary, yearly, CAD 345,000 - 395,000Department [Sales](https://jobicy.com/categories/seller.md) Employment type Full Time, Job posted16 Jul 2026Apply before16 Aug 2026Experience level Director Views / Applies 36 / 1 [About company](https://jobicy.com/company/sierra.md) * Share About [Sierra](https://jobicy.com/company/sierra.md) Sierra helps businesses build better, more human customer experiences with AI. [Computer Software](https://jobicy.com/company-category/software.md) * 2023 Actively Hiring Verified job posting This job post has been [manually reviewed](https://jobicy.com/tools/help-center/employee/how-does-jobicy-verify-the-legitimacy-of-remote-job-listings.md) for authenticity and compliance. ### AI Summary Sierra is seeking a Sales Director to lead healthcare sales, targeting enterprise customers like major health plans and providers. The role involves prospecting, managing relationships, negotiating complex deals, and shaping the go-to-market strategy. Candidates need 8-12+ years of enterprise sales experience with a track record of closing 6- and 7-figure ACV deals. The position offers a competitive salary range of $345,000-$395,000 CAD and is part of a fast-paced, collaborative environment focused on AI-driven customer experiences. ### Role DNA Job Complexity Easy Hard Pace & Pressure Relaxed Fast-paced Autonomy Level Guided Full Ownership Communication Load Independent Highly Collaborative AI Insight Requires 8-12+ years of proven enterprise sales experience with high-value deals ($1M+ quotas, 6-7 figure ACV) and deep healthcare industry knowledge, making it a challenging senior role. ### Salary Analysis Median Above Market CAD370,000CA Market CAD120k – 250k 0 CAD407k AI Insight The offered salary range of $345,000-$395,000 CAD is significantly above the typical Canadian market range for a Sales Director in Healthcare ($120,000-$250,000). This premium reflects the seniority, high expectations, and potential for influencing AI in healthcare. ### Core Skills Required [Sales Leadership](https://jobicy.com/jobs?search_keywords=Sales+Leadership.md) [Healthcare](https://jobicy.com/jobs?search_keywords=Healthcare.md) [Enterprise Sales](https://jobicy.com/jobs?search_keywords=Enterprise+Sales.md) [Customer Relationship Management](https://jobicy.com/jobs?search_keywords=Customer+Relationship+Management.md) [Negotiation](https://jobicy.com/jobs?search_keywords=Negotiation.md) [Strategic Planning](https://jobicy.com/jobs?search_keywords=Strategic+Planning.md) [Lead Generation](https://jobicy.com/jobs?search_keywords=Lead+Generation.md) [Cross-functional Collaboration](https://jobicy.com/jobs?search_keywords=Crossfunctional+Collaboration.md) [AI/ML Industry Knowledge](https://jobicy.com/jobs?search_keywords=AIML+Industry+Knowledge.md) [Go-to-Market Strategy](https://jobicy.com/jobs?search_keywords=GotoMarket+Strategy.md) ### Cover Letter Sample Dear Hiring Team, I am excited to apply for the Sales Director - Healthcare position at Sierra. With over 10 years of enterprise sales experience in healthcare technology, I have consistently exceeded $2M annual quotas and closed complex six-figure deals with major health plans and providers. My strength lies in building trusted relationships with C-level stakeholders and orchestrating cross-functional teams to deliver tailored AI solutions. At my previous role, I led the launch of a new healthcare AI platform, growing pipeline by 150% in the first year. I am drawn to Sierra's mission of transforming patient experiences through human-centric AI and would love to contribute to your early-stage GTM strategy. I look forward to discussing how my background aligns with your needs. Sincerely, [Your Name] Copy ### Sample Interview Questions Can you describe a complex healthcare enterprise deal you closed that required significant cross-functional collaboration?I led a deal with a national health plan where I coordinated with product, legal, and compliance teams to address data privacy concerns. By understanding their pain points around member engagement, I customized our AI agent solution, resulting in a $1.2M annual contract.How do you approach prospecting and building relationships with key decision-makers in the healthcare industry?I leverage industry events, referrals, and targeted research to identify p;ain points. I then tailor outreach to highlight value creation, often starting with a smaller proof-of-concept to build trust before engaging senior executives.What strategies have you used to manage a $1M+ quota in a competitive market?I focus on pipeline hygiene by qualifying leads rigorously, and I use a consultative selling approach to differentiate our solution. I also collaborate with marketing on account-based campaigns and regularly review forecasts with my team to adjust tactics.How do you stay updated on AI trends in healthcare and apply that knowledge in sales?I read industry reports, follow key analysts like Gartner, and attend healthcare AI conferences. I share insights with prospects to position myself as a thought leader and align our product's capabilities with emerging trends like value-based care.Describe a time you had to handle a difficult objection from a customer during a negotiation.A prospect was concerned about integration complexity. I arranged a technical deep dive with our engineering team to address their specific IT architecture, and provided case studies of similar integrations. This turned the objection into a positive discussion on scalability. ## 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 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](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 * 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. * Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds. * 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. ## What you’ll bring * 8-12+ 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. * 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/149377-sales-director-healthcare.md) * ![Upload CV](data:image/svg+xml;base64,PHN2ZyB4bWxucz0iaHR0cDovL3d3dy53My5vcmcvMjAwMC9zdmciIHdpZHRoPSI2NSIgaGVpZ2h0PSI2NSIgZmlsbD0ibm9uZSIgeG1sbnM6dj0iaHR0cHM6Ly92ZWN0YS5pby9uYW5vIj48ZyBjbGlwLXBhdGg9InVybCgjQSkiPjxwYXRoIGQ9Ik0wIDBINjVWNjVIMFYwWiIgZmlsbD0iIzAyOWFlYiIvPjxnIGZpbGw9IiNmZmYiIHN0cm9rZT0iI2ZmZiIgc3Ryb2tlLXdpZHRoPSIyIj48cGF0aCBkPSJNMzMuMDQ5IDE1LjQ1NGExLjQzIDEuNDMgMCAwIDAtMi4wOTcgMGwtNy41NzkgOC4xNDdhMS4zOCAxLjM4IDAgMCAwIC4wOSAxLjk3MyAxLjQ0IDEuNDQgMCAwIDAgMi4wMDgtLjA4OGw1LjEwOS01LjQ5MnYyMC42MWExLjQxIDEuNDEgMCAwIDAgMS40MjEgMS4zOTdjLjc4NSAwIDEuNDIxLS42MjUgMS40MjEtMS4zOTd2LTIwLjYxbDUuMTA5IDUuNDkyYTEuNDQgMS40NCAwIDAgMCAyLjAwOC4wODggMS4zOCAxLjM4IDAgMCAwIC4wOS0xLjk3M2wtNy41NzktOC4xNDZ6TTE2Ljc2OSAzOC40YzAtLjc3My0uNjItMS40LTEuMzg1LTEuNFMxNCAzNy42MjcgMTQgMzguNHYuMTAybC4yMTUgNi4yMjljLjIyMyAxLjY4LjcwMSAzLjA5NSAxLjgxMyA0LjIxOHMyLjUxIDEuNjA3IDQuMTcyIDEuODMzYzEuNi4yMTggMy42MzYuMjE4IDYuMTYuMjE4aDExLjI4bDYuMTYtLjIxOGMxLjY2Mi0uMjI2IDMuMDYxLS43MDkgNC4xNzItMS44MzNzMS41ODktMi41MzggMS44MTMtNC4yMThDNTAgNDMuMTEzIDUwIDQxLjA1NSA1MCAzOC41MDNWMzguNGMwLS43NzMtLjYyLTEuNC0xLjM4NS0xLjRzLTEuMzg1LjYyNy0xLjM4NSAxLjRsLS4xOSA1Ljk1OGMtLjE4MiAxLjM3LS41MTUgMi4wOTUtMS4wMjYgMi42MTJzLTEuMjI4Ljg1My0yLjU4MyAxLjAzOGMtMS4zOTUuMTktMy4yNDMuMTkzLTUuODkzLjE5M0gyNi40NjJjLTIuNjUgMC00LjQ5OC0uMDAzLTUuODkzLS4xOTMtMS4zNTUtLjE4NC0yLjA3Mi0uNTIxLTIuNTgzLTEuMDM4cy0uODQ0LTEuMjQyLTEuMDI2LTIuNjEyYy0uMTg3LTEuNDEtLjE5MS0zLjI3OS0uMTkxLTUuOTU4eiIvPjwvZz48L2c+PGRlZnM+PGNsaXBQYXRoIGlkPSJBIj48cGF0aCBmaWxsPSIjZmZmIiBkPSJNMCAwaDY1djY1SDB6Ii8+PC9jbGlwUGF0aD48L2RlZnM+PC9zdmc+) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. 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