At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. 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.

Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. 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.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. Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction. Operate as part of the customer's team:



Hold trusted relationships across the customer C-suite and working teams.

Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise. Influence how Sierra approaches its most important accounts and set the standard for the broader sales org. 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. of enterprise/strategic sales experience, owning the largest and most complex accounts. deals spanning business units and geographies.

Experience managing a $Mastery of complex deal structuring, risk navigation, and pricing. Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.

Experience operating alongside founders/executives in front of strategic customers. We build trust with our customers with our accountability, empathy, quality, and responsiveness.

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.

We care about our product being the best, and when it isn’t, we fix it. 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 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 advantages plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.

To do so, it is important to us that the diversity of our employees represents the diversity of our customers. 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. #

📌 Enterprise Sales Director - Strategic, Healthcare (Winnipeg)
🏢 Sierra
📍 Winnipeg