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. 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. 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.

Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product. 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. in an enterprise customer-facing sales role, identifying and closing large accounts.

Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. Ability to analyze market trends, identify opportunities, and make data-driven decisions. Proven track record of identifying and targeting potential enterprise clients through research, networking,



and cold calling. 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 perks 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 benefits 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, Healthcare (Winnipeg)
🏢 Neura Market
📍 Winnipeg