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 and Clay Bavor. 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. What you'll do Architect Sierra's most complex deals: 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. Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise. Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction. Shape strategy: Influence how Sierra approaches its most key accounts and set the standard for the broader sales org. Operate as an AI-native seller: Leverage AI tools across the full sales cycle-

📌 Enterprise Sales Director - Strategic (Toronto)
🏢 Sierra
📍 Toronto