Overview: Sierra is seeking an Enterprise Sales Director - Strategic to architect Sierra’s most complex deals across multiple business units and geographies. This remote-friendly role is based in the United States, with Sierra historically headquartered in San Francisco and with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney. You will lead multi-geo opportunities, build trusted relationships with C-suite stakeholders, and regularly engage Sierra’s co-founders in front of customers. What you’ll do: Lead and structure the largest, multi-BU, multi-geo opportunities, designing sophisticated deal terms and managing risk with precision. Integrate with the customer’s team, maintaining trusted relationships across the C-suite and key lines of business. Engage at the founder level, delivering founder-level presentations alongside Sierra’s co-founders. Operate with precision in messaging, positioning, and timing across all interactions. Shape account strategy and set the standard for the broader sales organization. Act as an AI-native seller, leveraging AI tools across the full sales cycle—from account research and personalized outreach to pipeline forecasting and deal execution—and continuously adopting new tools to work faster and smarter. What you’ll bring: 10–12+ years of enterprise/strategic sales experience with a track record of closing large, complex deals. Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies. Experience managing a $1M+ quota and running end-to-end

Overview: Sierra is seeking an Enterprise Sales Director - Strategic to architect Sierra’s most complex deals across multiple business units and geographies. This remote-friendly role is based in the United States, with Sierra historically headquartered in San Francisco and with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney. You will lead multi-geo opportunities, build trusted relationships with C-suite stakeholders, and regularly engage Sierra’s co-founders in front of customers. What you’ll do: Lead and structure the largest, multi-BU, multi-geo opportunities, designing sophisticated deal terms and managing risk with precision. Integrate with the customer’s team, maintaining trusted relationships across the C-suite and key lines of business. Engage at the founder level, delivering founder-level presentations alongside Sierra’s co-founders. Operate with precision in messaging, positioning, and timing across all interactions. Shape account strategy and set the standard for the broader sales organization. Act as an AI-native seller, leveraging AI tools across the full sales cycle—from account research and personalized outreach to pipeline forecasting and deal execution—and continuously adopting new tools to work faster and smarter. What you’ll bring: 10–12+ years of enterprise/strategic sales experience with a track record of closing large, complex deals. Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies. Experience managing a $1M+ quota and running end-to-end