Teams at Sierra

Provides hands-on IT support for the New York office, including macOS troubleshooting, global helpdesk queue management, hardware lifecycle, conference room AV, office networking, onboarding, SaaS administration, vendor coordination, and IT logistics. The role also supports office build-outs and moves, executes endpoint and workplace technology projects, improves processes, and documents solutions. Requires strong troubleshooting, organization, communication, and experience supporting technical users.

Lead and develop a regional enterprise sales team, own sales performance and forecast accuracy, and support complex $1M+ deals through negotiation and close. Hire, coach, and develop account executives; inspect pipeline quality; partner with Revenue Operations; and build a culture of accountability and collaboration. The role also contributes to go-to-market strategy and requires extensive enterprise sales and people leadership experience.

Own the enterprise technical pre-sales process, including customer discovery, solution scoping, business-value articulation, architecture reviews, platform demonstrations, prototypes, and technical proposals. Partner with Sales, Product, and Agent Engineering teams to improve Sierra’s AI solutions. Build executive and technical relationships, lead customer sales cycles, translate business problems into solutions, and communicate effectively with technical and non-technical audiences while using AI tools responsibly.