Jobs 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.

In this role, you'll create onboarding documentation and developer training programs, develop AI agents, and publish success stories to engage the technical community.

Provide commercial contracting support across SaaS, licensing, services, channel and vendor agreements. Build templates, playbooks, and workflows. Advise on IP, privacy, security, and AI-related regulatory issues. Collaborate cross-functionally with sales, operations, and product; negotiate complex deals and support scaling legal operations.

As a Sales Engineer, you will design and demo Sierra's Agent product, collaborating with Sales, Product and Engineering teams to meet customer needs and drive sales strategies.

This role involves leading a high-performing sales team, owning regional sales performance, and being involved in key deals while mentoring sales representatives.

Lead Sierra’s largest and most complex enterprise sales opportunities across business units and geographies. Build C-suite relationships, structure multi-million-dollar deals, manage risk and pricing, engage founders alongside customers, shape strategic account and sales approaches, and use AI tools throughout the sales cycle. The role requires executive-level communication, trusted-advisor credibility, and expertise managing complex six- and seven-figure contracts.

Lead complex enterprise sales deals for Sierra’s Consumer Business Insights vertical, managing prospecting through close for six- and seven-figure agreements. Build C-suite relationships, multi-thread accounts, manage deal risk, guide pricing and strategy, and engage executives and co-founders when appropriate. Operate as an AI-native seller by using AI tools for research, outreach, summarization, forecasting, and deal execution. Help raise team standards while identifying market opportunities and making data-driven decisions.

Lead enterprise sales for Sierra’s Consumer Business Insights vertical. Responsibilities include prospecting, building executive relationships, managing complex six- and seven-figure deals, negotiating contracts, developing sales strategies, closing large accounts, and collaborating with marketing, product, technical, legal, finance, and operations teams. The role also requires using AI tools for account research, outreach, call summaries, forecasting, and deal execution.

The Sales Director is responsible for prospecting, managing relationships with enterprise customers, negotiating deals, and developing sales strategies to achieve targets. They will collaborate cross-functionally and help define the sales motion in a growing team.

Lead end-to-end technical pre-sales for Sierra's AI platform: scope use cases, design and demo solutions, run technical/architecture reviews, and act as trusted technical advisor across the enterprise sales cycle while partnering with Sales, Product, and Engineering.

Own the end-to-end technical pre-sales process: scope customer use cases, design and demo Sierra's platform, lead technical and architecture reviews, and act as trusted technical expert throughout the enterprise sales cycle. Work cross-functionally with Sales, Product, and Agent Engineering to drive GTM and improve Agents. Lead early customer conversations, anticipate needs, and translate business problems into technical solutions.

Drive outbound prospecting and build relationships with commercial and enterprise customers to generate pipeline and revenue. Lead negotiations and close complex deals, collaborate with legal, finance, product, and GTM teams, develop and execute sales strategies, help define the company sales motion, and conduct market analysis to identify new opportunities.

Lead end-to-end technical pre-sales for enterprise financial services clients: scope use cases, demonstrate and architect Sierra's AI platform, drive technical reviews, collaborate with Sales/Product/Engineering, and support GTM to win and onboard customers.

Own and manage the full-cycle recruiting process, partner with hiring managers, execute sourcing strategies, and track recruiting metrics to enhance hiring.

Sell Sierra's AI customer-experience platform to enterprise customers by prospecting, building executive relationships, negotiating and closing complex multi-stakeholder deals, developing sales strategy, collaborating with GTM/product/technical teams, and using AI tools to automate tasks and improve pipeline and forecasting.

Sell Sierra's AI customer-experience platform to large financial services accounts. Generate leads, build executive relationships, negotiate and close complex 6- and 7-figure deals, develop sales strategy, and collaborate with product, technical, and GTM teams. Use AI tools to automate low-value tasks and focus on high-value customer relationships.

Lead Sierra's largest, most complex enterprise deals by designing deal structures, managing risk, and building trusted C-suite relationships. Influence account strategy, engage founders, and use AI-enabled tools across the sales cycle to close multi-million-dollar, multi-BU, multi-geo opportunities.

Lead enterprise sales for Brazilian Portuguese–speaking customers: prospect and generate leads, build and manage strategic relationships, negotiate and close complex six- and seven-figure deals, develop sales strategy and GTM motion, and collaborate cross-functionally to hit revenue targets.