Enterprise Sales Leader - Scale AI-Powered CX

Sierra; New York (NY); On-site; USD 180,000 - 320,000; Full time

Benefits offered by this job

Flexible PTO

Medical, dental, and vision

Life insurance

Retirement plan

Parental leave

Fertility benefits

Meals & snacks

Discretionary stipend

Alphorn lessons

Job summary

Sierra in San Francisco is seeking a VP of Enterprise Sales to lead our Americas region, building a high-performing team and closing strategic, multi-million deals.

You will guide sales strategy, partner with RevOps, and own forecasts while mentoring senior reps. This role emphasizes collaboration, data-driven decision making, and a deep network in enterprise tech. This position offers the opportunity to shape GTM with AI-powered products.

Qualifications

• 10–15+ years in enterprise customer-facing sales
• People leadership experience (5+ years)
• Experience closing $1M+ deals
• Strong communication skills (verbal & written)

Responsibilities

• Lead and develop a high-performing sales team across your region.
• Own regional performance, forecast accuracy, and pipeline quality.
• Be deeply involved in deals, supporting pricing, negotiations, and closing strategies

Skills

Leadership

Enterprise sales

Forecasting

Communication

Analytical thinking

Job description

Sierra in San Francisco is seeking a VP of Enterprise Sales to lead our Americas region, building a high-performing team and closing strategic, multi-million deals.

You will guide sales strategy, partner with RevOps, and own forecasts while mentoring senior reps. This role emphasizes collaboration, data-driven decision making, and a deep network in enterprise tech. This position offers the opportunity to shape GTM with AI-powered products.