Enterprise Sales Director Strategic Consumer Business Services

Skills

About the Role

You will lead large, complex opportunities for consumer business services accounts across business units and geographies. You will structure deals, manage risk, build C-suite relationships, engage founders with customers, shape account strategy, and use AI tools throughout the sales cycle.

Requirements

• 10–12+ years of enterprise or strategic sales experience
• Success closing multi-million-dollar, multi-stakeholder deals across business units and geographies
• Experience managing a $1M+ quota and complex six- and seven-figure ACV deals
• Deep C-suite relationships
• Expertise in complex deal structuring, risk navigation, and pricing
• Executive communication skills
• Familiarity with the AI landscape
• Experience working alongside founders or executives with strategic customers

Responsibilities

• Lead complex multi-business-unit and multi-geography sales opportunities
• Design sophisticated deal structures and manage deal risk
• Build trusted relationships with customer C-suite leaders and working teams
• Engage Sierra co-founders in customer-facing sales conversations
• Refine messaging, positioning, and timing across customer interactions
• Influence strategy for important accounts and set standards for the sales organization
• Use AI tools for account research, outreach, call summarization, forecasting, and deal execution

Benefits

• Unlimited paid time off
• Medical, dental, and vision benefits for employees and their families
• Life insurance and disability benefits
• Retirement plan dependent on country of employment
• Parental leave
• Fertility and family-building benefits through Carrot
• Lunch, snacks, and coffee
• Discretionary benefit stipend
• Free alphorn lessons
• Equity plan eligibility