Enterprise AI Sales Director — 7-Figure ACV & Equity

Sierra; United States; On-site; USD 150,000 - 350,000; Full time

Benefits offered by this job

Flexible (unlimited) paid time off

Medical, dental, and vision benefits

Life insurance and disability benefits

Retirement plan dependent on country

Parental leave

Fertility and family building benefits

Lunch, snacks and coffee

Discretionary benefit stipend

Free alphorn lessons

Job summary

Sierra is seeking an experienced Enterprise Sales professional to drive revenue with large accounts in a primarily in-person, global market. You will manage end-to-end complex deals, craft strategic plans, and work with cross-functional teams to deliver an industry-leading product.

You will navigate negotiations, forecast pipelines, and leverage AI tools to maximize efficiency while building strong customer relationships. This role emphasizes results, strategic thinking, and collaboration.

Qualifications

• 6-8 years of experience in an enterprise customer-facing sales role.
• Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
• Strong communication skills: exceptional verbal and written abilities.
• Analytical mindset: ability to analyze market trends and make data-driven decisions.
• Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.

Responsibilities

• Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling; build relationships with enterprise clients to drive revenue and pipeline.
• Manage relationships: Maintain strong relationships with decision-makers and stakeholders; serve as primary contact and exceed expectations.
• Negotiating & closing: Lead negotiations, address objections, and close deals; navigate contracts with legal and finance teams.
• Sales strategy & planning: Develop and execute strategies to meet targets; craft tailored presentations; collaborate with marketing.
• Collaborate cross-functionally: Work with GTM, product, technical, and operations teams to deliver the product.
• Operate as an AI-native seller: Leverage AI tools across the sales cycle to automate tasks and focus on high-value relationships.

Skills

Enterprise sales

Quota management

Communication

Analytical mindset

Lead generation

Job description

Sierra is seeking an experienced Enterprise Sales professional to drive revenue with large accounts in a primarily in-person, global market. You will manage end-to-end complex deals, craft strategic plans, and work with cross-functional teams to deliver an industry-leading product.

You will navigate negotiations, forecast pipelines, and leverage AI tools to maximize efficiency while building strong customer relationships. This role emphasizes results, strategic thinking, and collaboration.