Remote Enterprise AI Sales Director - Major Accounts

Zekai; United States; Remote; USD 180,000 - 270,000; Full time

Benefits offered by this job

Flexible unlimited PTO

Medical, dental, and vision benefits

Life insurance and disability

Retirement plan (country dependent)

Parental leave

Fertility and family-building benefits

Lunch and snacks

Discretionary benefit stipend

Free alphorn lessons

Job summary

Sierra seeks an experienced Enterprise Sales professional to independently drive complex, multi-year deals end-to-end in a fully remote role based in the United States. You will lead VP- and C-suite conversations, manage risk, and collaborate with leadership on pricing and strategy, leveraging AI tools to accelerate the sales process while building durable relationships across customer organizations.

If you thrive in a fast-paced, AI-driven environment, you will have opportunities for high

Qualifications

• 8–10 years of enterprise customer-facing sales experience.
• Experience managing a $1M+ quota and running end-to-end complex ACV deals.
• Proven ability to multi-thread and build trusted relationships across customer C-suites.
• Exceptional verbal and written communication.
• Analytical mindset—you analyze market trends, spot opportunities, and make data-driven decisions.

Responsibilities

• Independently drive complex enterprise deals end-to-end: manage a broad enterprise book with autonomy, leading 6- and 7-figure cycles from prospecting to close.
• Multi-thread to the C-suite: lead VP-level conversations and build durable C-suite relationships.
• Manage risk proactively: identify deal risk early and map stakeholders.
• Make the hard calls: set pricing, escalation timing, and deal strategy with leadership input.
• Leverage leadership & co-founders: engage for executive alignment when moving a deal forward.
• Raise the bar: act as a visible leader on deal teams and elevate standards.
• Operate as an AI-native seller: use AI tools across the sales cycle to research, outreach, forecasting, and execution.

Skills

Enterprise sales

Quota >$1M

C-suite relationships

Communication

Analytical mindset

Job description

Sierra seeks an experienced Enterprise Sales professional to independently drive complex, multi-year deals end-to-end in a fully remote role based in the United States. You will lead VP- and C-suite conversations, manage risk, and collaborate with leadership on pricing and strategy, leveraging AI tools to accelerate the sales process while building durable relationships across customer organizations.

If you thrive in a fast-paced, AI-driven environment, you will have opportunities for high