Enterprise AI Sales Director - Retail & Majors

Jobicy; United States; Remote; USD 180,000 - 320,000; Full time

Benefits offered by this job

Flexible (unlimited) paid time off

Medical, dental, and vision benefits

Life insurance and disability benefits

Retirement plan

Parental leave

Fertility and family building benefits

Lunch and snacks

Discretionary benefit stipend

Free alphorn lessons

Job summary

Sierra is seeking an experienced Enterprise Sales Executive to drive multi‑million deals end‑to‑end in the fast‑growing AI customer‑facing space. You will lead 6‑ and 7‑figure cycles, partner with C‑suite stakeholders, and shape deal strategy from prospecting to close in a highly autonomous role.

Based in San Francisco with growing North America offices, you’ll leverage Sierra’s AI platform to help retailers and brands grow revenue while delivering exceptional customer outcomes.

Qualifications

• 8–10 years of enterprise customer-facing sales experience.
• Experience closing 6- to 7-figure ACV deals with $1M+ quota.
• Proven ability to multi-thread and build trust with C-suite executives.
• Exceptional verbal and written communication and analytical mindset.

Responsibilities

• Independently drive complex enterprise deals end-to-end from prospecting to close.
• Lead VP-level conversations and build durable executive relationships.
• Map stakeholders and manage deal risk proactively.
• Collaborate with leadership to align pricing and strategy.
• Leverage AI tools across the sales cycle to improve efficiency.

Skills

Enterprise sales

CRM (Salesforce)

C-suite relationships

Negotiation

Data-driven

Tools

Salesforce

HubSpot

Job description

Sierra is seeking an experienced Enterprise Sales Executive to drive multi‑million deals end‑to‑end in the fast‑growing AI customer‑facing space. You will lead 6‑ and 7‑figure cycles, partner with C‑suite stakeholders, and shape deal strategy from prospecting to close in a highly autonomous role.

Based in San Francisco with growing North America offices, you’ll leverage Sierra’s AI platform to help retailers and brands grow revenue while delivering exceptional customer outcomes.