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SierraEnterprise Sales Director - Strategic
Sierra is seeking an Enterprise Sales Director - Strategic to lead major transactions for its leading customer-facing AI agent platform. The employer partners with prominent global…
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About This Role
Sierra is seeking an Enterprise Sales Director - Strategic to lead major transactions for its leading customer-facing AI agent platform. The employer partners with prominent global brands, including SoftBank, Sutter Health, SoFi, Rocket Mortgage, and The GAP, to revolutionize customer service and business growth. Founded by Bret Taylor and Clay Bavor, the company operates with a strong focus on core principles such as customer obsession, trust, craftsmanship, intensity, and family.…
Job Description
Sierra is seeking an Enterprise Sales Director - Strategic to lead major transactions for its leading customer-facing AI agent platform. The employer partners with prominent global brands, including SoftBank, Sutter Health, SoFi, Rocket Mortgage, and The GAP, to revolutionize customer service and business growth. Founded by Bret Taylor and Clay Bavor, the company operates with a strong focus on core principles such as customer obsession, trust, craftsmanship, intensity, and family.
This role suits an experienced enterprise sales professional capable of orchestrating complex, multi-million-dollar agreements across multiple geographic regions and business units. Responsibilities include shaping account strategies, establishing deep C-suite connections, utilizing AI tools across the entire sales pipeline, and collaborating directly with company co-founders during customer presentations.
Responsibilities
- Design sophisticated deal structures and manage risk for large multi-business-unit and multi-geography opportunities
- Establish trusted relationships with customer executives and working teams
- Engage and manage company co-founders during customer pitches
- Maintain high precision in timing, messaging, and positioning across all interactions
- Influence account strategies and help set standards for the broader sales organization
- Deploy AI tools throughout the sales cycle for tasks such as account research, outreach, pipeline forecasting, and deal execution
Requirements
- Possess ten to twelve or more years of strategic and enterprise sales background managing complex accounts
- Demonstrate a track record of closing multi-stakeholder, multi-million-dollar agreements spanning multiple geographies and business units
- Show experience managing quotas of one million dollars or greater and running end-to-end six and seven-figure annual contract value deals
- Bring deep and sustained relationships with C-suite executives
- Demonstrate mastery in pricing, risk navigation, and complex deal structuring
- Exhibit exceptional executive communication skills
Qualifications
- Deep familiarity with the artificial intelligence landscape with the ability to speak credibly to business and technical audiences
- Prior experience operating alongside executives and founders in front of strategic clients
- Background in building go-to-market strategies, sales motions, or sales teams from early-stage growth or scratch
Core Skills
Benefits
- Flexible and unlimited paid time off
- Medical, dental, and vision coverage for employees and their families
- Life insurance and disability benefits
- Retirement plan dependent on the country of employment
- Parental leave along with family building and fertility benefits through Carrot
- Lunch provided along with snacks and coffee
- Discretionary benefit stipend
- Free alphorn lessons
- Eligibility to participate in company equity plans
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
What is the salary for the Enterprise Sales Director position?
The salary ranges from USD 420,000 to 445,000 per year.
What remote work options are available for this role?
The posting does not specify remote or hybrid options, noting that Sierra is primarily an in-person company based in San Francisco with growing offices across North America, Europe, and Asia.
What level of experience is required?
Candidates must have 10 to 12 or more years of strategic and enterprise sales experience managing complex accounts, including closing multi-million-dollar deals and managing quotas of $1M+.
Sample Interview Questions
AI-generated questions tailored to this specific role — a preview of the full practice set.
