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Regional VP, Sales (South East Asia)

SierraSingaporeSales
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Salary
Not listed
Job type
Full-time
Experience
Executive · 10+ yrs
Posted
9 Oct 2026
Status
Open · checked 7d ago

About this role

This role suits an experienced sales leader with a background in managing enterprise teams who wants to direct regional operations in Singapore. The position is a Regional VP of Sales based in Singapore, focusing on driving performance and building customer relationships across Southeast Asia.

Role Overview

Sierra seeks a Regional VP of Sales for Southeast Asia to lead the commercial team and drive revenue growth from the Singapore office. The individual will oversee regional performance, guide enterprise account executives, and participate directly in high-stakes customer negotiations. The organization specializes in a customer-facing AI agent platform utilized by major international brands.

Key Responsibilities

Hire, onboard, mentor, and lead a high-performing team of enterprise and strategic account executives within Southeast Asia.
Manage regional performance metrics, maintain forecast accuracy, inspect pipeline quality, and partner with Revenue Operations.
Participate directly in client meetings and prospect discussions to support complex buying committees and late-stage deal closures.
Cultivate a workplace culture centered on accountability, continuous learning, and future leadership development.

Requirements

Possess 10 to 15 or more years of professional background in an enterprise customer-facing sales capacity, focusing on closing large accounts.
Demonstrate 5 or more years of people leadership history managing, mentoring, and developing enterprise sales teams.
Bring direct experience managing a quota of $1 million or higher and executing end-to-end complex deals.
Exhibit strong verbal and written communication capabilities alongside an analytical mindset for data-driven decision making.

Nice to Have

Familiarity with the artificial intelligence landscape, major market players, and emerging industry trends.
Background in building go-to-market strategies, sales teams, or sales motions from scratch or early-stage growth.

Skills and Tools

Enterprise sales management
Pipeline management and forecasting
Deal strategy and negotiation
Revenue operations collaboration
Market trend analysis

Salary and Benefits

Flexible, unlimited paid time off policies.
Medical, dental, and vision coverage for employees and their families.
Life insurance and disability benefits.
Country-dependent retirement plan options.
Parental leave alongside fertility and family-building support through Carrot.
Office perks including lunch, snacks, coffee, and discretionary benefit stipends.
Eligibility to participate in company equity plans and free alphorn lessons.

About the Company

Sierra provides a platform focused on customer-facing artificial intelligence agents, partnering with major global brands to alter customer service and business growth. Co-founded by Bret Taylor and Clay Bavor, the enterprise operates primarily in-person with growing global offices across North America, Europe, and Asia. Corporate culture and daily actions are governed by core values of trust, customer obsession, craftsmanship, intensity, and family balance.

How to Apply

Interested candidates should apply on the official company careers page.

Questions candidates ask

Where is this job located?

The position is based in Singapore.

How many years of total sales experience are required?

Candidates must have 10 to 15+ years of experience in an enterprise customer-facing sales role.

Is management experience required for this role?

Yes, applicants must have 5+ years of people leadership experience managing, mentoring, and developing a high-performing enterprise sales team.

What quota management background is expected?

Candidates need experience managing a $1M+ quota and running end-to-end complex deals.

What benefits are provided to full-time employees?

Benefits include flexible paid time off, medical, dental, and vision coverage, life and disability insurance, parental leave, family building benefits through Carrot, retirement plans, office meals and snacks, and a discretionary benefit stipend.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site