Regional VP, Sales (South East Asia)

Sierra
Singapore
On-site

Who this role is best for

A natural match if you have experience leading enterprise sales teams in AI or tech sectors.

Best fit for

  • Individuals with a deep understanding of AI markets and the ability to build go-to-market strategies from scratch.
    — “Experience Building GTM Strategies: Building sales teams and sales motions from scratch, or from early stage growth.”
  • Professionals who thrive in a culture of accountability, collaboration, and continuous improvement.
    — “Create a culture of accountability, learning, and collaboration.”

Things to consider

  • This role requires a strong commitment to regional performance and pipeline management.
    — “Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals.”
  • Candidates should be prepared for a high-intensity work environment with a focus on continuous self-improvement.
    — “We play to win. We care about our product being the best, and when it isn’t, we fix it.”

How to stand out

  • Highlight your experience in leading teams through complex enterprise sales cycles.
    — “Lead & develop a high-performing sales team - Hire, onboard, and develop Enterprise/Strategic AEs covering Southeast Asia.”
  • Demonstrate your track record in unblocking stalled deals and driving consistent execution.
    — “Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process.”
  • Showcase your analytical skills in interpreting market trends and making data-driven decisions.
    — “Analytical Mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.”
  • Demonstrate your ability to coach and develop sales representatives effectively.
    — “Coach reps on deal strategy, pipeline management, and execution.”
Pace · Fast PacedCollaboration · HighAutonomy · HighDecision Impact · Team

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • Leading a high-performing sales team
  • Achieving regional sales targets
  • Building and executing GTM strategies
Typical background
10-15 years of enterprise sales experience5+ years of people management experience

Skills & requirements

Required

Sales LeadershipEnterprise SalesPeople ManagementPipeline ManagementComplex Deal ManagementCommunication SkillsAnalytical Mindset

Preferred

AI Industry KnowledgeGTM Strategy

Stack & domain

Enterprise Customer-facing SalesDeal StrategyPipeline ManagementExecutionTeam DevelopmentLeadershipCommunicationAnalytical MindsetMarket TrendsData-driven DecisionsSalesEnterprise SalesCustomer Service

About the role

Original posting from Sierra via Ashby

ABOUT US

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.

We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.

Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.

WHAT YOU'LL DO

  • Lead & develop a high-performing sales team - Hire, onboard, and develop Enterprise/Strategic AEs covering Southeast Asia. Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.
  • Own regional performance - Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.
  • Be deeply involved in deals - Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.

WHAT YOU'LL BRING

  • 10- 15+ years of experience in an Enterprise customer-facing sales role, identifying and closing large accounts.
  • People Leadership Experience: 5+ years managing, mentoring, and developing a high performing enterprise sales team.
  • Enterprise Experience: Experience managing a $1M+ quota, and running end-to-end complex deals.
  • Strong Communication Skills: Exceptional verbal and written communication abilities.
  • Analytical Mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.

EVEN BETTER...

  • Industry Knowledge: Familiarity with the AI landscape, key players, and emerging trends.
  • Experience Building GTM Strategies: Building sales teams and sales motions from scratch, or from early stage growth.

OUR VALUES

  • Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
  • Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
  • Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
  • Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
  • Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.

WHAT WE OFFER

We want our benefits to reflect our values and offer the following to full-time employees:

  • Flexible (unlimited) paid time off
  • Medical, dental, and vision benefits for you and your family
  • Life insurance and disability benefits
  • Retirement plan dependent on country of employment
  • Parental leave
  • Fertility and family building benefits through Carrot
  • Lunch, as well as delicious snacks and coffee to keep you energized 
  • Discretionary benefit stipend giving people the ability to spend where it matters most
  • Free alphorn lessons

These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.

BE YOU, WITH US

We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Source: Sierra careers (Ashby)

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