Regional VP, Sales

Sierra; United States; On-site; USD 150,000 - 230,000; Full time

Benefits offered by this job

Flexible PTO

Medical, dental, and vision benefits

Life insurance

Retirement plan

Parental leave

Fertility benefits

Lunch and snacks

Equity plans

Free alphorn lessons

Job summary

Sierra in San Francisco is seeking an experienced Enterprise Sales Leader to drive growth across Korea. You will own regional performance, coach a high-performing sales team, and guide pricing and deal strategy from prospect to close.

You will join key customer conversations, manage a $1M+ quota, and collaborate with RevOps to ensure data quality and clear insights. Strong English and Korean communication are essential.

Qualifications

• 10–15+ years in an enterprise customer-facing sales role closing large accounts.
• 5+ years people leadership, mentoring and developing a high-performing enterprise sales team.
• Experience managing a $1M+ quota and running end-to-end complex deals.
• Analytical mindset to analyze market trends and identify opportunities with data-driven decisions.
• Strong English and Korean written and verbal communication.

Responsibilities

• Start selling as player/coach: prospect, build pipeline, manage customers and close deals.
• Lead & develop a high-performing sales team: hire, onboard, and develop AEs across Korea; coach on strategy and pipeline.
• Own regional performance: own regional number and forecast accuracy; inspect pipeline quality.
• Be deeply involved in deals: join key conversations; support pricing, negotiation, and close strategy.

Skills

Enterprise sales

People leadership

Quota management

Analytical mindset

English & Korean

Job description

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 and Clay Bavor. 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

• Start Selling - On day zero, you will be a player/coach. Prospect, build pipeline, manage customers, and close deals, We're looking for candidates who are coming from a leadership role, but are open to getting their hands dirty.

• Lead & develop a high-performing sales team - Over the next year, you will hire, onboard, and develop AEs across Korea. 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.

• Analytical Mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.

• Communication: Strong English and Korean written and verbal communication.

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.