Regional Sales Director at Sierra - AI Sales USA — Columbus
Traveler-Friendly Insight
This is an in-person, office-first role — Sierra explicitly states it is "primarily an in-person company based in San Francisco." This Regional Sales Director position requires hands-on team leadership, in-person client meetings, and deal navigation that makes it incompatible with a digital nomad or fully remote lifestyle.
As a Regional Sales Director managing enterprise deals ($1M+) and leading an in-person team, you should expect:
- Regular presence at Sierra's San Francisco headquarters
- Frequent travel to customer and prospect sites across your region
- Fixed collaboration hours aligned to US Pacific or Eastern time zones
For travelers interested in adjacent opportunities: If you want to work at an AI company with location flexibility, look instead for individual contributor enterprise AE or solutions engineering roles at AI-first companies — those positions sometimes offer partial remote arrangements. Alternatively, Sierra's growing offices in Europe and Asia may eventually offer roles with different geographic flexibility.
The discretionary benefit stipend could theoretically support coworking costs during short-term travel, but given the in-person mandate, this role is not suitable for nomadic work styles. Prioritize other opportunities if location independence is your primary criteria.
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 at the core of our actions and culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI and previously was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, most recently leading Google Labs, and earlier led Google's AR/VR effort, Project Starline, and Google Lens.
About the Consumer Business Services Team
Sierra partners with the businesses that power everyday life — from CPG brands to logistics networks, real estate and facilities teams, and energy and utility providers. Our agents handle everything from order tracking and account management to field service scheduling and billing support, tuned to the voice and workflows of each business.
This vertical spans a wide range of industries — consumer products, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, information & data services, consumer electronics, professional services, facilities management, construction, energy, and utilities — giving you the breadth to build relationships across some of the largest and most established companies in the world.
Join us to bring AI agents to the businesses that quietly run the economy — and help build technology that makes these essential services faster, more reliable, and more human for everyone who depends on them.
What You'll Do
Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region. 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: Extensive experience in enterprise customer-facing sales, identifying and closing large accounts.
People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team.
Enterprise experience: You've run and managed end-to-end complex deals ($1M+).
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, as well as fluency with AI tooling and workflows.
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 through 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 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. 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 continuously self-reflect to continuously self-improve.
Intensity: We know we don't have the luxury of patience. We play to win. 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. We are the best technology company for parents. We support 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 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.
Frequently Asked Questions
Is the Regional Sales Director role at Sierra remote or in-person?
What industries does the Consumer Business Services team cover?
What level of sales experience is required for this role?
Does Sierra offer equity compensation?
Is experience with AI or AI tooling required for this role?
