Senior Enterprise AE at Sierra AI - Career Growth

Sierra; San Francisco (CA); Hybrid; USD 200,000 - 350,000; Full time

Benefits offered by this job

Equity upside

Unlimited PTO

Job summary

Sierra AI is seeking a Senior Enterprise Account Executive to lead strategic deals in the AI-native SaaS space. You will own end-to-end enterprise sales, targeting large accounts with a $1M+ quota, and you will operate in a fast-paced, high-growth environment.

The role emphasizes AI-enabled selling and cross-functional collaboration across GTM, product, and finance. The ideal candidate has 6–8 years in enterprise sales, a track record of closing 6- to 7-figure ACV deals, and exceptional

Qualifications

• 6–8 years of enterprise sales experience
• Experience closing 6- to 7-figure ACV deals
• Ability to manage a $1M+ quota
• Strong communication and analytical skills

Responsibilities

• Prospecting & Lead Generation: Identify and target potential customers through research, networking, and cold calling.
• Manage Relationships: Build and maintain relationships with key decision-makers and stakeholders at our largest customers.
• Negotiating & Closing Complex Deal Cycles: Lead negotiations, address objections, and close deals with legal/finance stakeholders.
• Sales Strategy & Planning: Develop strategies to meet targets and tailor presentations/proposals for enterprise needs.
• Collaborate Cross-Functionally: Work with GTM, product, technical, and operations teams to deliver the product.
• Operate as an AI-Native Seller: Use AI tools across the sales cycle to automate low-value tasks and focus on relationships.

Skills

AI-native selling

Enterprise sales

Quota management

CRM proficiency

Job description

Senior Enterprise AE at Sierra AI - Career Growth — Remote

Career Trajectory: This is a senior individual contributor role (6–8 years experience, $1M+ quota) squarely in the enterprise AI SaaS sales space — one of the highest-earning and fastest-growing verticals in tech sales right now. Closing 6- and 7-figure ACV deals is a career-defining skill that translates across any enterprise software company.

Compensation Context: No salary is listed, but enterprise AEs at AI-native companies of Sierra's caliber in the US/Canada typically earn $200K–$350K OTE (base + commission), with equity upside at a high-growth startup. Sierra has raised significant funding and counts Fortune 500 clients, suggesting strong commission potential on large deals.

Skills You'll Develop:

• AI-native selling methodology — a genuinely differentiated and in-demand skill set
• Retail vertical expertise across a diverse customer base
• Cross-functional GTM collaboration in a fast-scaling startup

Company Stage & Culture: Sierra is a high-growth, high-intensity startup with world-class founders (Bret Taylor, Clay Bavor). Values like "Intensity" and "we don't have the luxury of patience" signal a demanding, fast-paced culture. The "Family" value and unlimited PTO suggest an attempt at balance, but this is not a lifestyle company.

Green Flags: Elite founding team, blue-chip client roster, AI-native product in a category experiencing explosive growth, equity participation. Red Flag to watch: Intensity culture may mean high expectations with limited ramp time — ask about quota attainment rates in interviews.

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. Previously, he was co-CEO of Salesforce and CTO of Facebook, and was one of Google's earliest product managers and co-creator of Google Maps. Clay spent 18 years at Google, where he led Google Labs, Project Starline (AR/VR), Google Lens, and the product and design teams for Google Workspace.

About the Retail Team

Sierra partners with a large and growing number of retailers — spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand's own voice.

Retail is where AI agents go beyond support to generate revenue — from product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales. Our team is redefining what an agent can do for a brand's top line, not just its cost line.

Join us to transform how the world's most-loved consumer brands engage their customers — and help build technology that makes shopping more personal, effortless, and delightful for everyone.

What You'll Do

Prospecting & Lead Generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.

Manage Relationships: Build and maintain strong relationships with key decision-makers and stakeholders at our largest customers. Serve as their primary point of contact and exceed their expectations.

Negotiating & Closing Complex Deal Cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.

Sales Strategy & Planning: Develop and execute sales strategies to meet or exceed targets. Craft tailored sales presentations and proposals that meet enterprise customer needs. Collaborate with the marketing team to implement effective sales campaigns.

Collaborate Cross-Functionally: Work closely with our broader GTM team as well as product, technical, and operations organizations to deliver our industry-leading product.

Operate as an AI-Native Seller: Leverage AI tools across the full sales cycle — account research, personalized outreach, call summarization, pipeline forecasting, and deal execution — to automate low-value tasks and reinvest time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter.

What You'll Bring

6–8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.

Enterprise experience: Managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.

Strong communication skills: Exceptional verbal and written communication abilities.

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

Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.

Even Better...

Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.

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 showing up professionally and personally.

Customer Obsession: We deeply understand our customers' business goals and relentlessly focus on driving outcomes, not just technical milestones. When a customer has 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 are proud of the products we produce and continuously self-reflect to 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, and we model it in our actions and processes. We support and respect each other and celebrate 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. 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.

Is this Enterprise Account Executive role at Sierra fully remote? Sierra describes itself as "primarily an in-person company," so this role is not fully remote. The Canada location hint suggests a hybrid or in-office arrangement at one of their North American offices, with likely travel for enterprise client meetings. What is the expected quota for this role? The posting specifies experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals, so candidates should expect a similar or higher quota at Sierra given the company's enterprise customer base. What industries does Sierra's Retail team focus on? The Retail team works across apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology — partnering with some of the world's most recognized consumer brands. Does Sierra offer equity compensation? Yes, eligible full-time employees can participate in Sierra's equity plans, subject to the terms of applicable plans and policies. What does 'AI-native seller' mean in this role? Sierra expects its AEs to actively use AI tools throughout the sales cycle — for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution — to replace low-value manual tasks and focus more time on high-value client relationships.

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