Senior Enterprise AE at Sierra AI - $1M+ Quota Role

Sierra; San Francisco (CA); Presencial; USD 200.000 - 280.000; Tempo integral

Benefícios oferecidos por esta vaga

Unlimited PTO

Fertility benefits

Equity plans

Resumo da vaga

Sierra AI is seeking a Senior Enterprise Account Executive for Lima. This role targets high-impact, multi-geo engagements with a $1M+ quota and multi-million ACV deals. You will collaborate with co-founders and senior executives, using AI-driven selling to drive outcomes.

You will lead complex negotiations, shape strategy across accounts, and advance Sierra’s enterprise footprint in a rapidly growing AI-native sales environment. Equity opportunities are available for eligible employees.

Qualificações

• 10–12+ years of enterprise/strategic sales experience.
• Proven success closing multi-million-dollar, multi-stakeholder deals.
• Experience managing a $1M+ quota and end-to-end 6- and 7-figure ACV deals.
• Deep C-suite relationships with executive buyers.
• Mastery of complex deal structuring, risk navigation, and pricing.
• Exceptional executive communication and trusted advisor presence.

Responsabilidades

• Architect Sierra's most complex deals across multiple BUs and geos.
• Operate as part of the customer's team with trusted relationships at the C-suite level.
• Engage founders in front of customers, delivering structured, founder-level pitches.
• Maintain precision in messaging, positioning, and timing across all interactions.
• Shape strategic account plans and set standards for the sales org.
• Operate as an AI-native seller, leveraging AI tools across the sales cycle.

Conhecimentos

Enterprise sales

C-suite relationships

Multi-million-dollar deals

Deal structuring

Pricing

Executive communication

AI-native selling

Descrição da vaga

Senior Enterprise AE at Sierra AI - $1M+ Quota Role in Lima

This is a senior-tier, high-impact enterprise sales role at one of the most credible AI startups in the market right now. Sierra is backed by elite co-founders (Bret Taylor, Clay Bavor) and counts Fortune 500 clients on its roster — this is genuine enterprise pedigree, not a stretch claim.

Compensation signals: No salary is listed, but Strategic Account Executives managing $1M+ quotas with 7-figure ACV deals at high-growth AI companies typically command $200K–$280K OTE in North American markets, with significant equity upside at a pre-IPO company of this profile. The equity plan mentioned is a material differentiator at this stage.

• Exposure to co-founder-level selling is rare and career-defining — few AE roles offer direct Bret Taylor-level engagement
• AI-native selling skills (leveraging AI tools across the sales cycle) are rapidly becoming a differentiator in enterprise sales hiring
• Retail vertical expertise in AI will be increasingly valuable as the sector accelerates automation

Green flags: Strong values framework with explicit "Family" balance commitment, unlimited PTO, fertility benefits, and a culture that openly discusses failure. These signal a more mature startup culture than the typical high-burn early-stage shop.

Watch for: The word "Intensity" as a core value, combined with "we don't have the luxury of patience," signals a demanding environment. Candidates should probe for realistic quota attainment rates and manager tenure 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, was previously co-CEO of Salesforce, and CTO of Facebook. Clay spent 18 years at Google, leading Google Labs, AR/VR (Project Starline), Google Lens, and Google Workspace product and design teams.

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 also 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

Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.

Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.

Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.

Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.

Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.

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 that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.

What You'll Bring

10–12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.

Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.

Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.

Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.

Mastery of complex deal structuring, risk navigation, and pricing.

Exceptional executive communication and a reputation for precision and trust.

Even Better...

Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.

Experience operating alongside founders/executives in front of strategic customers.

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, 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.

Is this Strategic Account Executive role at Sierra fully remote? No — Sierra describes itself as "primarily an in-person company" headquartered in San Francisco, with offices across North America, Europe, and Asia. The role requires significant in-person presence, though the location hint suggests Canadian-based candidates may be considered. What kind of quota and deal sizes does this role involve? The role requires experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure Annual Contract Value (ACV) deals across multiple business units and geographies. How much experience is required for this role? Sierra is looking for 10–12+ years of enterprise or strategic sales experience, with demonstrated success closing multi-million-dollar, multi-stakeholder deals at the C-suite level. Does Sierra offer equity to employees in this role? Yes — eligible full-time employees can participate in Sierra's equity plans, subject to the terms of applicable plans and policies. What makes Sierra's culture distinctive for a sales professional? Sierra emphasizes co-founder-level engagement in customer pitches (both Bret Taylor and Clay Bavor are actively involved), an AI-native selling approach using AI tools throughout the sales cycle, and a stated commitment to balancing intensity with family-friendly values.

Remote work & career advice that actually works.