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Enterprise Account Executive

About us

  • At Sierra, we’re building a platform to enable every company in the world to build their own autonomous AI agents for everything from customer service to commerce. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, and London.

  • 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 Family. 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

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

  • Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with 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 sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.

  • Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds. 

  • Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.

What you'll bring

  • 10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.

  • 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.

  • 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.

  • 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 (e.g., 401K, pension) with Sierra match

  • Parental Leave

  • Fertility and family building benefits through Carrot (U.S. only)

  • 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 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.

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Average salary estimate

$150000 / YEARLY (est.)
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$120000K
$180000K

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What You Should Know About Enterprise Account Executive, Sierra

Are you ready to take the lead as an Enterprise Account Executive at Sierra in New York? We’re on a mission to empower companies to create their own AI agents for everything from customer service to commerce, and we need your expertise to help us grow! As an Enterprise Account Executive, you’ll dive into prospecting and lead generation, targeting potential enterprise customers through strategic research, networking, and, yes, some good old cold calling. Building and managing relationships will be at the core of your role as you engage with key decision-makers, ensuring they’re not just satisfied, but delighted with our services. You’ll be on the front lines, negotiating and closing complex deals that pave the way for Sierra’s continued success. Additionally, your insightful sales strategies will shape how we interact with the market. Collaboration across teams is critical; you’ll work closely with our marketing, product, and technical teams to deliver the best customer experience. We seek someone who's had at least 10 years in enterprise sales with a proven record of closing significant accounts. If you have a knack for analyzing market trends and are passionate about the evolving AI landscape, this opportunity is for you. At Sierra, we’re not just a company; we’re a family, and we want you to be part of it!

Frequently Asked Questions (FAQs) for Enterprise Account Executive Role at Sierra
What are the responsibilities of an Enterprise Account Executive at Sierra?

As an Enterprise Account Executive at Sierra, your primary responsibilities will include prospecting and lead generation to identify potential enterprise customers. You'll build and maintain relationships with key stakeholders, manage the negotiation and closing of complex deals, and develop sales strategies that align with our business goals. Ensuring customer satisfaction and working collaboratively with our marketing and product teams are also critical parts of the role.

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What qualifications do I need to apply for the Enterprise Account Executive position at Sierra?

To apply for the Enterprise Account Executive role at Sierra, candidates should have at least 10 years of experience in a customer-facing sales position, ideally with a focus on enterprise clients. Experience managing a $1M+ sales quota and the capability to run end-to-end deals is crucial. Strong communication skills and an analytical mindset are also highly desirable.

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How does Sierra support its employees in the Enterprise Account Executive role?

Sierra supports its Enterprise Account Executives through a dynamic work environment that prioritizes trust and collaboration. With flexible paid time off, comprehensive medical and retirement benefits, and a focus on professional and personal growth, Sierra ensures that employees have the resources they need to excel in their roles while maintaining a healthy work-life balance.

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What does the sales strategy look like for the Enterprise Account Executive at Sierra?

The sales strategy for the Enterprise Account Executive at Sierra involves developing tailored approaches to meet enterprise customers’ specific needs. This includes crafting presentations and proposals to resonate with decision-makers. You’ll also collaborate with marketing to design and implement impactful sales campaigns, ensuring that the strategy aligns with Sierra's corporate objectives.

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Is prior experience in AI necessary for the Enterprise Account Executive role at Sierra?

While prior experience in the AI industry is beneficial, it is not strictly necessary for the Enterprise Account Executive position at Sierra. However, a general familiarity with the AI landscape and a strong understanding of key trends will certainly enhance your effectiveness in identifying opportunities and closing deals.

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Common Interview Questions for Enterprise Account Executive
How do you approach prospecting for new enterprise clients as an Enterprise Account Executive?

When answering this question, you should highlight your methods for researching potential clients, leveraging networking opportunities, and using cold calling effectively. Share specific strategies you have utilized in the past and give examples of how these approaches resulted in successful outcomes.

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Can you describe a complex deal you negotiated and how you handled objections?

In your response, provide a detailed example of a challenging negotiation scenario. Explain the steps you took to understand the client's concerns and how you addressed them. Highlight your communication skills and any tactics you used to turn objections into opportunities.

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What strategies do you implement to maintain relationships with key stakeholders?

Discuss the importance of regular communication and updates in your approach. Mention the techniques you use for relationship-building, such as personalized check-ins, and engaging with stakeholders through value-driven conversations about their goals and how Sierra can help achieve them.

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How do you analyze market trends to inform your sales strategies?

Your response should focus on the methodologies you use to gather and interpret data from market research, industry reports, and competitor analysis. Explain how this information informs your approach to prospecting, lead generation, and sales presentations.

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What role do collaboration and teamwork play in your sales approach?

Emphasize the collaborative nature of successfully closing deals. Provide examples of how you’ve worked with cross-functional teams such as marketing, product, and finance to align efforts and ensure a smooth sales process, which ultimately benefits the client.

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Describe a time you exceeded a sales target and how you achieved this success.

Highlight a specific instance where you not only met but surpassed your sales goals. Discuss the strategies you employed, the obstacles you overcame, and any innovative tactics you implemented to drive results.

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How do you prioritize leads when you have multiple prospects at once?

Discuss your method for evaluating leads based on various factors such as potential deal size, readiness to purchase, and relationship strength. Mention any tools or frameworks you use to help prioritize your efforts effectively.

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What techniques do you use to craft tailored sales presentations?

Explain how you customize your sales presentations by researching your prospects extensively. Highlight the importance of understanding their unique challenges and how you adapt your content to directly address their specific needs.

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How do you handle setbacks in the sales process?

Talk about how you remain resilient and view setbacks as opportunities for growth. Discuss the importance of learning from each experience and adjusting your strategies accordingly to improve future outcomes.

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What motivates you in the pursuit of sales as an Enterprise Account Executive?

Share your intrinsic and extrinsic motivations, such as the thrill of closing a deal, the satisfaction of helping clients solve problems, and the drive to achieve personal and team success. Mention how these motivations fuel your persistence in the sales process.

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DATE POSTED
March 14, 2025

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