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# Enterprise Sales Director – Majors

Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move.

[Apply for this job](#job-application)[View company](https://jobicy.com/company/sierra.md)Share26 Aug 2026Published39Listing views2Application actions25 Sep 2026Apply before  Opportunity details

## About this role.

AI SummarySierra is seeking an experienced Enterprise Sales Director to independently own complex major-account opportunities for its AI customer-experience platform. The role leads end-to-end enterprise sales cycles, including prospecting, executive relationship building, stakeholder mapping, pricing strategy, escalation management, and closing six- and seven-figure deals. Candidates need 8-10 years of enterprise sales experience, a history of managing $1M+ quotas, and strong C-suite communication skills. This is a high-autonomy, US-based remote or office-based position that emphasizes AI-native selling practices, customer outcomes, and disciplined deal execution.

## Role DNA

A quick view of the complexity, pace, ownership and collaboration implied by the job description.

### Job Complexity

5/5EasyHard

### Pace & Pressure

5/5RelaxedFast-paced

### Autonomy Level

5/5GuidedFull ownership

### Communication Load

5/5IndependentCollaborative

AI insightThis is a senior enterprise-sales position requiring ownership of long, high-value, multi-stakeholder deal cycles and sound judgment on pricing, risk, and executive engagement. Success depends on consistently navigating C-suite relationships, complex buying committees, and ambitious sales expectations with minimal supervision.

## Salary analysis

Estimated compensation compared with the broader US market for similar roles.

Estimated job medianMarket rate$322,500US market range$250k–$400k0$440k

AI insightThe disclosed yearly compensation range is $300,000-$345,000 USD, producing a midpoint of $322,500. For a US Enterprise Sales Director focused on major accounts at an AI software company, an estimated market compensation range is approximately $250,000-$400,000 USD annually; actual total compensation can vary substantially based on base-versus-variable mix, territory, quota, equity, and attainment.

## Core skills

Skills and capabilities most closely associated with this opportunity.

[Enterprise Sales](https://jobicy.com/jobs?search_keywords=Enterprise%20Sales.md)[Major Accounts](https://jobicy.com/jobs?search_keywords=Major%20Accounts.md)[Complex Deal Cycles](https://jobicy.com/jobs?search_keywords=Complex%20Deal%20Cycles.md)[C-Suite Selling](https://jobicy.com/jobs?search_keywords=C-Suite%20Selling.md)[Strategic Account Management](https://jobicy.com/jobs?search_keywords=Strategic%20Account%20Management.md)[Sales Strategy](https://jobicy.com/jobs?search_keywords=Sales%20Strategy.md)[Pipeline Forecasting](https://jobicy.com/jobs?search_keywords=Pipeline%20Forecasting.md)[AI Sales Tools](https://jobicy.com/jobs?search_keywords=AI%20Sales%20Tools.md)[Stakeholder Management](https://jobicy.com/jobs?search_keywords=Stakeholder%20Management.md)[Negotiation](https://jobicy.com/jobs?search_keywords=Negotiation.md)

Sample interview questionsDescribe a complex enterprise deal you owned from prospecting to close. How did you manage the buying process?I would outline the account strategy, the business problem being solved, the stakeholders involved, and the deal timeline. I would emphasize how I created a mutual action plan, aligned champions and executives, addressed risks early, and used measurable customer outcomes to earn consensus and close the opportunity.

How do you build and maintain relationships with C-suite stakeholders in a major account?

I begin with a clear understanding of the executive's strategic priorities, operating metrics, and industry pressures. I provide concise, relevant points of view, connect our solution to measurable business outcomes, and maintain credibility through consistent follow-through and thoughtful executive engagement.

What is your approach to identifying and mitigating risk in a six- or seven-figure deal?

I assess risk across executive sponsorship, compelling event, budget, technical validation, procurement, legal, and competitive positioning. I document these factors in an account and stakeholder map, assign actions and owners, and escalate early when executive alignment or resource support can materially change the outcome.

How have you used AI tools to improve your sales productivity and deal execution?

I use AI to accelerate account research, prepare tailored outreach, summarize calls, identify follow-up commitments, and improve forecast hygiene. The goal is not to automate relationship building, but to reduce administrative work so I can spend more time on customer strategy and high-value conversations.

How would you approach your first 90 days at Sierra?

I would rapidly learn Sierra's product, customer use cases, competitive landscape, and successful sales motions. I would prioritize territory and account segmentation, build account plans for the highest-potential prospects, establish internal partnerships, and create a qualified pipeline with clear next steps, stakeholder maps, and forecast discipline.

### About us

At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such as SoftBank, Uber, Rivian, CLEAR, and Sutter Health. 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 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](https://www.linkedin.com/in/brettaylor/) and [Clay Bavor](https://www.linkedin.com/in/claybavor/). 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

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Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.

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Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.

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Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.

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Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.

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Leverage leadership & co-founders: Bring in Sierra’s co-founders effectively for exec engagement when it moves a deal.

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Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team’s standard without being asked.

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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

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8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.

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

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Proven ability to multi-thread and build trusted relationships across customer C-suites.

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Exceptional verbal and written communication.

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Analytical mindset – you analyze market trends, spot opportunities, and make data-driven decisions.

### Even better…

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

### Our values

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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.

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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.

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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

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Medical, dental, and vision benefits for you and your family

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Life insurance and disability benefits

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Retirement plan dependent on country of employment

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Parental leave

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Fertility and family building benefits through Carrot

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Lunch, as well as delicious snacks and coffee to keep you energized

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Discretionary benefit stipend giving people the ability to spend where it matters most

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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.

Show more

[Apply now >](https://jobicy.com/jobs/151665-enterprise-sales-director-majors.md)

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