Enterprise Sales Director - Majors

Sierra; Toronto; Hybrid; CAD 180,000 - 300,000; Full time

Benefits offered by this job

Unlimited PTO

Medical, dental, and vision benefits

Life insurance

Equity plans

Job summary

Sierra is seeking a high-impact Enterprise Seller to independently drive multi‑million deals from prospecting to close. You will lead VP‑level conversations, build durable C‑suite relationships, and manage risk across complex sales cycles using AI-assisted tools.

You will operate at the senior level with a point of view on pricing and strategy, engaging Sierra’s co-founders when needed. Excellent communication and data-driven decision making are required.

Qualifications

• 8-10 years of enterprise customer-facing sales experience.
• Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
• Proven ability to multi-thread and build trusted relationships across customer C-suites.
• Exceptional verbal and written communication.
• Analytical mindset – you analyze market trends, spot opportunities, and make data-driven decisions.

Responsibilities

• Independently drive complex enterprise deals end-to-end, from prospecting to close.
• Multi-thread to the C-suite and build durable executive relationships across accounts.
• Identify and manage deal risk early; map stakeholders and coordinate actions.
• Make the hard calls on pricing, escalation timing, and deal strategy with senior guidance.
• Bring in Sierra’s co-founders effectively for executive engagement when needed.
• Elevate the team's standard and operate as a visible leader on deal teams.
• Leverage AI tools across the sales cycle to research accounts, outreach, and forecasting.

Skills

Enterprise sales

C-suite relationships

Communication skills

Analytical mindset

Deal closing

Job description

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 that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. 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

• 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.
• 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.
• Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
• 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.
• Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
• Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
• 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

• 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.
• Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
• Proven ability to multi-thread and build trusted relationships across customer C-suites.
• Exceptional verbal and written communication.
• Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.

Even better...

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

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 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.