Enterprise Sales Director - Majors
Drive complex enterprise deals and build C-suite relationships at Sierra, an AI-focused company based in San Francisco.
Posted by employer 3 months ago
First seen on Joblaze 2 months ago
Last verified on the company career page 1 day ago
Skills & Technologies
AI in the day-to-day
Leverage AI tools across the full sales cycle to automate low-value tasks and enhance customer relationships.
Requirements
- Experience
- 8–10 years
Not disclosed in this posting: compensation, visa sponsorship.
Benefits
Joblaze summary
The Enterprise Sales Director at Sierra is responsible for independently managing complex enterprise deals, guiding them from initial prospecting through to closure. This role requires a strong background in enterprise sales, particularly with 6- and 7-figure deals, and the ability to build relationships at the C-suite level. Ideal candidates will have 8-10 years of experience in customer-facing sales, with a focus on leveraging AI tools to enhance the sales process. Sierra emphasizes a culture of trust and customer obsession, making it a fitting environment for driven sales professionals.
Joblaze insights
- Listed about 2 months ago — first seen on Joblaze September 3, 2026. Last confirmed on Sierra's careers page November 10, 2026.
- This exact title is also open at 1 other location at Sierra: US - Remote.
- AI/ML appears in 20.8% of 559 comparable director sales/marketing roles in United States.
Quick facts
- Is the Enterprise Sales Director - Majors role remote?
- No — this is an on-site role in Canada - Remote.
- How much experience is required?
- 8–10 years of relevant experience for this Enterprise Sales Director - Majors role.
- Where is the role based?
- Sierra is hiring for this position in Canada - Remote.
- What's the tech stack?
- Joblaze extracted these technologies from the posting: AI/ML.
- What seniority level is this role?
- Sierra targets director candidates for this position.
- Is this full-time or contract?
- Full-time for this Enterprise Sales Director - Majors role at Sierra.
From the original posting
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.
Flexible (unlimited) paid time off
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Free alphorn lessons
Standard company text repeated across Sierra's postings is omitted here.
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