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Sierra

Enterprise Sales Director

RemoteCanada only
Published
Role
Sales
Experience
Senior
Employment
Full-time
CAD 305k–CAD 330k/yr
Check eligibility

Open to CA only. Set where you work from to check your eligibility.

No BS summary

Enterprise sales director with 6–8 years closing large enterprise accounts, managing $1M+ quotas, and running complex 6- and 7-figure ACV deals. Must be based in Canada and able to prospect, negotiate, and use AI tools across the sales cycle.

What you'll do

  • Identify and target potential customers through research, networking, and cold calling.
  • Build new relationships with enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
  • Build and maintain strong relationships with key decision-makers and stakeholders with the largest customers.
  • Serve as the primary point of contact for customers and exceed their expectations.
  • Lead negotiations with existing and prospective customers, address objections, and close deals.
  • Navigate contracts and agreements quickly and effectively with legal and finance stakeholders.
  • Develop and execute sales strategies to meet or exceed sales targets.
  • Craft tailored sales presentations and proposals for enterprise customer needs.
  • Collaborate with marketing to implement effective sales campaigns and presentations.
  • Work with the broader GTM team, product, technical, and operations organizations to deliver the product.
  • Leverage AI tools across account research, personalized outreach, call summarization, pipeline forecasting, and deal execution.
  • Automate low-value sales tasks and reinvest time into high-value customer relationships.
  • Continuously adopt and experiment with new tools to work faster and smarter.

What they require

  • 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
  • Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
  • Exceptional verbal and written communication abilities.
  • Ability to analyze market trends, identify opportunities, and make data-driven decisions.
  • Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
  • Preferred: Familiarity with the AI landscape, key players, and emerging trends.

Benefits

  • 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, snacks, and coffee
  • Discretionary benefit stipend
  • Free alphorn lessons
  • Eligible full-time employees can participate in Sierra's equity plans
🇺🇸 United StatesFinancial ServicesMid-size

Details

Apply routeDom
CAD 305k–CAD 330k/yr