Enterprise Sales Director, Financial Services

Posted 2 weeks ago

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About the role

  • Enterprise Sales Director growing Sierra’s AI customer-experience platform among Canadian banks, insurers, and financial-services firms. Managing complex enterprise deals, strategic relationships, negotiations, and AI-enabled sales execution.

Responsibilities

  • 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 relationships with key decision-makers and stakeholders at the largest customers
  • Serve as the primary point of contact and exceed customer expectations
  • Lead negotiations, address objections, and close complex deals
  • Navigate contracts and agreements with legal and finance stakeholders
  • Develop and execute sales strategies to meet or exceed targets
  • Create tailored sales presentations and proposals
  • Collaborate with marketing on sales campaigns and presentations
  • Work with the broader GTM team and product, technical, and operations organizations
  • Leverage AI tools across account research, outreach, call summarization, forecasting, and deal execution

Requirements

  • 6–8 years of experience in an enterprise customer-facing sales role
  • Experience managing a $1M+ quota
  • Experience 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 identifying and targeting enterprise clients through research, networking, and cold calling
  • Familiarity with the AI landscape, key players, and emerging trends is an advantage

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, as well as delicious snacks and coffee
  • Discretionary benefit stipend
  • Free alphorn lessons
  • Eligible full-time employees can participate in Sierra's equity plans
  • Offers commission

Job type

Full Time

Experience level

Lead

Salary

CA$305,000 - CA$370,000 per year

Degree requirement

No Education Requirement

Location requirements

RemoteCanada

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