Enterprise Sales Director - Strategic

Sierra
Canada, Toronto
Workplace: RemoteFull timeCAD 375,000 - 430,000 annuallyFunction: SalesExperience: 10+ yearsSkills: ["Precision","Trust","Executive communication","Risk navigation","Customer obsession"]

Own Sierra’s largest, most complex enterprise deals, architecting multi-BU, multi-geo deal structures while navigating risk and pricing with precision. Build trusted relationships across customer leadership and working teams, and confidently engage at the founder level. Use AI across the full sales cycle—account research, personalized outreach, call summaries, and forecasting—to automate low-value tasks and focus on high-impact customer relationships.

Loading

Loading job details...

Preparing the role view and application actions.

FursaFursa
Sierra
Sierra
6 days ago

Enterprise Sales Director - Strategic

✓ Verified Job

Canonical indexed version, validated from employer's careers page.

Source: Company careers pageValidated by: Fursa AI
Last checked: 4 hours agoStatus: Live

Job Summary

Own Sierra’s largest, most complex enterprise deals, architecting multi-BU, multi-geo deal structures while navigating risk and pricing with precision. Build trusted relationships across customer leadership and working teams, and confidently engage at the founder level. Use AI across the full sales cycle—account research, personalized outreach, call summaries, and forecasting—to automate low-value tasks and focus on high-impact customer relationships.
Location: Canada, Toronto
Workplace: Remote
Employment Type: Full time
Job Function: Sales
Seniority: Director level

Key Responsibilities

  • •Architect Sierra’s most complex enterprise deals, leading multi-BU, multi-geo opportunities with sophisticated deal structures and risk management.
  • •Operate as a trusted partner to customer teams and the customer C-suite.
  • •Engage regularly with Sierra’s co-founders and pitch with co-founder-like conviction in front of strategic customers.
  • •Shape account strategy and set the standard for the broader sales org.
  • •Use AI tools across the sales cycle (research, outreach, call summarization, forecasting) to automate low-value work and accelerate high-value relationship building.

Pay and Benefits

Salary: CAD 375,000 - 430,000 annually
Perks:Paid LeaveHealth InsuranceDentalVisionLife InsuranceDisabilityParental LeaveRetirementFertility Benefits

Key Requirements

  • •10-12+ years of enterprise/strategic sales experience owning the largest and most complex accounts.
  • •Proven success closing multi-million-dollar, multi-stakeholder deals across business units and geographies.
  • •Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
  • •Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.
  • •Strong deal structuring, risk navigation, and pricing expertise, paired with exceptional executive communication.
Experience:10+ yearsEnterprise salesStrategic salesAI
Skills:PrecisionTrustExecutive communicationRisk navigationCustomer obsession
Tech Stack:AI

Company Brief

Sierra
Develops advanced AI agents and tools focused on building autonomous, generalist machine learning systems to assist developers and enterprises in automating complex workflows, decision-making, and application-level tasks.
Industry: AI & Machine Learning
Website