AI-Native Enterprise Sales Director

Sierra; Toronto; On-site; CAD 180,000 - 320,000; Full time

Benefits offered by this job

Flexible time off (unlimited)

Medical, dental, vision benefits

Life insurance and disability benefits

Retirement plan (country dependent)

Parental leave

Fertility and family building benefits

Lunch and snacks

Discretionary benefit stipend

Free alphorn lessons

Job summary

Sierra is seeking a Senior Enterprise Sales leader in Toronto to own the largest, most complex accounts. You will architect multi-BU, multi-geo deals and manage relationships at the C-suite level, including engaging founders in strategic discussions.

You will drive end-to-end 6- to 7-figure ACV deals, navigate complex pricing and risk, and leverage AI tools to accelerate the sales cycle while delivering trusted, precise outcomes.

Qualifications

• 10-12+ years of enterprise/strategic sales experience.
• Proven success closing multi-million-dollar, multi-stakeholder deals across geographies.
• Experience managing a $1M+ quota and end-to-end 6- to 7-figure ACV deals.
• Deep, sustained C-suite relationships and ability to engage as a peer with executives.
• Mastery of complex deal structuring, risk navigation, and pricing.
• Exceptional executive communication and trusted, precise collaboration.

Responsibilities

• Architect Sierra's most complex deals across multiple BU and geographies.
• Operate as part of the customer's team with trusted relationships at C-suite level.
• Engage founders level and co-founders in front of customers with conviction.
• Bring precision to messaging, positioning, and timing across interactions.
• Shape strategy and set the standard for the broader sales org.
• Operate as an AI-native seller, leveraging AI tools across the full sales cycle.

Skills

Enterprise sales

Multi-million deals

Quota management

C-suite relationships

Deal structuring

Executive communication

Job description

Sierra is seeking a Senior Enterprise Sales leader in Toronto to own the largest, most complex accounts. You will architect multi-BU, multi-geo deals and manage relationships at the C-suite level, including engaging founders in strategic discussions.

You will drive end-to-end 6- to 7-figure ACV deals, navigate complex pricing and risk, and leverage AI tools to accelerate the sales cycle while delivering trusted, precise outcomes.