Enterprise Sales Director

About the role

You will architect Sierra's most complex deals, leading the largest multi-business unit and multi-geography opportunities with precision and conviction. You will operate as part of the customer's team, holding trusted relationships across their C-suite and working teams while engaging at the founder level. In these interactions, you will be trusted to regularly engage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise. You will bring exacting craft to messaging, positioning, and timing across every interaction, shaping strategy for Sierra's most important accounts and setting the standard for the broader sales organization. As an AI-native seller, you will leverage AI tools across the full sales cycle, including 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.

Key facts

What you'll do

• Architect Sierra's most complex deals, designing sophisticated deal structures and managing risk with precision and conviction for our largest multi-BU, multi-geo opportunities.
• Operate as part of the customer's team, holding trusted relationships across the customer C-suite and working teams to drive outcomes and alignment.
• Engage at the founder level, regularly managing Sierra's co-founders in front of customers and pitching with co-founder-like conviction and expertise.
• Bring precision to everything, operating with exacting craft in messaging, positioning, and timing across every customer interaction.
• Shape strategy, influencing how Sierra approaches its most important accounts and setting the standard for the broader sales organization.
• Operate as an AI-native seller, leveraging AI tools across the full sales cycle for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution.
• Automate low-value tasks to reinvest time into high-value customer relationships, continuously adopting and experimenting with new tools to work faster and smarter.
• Build and refine GTM motions, including building sales teams and sales motions from scratch or from early stage growth where needed.
• Own and exceed a $1M+ quota, running end-to-end complex 6- and 7-figure ACV deals across multiple stakeholders and business units.
• Establish deep, sustained C-suite relationships, demonstrating gravitas to be treated as a peer by executive buyers and steering complex consensus processes.
• Master complex deal structuring, risk navigation, and pricing to protect Sierra's interests while driving mutually beneficial outcomes.
• Communicate with exceptional executive presence, maintaining a reputation for precision, trust, and reliability in every engagement.

Requirements

• 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts in a high-touch, consultative environment.
• Demonstrated success closing multi-million-dollar, multi-stakeholder deals that span business units and geographies with clear, documented outcomes.
• Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals from inception to close and expansion.
• Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers in enterprise environments.
• Mastery of complex deal structuring, risk navigation, pricing, and contract negotiation across multiple jurisdictions and business units.
• Exceptional executive communication skills, with a reputation for precision, trust, and consistency in fast-paced, ambiguous situations.
• Proven ability to operate independently with high ownership, judgment, and integrity while managing multiple concurrent complex deals.
• Comfort working alongside founders and executive leadership teams, influencing decisions at the highest level with clarity and conviction.

Nice to have

• Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike, translating complex concepts into clear business outcomes.
• Experience operating alongside founders/executives in front of strategic customers, including managing executive-level conversations and expectations.
• Experience building GTM strategies from scratch or from early stage growth, including building sales teams, playbooks, and sales motions that scale.

Practical notes

This role is full-time and remote based in Canada.