Enterprise Sales Director

About the role

You will architect and own Sierra's most complex, multi-billion dollar enterprise opportunities across a portfolio of business units and global regions. You will operate as a trusted extension of the customer's C-suite, holding executive-level relationships with peer gravitas and conviction. You will engage at the founder level, regularly interacting with Sierra's co-founders and bringing founder-like credibility into every strategic conversation. You will bring surgical precision to messaging, positioning, and timing, ensuring every interaction reflects the highest standard of craftsmanship. You will shape the strategic direction of key accounts, setting playbooks and standards that influence the broader sales organization. You will leverage AI-native tools to automate low-value tasks, using insights from data and call intelligence to deepen relationships and execute complex deals. You will navigate intricate risk, pricing, and structuring challenges with clarity and confidence, driving outcomes that align with both customer and Sierra objectives. You will partner closely with healthcare customers to transform the patient experience through AI, making care more accessible, human, and affordable.

Key facts

What you'll do

Architect Sierra's largest and most complex multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision.

Operate as a trusted member of the customer's team, holding C-suite and working-level relationships with executive presence and accountability.

Engage at the founder level, regularly interacting with Sierra's co-founders and pitching with their conviction and expertise in front of strategic customers.

Bring exacting craft to messaging, positioning, and timing, ensuring precision across every customer interaction and deliverable.

Shape strategy for Sierra's most important accounts, defining standards and playbooks that influence the broader sales organization.

Leverage AI-native tools across the full sales cycle, including 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 new tools to work faster and smarter than traditional methods.

Operate with the intensity and ownership required to move complex healthcare deals forward, aligning with the mission of transforming patient care through AI.

Build and maintain deep, sustained C-suite relationships in the healthcare sector, earning trust and enabling outcomes that make care more accessible and affordable.

Serve as a go-to strategic advisor for healthcare customers, using domain expertise and executive communication to solve high-stakes problems.

Requirements

Bring 10-12+ years of enterprise or strategic sales experience, owning the largest and most complex accounts in competitive environments.

Demonstrate a track record of closing multi-million-dollar, multi-stakeholder deals that span business units and geographies with measurable impact.

Manage a $1M+ quota and run end-to-end complex 6- and 7-figure ACV deals from discovery through execution and expansion.

Maintain deep, sustained C-suite relationships and exhibit the gravitas necessary to be treated as a peer by executive buyers in healthcare and technology.

Master complex deal structuring, risk navigation, pricing, and contracting nuances across multiple jurisdictions and business units.

Exhibit exceptional executive communication skills, with a reputation for precision, clarity, and trust in fast-paced, high-stakes settings.

Operate effectively in a matrixed environment, aligning cross-functional teams including product, legal, finance, and implementation to close large deals.

Show comfort with AI-native workflows and a commitment to using data and intelligence to refine sales behaviors and outcomes over time.

Nice to have

Deep familiarity with the AI landscape and the ability to speak credibly to both technical and business stakeholders with clarity and insight.

Experience operating alongside founders and executives in front of strategic customers, with a history of co-sell and partnership success.

Practical notes

This is a full-time role.

The role is remote-based from Canada.

Travel may be required as part of customer and prospect engagement.

Visas may be required for certain candidates depending on location and work authorization status.

Candidates must be able to start within a reasonable timeframe as defined by hiring timelines.

This role reports to the Enterprise Sales leadership and works closely with the healthcare go-to-market team.