Enterprise Sales Director, Healthcare

About the role

You will own the end-to-end enterprise sales cycle for healthcare customers, driving new business and strategic expansion within some of the most regulated and complex buying environments in the industry. You will act as the primary external leader for a portfolio of the most critical healthcare accounts, aligning your efforts with the company's mission to build more human customer experiences using AI. You will leverage deep industry expertise to navigate multi-stakeholder buying committees and influence outcomes that shape the future of patient and member interactions. You will partner closely with internal teams to ensure every deal is executed with precision, compliance, and long-term strategic value. You will use data and insight to prioritize the highest impact opportunities and consistently exceed demanding revenue and pipeline targets. You will embody the culture of the organization by demonstrating the highest standards of trust, craftsmanship, and intensity in every interaction.

Key facts

What you'll do

Conduct in-depth research to identify and prioritize enterprise healthcare prospects, mapping stakeholder ecosystems and buying committees to inform targeted outreach strategies.

Lead complex, multi-threaded conversations with key decision-makers, establishing credibility as a trusted advisor while articulating the strategic value of AI-driven patient and member experiences.

Develop and own a strategic account plan for each major healthcare customer, aligning product capabilities with business outcomes, regulatory considerations, and operational realities.

Navigate multi-year, high-visibility contract negotiations, managing objections, trade-offs, and stakeholder alignment to close deals that balance speed with long-term partnership value.

Collaborate with legal, finance, and technical teams to design and execute solutions that meet the specific needs of large health plans, provider networks, and healthcare platforms.

Build and maintain executive-level relationships with C-suite leaders and operational stakeholders, ensuring they see Sierra as a strategic partner in transformation initiatives.

Leverage AI-native tools to streamline sales workflows, from account research and personalized outreach to pipeline forecasting and call analysis, increasing efficiency without sacrificing relationship depth.

Partner with marketing to develop compelling narratives, case studies, and proof points that resonate specifically with healthcare buyers and their unique decision criteria.

Collaborate cross-functionally with product and operations teams to surface customer feedback, prioritize features, and align on solutions that strengthen our industry position.

Analyze pipeline health, win/loss patterns, and market signals to refine strategies, adjust tactics, and consistently overachieve against revenue and quota objectives.

Champion the adoption of new sales technologies and methodologies, setting an example for peers by using data to drive decisions and outcomes.

Represent Sierra at key industry events, conferences, and customer forums, strengthening the brand's presence within the healthcare ecosystem.

Own the end-to-end sales process from initial discovery through contract signing and expansion, ensuring alignment with compliance standards and internal governance.

Educate stakeholders on the ethical and practical applications of AI in healthcare, reinforcing trust and transparency with patients, providers, and payers.

Requirements

Bring 6-8 years of enterprise customer-facing sales experience, with a proven ability to identify, engage, and close large accounts in complex environments.

Demonstrate a track record of managing $1M+ annual quotas and executing end-to-end deals with multi-figure annual contract values in regulated industries.

Show exceptional verbal and written communication skills, with the ability to synthesize technical concepts into clear, compelling narratives for executive audiences.

Apply an analytical mindset to interpret market trends, competitive dynamics, and customer data, making decisions that are firmly grounded in evidence.

Consistently prospect and generate new enterprise-level opportunities through research, networking, and disciplined cold outreach to senior stakeholders.

Operate effectively in ambiguous, fast-paced environments, balancing competing priorities while maintaining rigorous attention to detail and quality.

Exhibit strong judgment and integrity when navigating confidential, sensitive, and high-stakes conversations involving patient data and regulatory requirements.

Commit fully to Sierra's values of trust, customer obsession, craftsmanship, intensity, and family, ensuring your actions reinforce our culture every day.

Nice to have

Demonstrated familiarity with the AI landscape, including key players, emerging use cases, and the implications for healthcare delivery and operations.

Practical notes

This is a full-time role based in Canada with remote work arrangements.

Eligibility: You must be legally authorized to work in Canada without sponsorship.

Hiring process timeline: We move quickly, so if you are interested and qualified, please apply as soon as possible.