Enterprise Sales Director – Healthcare

About the role

Join Sierra’s fast‑growing Healthcare team as an Enterprise Sales Director. You will own the full sales cycle for large‑scale AI‑driven customer‑facing solutions, helping health plans, providers and diagnostics companies transform patient interactions.

Key responsibilities

• Identify and prospect enterprise healthcare customers through research, networking and cold outreach.
• Build and nurture relationships with key decision‑makers, serving as the primary point of contact.
• Lead complex negotiations, address objections and close multi‑million‑dollar deals.
• Develop and execute sales strategies, crafting tailored presentations and proposals.
• Collaborate with marketing, product, technical and operations teams to deliver the solution.
• Leverage AI tools across the sales cycle to automate low‑value tasks and improve efficiency.

Required profile

• 6–8 years of enterprise‑facing sales experience, consistently meeting $1M+ quotas.
• Proven track record of closing 6‑ and 7‑figure ACV deals.
• Exceptional verbal and written communication abilities.
• Analytical mindset with data‑driven decision making.
• Demonstrated success in prospecting and lead generation.
• Familiarity with the AI landscape and emerging industry trends (preferred).

What we offer

• Unlimited paid time off and flexible work arrangements.
• Medical, dental and vision coverage for employees and families.
• Life insurance, disability benefits and retirement plans (where applicable).
• Parental, fertility and family‑building benefits.
• Equity participation for eligible full‑time employees.
• Free lunch, snacks, coffee and discretionary benefit stipend.