← All roles

Enterprise Sales Director - Majors, Healthcare

Sierra· Sales
Apply on company site
Remote$315k - $355kFull-timePosted 3mo ago

About the role

Senior enterprise sales leader responsible for driving 6- and 7-figure deals in the healthcare space, managing complex end-to-end cycles, and engaging C-suite stakeholders for Sierra’s AI-powered customer-facing solutions.

Responsibilities

  • Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
  • Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.
  • Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
  • Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.
  • Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
  • Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
  • Operate as an AI-native seller: Leverage AI tools across the full sales cycle to automate low-value tasks and reinvest time into high-value customer relationships, while continuously adopting and experimenting with new tools

Qualifications

  • 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.
  • Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
  • Proven ability to multi-thread and build trusted relationships across customer C-suites.
  • Exceptional verbal and written communication.
  • Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.

Skills

Required:Enterprise salesC-suite engagement

Benefits

  • Flexible (unlimited) paid time off
  • Medical, dental, and vision benefits for you and your family
  • Life insurance and disability benefits
  • Retirement plan dependent on country of employment
  • Parental leave
  • Fertility and family building benefits through Carrot
  • Lunch, as well as delicious snacks and coffee
  • Discretionary benefit stipend
  • Free alphorn lessons
Last updated Sep 30, 2026. Interested? Apply on the company site.
Sierra logo

About Sierra

Better customer experiences. Built on Sierra.

Sierra helps businesses build better, more human customer experiences with AI.

AICustomer ExperienceCustomer SupportVoiceai-agents-and-applicationsorchestrationvoice-ai-stackwing-list-2026
Company profileWebsite

More open roles at Sierra