At a Glance
- Tasks: Drive enterprise sales in healthcare, building relationships and closing high-value deals.
- Company: Join Sierra, a leading AI platform transforming customer experiences.
- Benefits: Enjoy flexible time off, health benefits, and a supportive work culture.
- Other info: Diverse and inclusive workplace that values your unique experiences.
- Why this job: Make a real impact in healthcare by leveraging AI for better patient experiences.
- Qualifications: 6-8 years in enterprise sales with strong communication and analytical skills.
The predicted salary is between 110700 - 135300 $ per year.
About us
At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such as SoftBank, Uber, Rivian, CLEAR, and Sutter Health. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family.
About the Healthcare team
Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
What you'll do
- Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
- Manage relationships: Build and maintain strong relationships with key decision‑makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
- Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
- Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers' needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
- Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry‑leading product.
- Operate as an AI-native seller: Leverage AI tools across the full sales cycle to automate low-value tasks and reinvest that time into high-value customer relationships.
What you'll bring
- 6-8 years of experience in an enterprise customer‑facing sales role, identifying and closing large accounts.
- Enterprise experience: Experience managing a $1M+ quota and running end‑to‑end complex 6- and 7‑figure ACV deals.
- Strong communication skills: Exceptional verbal and written communication abilities.
- Analytical mindset: Ability to analyze market trends, identify opportunities, and make data‑driven decisions.
- Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
- Even better... Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Our values
- Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness.
- Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes.
- Craftsmanship: We get the details right, from the words on the page to the system architecture.
- Intensity: We know we don’t have the luxury of patience. We play to win.
- Family: We know that balance and intensity are compatible, and we model it in our actions and processes.
What we offer
- 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 to keep you energized
- Discretionary benefit stipend giving people the ability to spend where it matters most
- Free alphorn lessons
Be you, with us
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We encourage you to apply even if your experience doesn't precisely match the job description.
Enterprise Sales Director, Healthcare in Winnipeg employer: Sierra
Sierra is an exceptional employer that fosters a vibrant work culture rooted in trust, customer obsession, and craftsmanship. Located in the heart of San Francisco, we offer flexible paid time off, comprehensive health benefits, and unique perks like free alphorn lessons, all while supporting employee growth through collaboration and innovation in the rapidly evolving AI landscape. Join us to be part of a team that values balance and intensity, ensuring that your professional journey is both rewarding and fulfilling.
