39 of 3,156 remote jobs

Featured, then newest · Page 1 of 2

Filters

Enterprise Sales Director - Majors, Healthcare

Sierra

Canada

today

Strategic Finance, Ads

OpenAI

Hybrid — San Francisco · New York City

today

Senior Lead, AI Pricing & Margin Strategy

Squarespace

Hybrid — New York City · New York

today

Senior Product Manager, Domains

Squarespace

New York City · New York

today

General Manager, SMB - US-Based

Toptal

United States

today

General Manager, Industrial Products and Services

Toptal

Canada

today

General Manager, Industrial Products & Services - US Based

Toptal

Anywhere

today

Senior AI Solution Sales Executive

Instacart

United States · United States

today

Director, Product Management - Cloud Security and Shared Capabilities

Datadog

Hybrid — Paris, France · Paris

today

Strategic Account Executive - Israel

Datadog

Israel, · Israel · Tel Aviv

today

Major Account Manager

Datadog

Hybrid — Boston, Massachusetts, USA; New York, New York, USA · Boston · New York · Florida · North Carolina · Rhode Island

today

Strategic Account Executive (Higher Education)

Datadog

Hybrid — Melbourne, Australia; Sydney, Australia · Sydney

today

Regional Director - Enterprise Sales

Datadog

Hybrid — Osaka, Japan · Japan

today

Strategic Account Executive

Datadog

Hybrid — Sao Paulo, Brazil · Brazil · Sao Paulo

today

Strategic Account Executive

Datadog

Hybrid — Boston, Massachusetts, USA · Boston

today

Director of Pricing & Monetization

PagerDuty

Hybrid — San Francisco

today

Strategic Finance, GTM

Descript

San Francisco, CA or Remote, US · San Francisco

today

Lead Product Manager, Pricing Lifecycle

Orb

Hybrid — HQ-San Francisco

today

Implementation Architect- San Francisco HQ

Orb

Hybrid — HQ-San Francisco

today

Deal Desk Manager, AMER

Cockroach Labs

Hybrid — New York, NY

today

General Manager & Director, GTM Strategy

Justworks

Hybrid — New York, New York · New York, NY

today

Senior Product Manager, Verifications

Checkr

Hybrid — Denver, Colorado, United States; San Francisco, California, United States · Denver · San Francisco

today

Director of Ad Sales - West

Duolingo

California

today

Show more · 14 left

Enterprise Sales Director - Majors, Healthcare

Sierra

CanadaListed todayPosted by the employer Jul 16, 2026Listing ends Dec 28, 2026

Compensation: CA$370k–CA$395k
Location: Canada
Fully remoteMore jobs: Canada
Employment: Full-time
Category: Sales

Role skills

forecasting ai deal strategy research pricing enterprise sales

Apply on jobs.ashbyhq.comExternal application — you finish on the employer's site.

Tailor my résumé Apply now

About the job

5 min read7 sections

ABOUT US

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. 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 a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.

Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.

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.
Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
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

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- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.

WHAT YOU'LL BRING

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.

EVEN BETTER...

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. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.

WHAT WE OFFER

We want our benefits to reflect our values and offer the following to full-time employees:

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

These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.

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 believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Role signals

Benefits: , , , , , , , , ,

About Sierra

Sierra helps companies deliver personalized customer experiences across various channels. The company's platform enables businesses to build and optimize AI age…Based on an AI summary from sierra.ai