# Enterprise Sales Engineer - Strategic, Healthcare at Sierra > Onsite · Canada · Unspecified · Software engineering · open. Source: https://alderhq.app/jobs/ashby%3ASierra%3Af56d33c3-897f-4a1c-85a4-6912889d00a3 (read 2026-11-05). ## Facts (observed) - Company: [Sierra](https://alderhq.app/companies/sierra) - Location text: Toronto - Where it can be done from (inferred): Onsite · Canada (evidence: "Location: Toronto") - Posted: 2026-10-23 (13 days ago) - First seen by alder: 2026-11-02 · last verified: 2026-11-04 - Reposted: 0 times · edited: 0 times - Apply on the employer's site: https://jobs.ashbyhq.com/Sierra/f56d33c3-897f-4a1c-85a4-6912889d00a3 ## Pay and sponsorship - Posted pay: CAD 355k–CAD 365k per year (from the listing's pay field) - Market band for similar posted roles (Toronto, n 62): p25 CAD 115k, median CAD 135k, p75 CAD 213k ## Description (the employer's text) ### 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 and Clay Bavor. 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 Go deep on a few accounts. Learn each customer's business well enough that you could be wearing their badge in their hallways Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle Decide when to bring in Agent Development, Product, Security, Legal, and Sierra leaders, and what each of them needs to do. You keep everyone aimed at the same goal Raise the bar for the SE team: mentor others, set standards for demos and pilots, and write the playbooks for Strategic deals and GTM processes Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases Share what you see across your largest accounts with Product leadership and inform roadmap ### What you'll bring 7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales Experience in leading the sales process with Strategic customers with deal sizes of $1M+ consistently Past experience in demo building, and presenting, and working with customers or clients in the GTM function Strong experience in relationship-building with prospect stakeholders, including C-suite executives and technical leaders Experience leading architecture, integration, and security discussions with enterprise architects, engineering leaders, and security teams Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it Experience growing accounts past initial sale and defining customer roadmaps to facilitate growth Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience --- Data: alder (https://alderhq.app). Cite https://alderhq.app/jobs/ashby%3ASierra%3Af56d33c3-897f-4a1c-85a4-6912889d00a3 and the date you read it. Observed facts come from the employer's own listing; location reach, level, family and skills are inferences.