Jobs

Enterprise Sales Engineer - Strategic, Financial Services

Sierra

Apply on Ashby
Location
Toronto, Ontario, Canada
Track
AI Sales / GTM
Salary
$355K–$365K / yr
Posted
October 23, 2026
Source
Ashby

Job description

About us

About the Financial Services team

  • Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.
  • Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.
  • Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and 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

Even better...

  • Experience translating code, technical logic and user requirements to product and engineering requirements
  • Selling a technical AI product

Similar roles

Get roles like this in your inbox

New agentic AI jobs, curated every Thursday. No spam.

Apply on Ashby