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Added 1 day ago
GL
Senior Mortgage Underwriter
Gold Lion Mortgages Inc
Calgary, AB
- Full-time
Package submissions through Canadian origination systems (e.g., Finmo, Velocity, Filogix Expert) with clear, persuasive notes highlighting deal strengths, risks, and mitigants.
Added 2 days ago
BC
Team Lead, Marketing Digital Platforms
BBA Consultants
Mont-Saint-Hilaire, QC · Mont-St-Hilaire, QC
- Full-time
You'll be the platforms expert on the team, making sure they perform, deliver a quality experience and carry accurate information at all times. Digital is moving fast, and we'll be counting…
Added 2 days ago
FI
Database Administrator
Flexstaf I.T. Inc.
Toronto, ON
- Contract
Microsoft Certified: Azure Solutions Architect Expert (AZ-305)
Added 2 days ago
M
RQ00834 - Database Administrator - Intermediate
Maarut
Toronto, ON
- Contract
Microsoft Certified: Azure Solutions Architect Expert (AZ-305)
Added 2 days ago
Senior Lending Advisor - Scotia Plaza, Toronto, ON
Scotiabank
Toronto, ON
As a Senior Lending Advisor, you’ll help clients achieve their homeownership goals by delivering expert mortgage advice, strengthening relationships, and driving lending growth.
Added 2 days ago
RT
Senior Database Administrator
Russell Tobin
Toronto, ON
- $55 to $60 CAD / hour
- Contract
Microsoft Certified: Azure Solutions Architect Expert (AZ-305)
Added 2 days ago
S
Senior Database Administrator
StafinGo
Toronto, ON · Greater Toronto Area, Canada
- $55 to $70 CAD / hour
- Contract
Stafingo Is Hiring | Senior Database Administrator – SQL Server, Azure, Microsoft Dynamics GP & Salesforce in GTA-Fully Onsite
Added 2 days ago
C
Vice President, Sales & Marketing
CYBERWELL
ON · Ontario, Canada
- Full-time
…backed by WELL Health Technologies. We have deliberately united expert capabilities across proactive defense, offensive security, governance and risk, and technology solutions to support…
Added 2 days ago
B
Database Administrator- Dynamics GP
Bevertec
Toronto, ON
- Contract
Microsoft Certified: Azure Solutions Architect Expert
Added 2 days ago
S
Head of Data Systems (Google Stack)
Stacktics
Toronto, ON
- Full-time
Act as Stacktics' primary Data Systems expert, ensuring to maintain and continuously grow personal expertise, and sharing information with other Stacktics team members, client stakeholders…
Added 3 days ago
CC
Analyst, Insights and Pipeline Management
Canadian Cancer Society
Prince George, BC
- $52,000 to $59,000 CAD / year
- Full-time
Serve as the Salesforce subject‑matter expert for the Corporate Giving team, including managing updates, creating and editing reports, supporting process changes, and building campaigns.
Added 3 days ago
H
Expert Acceleration & Operations Manager
Haleon
Mississauga, ON
- Full-time
Lead the performance and operational capabilities across our Expert organization. Help to create simplified solutions enabling our sales teams (virtual & field) to maximize their…
Added 3 days ago
FR
Operations Coordinator - Client Service Administration and Process Support - Toronto
Fitch Ratings
Toronto, ON
- $45,000 to $55,000 CAD / year
- Full-time
…unrivaled breadth and depth, the company delivers learning solutions for apprentices, graduates, and those with 10+ years’ experience in Financial Services. Our offerings include expert…
Added 3 days ago
S
Enterprise Sales Engineer, Financial Services
Sierra
Toronto, ON
- $270,000 to $280,000 CAD / year
- Full-time
…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…
Added 3 days ago
S
High Growth Enterprise Sales Engineer
Sierra
Toronto, ON
- $210,000 to $220,000 CAD / year
- Full-time
…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…
Added 3 days ago
S
Enterprise Sales Engineer, Consumer Business Services
Sierra
Toronto, ON
- $270,000 to $280,000 CAD / year
- Full-time
…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…
Added 3 days ago
S
Enterprise Sales Engineer - Strategic, Retail
Sierra
Toronto, ON
- $355,000 to $365,000 CAD / year
- Full-time
…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…
Added 3 days ago
S
Enterprise Sales Engineer - Strategic, Healthcare
Sierra
Toronto, ON
- $355,000 to $365,000 CAD / year
- Full-time
…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…
Added 3 days ago
S
Enterprise Sales Engineer - Strategic, Financial Services
Sierra
Toronto, ON
- $355,000 to $365,000 CAD / year
- Full-time
…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…
Added 3 days ago
S
Enterprise Sales Engineer - Majors, Retail
Sierra
Toronto, ON
- $325,000 to $335,000 CAD / year
- Full-time
…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…
Added 3 days ago
S
Enterprise Sales Engineer - Strategic, Consumer Business Services
Sierra
Toronto, ON
- $355,000 to $365,000 CAD / year
- Full-time
…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…
Added 3 days ago
S
Enterprise Sales Engineer - Strategic
Sierra
Toronto, ON
- $355,000 to $365,000 CAD / year
- Full-time
…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…
Added 3 days ago
S
Enterprise Sales Engineer - Majors, Consumer Business Services
Sierra
Toronto, ON
- $325,000 to $335,000 CAD / year
- Full-time
…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…
Added 3 days ago
S
Enterprise Sales Engineer - Majors
Sierra
Toronto, ON
- $325,000 to $335,000 CAD / year
- Full-time
…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…
Added 3 days ago
S
Enterprise Sales Engineer
Sierra
Toronto, ON
- $260,000 to $270,000 CAD / year
- Full-time
…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…

Sierra

Enterprise Sales Engineer - Majors

Toronto, ON, Canada

$325,000 to $335,000 CAD / year · Full-time

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Job details

Pay: $325,000 to $335,000 CAD / year
Job type: Full-time
Experience: 4-6+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales
Posting language: English
Posted: Oct 23, 2026

Original job description

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.

What you'll do

Be the primary partner to your Sales counterparts helping to win deals and grow customers
Go from first discovery to a tailored, working agent in days, not weeks, across prospects and existing customers
Work with every team involved in the decision: CX, IT, security, procurement, and executive sponsors
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
Mentor newer SEs and contribute reusable assets for your industry or team
Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases
Go deep on your industry, the patterns, and winning motions to scale your work

What you'll bring

4-6+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales
Experience in leading the sales process with large Enterprise customers with deal sizes ranging $500-$1M
Past experience in demo building, and presenting, and working with customers or clients in the GTM function
Experience in relationship-building with prospects, including executives and technical leaders
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
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
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

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.

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More about this job

Responsibilities

You will act as the primary technical partner to sales counterparts to scope use cases, design demos, and lead technical reviews for enterprise prospects. Additionally, you will manage the end-to-end pre-sales process and support accounts through launch and expansion.

Requirements

Candidates must have 4-6+ years of experience in Sales or Solutions Engineering with a track record of managing large enterprise deals. A bachelor's degree is required, along with strong skills in technical presentation and the ability to translate complex business problems into AI-driven solutions.

Skills

Sales Engineering
Solutions Engineering
Technical Sales
Enterprise Sales
Demo Building
Technical Architecture
Relationship Building
AI Tools
Solution Design
Technical Proposals
Account Management
Customer Discovery
Business Value Articulation
Product Requirements
Technical Logic

Benefits

Flexible unlimited paid time off
Medical benefits
Dental benefits
Vision benefits
Life insurance
Disability benefits
Retirement plan
Parental leave
Fertility and family building benefits
Lunch
Snacks and coffee
Discretionary benefit stipend
Alphorn lessons
Equity plans

Visa sponsorship

Not detected in the job text

Keywords

AI Agents
Enterprise Sales
Sales Engineering
Solutions Engineering
GTM
Customer Success
IT
Security
Procurement
Architecture Review
Technical Expert
Agent Development
Computer Science
Product Requirements
Engineering Requirements
Technical AI Product
SaaS
Discovery
Prototyping
Account Expansion

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