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Enterprise Sales Director, Financial Services

SierraCanada - RemoteSales
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Salary
$325K - $370K CAD
Job type
Full-time
Work mode
Remote
Posted
5 Aug 2026
Status
Open · checked 7d ago

About this role

This remote Enterprise Sales Director position at Sierra focuses on driving growth and shaping AI strategies for top financial services institutions across Canada. The role suits an experienced sales professional with a background in managing complex enterprise accounts and closing high-value deals.

Role Overview

Sierra is seeking an Enterprise Sales Director to join its Financial Services team on a remote basis in Canada. The position involves partnering with major banks, neobanks, insurers, and financial ecosystems to help them implement customer-facing AI agents. The decisions made in this role impact millions of end customers and substantial economic activity, transforming how financial institutions interact with their clients during critical moments.

Key Responsibilities

Prospect and generate leads by targeting potential clients through networking, research, and cold calling to expand enterprise relationships.
Manage and maintain strong connections with key decision-makers and stakeholders at major client organizations.
Lead negotiations for complex deal cycles, navigating contracts and agreements alongside legal and finance teams.
Formulate and execute sales sales strategies to achieve or exceed targets, crafting tailored presentations with the marketing team.
Collaborate cross-functional with GTM, product, technical, and operations groups to deliver industry-leading solutions.
Act as an AI-native seller by utilizing automated tools across the sales cycle for research, forecasting, outreach, and deal execution.

Requirements

Possess 6 to 8 years of professional experience in an enterprise customer-facing sales role focused on identifying and closing large accounts.
Bring proven enterprise experience managing a $1 million plus quota while running complex 6- and 7-figure ACV deals.
Demonstrate exceptional verbal and written communication abilities.
Exhibit an analytical mindset capable of assessing market trends, recognizing opportunities, and making data-informed choices.
Display a documented history of prospecting and lead generation targeting enterprise clients.

Nice to Have

Familiarity with the artificial intelligence landscape, key players in the industry, and emerging market trends.

Skills and Tools

Enterprise account management and quota ownership
Contract negotiation and deal cycle execution
Lead generation, prospecting, and cold calling
Market analysis and data-driven planning
AI-native sales tools for outreach, research, pipeline forecasting, and call summarization

Salary and Benefits

Annual salary ranging from $325,000 to $370,000 CAD
Flexible, unlimited paid time off policies
Comprehensive medical, dental, and vision coverage for employees and their families
Life insurance and disability coverage
Country-dependent retirement plans and eligible equity plan participation
Parental leave alongside fertility and family building benefits via Carrot
Discretionary benefit stipend and complimentary alphorn lessons

About the Company

Sierra creates leading platforms for customer-facing artificial intelligence agents, partnering with major global brands to transform customer service and business growth. Co-founded by industry veterans Bret Taylor and Clay Bavor, the company operates on core values centered around trust, customer obsession, craftsmanship, intensity, and family support.

How to Apply

Interested candidates should visit the official Sierra careers page to submit an application and learn more about open opportunities.

Questions candidates ask

What is the salary range for this remote role in Canada?

The annual salary for the Enterprise Sales Director, Financial Services position is between $325,000 and $370,000 CAD.

How many years of experience are required?

Candidates must have 6 to 8 years of experience in an enterprise customer-facing sales role identifying and closing large accounts.

Is this position remote?

Yes, this role is designated as Canada - Remote.

What specific industry does this sales team focus on?

The team focuses exclusively on financial services customers, including systemically important banks, neobanks, insurers, and vertically integrated ecosystems.

What kind of benefits are provided to full-time employees?

Benefits include flexible paid time off, medical, dental, vision, life and disability insurance, retirement plans, parental leave, Carrot family-building benefits, a discretionary stipend, and free alphorn lessons.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site