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Enterprise Sales Director, Financial Services

SierraUS - RemoteSales
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Salary
$280K - $300K USD
Job type
Full-time
Work mode
Remote
Posted
5 Aug 2026
Status
Open · checked 7d ago

About this role

The Enterprise Sales Director, Financial Services role at Sierra is a remote position based in the US, designed for seasoned sales professionals who excel at managing complex 6- and 7-figure accounts. This opportunity suits candidates with a strong background in enterprise software sales who want to drive adoption of conversational AI platforms among major financial institutions.

Role Overview

Sierra is looking for an Enterprise Sales Director to join the Financial Services team on a full-time remote basis. In this position, the individual will lead end-to-end sales cycles, cultivate relationships with key decision-makers at prominent banks and insurers, and act as an AI-native seller to automate routine tasks while focusing on high-value client connections.

Key Responsibilities

Identify and target potential enterprise clients through proactive research, professional networking, and cold calling.
Drive revenue growth, expand the sales pipeline, and secure deployment capacity across major accounts.
Build and maintain trusted relationships with high-level stakeholders, acting as the primary point of contact.
Lead negotiations for complex deal cycles, resolving objections and navigating contracts swiftly alongside legal and finance teams.
Formulate and execute strategic sales plans, craft tailored proposals, and collaborate with marketing on campaigns.
Partner cross-functionally with product, technical, operations, and go-to-market teams to deliver top-tier solutions.
Utilize modern AI tools throughout the sales cycle for account research, personalized outreach, call summarization, and pipeline forecasting.

Requirements

Possess 6 to 8 years of professional experience in an enterprise customer-facing sales role, successfully identifying and closing large accounts.
Bring hands-on enterprise experience managing quotas of $1M+ and running complex end-to-end sales agreements.
Demonstrate exceptional verbal and written communication skills.
Apply an analytical mindset to evaluate market trends, spot new opportunities, and make data-driven choices.
Display a documented history of prospecting and lead generation success with enterprise organizations.

Nice to Have

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

Skills and Tools

Enterprise sales strategy and execution
Complex contract negotiation and closing
Lead generation and prospecting
Cross-functional collaboration
AI-native sales tools for forecasting and research
Market analysis and data-driven decision making

Salary and Benefits

Annual salary range between $280,000 and $300,000 USD
Flexible, unlimited paid time off policies
Comprehensive medical, dental, and vision coverage for employees and families
Life insurance and disability coverage
Retirement plan options based on employment location
Parental leave alongside fertility and family-building support through Carrot
Discretionary benefit stipends and complimentary alphorn lessons
Participation in company equity plans for eligible full-time staff

About the Company

Sierra operates as a leading platform for customer-facing artificial intelligence agents, partnering with globally recognized brands to revolutionize customer service and business growth. Co-founded by industry veterans Bret Taylor and Clay Bavor, the organization is anchored by core cultural pillars centered on trust, customer obsession, craftsmanship, intensity, and family balance.

How to Apply

Interested applicants should visit the official Sierra careers page to submit their application for the Enterprise Sales Director, Financial Services position.

Questions candidates ask

Is this job remote?

Yes, this position is fully remote within the United States.

What is the salary range for this role?

The annual salary is between $280,000 and $300,000 USD.

How many years of experience are required?

Candidates must have 6 to 8 years of experience in an enterprise customer-facing sales role.

What department does this role belong to?

This position is part of the Sales department, specifically focusing on the Financial Services team.

What benefits are offered?

Full-time employees receive flexible paid time off, medical, dental, vision, life and disability insurance, parental leave, fertility benefits through Carrot, equity plan participation, retirement plans, discretionary stipends, and alphorn lessons.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site