Enterprise Sales Director, Financial Services

This is a fully remote position, open to applicants in Canada.

📋 Description

• Identify and engage potential customers through research, networking, and cold outreach.

• Establish new relationships with enterprise clients and prospects to enhance revenue, pipeline, and deployment capabilities.

• Cultivate and maintain relationships with key decision-makers and stakeholders among major clients.

• Act as the primary contact and aim to exceed customer expectations.

• Lead negotiations, tackle objections, and finalize intricate deals.

• Navigate contracts and agreements in collaboration with legal and finance teams.

• Develop and implement sales strategies to achieve or surpass targets.

• Craft customized sales presentations and proposals.

• Collaborate with the marketing team on sales initiatives and presentations.

• Partner with the broader Go-To-Market (GTM) team as well as product, technical, and operations departments.

• Utilize AI tools for account research, outreach, call summarization, forecasting, and deal execution.

⛳️ Requirements

• 6–8 years of experience in a customer-facing sales position within the enterprise sector.

• Proven experience managing a quota exceeding $1M.

• Background in handling complex end-to-end deals with 6- and 7-figure Annual Contract Value (ACV).

• Outstanding verbal and written communication skills.

• Capability to analyze market trends, identify opportunities, and make informed, data-driven decisions.

• Demonstrated success in identifying and targeting enterprise clients through research, networking, and cold outreach.

• Familiarity with the AI industry, including key players and emerging trends is a plus.

🏝️ Benefits

• Flexible (unlimited) paid time off.

• Comprehensive medical, dental, and vision coverage for you and your family.

• Life insurance and disability coverage.

• Retirement plan based on your country of employment.

• Parental leave.

• Fertility and family-building benefits through Carrot.

• Lunch provided, along with a variety of snacks and coffee.

• Discretionary benefit stipend.

• Complimentary alphorn lessons.

• Eligible full-time employees can take part in Sierra's equity plans.

• Commission opportunities available.