Enterprise Sales Director

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

📋 Description

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

• Establish new relationships with enterprise clients and prospects to drive revenue, pipeline growth, and deployment capacity.

• Cultivate and sustain relationships with key decision-makers and stakeholders within major customer accounts.

• Act as the primary liaison for key customers, consistently surpassing their expectations.

• Lead negotiations with current and prospective clients, manage objections, and finalize complex deals.

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

• Develop and implement sales strategies aimed at achieving or exceeding sales objectives.

• Create customized sales presentations and proposals tailored for enterprise clients.

• 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, personalized outreach, call summarization, pipeline forecasting, and deal execution.

• Continuously adopt and experiment with innovative tools to automate low-value tasks, allowing a greater focus on customer relations.

⛳️ Requirements

• 6–8 years of experience in an enterprise-facing sales role, with a focus on identifying and closing large accounts.

• Proven experience managing a quota of $1M or more.

• Expertise in handling end-to-end complex 6- and 7-figure annual contract value (ACV) deals.

• Outstanding verbal and written communication skills.

• Capacity to analyze market trends, spot 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 landscape, 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 benefits.

• Retirement plan based on the country of employment.

• Parental leave.

• Fertility and family building benefits through Carrot.

• Lunch, as well as tasty snacks and coffee to keep you energized.

• Discretionary benefit stipend allowing individuals to spend in areas that matter most to them.

• Complimentary alphorn lessons.

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