Enterprise Sales Director , Retail

Sierra

1d • $260,000 - $280,000 • Onsite

About The Position

Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.

Requirements

• 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
• Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
• Exceptional verbal and written communication abilities.
• Ability to analyze market trends, identify opportunities, and make data-driven decisions.
• Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.

Nice To Haves

• Familiarity with the AI landscape, key players, and emerging trends.

Responsibilities

• Identify and target potential customers through research, networking, and cold calling.
• Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
• Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers.
• Serve as their primary point of contact and exceed their expectations.
• Lead negotiations with existing and prospective customers, addressing objections and closing deals.
• Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
• Develop and execute sales strategies to meet or exceed sales targets.
• Craft tailored sales presentations and proposals that meet our enterprise customers needs.
• Collaborate with our marketing team to implement effective sales campaigns and presentations.
• Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
• Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed