# Sales Director – Retail Remote from[Canada](https://jobicy.com/job-region/canada.md)Salary, yearly, CAD 345,000 - 395,000Department [Sales](https://jobicy.com/categories/seller.md) Employment type Full Time, Job posted16 Jul 2026Apply before16 Aug 2026Experience level Director Views / Applies 43 / 2 [About company](https://jobicy.com/company/sierra.md) * Share About [Sierra](https://jobicy.com/company/sierra.md) Sierra helps businesses build better, more human customer experiences with AI. [Computer Software](https://jobicy.com/company-category/software.md) * 2023 Actively Hiring Verified job posting This job post has been [manually reviewed](https://jobicy.com/tools/help-center/employee/how-does-jobicy-verify-the-legitimacy-of-remote-job-listings.md) for authenticity and compliance. ### AI Summary Sierra is seeking a Sales Director to drive enterprise sales for its AI-powered customer experience platform, targeting major retailers. The role involves prospecting, managing relationships with key decision-makers, negotiating complex deals, and developing sales strategies. Candidates need 8-12+ years of enterprise sales experience with a track record of closing large accounts ($1M+ quota). This position offers significant autonomy and cross-functional collaboration with product, marketing, and operations teams. The compensation is highly competitive, reflecting the seniority and impact of the role. ### Role DNA Job Complexity Easy Hard Pace & Pressure Relaxed Fast-paced Autonomy Level Guided Full Ownership Communication Load Independent Highly Collaborative AI Insight The role requires extensive experience (8-12+ years), enterprise sales acumen, and the ability to close complex multi-million dollar deals, making it challenging. However, clear expectations and a defined structure prevent it from being the highest difficulty level. ### Salary Analysis Median Above Market CAD370,000CA Market CAD120k – 200k 0 CAD407k AI Insight The offered median salary of $370,000 CAD is significantly above the typical Canadian market range for a Sales Director in retail ($120,000 - $200,000 CAD), reflecting the seniority, complexity, and high-stakes nature of enterprise AI sales, as well as the company's premium compensation structure. ### Core Skills Required [Sales](https://jobicy.com/jobs?search_keywords=Sales.md) [Enterprise Sales](https://jobicy.com/jobs?search_keywords=Enterprise+Sales.md) [Lead Generation](https://jobicy.com/jobs?search_keywords=Lead+Generation.md) [Negotiation](https://jobicy.com/jobs?search_keywords=Negotiation.md) [CRM](https://jobicy.com/jobs?search_keywords=CRM.md) [AI Industry](https://jobicy.com/jobs?search_keywords=AI+Industry.md) [Retail](https://jobicy.com/jobs?search_keywords=Retail.md) [Business Development](https://jobicy.com/jobs?search_keywords=Business+Development.md) [Account Management](https://jobicy.com/jobs?search_keywords=Account+Management.md) [Strategic Planning](https://jobicy.com/jobs?search_keywords=Strategic+Planning.md) ### Cover Letter Sample Dear Hiring Manager, I am writing to express my strong interest in the Sales Director - Retail position at Sierra. With over 10 years of enterprise sales experience, including consistently exceeding $1M quotas and closing complex, multi-million dollar deals, I am confident in my ability to drive revenue growth for your innovative AI platform. My background includes building strategic relationships with C-level executives, leading cross-functional negotiations, and developing data-driven sales strategies that align with customer needs. I am particularly drawn to Sierra's mission to transform customer experiences through AI and its strong retail focus. My experience in the retail technology space and my analytical mindset enable me to identify market opportunities and craft tailored solutions for major brands. I am eager to leverage my skills in prospecting, relationship management, and deal closure to help Sierra scale its presence in the retail sector. Thank you for considering my application. I look forward to the opportunity to discuss how my experience and passion align with Sierra's goals. Sincerely, [Your Name] Copy ### Sample Interview Questions Describe a complex enterprise deal you closed that involved multiple stakeholders and a long sales cycle. How did you navigate the process?I closed a $2M deal with a large retailer where the buying committee included IT, marketing, and operations leads. I built relationships with each, tailored demonstrations to their specific pain points, and engaged internal experts to address technical concerns. I managed the timeline by setting clear milestones and following up consistently.How do you approach prospecting for new enterprise accounts in the retail sector?I use a mix of industry research, networking at events, and leveraging existing connections. I identify key decision-makers through LinkedIn and company org charts, then craft personalized outreach highlighting how our solution addresses their specific challenges, such as customer service automation or revenue growth.How would you develop a sales strategy for a new AI product targeting retailers?I would start by analyzing market trends and competitor offerings, then segment retailers by size and need. I’d prioritize high-potential accounts, create tailored value propositions, and collaborate with marketing to build targeted campaigns. Metrics like pipeline velocity and win rates would guide ongoing adjustments.Can you provide an example of how you handled a difficult negotiation where the client had objections about pricing or value?A client felt our solution was too expensive. I listened to their concerns, then demonstrated ROI through a case study from a similar retailer. I offered a phased implementation to reduce upfront cost, and we ultimately agreed on a three-year contract with volume discounts, securing a win-win.How do you balance autonomy with collaboration when working cross-functionally with product and marketing teams?I take ownership of my targets but regularly sync with product to understand roadmap updates and with marketing to align on campaigns. For example, I set up biweekly meetings to share customer feedback, which helps product prioritize features and marketing create relevant content. ## About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are [Bret Taylor](https://www.linkedin.com/in/brettaylor/) and [Clay Bavor](https://www.linkedin.com/in/claybavor/). Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google’s earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ## About the Retail team * 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. ## What you’ll do * Prospecting & lead generation: 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. * Manage relationships: 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. * Negotiating & closing complex deal cycles: 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. * Sales strategy & planning: 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. * Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds. * Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product. ## What you’ll bring * 8-12+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. * Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex 6- and 7-figure ACV deals. * Strong communication skills: Exceptional verbal and written communication abilities. * Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions. * Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling. ## Even better… * Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends. * Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth. ## Our values * Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. * Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. * Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. * Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. * Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. ## What we offer We want our benefits to reflect our values and offer the following to full-time employees: * 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 These benefits are further detailed in Sierra’s policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra’s equity plans subject to the terms of the applicable plans and policies. ## Be you, with us We’re working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn’t precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class. Show more [Apply now >](https://jobicy.com/jobs/149376-sales-director-retail.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. 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