# Sales Director – Financial Services 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 36 / 4 [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 for its Financial Services team to drive revenue and manage relationships with major banks and insurers. The role involves prospecting, negotiating complex deals, and shaping the go-to-market strategy for an AI-powered customer experience platform. Candidates need 8-12+ years of enterprise sales experience with a $1M+ quota and a track record of closing 6- and 7-figure contracts. The position is based in San Francisco but offers a salary in CAD, reflecting a global compensation structure. This is a high-impact role at a fast-growing startup that values trust, customer obsession, and craftsmanship. ### 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 enterprise sales experience, managing large quotas, and complex deal cycles, making it challenging but not the highest difficulty due to the support of a growing team. ### Salary Analysis Median Above Market CAD370,000CA Market CAD150k – 300k 0 CAD407k AI Insight The offered salary of CAD $345,000–$395,000 significantly exceeds the typical Canadian market range for Sales Directors in financial services, which is $150,000–$300,000. This suggests a highly competitive compensation package, likely reflecting the seniority, global scope, and high expectations of the role. ### Core Skills Required [Enterprise Sales](https://jobicy.com/jobs?search_keywords=Enterprise+Sales.md) [Financial Services](https://jobicy.com/jobs?search_keywords=Financial+Services.md) [B2B SaaS](https://jobicy.com/jobs?search_keywords=B2B+SaaS.md) [Account Management](https://jobicy.com/jobs?search_keywords=Account+Management.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) [Strategic Planning](https://jobicy.com/jobs?search_keywords=Strategic+Planning.md) [Relationship Building](https://jobicy.com/jobs?search_keywords=Relationship+Building.md) [AI](https://jobicy.com/jobs?search_keywords=AI.md) ### Cover Letter Sample Dear Hiring Manager, I am writing to express my strong interest in the Sales Director – Financial Services position at Sierra. With over 10 years of enterprise sales experience, including managing $1M+ quotas and closing complex 6- and 7-figure deals, I am confident I can drive meaningful results for your team. My background includes building relationships with systemically important financial institutions and navigating intricate contract negotiations. I am particularly excited about Sierra’s mission to humanize customer experiences with AI and would love to contribute to your growth in the financial services sector. Thank you for considering my application. I look forward to discussing how my skills align with your needs. Copy ### Sample Interview Questions Can you describe a complex deal you closed that required navigating multiple stakeholders and objections?In my previous role, I led a deal with a top-five bank that involved six-month negotiations, legal hurdles, and competing priorities. I built relationships with key decision-makers, addressed technical concerns by involving product experts, and structured a phased rollout that aligned with their budget. The deal closed at $2.5M ACV.How do you approach prospecting and lead generation for enterprise accounts?I use a combination of market research, leveraging LinkedIn and industry events, and warm introductions from existing clients. I prioritize accounts based on strategic fit and potential revenue, then craft personalized outreach that highlights value propositions tailored to their pain points.Describe a time you had to adjust your sales strategy due to market changes or internal feedback.When a competitor launched a similar product, I pivoted our messaging to emphasize our AI’s unique ability to handle sensitive financial data. I worked with marketing to create case studies and led team training on competitive positioning, which reversed a pipeline decline.How do you collaborate with cross-functional teams like product and legal to close deals?I involve product early to demonstrate capabilities and address technical questions, and I loop in legal during contract drafting to preempt issues. I use regular syncs to ensure alignment and manage expectations, resulting in smoother negotiations.What metrics do you use to measure your success in enterprise sales?I track pipeline velocity, win rates, average deal size, and quota attainment. I also monitor customer satisfaction and retention, as long-term relationships are key in financial services. ## 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 Financial Services team * Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world’s leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity. * Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle – the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one. * Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable 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/149378-sales-director-financial-services.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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