Regional Sales Director, Platform - Canada

Your work days are brighter here. We’re obsessed with making hard work pay off, for our people, our customers, and the world around us. As a Fortune 500 company and a leading AI platform for managing people, money, and agents, we’re shaping the future of work so teams can reach their potential and focus on what matters most. The minute you join, you’ll feel it. Not just in the products we build, but in how we show up for each other. Our culture is rooted in integrity, empathy, and shared enthusiasm. We’re in this together, tackling big challenges with bold ideas and genuine care. We look for curious minds and courageous collaborators who bring sun-drenched optimism and drive. Whether you're building smarter solutions, supporting customers, or creating a space where everyone belongs, you’ll do meaningful work with Workmates who’ve got your back. In return, we’ll give you the trust to take risks, the tools to grow, the skills to develop and the support of a company invested in you for the long haul. So, if you want to inspire a brighter work day for everyone, including yourself, you’ve found a match in Workday, and we hope to be a match for you too.

About the Team

Workday is building a new specialized sales team focused on selling platform, data, analytics, AI, and extensibility solutions into the Office of the CIO. This team will partner with enterprise customers to help IT leaders modernize their technology strategies, unlock business value from Workday’s platform, and align innovation roadmaps to strategic business outcomes. The Revenue organization at Workday balances integrity, innovation, accountability, and collaboration. We are looking for an experienced sales leader who can build trusted executive relationships, coach high performing sellers, and help accelerate market adoption in a dynamic growth area for Workday

About the Role

You are an experienced enterprise sales leader who combines technical fluency, executive presence, and disciplined sales execution. You have led teams through complex, multi stakeholder sales cycles and are comfortable engaging directly with CIOs, CTOs, and senior IT leaders. You know how to coach sellers, orchestrate internal resources, shape executive-level value propositions, and create accountability around pipeline generation, forecast accuracy, and revenue performance. You bring credibility in conversations about cloud architecture, data strategy, AI, integration, security, and enterprise transformation, and you can help your team position Workday as a strategic platform within a customer’s broader technology ecosystem.

Key Focus & Responsibilities

• Team Leadership & Coaching: Use your experience to lead, coach, and mentor a field sales team of specialized Account Executives. Drive a culture of accountability, performance, and continuous development.
• Deal Strategy & Orchestration: Lead a team focused on driving complex platform sales cycles ($500K+ ARR) by orchestrating internal teams of pre-sales, value management, bid management, and sales support from initial discovery through negotiation and closing.
• SOW, Roadmap, & Deal Governance: Oversee your team's operational accountability for generating and executing formal AI/Platform Statements of Work (SOWs) and delivering 1–3 year phased technology roadmaps.
• Forecasting & Business Modeling: Maintain accurate forecasting data and business modeling for senior leadership, while helping your team operationalize a "time to engage" strategy based on corporate triggers.
• Hyperscaler & Partner Co-Selling: Employ effective selling strategies by pulling together different business units to maximize sales, guiding your team to co-sell joint platform solutions with cloud hyperscaler partners (AWS, GCP) and Global System Integrators (GSIs).

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About You

Basic Qualifications M4 Regional Sales Director, Platform:

• 8+ years experience selling cloud/SaaS/ERP/analytics solutions, with a specific focus on complex platform, enterprise data, or AI/analytics solutions directly to the Office of the CIO or CTO.
• 8+ years experience managing complex sales cycles from start to finish with a track record of successful revenue/quota attainment.
• 5+ years experience as a leader in a team selling environment.

M5 Regional Sales Director, Platform:

• 2+ years of field sales management experience at a SaaS company, ideally focused on new business acquisition, with an additional 8+ years as a field sales representative.
• 8+ years experience selling cloud/SaaS/ERP/analytics solutions, with a specific focus on complex platform, enterprise data, or AI/analytics solutions directly to the Office of the CIO or CTO.
• 8+ years experience managing complex sales cycles from start to finish with a track record of successful revenue/quota attainment.
• 5+ years experience as a leader in a team selling environment.

Other Qualifications

• Domain & Technical Fluency: Strong technical credibility in modern enterprise IT architectures, cloud data foundations, API orchestration, data privacy/security, and AI/ML platform integration.
• oCIO Persona Fluency: Speaks the language of IT leadership. Understands the strategic competitive landscape by staying up to date with trends and customer needs so you can effectively coach your team to position Workday solutions.
• Cross-Functional Orchestration: Proven experience pulling together different business units to maximize on sales and position Workday's extensibility, analytics, and autonomous agent capabilities as an interoperable component of a client's wider IT stack.
• Dynamic Leadership: Self-starter attitude with the ability to work in a dynamic environment, empowering your team to challenge legacy IT assumptions, frame clear TCO models, and align technology roadmaps to strategic business goals.

Workday Pay Transparency Statement

Workday pay ranges vary based on work location. As a part of the total compensation package, this role may be eligible for the Workday Bonus Plan or a role-specific commission/bonus, as well as annual refresh stock grants. Recruiters can share more detail during the hiring process. Each candidate’s compensation offer will be based on multiple factors including, but not limited to, geography, experience, skills, job duties, and business need, among other things. For more information regarding Workday’s comprehensive benefits, please [click here]( Primary Location: CAN.ON.Toronto Primary Location Base Pay Range: $170,000 CAD - $255,000 CAD Primary CAN Base Pay Range: $170,000 - $255,000 CAD

Our Approach to Flexible Work

With Flex Work, we’re combining the best of both worlds: in-person time and remote. Our approach enables our teams to deepen connections, maintain a strong community, and do their best work. We know that flexibility can take shape in many ways, so rather than a number of required days in-office each week, we simply spend at least half (50%) of our time each quarter in the office or in the field with our customers, prospects, and partners (depending on role). This means you'll have the freedom to create a flexible schedule that caters to your business, team, and personal needs, while being intentional to make the most of time spent together. Those in our remote "home office" roles also have the opportunity to come together in our offices for important moments that matter. Pursuant to applicable Fair Chance law, Workday will consider for employment qualified applicants with arrest and conviction records. Workday is an Equal Opportunity Employer including individuals with disabilities and protected veterans. Workday is committed to providing reasonable accommodations for qualified individuals during our application process, in order to perform one or more essential functions of their job, as well as regarding the use of AI tools for employment decision-making to any degree. Please see below for more details including how to request an accommodation as a qualified veteran, due to a disability or for religious reasons, or as otherwise provided under applicable law. Workday prohibits taking adverse action against any candidate or employee for reporting a possible violation of this policy, requesting one or more work accommodations, exercising a privacy right, or cooperating in an investigation in accordance with applicable law. Any employee who retaliates against a candidate or employee for doing so may be subject to disciplinary action, up to and including termination of employment, to the fullest extent allowable under applicable law. If you require a reasonable accommodation, you may email [View email address on joinrs.com](mailto:View email address on joinrs.com), as far in advance as possible. Are you being referred to one of our roles? If so, ask your connection at Workday about our Employee Referral process!At Workday, we value our candidates’ privacy and data security. Workday will never ask candidates to apply to jobs through websites that are not Workday Careers. Please be aware of sites that may ask for you to input your data in connection with a job posting that appears to be from Workday but is not. In addition, Workday will never ask candidates to pay a recruiting fee, or pay for consulting or coaching services, in order to apply for a job at Workday.