Sales Sr. Director (Winnipeg)

What You’ll Do As a Senior Director Sales Manager, you’ll own a portfolio of strategic accounts and new business pursuits, leading complex, multi-tower opportunities from origination through close. You’ll partner with regional leadership, delivery, solution, and alliance teams to build pipeline and shape priority wins. Key Responsibilities Own sales outcomes for a portfolio of strategic accounts and new logo pursuits across Canada Shape go-to-market strategy in partnership with regional leadership, sales, delivery, and ecosystem partners Lead end-to-end sales cycles for complex, end-to-end engagements — including pipeline generation, deal shaping, commercial constructs, proposals, and closing Develop and own executive and C‑suite relationships, engaging clients through workshops, value‑based presentations, and strategic reviews Partner with Microsoft and ecosystem partners to co‑sell, originate, and grow pipeline Mentor and influence sales colleagues, solution architects, and pursuit teams; contribute to building reusable sales assets Manage a team of 20 Business Development Managers, with a robust focus on coaching, mentoring, and performance development Maintain accurate pipeline forecasting, sales reporting, and commercial discipline Strengthen market presence and brand awareness through industry engagement, networking, and thought leadership Qualifications What you’ll bring: You’re a senior, client‑focused seller with a strong track record of growing technology services revenue, shaping complex deals, and building long‑term executive relationships.

You communicate clearly, influence effectively, and thrive in a matrixed environment. Experience 12+ years of sales/solution leadership experience in IT services, consulting, or digital transformation (Microsoft ecosystem strongly preferred) Proven ability to meet or exceed multi‑million‑dollar sales targets and influence senior stakeholders, including C‑level Experience selling across Microsoft technologies — cloud (Azure), modern workplace, business apps, and data/AI Strong deal shaping, commercial acumen, and business case development for complex, multi‑tower engagements Bachelor’s degree in business or technology (or equivalent experience) Skills Exceptional executive presence and ability to build long‑term, trusted client relationships Strong influencing and communication skills across internal and external senior stakeholders Strategic mindset with strong pipeline, opportunity, and forecast management Ability to lead in a matrixed, fast‑paced, global environment Preferred Qualifications Experience selling managed services, outsourcing, or large transformation deals Experience integrating service partners and ecosystem players into commercial constructs Microsoft Certifications and/or relevant industry certifications How Success Is Measured Success in this role is measured by revenue growth, deal conversion, pipeline health, and client satisfaction outcomes across your portfolio. Compensation & Location Toronto: $190,000 - $215,000 Calgary: $190,000 - $215,000 Vancouver: $190,000 - $215,000 Ottawa: $190,000 - $215,000 Montreal: $190,000 - $215,000 In addition to base pay, this sales role is eligible for additional incentive compensation under the Sales Achievement Bonus Plan based on achievement toward individual sales targets, subject to plan terms. #J-18808-Ljbffr