Job Title: Sales Representative– Microsoft Data & AI Consulting Services
Employment: Full-time
Location: Toronto, CanadaOSI Digital is a global consulting firm with over three decades of experience helping organizations accelerate their digital transformation. As a trusted partner, we enable enterprises to reimagine what’s possible with their data, from building scalable cloud ecosystems to infusing AI into everyday decision-making, we deliver end-to-end solutions across modern data platforms, advanced analytics, AI/ML, and cloud enablement, helping businesses unlock agility, intelligence, and measurable growth.
As part of our growing Data Analytics Practice, we are seeking a seasoned Sales Representative who can build and expand our Microsoft stack-based data analytics business, focusing on developing and closing new business opportunities in Microsoft’s data and AI landscape.
Role Summary
We’re seeking a strategic sales representative with a proven ability to close complex Data and AI consulting engagements and acquire new enterprise clients within the Microsoft ecosystem. This position is ideal for a seasoned professional with a strong record of driving revenue growth through consultative selling, building executive-level relationships, and uncovering high-value opportunities across Data Engineering, Data warehousing, Analytics, and AI solutions. The role demands a true hunter mindset, someone skilled at identifying, pursuing, and converting new business opportunities within Microsoft’s Data & AI landscape.
The candidate will be responsible for generating new business, building long-term client relationships, and driving revenue growth through consultative selling of Microsoft Stack – Data, Analytics, Visualizations & AI Solutions.
Key Responsibilities:
- Identify and qualify potential customers through outbound prospecting, networking, events, and inbound inquiries.
- Leverage your current network to solicit and provide our Data Analytics consulting services in the Microsoft stack.
- Stay current with Microsoft’s Data & AI roadmap, industry trends, and competitor offerings to shape positioning and differentiate OSI in the marketplace.
- Drive go-to-market strategies in collaboration with marketing and leadership teams. Ensure our sales strategy is perfectly aligned with Microsoft’s newest offerings and incentives, positioning us ahead of the competition.
- Negotiate pricing, contract terms, and close deals to meet or exceed sales quotas and revenue targets.
- Manage the full sales lifecycle - from lead generation to deal closure and handoff to delivery.
- Coordinating with internal practice leads to craft compelling proposals, SOWs, and pricing strategies aligned to client needs.
- Define ideal customer profiles (ICPs) and target account lists, mapping key decision-makers such as CIOs, CDOs, and VPs of Data, IT, and Finance.
- Build and nurture long-term client relationships to maintain a strong pipeline of qualified leads.
Required Qualifications:
- Bachelor’s degree in business, Marketing, Engineering, or a related field required; MBA preferred.
- Minimum of 5+ years of experience in IT services, technology, or consulting sales focused on Data, Analytics, Cloud Solutions, and AI, including at least 4+ years of demonstrated success selling within the Microsoft technology ecosystem.
- Strong conceptual and commercial understanding of Microsoft’s Data and AI services, including Microsoft Fabric, Azure Synapse Analytics, Azure Data Factory, Power BI, and Azure Machine Learning.
- Experience selling both project-based consulting and managed services is highly desirable.
- Experience in Account Management, including generating new business and exceeding consumption-based revenue targets.
- Established connections within Microsoft’s sales and partner ecosystem, as well as relationships with enterprise customers leveraging Microsoft technologies.
- Demonstrated success in positioning and selling complex consulting and professional services by aligning business challenges with data- and AI-driven solutions.
- Skilled in developing go-to-market strategies, defining ideal customer profiles (ICPs), and building targeted account plans to drive pipeline growth and new logo acquisition.
- Exceptional ability to articulate business value, deliver compelling proposals, and present to C-level and VP-level executives.
- In-depth awareness of industry trends, competitive landscape, and Microsoft partnership programs to identify differentiation opportunities.
Preferred Qualifications:
- Established relationships with Microsoft account teams and partner organizations, experience with co-sell and commercial marketplace motions.
- Familiarity with data-driven transformation initiatives across industries such as manufacturing, healthcare, financial services, construction, and retail.
- Microsoft Solution Sales or Azure-related certifications (e.g., Microsoft Certified: Azure Fundamentals, Data & AI Fundamentals) are a plus.
- Proven experience selling data and analytics solutions within adjacent ecosystems such as Snowflake, Databricks, Tableau, and other non-Microsoft cloud platforms.
How to Apply
Send your resume and a brief note describing two recent net-new Microsoft Data/AI wins (problem, solution, TCV, your role, outcome).
