Digital Strategy & Transformation Consulting Services

Strategy-Driven Digital Transformation | Turning Strategic Thinking into Digital Reality

Mid-sized businesses and nonprofits know they must embrace digital change to stay relevant and effective. Over 75% of mid-market companies plan to boost IT spending next year, but less than half have a digital strategy to guide those investments. Likewise, 90% of Canadian nonprofits rank digital transformation as a top priority, yet about one in four lack the skilled staff to execute it. This has resulted in underperforming returns of their technological investments due to fragmented systems, limited IT resources, or teams hesitant to adopt change.

Without a clear roadmap, mid-sized business and non-for-profits are at risk of falling behind or missing opportunities as their digital efforts are not aligned to a bigger strategic picture.

At The Planning Group, we specialize in the intersection of strategy and technology. We help organizations develop practical, purpose-driven digital strategies that bridge the gap between high-level goals and everyday execution. With over 20 years of strategic consulting experience, we treat digital transformation as a business decision, not just a technology project. Our strategy-first, people-centered approach ensures that every initiative supports your mission, strengthens operations, and delivers measurable value.

As a boutique firm, our senior advisors work directly with your team by guiding you from early planning through to execution and adoption. Whether you're modernizing systems, rethinking digital services, or aligning leadership around a digital roadmap, we’ll help you move forward with clarity and confidence.

Through our work, clients gain:

• Strategic alignment for digital investments. We create a roadmap focused on high-impact, tech-enabled initiatives that support your business goals.
• Alignment and buy-in across teams and leadership. We build shared understanding and commitment, helping boards and executives champion the digital journey.
• Actionable and tailored transformation plans. We deliver a clear, step-by-step roadmap aligned to your capacity, budget, and timeline - no one-size-fits-all templates.
• Stronger change readiness. We equip your team with the training and change management tools to embrace new systems and workflows.
• Improved collaboration between business and IT. We connect technical and strategic conversations, ensuring technology solutions meet real business needs, and business leaders stay engaged in the tech journey.
• Stronger digital services and results. Expect faster processes, more customer-focused tools, and better outcomes for your mission.

If you’re looking for clarity on how to modernize your technology, enhance your digital services, or align your leadership around a digital game plan, The Planning Group will help you get there with alignment and confidence. We turn digital transformation into a driver of your mission and business success, ensuring your technology investments truly advance your organization’s goals.

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