Senior Strategist, Future Strategy & Innovation

Dig Insights unites strategy, human understanding, and technology to help brands move decisively, in a world that won’t wait. We work with insights and marketing professionals at some of the world’s most well-loved brands, powering their brand and innovation decision-making. Dig One is our agile technology platform, used by our people and our clients, to deliver smarter and faster decisions.  

Our clients span verticals including CPG, QSR, retail, technology, financial services, and telecommunications. Our work is led by a team of over 250 strategists, insights consultants, developers, and data scientists. We work for a global client base out of offices in Toronto, Chicago, London, and Singapore. 

Since we started in 2010, we’ve been focused on setting a new standard for the insights industry – challenging the traditional model and building for what comes next. That means hiring people who are bright, creative, resourceful, and kind. People who succeed at Dig are curious, question established norms and are passionate about helping our clients to move their businesses forward. If you want to join a team that takes themselves just seriously enough to produce great work, we’d love to welcome you. 

As we continue to grow, both geographically and in our expertise, we are looking for people who want to join a high-growth and highly collaborative company. 

About the Role 

Your primary responsibilities will include, but are not limited to: 

Research & Reporting 

• Invest the time necessary to develop an intimate knowledge of the client’s business in order to understand what impact the research, insights and recommendations will have upon it. 
• Tie in client documents to the final trend findings 
• Monitor a variety of sources in order to identify trends and opportunity spaces. From Instagram, blogs and online experts to books, magazines, and the intellectual products of trade/industry conferences. 
• Conduct research and analysis to identify emerging trends and anticipate future challenges in various industries and sectors. Develop an outline and turn your findings into a synthesized report. 
• Should be able to provide recommendations that demonstrate clear ties to the client’s business. 
• Develop strategic foresight and implementation plans for design, business, policy innovations, or organizational change. 
• Translate research/insights into workshop materials that can be leveraged during innovation workshops and sessions with the client. 

Creative Ingenuity 

• Apply design-thinking methodologies to research and test innovative ideas. Study in-market examples of emerging trends and cultural shifts and continuously evolve your research approach. 
• Bring new ideas to the table in terms of how we are executing the work. 
• The ability to create your own report templates (in collaboration with the Director). 
• Present research findings in a compelling, inspiring way—not just detailed analysis, but narratives that energize and engage the team. 

Presenting & Facilitation 

• Strong presentation capabilities: share your findings to your colleagues and clients in a way that shows your passion for the work and the breadth of your knowledge. 
• Aid in the organization and facilitation of workshops and working sessions with clients. 

Project Management 

• Coordinate and collaborate with cross-functional teams on qualitative and quantitative research to develop innovative solutions that address clients' future needs and challenges. 
• Proactive workflow management to hit deadlines. 
• Own your project timelines by prioritizing effectively, flagging roadblocks before they become issues, collaborating across teams, and proactively setting up conditions for success. 

Key Demonstrable Traits and Skills 

While a trends background isn’t required, the traits and transferable skills below can strongly contribute to success in this role: 

• Analytical Thinking – Our projects often begin with broad, ambiguous topics. The ideal candidate should be comfortable navigating uncertainty and able to break down complex challenges into clear steps for investigation, synthesis, and insight development. 
• Strategic Mindset – Our work influences the long‑term trajectory of the clients who partner with us. It’s important that the candidate can take conceptual ideas and ground them within a client’s business, brand, or innovation strategy. 
• Creative Curiosity – Our methodologies are robust and require a mindset of exploration: asking “what if,” building on possibilities, and identifying early-edge signals and emerging opportunities that could shape category change. 
• Adaptable Perspective‑Taking – As new research and information surface, our thinking must evolve. This role requires openness to shifting perspectives rather than becoming attached to fixed ideas—allowing the future to emerge through the process. 
• Passionate Dynamism – This work is a privilege, and the candidate’s energy and attitude influence client relationships, deliverables, and collaboration with team members and cross-functional partners. Every choice should support producing the strongest possible final output. 

Previous Experience 

• 5+ years in a similar role, which may include design, brand, innovation, or business strategy. 
• Recent experience in a client-facing capacity. 
• Strong presentation abilities, including articulating a point of view and thinking on your feet. 
• A self‑starter who thrives in a remote environment and communicates effectively. 

Work Perks:

• A hybrid-remote work environment, where employees have the flexibility to work remotely or from one of our offices
• Unlimited vacation policy
• Reimbursement for health and wellness classes/memberships and continuous learning
• RRSP / 401K employer matching program
• Offices in Toronto and Chicago, located steps to public transportation in the downtown core
• Regular social events such as charity poker nights, trivia events, team building days, and more!

To find out more about us visit us at www.diginsights.com

Our culture is built on 5 core values: Energy, Excellence, Evolution, Equality and Empathy. We believe that our success is dependent on the diverse talents, skills, and ideas of its staff. We are committed to creating an inclusive work environment and encourage applications from all qualified candidates including those in the BIPOC and LGBTQ communities, and from people with disabilities.

We thank you for your interest in Dig Insights, however, only candidates who are chosen for an interview will be contacted.