Director of Sales - Strategy & Innovation

Director of Sales – Future Strategy & Innovation

Join Dig Insights to shape and scale future strategy & innovation (FSI) solutions.

Dig Insights is a tech-enabled research company that helps global consumer brands move beyond consumer‑centric to decision‑centric markets. Our proprietary SaaS platform, Upsiide, reinvents how enterprises screen, optimize, and build business cases for innovation.

The Director of Sales – Future Strategy & Innovation leads the commercial strategy to grow FSI solutions across priority accounts and new business opportunities.

• Partner with the Head of FSI delivery to identify priority spaces, target accounts, and high‑potential buyers within innovation, R&D, and strategy roles.
• Advance complex, consultative FSI opportunities from early‑stage needs through proposal development and close, shaping compelling capability narratives and persuasive pitch materials.
• Drive the full sales cycle for FSI pursuits in collaboration with FSI VPs, managing qualification, pricing strategy, sales process orchestration, and commercial workflows.
• Represent FSI within account strategy, coordinating opportunities and ensuring integration into account plans.
• Act as the commercial brain behind FSI solutions – productize streamlined offerings, shape upsell paths, and translate ideas into market‑ready value propositions grounded in trend, foresight, and cultural intelligence.
• Deliver against the FSI booking quota, managing forecasting, pipeline advancement, and win strategies, while owning Hub Spot usage and reporting.
• Collaborate across Strategic Growth, Insights Consulting, Upsiide, and Marketing to align outreach and early‑funnel opportunity development.
• Lead discovery conversations with current and prospective clients to surface future‑focused challenges, opportunities, and growth ambitions.
• Act as steward and ambassador for the Future Strategy & Innovation practice, bringing a strong understanding of its approaches and point of view into client and commercial conversations.

• 8‑10+ years in insights, innovation, market research, brand/strategy consulting, or related commercial roles, with a focus on trends, foresight, and cultural intelligence.
• Intellectual curiosity to deeply understand and authentically represent FSI program approaches.
• Proven ability to source, shape, and advance complex commercial opportunities with multi‑method background (quantitative, qualitative, technology, syndicated, etc.).
• Existing network or ability to grow network of innovation, strategy, R&D, and insights functions, primarily in CPG, Retail, Financial Services, QSR, Healthcare, and Technology.
• Strong capability in structuring pitches, developing proposals, and managing multi‑step sales processes.
• Demonstrated success in early‑stage business development or opportunity creation roles.
• Executive communication skills with the ability to run discovery calls, articulate value, and influence internal partners.
• Experience navigating cross‑functional environments with multiple stakeholders and distributed teams.

This role offers the opportunity to help shape and scale a differentiated offering while driving measurable commercial impact through complex, consultative sales. If you’re motivated by advancing future‑focused opportunities and owning results, we encourage you to apply.

• Hybrid‑remote work environment with 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!

Our culture is built on five core values:
Energy, Excellence, Evolution, Equality, and Empathy. 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.

Visit  and apply through our career portal.

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