Director of Digital Sales

Are you a client-facing sales leader who builds relationships through meetings, presentations, and genuine connection not from behind a desk?

Our client a rapidly growing Toronto-based digital consulting and technology partner is seeking a dynamic Director of Digital Sales to spearhead business growth across North America. This is a true sales leadership role for someone who thrives on face time with clients, strategic conversations, and closing meaningful deals. If you’re energized by being out in the field, building trust with decision-makers, and driving revenue through consultative selling, this opportunity is for you.

About the Company

This consulting firm is a trusted technology partner specializing in UI/UX design, SEO, and custom development projects. They also provide ongoing infrastructure support and maintenance, positioning themselves as long-term collaborators invested in their clients’ success.

Their clients include large non-profit organizations, medium-sized businesses, startups, and pharmaceutical campaign teams entities that value impact-driven design, technical execution, and continuous optimization.

The firm is also at the forefront of helping clients integrate AI into their operations, driving smarter decision-making, improved user experiences, and operational efficiency.

Your Role

As the Director of Digital Sales, you will be the face of the company in the market. This is a high-touch, relationship-driven role focused on client meetings, presentations, networking, and strategic deal-making not lead generation or email campaigns. You’ll own revenue growth, lead the full sales cycle from first handshake to signed contract, and serve as a trusted advisor to prospects navigating their digital transformation.

While marketing activities remain outside your scope, you’ll provide strategic input to ensure campaigns and messaging align with what resonates in the field.

Key Responsibilities

Sales Leadership & Revenue Growth

• Own and drive the full sales cycle, with a focus on in-person meetings, presentations, and relationship building

• Develop and execute a sales strategy targeting clients across North America

• Identify, pursue, and close new business across key sectors including nonprofit, startup, pharma, and digital-first SMBs

• Deliver compelling pitches and tailored proposals that span development, design, SEO, infrastructure support, and AI integration

Client Engagement & Strategic Advisory

• Be present attend industry events, conduct discovery meetings, and build lasting relationships with key stakeholders

• Understand client challenges deeply and craft personalized solutions that address real business problems

• Act as a trusted advisor, guiding prospects through complex buying decisions

Cross-Functional Collaboration

• Partner with account management and delivery teams to ensure seamless handoffs and client satisfaction

• Provide market and client insights to leadership, advising on how marketing activities can better support sales objectives

• Participate in pipeline reviews and contribute to refining service offerings based on frontline feedback

Market Intelligence

• Stay ahead of trends in AI, digital transformation, and emerging technologies to identify growth opportunities

• Serve as the bridge between client feedback and internal innovation

What You Bring

• Proven track record of success in B2B sales leadership, preferably in digital services, consulting, or technology partnerships

• A relationship-first approach you build trust through face-to-face interaction, not automation

• Experience owning and closing complex, consultative sales cycles

• Strong understanding of digital design, UX, web/app development, and SEO services

• Ability to translate technical solutions into compelling business value for non-technical executives

• Exceptional presentation, negotiation, and communication skills

• Comfortable traveling within North America for client meetings and industry events

• Self-motivated, entrepreneurial, and energized by a fast-paced, high-growth environment

Why This Role

• A true sales role meetings, presentations, and meaningful client interaction, not desk-bound lead gen

• Terrific offices in Liberty Village with hybrid flexibility (1 day remote per week)

• Remote-first culture for team members beyond the GTA

• Direct access to company leadership and the opportunity to shape the sales function

• Fast-paced environment with measurable impact and significant earning potential

• Weekly team lunches and a collaborative, energetic culture

• Comprehensive health and dental benefits