Director of Sales

Director of Sales

Toronto, ON, Canada

Full Time

Job Description

This is a hands-on, commercially driven role to own new business development and build the foundation of a high-performing sales organization. You won't inherit a large team or an established sales engine. To start, you'll personally generate pipeline, lead discovery, develop strategic opportunities, and close new business. You'll work closely with the founders to sharpen our go-to-market strategy, improve our sales process, and identify the markets and use cases where Giftagram wins.

As you prove the motion and hit targets, you'll build, lead, and develop the sales team beneath you. It's ideal for someone who enjoys both selling and building, and can move between executive conversations, hands-on prospecting, complex deal strategy, and repeatable process.

What you'll do:

Drive new revenue

• Own the full sales cycle, from prospecting and discovery through proposal, negotiation and close.
• Build and maintain a healthy pipeline of mid-market and enterprise opportunities.
• Develop relationships with senior decision-makers across marketing, client experience, sales, HR, procurement and operations.
• Lead consultative conversations that connect our capabilities to real customer and employee use cases.
• Develop strategic account plans and navigate multi-stakeholder deals.
• Meet and exceed new revenue and pipeline targets.

Build the sales engine

• Develop a repeatable outbound strategy across priority industries, accounts and buyer personas.
• Improve conversion of inbound, referral and partner-generated opportunities.
• Create the playbooks, reporting and performance metrics needed to scale, with strong forecasting and CRM discipline.
• Test and refine positioning, packaging, pricing and messaging based on market feedback.
• Identify the right technology, data and tools to support an efficient sales organization.

Build and lead the team

• As revenue grows, define roles, compensation, territories and performance expectations, then recruit, onboard and coach the team.
• Build a culture of ownership, urgency and accountability, and lead by example by staying active in prospecting and key deals.

Shape our commercial strategy

• Partner with the founders on go-to-market strategy, revenue planning and market expansion.
• Collaborate with Marketing on demand generation, account-based initiatives and sales enablement, and with Client Success on expansion and a seamless handoff from sale to implementation.
• Work with Curation, Merchandise, Operations and Product to ensure proposed solutions are commercially sound and operationally achievable.
• Bring customer and market insights back into company strategy, and represent Giftagram at industry events and across the corporate gifting and employee experience ecosystem.

What you'll bring

• 7+ years of progressive B2B sales experience, ideally in SaaS, corporate services, employee experience, marketing technology, branded merchandise or another solution-led environment.
• A proven record of generating pipeline and closing mid-market and enterprise business with multiple stakeholders and longer, consultative cycles.
• Experience building or meaningfully improving an outbound sales motion.
• Strong commercial judgment across forecasting, pricing, proposals and deal structuring, with a practical, data-informed approach to sales operations and CRM.
• Experience coaching or mentoring sellers, or clear readiness to build and lead a team.
• Confidence with executives, and the ability to move between strategy and execution without losing momentum.
• An entrepreneurial mindset, comfort in an evolving high-growth environment, and a genuine appreciation for thoughtful customer experiences and strong brands.

You'll thrive here if you're

A builder energized by creating something from the ground up, and a strong individual seller who wants to grow into a broader leadership mandate. You're comfortable prospecting and opening doors, not only working opportunities others generate. You're curious and consultative, skilled at uncovering the business need behind a gifting request, highly accountable, and motivated by measurable results.

Why join Giftagram

Own a critical growth function at an established company entering its next stage, working directly with the founders and influencing go-to-market strategy.

Sell a differentiated platform that combines technology, curation, branded merchandise, and fulfillment to recognizable brands and meaningful enterprise opportunities.

Build the sales organization you'll ultimately lead.

Competitive base salary plus uncapped performance-based commission and the opportunity to participate in the company's long-term growth.

Join a collaborative team that values thoughtfulness, ownership, transparency and continuous improvement.

Location

Toronto-based hybrid. We value in-person collaboration while offering flexibility in how the team works.

Interested in connecting?

Even if you're not actively looking, we'd be glad to connect with experienced sales leaders who are excited to build, sell and shape the next stage of Giftagram's growth.

About Giftagram

Giftagram is a corporate gifting platform that helps leading organizations build stronger relationships through thoughtful, memorable gifting. Our technology and services make it easy for companies to run gifting across the customer and employee journey, from client appreciation and milestone recognition to events, branded merchandise and company-wide programs. We handle the full experience: gift curation, recipient choice, branded digital experiences, logistics, fulfillment, budgets and reporting.

We work with organizations including Wealthsimple, Shopify, SpaceX, Colliers and Relay Financial. As we enter our next stage of growth, we're looking for an entrepreneurial sales leader to help build and scale our sales function.