Head of Sales

Overview

As Head of Sales, you will lead and execute our commercial growth plan. You’ll build and manage a high-performance sales organization, define pricing and packaging strategies, own partner-ecosystem growth, and optimize all revenue-driving functions. You’ll work closely with product, marketing and customer-success to ensure we’re hitting targets and delivering exceptional value to our clients. You will be one of the few early executive hires, as the role is strategic, hands-on and instrumental in shaping our future success.

• Develop and execute a comprehensive revenue growth strategy across direct sales, channel/partners, and enterprise accounts in the GTA, Canada and internationally.
• Build, lead and scale a results-driven sales organization (AEs, BDRs, channel sellers) including hiring, training, coaching and performance management.
• Define and optimize sales process, pipeline management, forecasting, and go-to-market motions.
• Set pricing, packaging and promotion strategy in conjunction with product and finance to optimize revenue, margin, and market penetration.
• Own quota-setting, territory design and attainment tracking; be accountable for P&L of revenue operations.
• Cultivate strategic partnerships (resellers, alliances, referrals) to accelerate revenue reach and open new channels.
• Collaborate with marketing to drive demand generation, lead qualification, brand positioning and market differentiation.
• Work with customer success and product to ensure adoption, renewal and expansion — helping convert customers into advocates.
• Use data-driven insights to improve sales effectiveness continuously, conversion rates, deal size, sales cycle and churn.
• Act as a senior leader and culture driver: you’ll help recruit, mentor, and scale the commercial team to match our growth ambition.

As Head of Sales, you will lead and execute our commercial growth plan. You’ll build and manage a high-performance sales organization, define pricing and packaging strategies, own partner-ecosystem growth, and optimize all revenue-driving functions. You’ll work closely with product, marketing and customer-success to ensure we’re hitting targets and delivering exceptional value to our clients. You will be one of the few early executive hires, as the role is strategic, hands-on and instrumental in shaping our future success.

• 15+ years of enterprise SaaS sales or Services Sales leadership experience, ideally in IDP, document automation or workflow / productivity tools or Digital Services.
• Proven track record of building and scaling a sales organization from early stage to growth scale (GTA or North America).
• Strong commercial acumen: you’ve set pricing/packaging, owned P&L, strong vision for acquiring/expanding high-value enterprise accounts.
• Comfortable wearing many hats: you’ll be hands-on now (closing deals, building pipeline) and strategic for tomorrow (building team, systems, strategy).
• Outcomes-oriented and metrics-driven you live by quota, conversion, average deal size, pipeline velocity, retention metrics.
• Excellent communicator and relationship-builder: ability to engage C-Suite, Board, partners and make the case for transformation.
• A self-starter with strong entrepreneurial spirit, comfortable in a fast-moving environment.
• Located in or near the Greater Toronto Area, comfortable with hybrid work and travel to partner or any local or regional events as necessary to represent the product and the company.

• Hybrid / flexible work environment.
• Access to cutting-edge AI, cloud, and data engineering tools and projects.
• Fast-track career growth opportunities for high-performance talent.
• Inclusive, global and mission-driven culture.
• Competitive group benefits plan (health/dental/vision, etc.).
• Professional development support: training, conferences, certifications.
• Company-sponsored team-building, wellness initiatives and inclusive culture.
• Equity participation in company success.
• PTO/vacation policy that supports work-life balance.

• Staggered Competitive base salary (commensurate with experience) plus attractive variable incentive tied to revenue targets.
• Equity stake in…