Lead a team of Account Executives focused on the Commercial (mid-market) segment to own, manage, and exceed revenue outcomes
Engage with executive-level stakeholders at established e-commerce organizations and drive complex sales cycles to close new business
Partner with Account Executives on strategic deal execution, including executive engagement, multi-threading, and complex negotiations
Act as an active coach and mentor, leveraging call reviews, pipeline inspections, and deal strategy sessions to elevate performance
Collaborate cross-functionally with Marketing, Partnerships, and Customer Success to strengthen market positioning and accelerate sales cycles
Drive accountability through weekly activity reviews, ensuring balanced pipeline development, forecasting accuracy, and consistent conversion metrics
Use sales analysis and data-driven insights to inform strategy, improve execution, and optimize performance across the team
Ensure coaching frameworks, enablement resources, and ongoing training programs are fully leveraged to ramp, develop, and retain top talent
Provide input into GTM strategy and the design of scalable processes, reporting, and tools to support Commercial sales growth
Identify, share, and implement best practices that elevate the team’s ability to win in competitive, complex environments
Stay up-to-date on product roadmap, industry trends, and the evolving competitive landscape to ensure the team is positioned as consultative experts
Shape sales leadership, scale the Commercial team, and contribute to go-to-market strategy for a conversational AI platform for ecommerce
Requirements
3+ years of Account Executive Leadership experience, ideally with at least one year being in enterprise sales. At least 1 year leading Commercial or Mid-Market teams and a previous career as an individual contributor
Direct experience in SaaS organizations with complex deal cycles and multi-stakeholder sales processes. Bonus points if it's within E-commerce.
Proven track record of driving both personal and team quota attainment in Commercial segments
Experience scaling teams and building repeatable sales processes in high-growth environments
Passion for and polish within, learning, coaching, and developing future sales leaders
Comfortable as both a strategic leader and hands-on contributor when needed
Experienced people leader: you are a proven coach, mentor, and motivator who builds high-performing teams
Track record of driving growth and consistently exceeding targets within the Commercial or Mid-Market SaaS space
Strong understanding of how to sell SaaS solutions to executive stakeholders, with an emphasis on ROI, scalability, and measurable business outcomes
Demonstrated ability to manage complex sales cycles, negotiate large contracts, and navigate multi-stakeholder environments
Adept at cross-functional collaboration and influencing across teams to drive shared outcomes
Strong communicator and executive presence; confident leading customer-facing discussions and internal strategy sessions
History of operational excellence, including quota attainment, pipeline management, and forecasting accuracy
Self-aware and highly engaged leader, present “on the floor” with your team, invested in their growth, success, and overall engagement
Willingness/ability to commit to a hybrid work environment that involves working in the office 2 days per week (Wednesday & Thursday)
Must be legally authorized to work in the job location or indicate visa/sponsorship needs via application form
Benefits
🏖️ 5-week vacation
🤕 Paid sick leave (15 days)
🌏 6 weeks full remote/year
🧸 Paid parental leave (16 weeks)
🍽️ CAD $400/month for lunch expenses (you’ll have your own Gorgias credit card)
🏥 We provide private health insurance and retirement pension
💆🏻♀️ Get up to CAD $900 to set up your workstation at home (working from home should feel breezy)
📚 Get up to CAD $2600 of learning material and wellness support per year! This includes CAD 1950 for learning material (such as books, courses, and individual coaching sessions) directly linked to your job scope, as well as a CAD 650 wellness budget. Take advantage of these resources to grow in your role and prioritize your personal development and wellness.
🥰 Every quarter, we organize an online company-wide summit to discuss where we’re going and strengthen social bonds. Once per year, we organize offsite team retreats and company retreats!
📚 Get up to $2000 of learning material (includes books, courses, training sessions that can be easily identified and linked with your job scope)
🥰 Every quarter we organize a company-wide summit to discuss where we're going and strengthen the social bonds (once the health situation allows it, we'll transform these summits into offsites!)
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