Senior Account Executive — US & Canada
Indexed description
We are a lean, focused team. This is not a role for someone who relies on a large support organisation. It is a role for someone energised by ownership, who wants to be close to the product, close to the customer, and genuinely excited about the future of retail technology.
🚀 What You'll Do
- Own the full enterprise sales cycle end-to-end: prospecting, qualification, discovery, solution design, commercial negotiation, and close.
- Build and manage a pipeline of enterprise retail brands across North America, with a focus on the Eastern and Central regions.
- Engage with C-suite and VP-level stakeholders across IT, Operations, and Retail leadership. You are a peer in these conversations, not a pitch machine.
- Bring a consultative approach: invest time in understanding a prospect's business and pain points before presenting solutions.
- Collaborate with our SVP, Sales and our Solutions Engineering team on complex, multi-stakeholder opportunities.
- Participate in industry events, retail tradeshows, and store visits, including key events in New York and across North America.
- Contribute pipeline intelligence, competitive insights, and account strategy to the broader go-to-market team. Leverage AI tools to improve sales processes and drive efficiency
- Enterprise-level deals with multi-year contracts and meaningful ACV. These are strategic, board-level investments for our customers.
- Complex, multi-stakeholder buying committees spanning IT, Operations, and Retail leadership. You will need to build consensus across functions, not just win one champion.
- Longer sales cycles that reward patience, rigour, and relationship-building over quick wins.
- A blended revenue model combining committed subscription and consumption-based components. Our commission structure is designed to reward you meaningfully at signing.
- Territory: United States and Canada.
- 5–7 years of B2B SaaS or enterprise technology sales experience, with a quota-carrying, closing role throughout.
- Demonstrated ability to run complex, multi-stakeholder enterprise deals independently and without heavy internal support.
- Executive presence: comfortable and credible in C-suite and VP-level conversations from day one.
- Hungry and coachable, motivated by ownership and results, not by the size of the support team around you.
- Comfortable with longer sales cycles and a commission structure that rewards meaningfully at signing: you think in quarters.
- Experience selling into retail, retail-adjacent, or commerce verticals is a genuine plus, though not a hard requirement.
- Based in Canada (Eastern or Central time zone preferred); remote-first.
Our diversity is our greatest strength. Our team comprises over 40 nationalities, fostering a melting pot of unique perspectives, cultural experiences, and innovative ideas. Join us in our mission to bring the joy back to retail.
🔥 Perks & Benefits
Generous PTO & R&R: We prioritise your wellbeing with a generous leave policy and a culture that encourages you to recharge.
Professional Growth: A dedicated personal development budget and a learning-centric environment to help you advance.
Flexible Working: Remote-first with flexibility to create a working environment that suits your lifestyle.
Balanced Work-Life: Life-friendly working hours designed to help you maintain a fulfilling career and personal life.
Financial Rewards: Employee stock options alongside a competitive uncapped commission plan.
Create a free Caio profile to unlock more results and save your role and location preferences.
Unlock free search