Enterprise Account Executive

Senior Director of Sales | Bucketlist Rewards and Recognition Bucketlist Rewards is seeking a highly experienced Enterprise Account Executive to accelerate our growth within the enterprise segment. You will focus exclusively on acquiring new customers, navigating complex buying cycles with multiple stakeholders, and working directly with senior HR, Total Rewards, and C‑Suite leaders. If you thrive in strategic sales environments, love solving big organizational challenges, and want to help shape the future of recognition and rewards at scale, this is the role for you. This is a unique opportunity to join a fast‑growing technology company where creativity, experimentation, and innovation fuel our success. About Us Bucketlist Rewards provides a leading B2B SaaS solution that allows organizations of all sizes to introduce effective rewards and recognition programs to its workforce. Our goal is to provide companies with an easy‑to‑use web platform that enables employers to reward team members in a meaningful way that matters to them, while achieving great business results and building better organizational cultures. When it comes to great company culture, the Bucketlist team walks the talk and we are proud to be Great Place to Work certified Key Responsibilities Own and drive full‑cycle enterprise sales for organizations, managing long and often complex purchasing processes involving multiple stakeholders. Deliver highly strategic, tailored demonstrations of our SaaS platform based on each enterprise’s goals, operational structure, and change‑management considerations. Develop deep discovery to understand customer priorities, workforce challenges, buying criteria, procurement processes, budget structures, and decision authority. Build and execute strategic account plans to engage executive sponsors, influence decision‑making groups, and guide prospects through multi‑step evaluation. Collaborate closely with internal teams (Product, Customer Success, Marketing) to design custom solutions and business cases for high‑value enterprise prospects. Meet and exceed monthly and quarterly revenue targets for the enterprise segment. Continuously refine your sales process and adopt best practices to improve win rates. Proactively supplement your pipeline through targeted outbound engagement, ABM‑style outreach, and strategic networking with enterprise HR and business leaders. Required Skills for Success 5+ years of enterprise sales experience, with a proven track record selling into organizations with 5,000+ employees. Understands MEDDPICC sales qualification and can align the sales process to it. Demonstrated success managing complex, multi‑stakeholder deals with long sales cycles and multi‑departmental buying committees. Strong executive presence and ability to speak confidently with HR leaders, Total Rewards leaders, Procurement, IT, Finance, and other senior decision‑makers. Can effectively communicate ROI to both champions and decision makers. Exceptional discovery skills and the ability to build compelling ROI, business cases, and change‑management narratives for enterprise‑scale initiatives. Outstanding written, verbal, presentation, and interpersonal communication skills. Highly organized and capable of managing numerous strategic accounts simultaneously. Demonstrated ability to open new enterprise conversations and create pipeline in key target accounts. A true closer: competitive, persistent, and deeply motivated by winning high‑value deals. Strong customer empathy and a consultative, insight‑driven sales approach. A self‑starter. This is a role that requires your drive and expertise to be successful. Nice to Have Experience selling HR tech, SaaS platforms, or employee engagement/recognition solutions. Experience with global enterprises or multi‑national organizations. Track record of being a top performer in past sales organizations (presidents club recipient, top performer etc.). The Perks Growth Opportunities: Join a growing company where you’ll be part of a high‑performing team with lots of potential. Remote Work: We are a distributed workplace (100% remote). This position is open to anyone residing and able to work in Canada on a remote basis. Wellness Days: In addition to paid vacation days, we offer flexible paid time off to fit individual needs. Comprehensive Benefits Package: Includes health, dental, vision care, EFAP, and more. Annual Bucketlist Benefit: An additional paid day off and $$ to spend to help check items off your own bucket list Rewards and Recognition: We drink our own champagne We’ll help you achieve not just your career goals but your personal goals as well Compensation Compensation: The anticipated on target earnings (OTE) range for this role is $200,000 to $350,000 CAD annually. The starting base salary will depend on a number of factors including skills, experience and market demands. The OTE range listed includes base salary and commissions, which are dependent on performance. Seniority level Mid‑Senior level Employment type Full‑time Job function Sales and Business Development Industries Human Resources Services and Information Services EEO Statement At Bucketlist Rewards, we are committed to fostering a diverse, equitable, and inclusive workplace. We believe that varied perspectives drive innovation and creativity, and we welcome applicants from all backgrounds and experiences. We encourage individuals from underrepresented groups to apply, as we strive to build a team that reflects the diverse communities we serve. We are dedicated to creating an environment where everyone feels valued, respected, and empowered to contribute their best work. #J-18808-Ljbffr