Senior Account Executive, Mid-Market

Job description

Accountabilities Drive new business revenue within an assigned mid-market segment by developing and advancing qualified sales opportunities. Partner with Sales Development to target strategic accounts while independently self-sourcing opportunities on a recurring basis. Manage complex, multi-stakeholder sales cycles from initial discovery through proposal, negotiation, close, and transition to the Customer Experience team. Conduct compelling product demonstrations and deliver a consultative sales experience tailored to each prospect’s business challenges, priorities, and desired outcomes. Build trusted relationships with senior leaders and C-level executives, uncovering both stated and underlying business needs. Prepare and negotiate commercial proposals, collaborating with senior leadership when required to secure larger or strategically important opportunities. Consistently achieve or exceed quarterly sales targets while maintaining accurate forecasts and pipeline visibility. Develop strong partnerships with customers and internal teams to ensure successful handoffs and long-term customer value. Collaborate with Product teams by sharing customer insights, market trends, and feedback that can inform future product development. Stay adaptable in a fast-paced environment, proactively identifying opportunities to improve sales processes, customer engagement, and broader go-to-market initiatives. Requirements 5+ years of sales experience in an Account Executive or comparable role, preferably within B2B SaaS, with a demonstrated record of strong sales performance. Proven experience managing complex sales cycles involving multiple stakeholders within larger or enterprise organizations, from prospecting through close. Demonstrated ability to self-source opportunities and build pipeline within target accounts. Strong consultative selling, discovery, negotiation, presentation, and closing skills, with the ability to connect solutions to measurable customer needs. Experience developing relationships with senior decision-makers and C-suite executives. Proficiency with Salesforce or comparable CRM platforms, along with sales and prospecting tools such as LinkedIn Sales Navigator, Outreach, and web-conferencing platforms. Excellent organizational, prioritization, and time-management skills, with the ability to manage multiple opportunities and sales activities effectively. Strong communication and presentation abilities, including confidence delivering product demonstrations remotely. A proactive, self-directed mindset with the ability to operate independently, take initiative, and contribute ideas in an evolving environment. Curiosity, adaptability, resilience, and a willingness to experiment, learn, and take on new challenges. Strong commercial judgment and customer empathy, with the ability to listen carefully and identify both explicit and latent customer needs. Post-secondary degree or equivalent experience. Candidates should reside in the Greater Toronto Area and be able to access a downtown Toronto coworking location for occasional sales-team gatherings. Benefits Competitive compensation: CA$90,000–CA$110,000 base salary, plus approximately CA$130,080 in commission and equity eligibility. Remote-first flexibility: Work remotely while remaining connected with distributed teams and occasional in-person collaboration opportunities. Health and wellness: Comprehensive health and wellness benefits designed to support physical and mental well-being from day one. Professional development: Dedicated professional mastery support and ongoing opportunities to develop your skills and advance your career. Sales enablement: Structured onboarding and ramp support from the Revenue Enablement team to help you succeed in the role. Technology: Company-provided MacBook, monthly phone and internet subsidy, and a work-from-home budget for your home office. Performance support: Regular feedback, one-on-one conversations, and structured performance development. AI and innovation: An environment that encourages experimentation with AI, automation, and new approaches to driving business impact. Culture and connection: Opportunities to participate in town halls, AMAs, celebrations, and other initiatives designed to foster connection in a remote-first environment. Employee Resource Groups: Access to employee-led communities supporting learning, connection, and inclusion. Career impact: The opportunity to contribute directly to business growth while developing your career in a high-performing SaaS sales environment. How Jobgether works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best! Why Apply Through Jobgether? Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time. #LI-CL1 This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior Account Executive, Mid-Market based in Canada. This is a high-impact, revenue-generating role focused on driving new business across the mid-market segment, serving organizations with approximately 251–2,500 employees.You’ll own complex B2B SaaS sales cycles from prospecting and discovery through negotiation, close, and customer handoff.The role combines strategic selling, consultative discovery, executive relationship-building, and strong commercial execution.You’ll work closely with Sales Development, Customer Experience, Product, and senior leadership to create exceptional buying experiences and accelerate growth.Success requires curiosity, resilience, strong business acumen, and the ability to uncover customer challenges and translate them into compelling solutions.The position is remote-first, with candidates expected to be based in the Greater Toronto Area and able to access a downtown Toronto coworking space for occasional team gatherings.It offers significant autonomy, strong earning potential, professional development, and the opportunity to make a measurable impact in a fast-moving SaaS environment.