Senior Account Executive, Mid-Market

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.