Expansion Account Executive, Mid-Market

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for an Expansion Account Executive, Mid-Market based in Canada.

The Expansion Account Executive, Mid-Market will own a portfolio of customers from post-sale handoff through renewal and expansion.
You’ll play a central role in strengthening customer relationships while identifying opportunities to grow revenue within existing accounts.
The position combines strategic account management, proactive prospecting, consultative selling, product demonstrations, and commercial ownership.
You’ll navigate complex mid-market deals, engage multiple stakeholders, and build trusted partnerships with customers in English-speaking markets.
Working in a fast-paced, high-growth environment, you’ll have significant responsibility for your pipeline, forecasts, and customer outcomes.
You’ll collaborate across teams while using modern sales technology to manage opportunities and deliver a consistently excellent customer experience.
This is an ideal opportunity for a customer-focused sales professional who thrives on ownership, growth, and meaningful commercial impact.

• Own a defined book of business from post-sale handoff through renewal and expansion, developing deep knowledge of customers, their objectives, and their operational needs.
• Build and maintain strong relationships with mid-market customers, acting as a trusted partner and primary point of contact throughout the customer lifecycle.
• Identify, develop, and close expansion opportunities within existing accounts, using customer success and business needs to drive sustainable revenue growth.
• Proactively prospect within the existing customer base to uncover new use cases, stakeholders, teams, and opportunities for additional value.
• Conduct engaging quarterly business reviews to assess customer satisfaction, demonstrate product capabilities, identify opportunities for improvement, and communicate measurable business value.
• Lead tailored product demonstrations and presentations that connect customer challenges with relevant solutions and outcomes.
• Manage multiple customer requests, demos, proposals, follow-ups, negotiations, and internal processes simultaneously while maintaining exceptional organization and attention to detail.
• Become highly proficient in the sales technology stack, including CRM, prospecting, outreach, and communication platforms.
• Own and maintain an accurate sales pipeline, forecasting monthly and quarterly expansion opportunities with a target accuracy of approximately +/-15%.
• Maintain meticulous and timely documentation of customer interactions, opportunities, deals, and account progress.
• Embrace an entrepreneurial, hands-on approach and contribute to building scalable processes in a rapidly evolving environment.

Requirements

• At least 4 years of sales experience, with substantial experience in account management, customer expansion, or a similar role within the mid-market segment.
• Demonstrated success growing existing B2B accounts and consistently generating revenue through expansion opportunities.
• Experience managing larger or complex deals, navigating multi-stage sales cycles, and influencing multiple stakeholders.
• Strong analytical and presentation skills, with the ability to translate data and customer insights into compelling business conversations.
• Proven ability to deliver effective product demonstrations and lead high-impact quarterly business reviews.
• Exceptional organizational skills and attention to detail, with the ability to manage multiple priorities without allowing important tasks or opportunities to fall through the cracks.
• Excellent interpersonal and communication skills, with the ability to establish trusted relationships with customers and collaborate effectively with internal teams.
• Adaptability and resilience, with the ability to perform effectively in a fast-paced, high-growth, and frequently changing sales environment.
• A positive, creative, ambitious, and customer-obsessed mindset, combined with strong personal integrity and a willingness to take ownership.
• Curiosity and a growth mindset, with a genuine interest in learning about customers’ industries and continuously improving through coaching and feedback.
• Bachelor’s degree or higher, ideally in a relevant discipline.
• Professional fluency in English, both written and verbal, as the role supports customers primarily across the US and English-speaking Canada.
• Experience with modern sales technology such as Salesforce, Salesloft/Outreach, ZoomInfo/DiscoverOrg, or comparable platforms is an advantage.
• Startup or entrepreneurial experience is a plus.
• Experience with CMMS, maintenance, facility operations, or related software is a bonus.
• Demonstrated success working independently in a remote environment is an advantage.

Benefits

• Competitive compensation: Attractive salary package with opportunities for meaningful equity.
• Healthcare: Health, dental, and vision coverage.
• Retirement: Access to a retirement savings program, including RRSP enrollment for eligible Canadian employees.
• Paid time off: Flexible “take what you need” PTO policy.
• Equity opportunities: Meaningful participation in the company’s long-term growth through equity.
• Global environment: Collaborate with talented colleagues across the world in a diverse and distributed workplace.
• Merit-driven culture: Ideas, initiative, and strong performance are recognized and celebrated.
• Growth environment: Join a high-growth organization where you can take ownership, develop your skills, and make a visible commercial impact.
• Inclusive workplace: Work in an environment committed to creating opportunities for people from diverse backgrounds, experiences, and perspectives.