Account Executive in Winnipeg

About CultureAlly

CultureAlly is a fast-growing workplace culture and training company, recognized by The Globe and Mail as one of the Top Growing Companies in 2026. We partner with leading organizations across North America to deliver impactful training, consulting, and eLearning experiences that elevate workplace culture and drive meaningful organizational change.

Role Overview

As an Account Executive, you'll guide organizations through the buying journey - from initial discovery through solution recommendation, proposal, negotiation, and close. You'll work with qualified inbound opportunities while proactively developing relationships within target accounts, helping HR and business leaders build stronger workplace cultures through CultureAlly's training and learning solutions.

We're looking for an experienced, commercially driven sales professional who can establish credibility with senior stakeholders, lead thoughtful discovery conversations, and independently manage an active pipeline. You'll bring strong sales judgment, organization, and a proactive approach to following up, building relationships, and closing business. You'll also maintain relationships with existing clients, identifying opportunities for repeat business, renewals, and additional training needs.

Reporting to the Director of Sales & Operations, you'll collaborate closely with Marketing and Operations, maintain accurate forecasts, and take ownership of delivering an exceptional buying experience that leads to long-term client partnerships.

What You'll Do:

• Own and manage a pipeline of qualified sales opportunities from discovery through close.
• Convert inbound opportunities while proactively developing additional business through strategic prospecting, account development, referrals, and re-engagement of existing clients.
• Respond promptly to inbound inquiries generated through marketing campaigns and referrals.
• Build and maintain relationships with HR, Learning & Development, and business leaders through consistent communication and proactive follow-up.
• Conduct consultative discovery conversations to understand client objectives, challenges, timelines, and buying process.
• Recommend tailored training and learning solutions that align with each client's goals.
• Prepare proposals, pricing, and presentations that clearly communicate value.
• Manage multiple opportunities simultaneously, maintaining clear next steps and accurate forecasts.
• Identify opportunities for repeat business, renewals, and account expansion through ongoing client engagement.
• Maintain accurate HubSpot CRM records, including activities, opportunity stages, notes, and forecasts.
• Collaborate with Marketing and Operations to ensure a seamless client experience from first conversation through delivery.
• Meet and exceed monthly and quarterly revenue targets.

You Should Have:

• 5 to 10+ years of B2B consultative sales experience with responsibility managing opportunities from discovery through close.
• Experience selling corporate training, learning solutions, or professional services to HR, Learning & Development, and executive stakeholders.
• A proven track record of consistently achieving or exceeding sales quotas, with the ability to clearly articulate personal revenue contributions, average deal sizes, sales cycles, and conversion performance.
• Strong consultative selling skills, including discovery, active listening, solution recommendations, negotiation, and closing.
• Proven experience managing a high-volume pipeline of consultative sales opportunities, including navigating complex buying processes, engaging multiple stakeholders, and managing larger strategic opportunities when needed.
• Strong organizational and time-management skills, with experience using HubSpot or a similar CRM for pipeline management and forecasting.
• A proactive, self-directed approach to sales, with the ability to work independently and collaborate effectively across teams.
• A customer-first mindset, strong relationship-building skills, and a genuine interest in helping organizations improve workplace culture.
• Familiarity with solution selling methodologies (SPIN, MEDDICC, etc.).

Compensation & Benefits:

• Total Compensation: On-target earnings (OTE): $150,000 - $175,000 CAD (base salary + uncapped commission with additional earning potential through accelerators for exceeding sales targets).
• Comprehensive health and dental benefits.
• Remote-first team: work from anywhere in Canada.
• 3 weeks vacation plus 3 flexible leave days for personal, cultural, or religious observances.

Other Details:

• Fully remote role based in Canada.
• Standard hours: 9 a.m. – 5 p.m. EST (flexibility required for client scheduling).
• Occasional travel within North America for team and company meetings may be required.