At BIG Digital, we build technology people actually see, touch, and experience in the real world.

Our interactive technology powers experiences for some of the world’s biggest brands and Fortune 100 organizations across retail, sports and entertainment, healthcare, live events, and enterprise environments.

We bring hardware, software, AI, analytics, and managed services together to solve complex business challenges and create experiences that engage millions of consumers.

And we’re growing.

We’re looking for an exceptional Enterprise Account Executive who knows how to open doors, build relationships at the highest levels, and turn complex opportunities into significant business.

This isn’t a role where you’ll inherit a territory and wait for leads.

We want a builder.

Someone who gets excited about creating opportunities. Someone who can walk into a conversation with a major brand, retailer, venue, agency, or enterprise organization, understand what they’re trying to accomplish and bring together the right technology to make it happen.

If you’re energized by big ideas, complex deals, recognizable clients, and the opportunity to help shape the next stage of a growing technology company, we should talk.

The Role This is a strategic enterprise sales role for someone who can create opportunities, navigate complex organizations, and close meaningful business.

You’ll own the sales process from prospecting through close, working directly with senior decision-makers to understand business challenges and develop integrated technology solutions that combine hardware, software, AI, analytics, and services.

You’ll report directly to the Chief Growth Officer and work closely with leadership,



marketing, product, and operations.

What You’ll Do

Build and manage a strong enterprise pipeline

Prospect and develop new strategic accounts across North America

Build relationships with senior executives and decision-makers

Lead consultative sales engagements from discovery through close

Develop proposals and solutions that address real business challenges

Negotiate and close complex enterprise opportunities

Grow existing accounts into long-term partnerships

Collaborate with internal teams to develop and deliver winning solutions

Represent BIG Digital at client meetings, trade shows, and industry events

Maintain accurate pipeline and forecasting within CRM

What We’re Looking For You’re a builder. You know how to open doors, create opportunities, and turn relationships into long-term business.

Ideally, you have:

[5+] years of enterprise B2B sales experience

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A proven record of meeting or exceeding sales targets

Experience selling integrated technology solutions that combine hardware and software, ideally with SaaS, services, analytics, or other components.

Strong presentation, negotiation, and communication skills

Confidence working with executive-level decision-makers

Strong prospecting and new-business development capabilities





Practical fluency with AI and modern sales tools

Experience in retail technology, digital signage, experiential marketing, sports and entertainment, SaaS, AV, customer engagement technology, or related industries is an advantage.

An existing network within major brands, retailers, agencies, sports organizations, venues, or enterprise clients is a significant advantage.

Travel This role includes travel throughout Canada and the United States for client meetings, trade shows, conferences, and customer presentations.

What Success Looks Like Within your first year, you’ll:

Open new strategic accounts

Close significant six- and seven-figure enterprise opportunities

Expand existing customer relationships

Help drive BIG Digital’s next stage of growth

Competitive base salary, advantages and commission/bonus structure.

Additional compensation and benefits include:

Uncapped commission

Quarterly incentive program

Annual bonus opportunities

Health and dental benefits

Paid vacation

Hybrid work environment

Why BIG Digital? You won’t be selling technology hidden behind a login screen.

You’ll be selling highly visible, real-world experiences used by leading brands and millions of consumers, while helping customers rethink how they engage people across physical spaces.

BIG Digital is growing, and this role will play a meaningful part in what comes next.

Ready to build something BIG?

We’d like to hear from you.

We’d love to hear from you.

BIG Digital is an equal opportunity employer and is committed to creating an inclusive workplace.

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📌 Enterprise Account Executive (Winnipeg)
🏢 Big Digital
📍 Winnipeg