About Loop

Loop is a fast-growing FinTech high growth startup that enables businesses to seamlessly manage money around the world so our clients can access more markets, accelerate their growth and simplify their operations with the only truly cross-border banking platform. Loop is enabling the next generation of businesses to thrive around the world and we are looking for ambitious people to join our mission.

About the Role

Hi, I’m James, Head of Growth at Loop. I am hiring a Senior Outbound Account Executive to help drive Loop’s next stage of growth. You’ll own the full sales cycle - running discovery, crafting tailored solutions, and closing deals that move the business forward. If you’re a results-driven individual who thrives in a fast-paced startup environment, this role is for you.

This role is an onsite position 5 days per week at our downtown Toronto office (Adelaide and Spadina).

Where You Come In

We’re looking for a proactive, ambitious sales professional to take the lead on Loop’s outbound motion. You’ll form relationships with business owners and finance executives, uncover their pain points, and help them understand exactly how Loop can make their financial operations smoother and more effective.

You’ll be expected to build your own pipeline of leads through outbound activities, running strong discovery calls, manage full deal cycles, and build trust that converts interest into new business.

As one of our first sales hires, you’ll start by owning the full outbound sales motion, and as we grow, you’ll have an opportunity to help shape the playbook and the team around it.

What You'll Be Doing

Full-Cycle Sales Execution

• Own the entire sales process from discovery to close with a strong understanding of the KPIs required to deliver results.
• Run thoughtful discovery conversations that uncover customer needs and align Loop’s solutions to their goals.
• Deliver engaging product demos that clearly communicate value and differentiation.
• Put together pitch decks and proposals for the customers you are engaging with.
• Build strong relationships with prospects and key decision-makers to drive trust and momentum.
• Maintain a healthy, well-managed pipeline and deliver accurate forecasts in our CRM.
• Close business and achieve quota attainment consistently.

Customer Insights & Strategy

• Act as the voice of the customer to gather and share feedback to inform product and GTM decisions.
• Identify emerging patterns, use cases, and opportunities for new segments or verticals.
• Refine messaging, positioning, and demo strategy.

Experimentation & Feedback Loops

• Continuously test new approaches to discovery, demos, and closing tactics to improve performance.
• Leverage data and insights to optimize the sales process and increase win rates.
• Contribute to the development of Loop’s sales playbook and help define what “success” looks like for the sales function.

What We’re Looking For

Must-Have Skills & Experience

• 3+ years of full-cycle closing experience selling to small to midmarket sized companies.
• Consistent track record of hitting or exceeding a $1M+ annual quota. Experience using Salesforce (or similar CRM), and outbound prospecting tools.

Mindset & Style

• You’re proactive, curious, driven and highly perseverant.
• You take ownership of outcomes and thrive in an unstructured, fast-moving environment.
• You combine hustle with thoughtfulness — always focused on creating real value for customers.
• You’re adaptable, collaborative, and eager to help build something from the ground up.

It's a Bonus if You Have

• Experience selling payments or other financial products
• Experience working with small teams, particularly at start-ups.

What's in it for you?

• Opportunity to build the sales function in a high-growth fintech startup.
• Strong support from the Loop team to help achieve your targets.
• Competitive salary, opportunity to develop a commission structure, and potential for equity.
• Chance to work in an energetic, fast-paced, and collaborative startup culture.

What we offer

• Salary range CAD$70,000-$85,000 base annual, commensurate with experience
• A rewarding commission structure based on closed business providing an OTE of CAD$150,000-200,000 (commission not guaranteed)
• Equity ranging 0.01-0.1%
• 3 weeks vacation
• Enrollment in group's health benefits after probation period
• This role is onsite in our downtown Toronto office
• Kitchen full of snacks and drinks to keep you going throughout the day
• Catered lunch on Fridays (we take recommendations!)

Interview Process

• 30 minutes video call to discuss the opportunity and the organization with Mandy, People and Business Operations Specialist
• 60 minutes in person meeting with James, Head of Growth and Hassan, Account Executive
• 60 minutes in person meeting with Sarah, Chief of Staff and Cato, CEO and Co-Founder
• Background check and offer

How to Apply

To apply for this position, please click “apply” and share your resume, alongside a brief paragraph about yourself and your previous experience. Your application will be reviewed by our recruiters and hiring managers; we do not use AI tools for screening or selection.

Loop is committed to creating a diverse culture. We encourage you to apply regardless of who you are or where you came from - what matters is the journey ahead. Put simply, if you’re unsure about your qualifications for this position, we’d still encourage you to apply!