Sales Lead

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 Sebastian, Director of Revenue Operations at Loop. We’re looking for a Sales Lead to lay the foundation for Loop’s outbound sales engine. If you’re a player-coach who thrives in a fast-paced startup environment and knows how to build and scale outbound sales teams targeting SMBs, 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 an entrepreneurial and hands-on sales leader to build and lead our outbound SMB sales function. You will start by personally owning pipeline development and closing deals, but simultaneously work on hiring, coaching, and scaling a high-performing inside sales team.

This is not a pure management role, you’ll be expected to lead from the front. You’ll be responsible for building a pipeline and closing new business while also creating the sales playbook, and building a culture of execution and accountability. You’ll work closely with Loop’s leadership, product, and growth teams to ensure sales is tightly aligned with company goals.

What You'll Be Doing

Hands-On Sales Execution

• Prospect, pitch, and close deals with SMBs across Canada.
• Manage the full sales pipeline, including your own pipeline in the early stages.
• Continuously refine messaging, cadence, and outbound strategies based on what works.
• Own the early-stage customer experience post-sale, ensure successful onboarding, delivery on what was promised, and revenue realization.
• Act as a bridge between sales and operations to ensure a smooth handoff and high customer satisfaction.
  
  

Team Building & Leadership

• Recruit, onboard, and coach a team of outbound-focused BDRs and/or AEs.
• Design and implement structured onboarding programs to ramp new hires quickly and effectively.
• Build a culture of performance, learning, and accountability—setting high expectations and giving your team the tools to meet them.
• Conduct regular 1:1s, pipeline reviews, and call coaching sessions to improve team capability and execution quality.
• Act as a mentor and motivator—bringing energy, urgency, and discipline to every part of the sales motion.
  
  

Sales Strategy & GTM Infrastructure

• Develop and implement a scalable outbound sales playbook.
• Define sales KPIs and report performance regularly to the leadership team.
• Work with RevOps and Growth Marketing to to build a best in class GTM tech stack, refine ideal customer profiles, lead scoring, and messaging for outbound channels.
  
  

Experimentation & Feedback Loops

• Constantly test new tactics—channels, scripts, incentives, etc.—to find the most effective paths to conversion.
• Serve as the feedback loop between customers and Loop’s product/growth teams to help refine our offerings and go-to-market approach.Become an expert in understanding Loop’s products and how they can add value to customers. Be able to understand where Loop fits into the financial services ecosystem for customers so that you can position Loop’s solution in a compelling manner.
  
  

What We’re Looking For

Must-Have Skills & Experience

• 5+ years of sales experience selling to SMB customers.
• 1+ years of experience building and leading outbound teams (BDRs or AEs).
• Demonstrated ability to drive consistent performance across individual contributors via coaching, clear process, and cultural leadership.
• Experience developing outbound sales playbooks.
• Strong organizational skills and ability to manage multiple priorities in a fast-moving environment.
• Ability to distill complex products into simple, compelling messages.
  
  

Mindset & Style

• You’re a “roll-up-your-sleeves” leader who leads by example.
• You’re hungry, ambitious, and obsessed with hitting targets.
• You’re as comfortable with outreach and closing as you are in 1:1s or performance reviews.
• You take full ownership of outcomes and find ways around obstacles.
  
  

It's a Bonus if You Have

• Experience in B2B Software or Financial Services.
• Experience working with small teams, particularly at start-ups.
• One year of experience in a management position.
  
  

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.
  
  

People You'll Be Working With

• Sebastian, Director of Revenue Operations
• Hassan, Sales Development Representative
• Jeff, Head of Operations
• Cato, CEO and Co-Founder
• Sarah, Chief of Staff
  
  

What We Offer

• Salary range CAD$80,000 - $95,000 base annual, commensurate with experience
• A rewarding commission structure for successful lead conversions
• 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 Mondays (we take recommendations!)
  
  

Interview Process

• 30 minutes video call to discuss the opportunity and the organization with Sebastian, Director of Revenue Operations
• 60 minutes in person meeting with 2 team members
• 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 submit along with your resume and a brief paragraph about yourself and an overview of how you would plan to build a sales team at Loop.

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!