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About the Role

You will lead and scale the Toronto Working Capital sales team, which today has five people. You are accountable for people and performance, raising the standard, and growing the team. You manage to the data, build world-class onboarding, training and coaching, and partner across the organization. You are a great communicator who brings professionalism and builds a culture where high performance and having fun go hand in hand. You and the Montreal Sales Leader share the same standards, back each other up, and share responsibility for scaling the business.

Responsibilities

Lead, develop and scale a high-performing Toronto sales team
Assess the team, then set a clear plan for each person against shared standards
Keep a constant pulse on the sales floor, focusing the team on revenue-generating activity
Work with each team member daily toward their goals and the goals of the business
Own the daily, weekly, monthly and quarterly performance of the Toronto team
Work directly with anyone who is behind to get them to target
Set clear expectations and standards for every role, communicate them in writing, and enforce accountability consistently
Define each role in writing: what it is, what success and failure look like, and the pathway for growth
Put structured performance improvement plans in place for underperformers
Run quarterly performance reviews
Make timely decisions when someone is not the right fit
Own hiring for Toronto sales roles end to end: sourcing, interviewing and making the final decision
Grow Toronto from its current five to match the size and output of Montreal, with a defined plan, timeline and hiring order
Decide which roles to add first based on pipeline, lead volume and team gaps
Use role scorecards, defined interview stages and a standing candidate pipeline, aligned with Montreal's process
Keep Toronto properly staffed, monitor turnover and work to minimize it
Be the primary contact for Toronto personnel issues and conflict resolution
Oversee scheduling and vacation planning for the Toronto team
Own onboarding for every new Toronto hire and ensure they reach full productivity
Bring the current team in line with shared onboarding and training standards
Build onboarding documentation and presentations for each role jointly with the Montreal Sales Leader
Include daily, weekly and monthly plans, system training, sales training and all other required modules in onboarding
Put targets and expectations inside the onboarding documents, with clear Week 1, Month 1 and Quarter 1 goals, and ramp benchmarks
Run existing team members through onboarding and training modules
Personally onboard each new hire and own their ramp until they reach full productivity
Review and improve the onboarding program after every cohort
Use AI to help build and improve onboarding and continuing education
Coach and train the Toronto team through role-play, call coaching, and group and one-on-one sessions
Help design, build and launch Vault University with the Montreal Sales Leader
Deliver Vault University to the Toronto team and keep improving it based on results
Run coaching as a structured, repeatable process with a written coaching and training plan for each role
Set training priorities based on performance gaps, and lead sessions on pricing, objection handling, discovery and deal troubleshooting
Track coaching and training against clear metrics
Co-build playbooks, documentation and a searchable resource library with the Montreal leader
Review performance data, identify gaps in conversion, activity and pipeline, and manage directly to them
Use AI and data to find root causes, analyze closed and lost deals, and learn what top performers do differently
Track and improve key metrics, including approved-to-funded ratio, conversion rates, dials, deal size and pipeline health
Own key Toronto revenue initiatives, such as the repaid book, BDR funding and decline management
Oversee pipeline and queue performance across all lead sources, allocate leads based on performance, and make sure stalled deals are followed up
Present Toronto performance plans and results to [CRO], with analysis and follow-ups delivered on time
Learn every system used by the teams, including the CRM, Flinks and supporting tools
Help build the documentation, systems and processes the organization needs to run efficiently and scale
Continuously remove inefficiencies so the team spends more time selling
Drive adoption of new processes, tools and initiatives
Understand how every department in the Working Capital division works from beginning to end
Become an expert on the full process
Build bridges and lasting relationships between departments
Resolve friction that affects deals, performance or the customer experience
Work with originator partners to align on goals and hold the relationship accountable for performance and communication
Own the culture of the Toronto team and be the leader the team looks to
Build trust quickly with the existing team and carry what's working into the next stage of growth
Communicate clearly and consistently with the team, leadership, Montreal and partners
Bring professionalism to the team, set expectations for how everyone works and represents the company, and model them
Build genuine relationships and lead with empathy
Organize in-office and out-of-office events, games and activities that build a strong team dynamic, and celebrate wins
Keep the team engaged and motivated, and address morale concerns before they affect performance

Requirements

5+ years of sales leadership experience, ideally in a high-volume, inside sales environment
A proven record of taking over and scaling high-performing sales teams, ramping new hires quickly and keeping turnover low
Experience assessing an existing team, building trust with it, and raising the standard
Strong performance management skills: setting standards, holding people accountable and handling difficult conversations
Experience building formal, repeatable onboarding, training and coaching programs from the ground up, with measurable results
Experience building the documentation, systems and processes that make a sales organization efficient and scalable
A collaborative style: you're a true partner to a peer leader and can share ownership and credit
Strong analytical skills and comfort using data and AI tools to diagnose problems and drive decisions
Exceptional verbal and written communication and a polished, professional presence
A warm, human leadership style that holds a high bar and follows through on commitments
Experience in lending, fintech, financial services or working capital is a strong asset
Bilingual English/French, an asset
Able to work on-site in Toronto

Skills

Sales leadership
People management
Performance management
Hiring
Onboarding
Training
Coaching
Data analysis
AI tools
Communication
Collaboration
Lending
Fintech
Financial services
Working capital

Location

Toronto, ON

Work Type

On-site
Full-time

Experience Level

Senior

Benefits

Compensation range and bonus structure
Vacation
Benefits
Other perks