Senior Sales Manager, Working Capital (Toronto)

Senior Sales Manager, Working Capital (Toronto)

Location:
Toronto, ON (on-site)

A bout the Role and Team Structure

You will lead and scale the Toronto Working Capital sales team, which today has five people. You are first and foremost accountable for people and performance. You step in as the team's leader, learn what each person does well, raise the standard, and grow the team to match Montreal's size and output. You manage to the data, build and run world-class onboarding, training and coaching, and partner across the organization to make the whole process run better. You are a great communicator who brings professionalism to the team and builds a culture where high performance and having fun go hand in hand.

Toronto and Montreal are separate teams, each with its own leader, run as one sales organization. You and the Montreal Sales Leader share the same standards, back each other up, and share responsibility for scaling the business.

Partnership with Montreal

- Share in scaling the business and in combined performance

- Share best practices, wins and lessons in both directions, and bring the two teams together as one organization

- Co-develop and share structured, documented coaching, training and onboarding practices so every rep gets the same experience in both cities

- Work with the Montreal Sales Leader as co-owners of one sales organization and as each other’s backup, covering leadership, training and onboarding at either office when needed

People Leadership and Performance Management

You are the single accountable leader for every person on the Toronto team.

People leadership

- Lead, develop and scale a high-performing Toronto sales team

- Get to know each current team member quickly: their strengths, gaps, goals and what motivates them

- Assess the team in your first 60–90 days, then set a clear plan for each person against the shared standards

- Keep a constant pulse on the sales floor, with a real-time presence that keeps the team focused on revenue-generating activity and ensures issues are heard and addressed as they arise

- Work with each team member daily toward their goals and the goals of the business

- Set the standard for showing up on time, fully engaged and giving full effort

- Be the escalation point for performance and personnel challenges in Toronto

Performance management

- Own the daily, weekly, monthly and quarterly performance of the Toronto team, and 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, so each person knows exactly how they are measured

- Put structured performance improvement plans in place for underperformers: repeatable, tracked, clearly communicated and focused on results

- Run quarterly performance reviews covering where each person is, where they want to be, and a clear plan to close the gap

- Make timely decisions when someone is not the right fit

Hiring and Scaling the Team

- 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 the gaps you find in the current team

- 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 by retaining and developing strong performers

- Be the primary contact for Toronto personnel issues and conflict resolution

- Oversee scheduling and vacation planning for the Toronto team

Onboarding and Ramp

You own onboarding for every new Toronto hire and are accountable for how fast they reach full productivity. You also bring the current team in line with the shared onboarding and training standards.

- Build onboarding documentation and presentations for each role jointly with the Montreal Sales Leader: simple, well designed, scalable and repeatable

- Include daily, weekly and monthly plans, system training (the CRM, Flinks and every other tool the teams use), sales training and all other required modules

- Put targets and expectations inside the onboarding documents, with clear Week 1, Month 1 and Quarter 1 goals for each role, and ramp benchmarks (time to first deal, activity and conversion targets) so progress is visible and measurable

- Run existing team members through any onboarding and training modules they haven't yet had, so everyone in both offices works to the same standard

- Personally onboard each new hire and own their ramp until they reach full productivity

- Review and improve the program after every cohort, using new-hire feedback and ramp results

- Use AI to help build and improve onboarding and continuing education

Training, Coaching and Vault University

- 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: a formal ongoing training program that follows onboarding, with a curriculum, calendar and clear learning goals for each role

- Once launched, 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, so every rep knows which trainings and coaching they receive, how often, and from whom

- 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 (sessions held vs. planned, rep understanding, performance lift)

- Co-build playbooks, documentation and a searchable resource library with the Montreal leader so practices stay identical across both offices

Data-Driven Leadership and Revenue Ownership

- 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

Systems, Process and Cross-Functional Partnerships

- Learn every system used by the teams, including the CRM, Flinks and supporting tools, so you can answer any question

- 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, and drive adoption of new processes, tools and initiatives

- Understand how every department in the Working Capital division works from beginning to end, and become an expert on the full process

- Build bridges and lasting relationships between departments, and 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 [confirm ownership by office]

Toronto Culture and Communication

- Own the culture of the Toronto team and be the leader the team looks to, including through the transition to new leadership

- 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, so every expectation, priority and change is understood

- 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, creating a high-performance culture that is also fun to be part of

- 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

What You Bring

- 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

What We Offer

- Compensation range and bonus structure

- Vacation

- Benefits

- Other perks