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