Sales Manager / Sales Coach-Trainer, Working Capital

Sales Manager / Sales Coach-Trainer, Working Capital

This role trains, coaches and motivates the Working Capital sales team, and uses AI to streamline our process, rebuild our reporting and run automated quality and compliance checks. It also distributes leads, backs up the Toronto sales manager, helps run the office and its culture, and leads the team when the Director of Sales is away.

About the role

You are the right hand to the Director of Sales on the sales floor. You help train, coach and motivate the team, build the tools and documents that make them better, use AI and data to manage performance, and keep leads moving to the right people. When the Director is sick or on vacation, you lead the team and drive it to results.

You work under the Director's guidance across the Account Executive, Account Management and BDR teams, alongside the AM Manager, the BDR Team Lead and Sales Support, and you partner with the Toronto Senior Sales Manager. The Director decides how onboarding, training, coaching and documentation are designed. You help create and deliver them, and you carry the day-to-day.

Reports to: Director of Sales

Works with: Account Executives, the AM Manager, the BDR Team Lead and Sales Support

Location: Montreal, on-site, with travel to Toronto as needed

Training and coaching

You carry the day-to-day delivery of onboarding, coaching and ongoing training, working from the programs the Director designs.

• Deliver onboarding for new hires in each role, and own their ramp against Week 1, Month 1 and Quarter 1 goals
• Run coaching as a structured, repeatable process: call reviews, role-play, deal reviews, and group and one-on-one sessions
• Help build and deliver Vault University, the ongoing training program that follows onboarding, with a curriculum, calendar and clear learning goals for each role
• Lead sessions on pricing, objection handling, discovery and deal troubleshooting, based on the gaps the data shows
• Keep every rep's coaching plan current, so each person knows which trainings and coaching they get, how often, and from whom
• Track coaching and training against clear metrics: sessions held versus planned, rep understanding and performance lift
• Coach the AM Manager and the BDR Team Lead on how to coach their own teams, when the Director asks

Documentation and motivation

You turn what works into materials the whole team can use, and you keep the energy on the floor high.

• Build onboarding documents, playbooks, presentations and a searchable resource library, with the Director approving what is released
• Use AI to create training materials and continuing education that are simple, well designed and easy to repeat
• Capture what top performers do differently and turn it into scripts, call guides and checklists
• Run contests, challenges and team activities that push the team toward its goals
• Recognize wins in the huddles and across the floor, and help celebrate achievements
• Keep a pulse on morale and flag concerns to the Director before they affect performance

Performance management through AI and data

You use AI, reporting and data to show each rep where they are strong and where they are weak, and to push the team toward its targets.

• Build and maintain AI tools, dashboards and reports that track dials, submissions, conversions by lead source and industry, approved-to-funded ratio, deal size and pipeline health
• Use AI and data to find root causes, review closed and lost deals, and learn what top performers do differently
• Set coaching priorities from the gaps the data shows, and follow up to confirm the performance improves
• Work directly with anyone who is behind target, daily and weekly, to get them back on pace
• Hold reps to the written standards for their role, and support the Director's performance improvement plans and quarterly reviews with data and notes
• Flag performance and personnel issues to the Director early, and bring a recommendation

Streamlining our process with AI

You take the way we sell today and use AI to make it faster, simpler and more consistent.

• Map our sales process from lead to funding, and find the steps that can be automated, shortened or removed
• Rebuild our reporting so the team and leadership see the right numbers, in near real time, with less manual work
• Build AI-powered tracking and coaching tools that tell each rep what to do next and where to improve
• Create efficiencies that give reps more time to sell, and measure the time saved
• Test new tools and automations, document what works and roll it out to the team
• Keep the whole system documented, so it can be maintained and handed over

Quality assurance and automated spot checks

You build and run the system that checks whether the team is selling our advances correctly and staying compliant, using AI tools to automate the checks and review activity at scale instead of sampling a few calls.

• Build out AI tools that automate the checks on calls and activity, with regular reports to the Director and, where needed, to compliance
• Check that reps never describe our advances as loans, and that they present them accurately as a purchase of future revenues, in line with our agreement and compliance rules
• Check that reps ask for the credit check consent properly, at the right point in the conversation
• Detect fake or padded dialing, such as very short calls, repeated dialing of the same numbers, or activity that does not match call logs
• Check that calls meet the agreed criteria: required disclosures, accurate terms, no promises of guaranteed outcomes, and a dated next step
• Review flagged calls with the Director, and turn the findings into coaching and training
• Track trends by rep, lead source and product, and report compliance and quality results on a regular schedule
• Make sure call monitoring follows our recording consents, privacy policy and applicable law, with advice from compliance and legal

Lead distribution and pipeline

You make sure leads reach the right people quickly and fairly, with Sales Support helping with the logistics.

• Distribute leads across the team based on performance and results, so every rep has a healthy, fair mix
• Review the lead mix regularly and adjust it using conversion and funded volume
• Watch speed to lead: BDR transfers within 1 minute, marketing leads within minutes and DRs within minutes of receipt
• Monitor pipeline and queue performance across all lead sources, and make sure stalled deals are followed up
• Report on lead source performance to the Director, with recommendations

Leading the team when the Director is away

When the Director is sick or on vacation, you run the floor so the team never loses momentum.

• Lead the daily morning meeting and set the priorities for the day
• Keep the team focused on revenue-generating activity and on pace to its funding targets
• Handle deal blockers and escalations with credit and fulfillment, and listen live to decision calls
• Keep coaching sessions, training and lead distribution running as planned
• Handle day-to-day issues and escalate personnel matters to the Director, or to the designated contact while the Director is away
• Keep morale and standards high, so the team sees you as a leader in the Director's place
• Hand the Director a short summary of results and open items on their return

Supporting Toronto

You back up the Toronto Senior Sales Manager and help the Toronto team succeed.

• Support the Toronto sales manager where needed, and act as their backup when they are away
• Travel to Toronto when needed to support training, onboarding, coaching and the day-to-day running of the floor
• Share the tools, reports, spot checks and training you build, so both offices work to the same standards
• Help keep onboarding, coaching and training practices consistent between Montreal and Toronto

Office, events and culture

You help run the office and build the culture, together with the Director, so the team has a place where high performance and fun go hand in hand.

• Help manage the office day to day and keep it a professional, productive environment
• Plan and coordinate events, including in-office and out-of-office events and team-building activities that build a strong team dynamic
• Make sure the office is stocked with the supplies and items the team needs, and reorder before anything runs out
• Coordinate with IT so every team member has the equipment they need, including new hires ready on day one
• Share responsibility with the Director for office culture and environment, and act on what the team tells you
• Keep the team engaged and flag morale concerns to the Director early

Systems and process

You know how the whole process works, so you can answer any question and fix what slows the team down.

• Learn every system the teams use, including the CRM, Flinks and supporting tools, and teach them to new and existing reps
• Understand how credit, fulfillment and account management work from beginning to end, and build relationships with those teams
• Spot inefficiencies and bring solutions, so the team spends more time selling
• Drive adoption of new processes, tools and initiatives, and keep documentation up to date

What you bring

• 3+ years in sales, including experience coaching, training or managing sales reps, ideally in a high-volume, inside sales environment
• A record of developing reps and lifting their results
• Experience building onboarding, training and coaching materials that people actually use
• Hands-on experience using AI and automation to streamline processes, rebuild reporting and build tracking, coaching and quality-check tools, and the skill to turn data into coaching and action
• The ability to lead a team with credibility when your manager is away, and a willingness to travel to Toronto when needed
• Strong performance management skills, including difficult conversations
• A motivating, positive style that holds a high bar and follows through
• Strong communication, a polished presence and good judgment
• The ability to learn systems and processes quickly and explain them simply
• Experience in lending, fintech, financial services or working capital is a strong asset
• Bilingual English/French, an asset

What we offer

• Compensation range and bonus structure
• Vacation
• Benefits
• Other perks, including a growth path toward Director or senior sales leadership