Director, Acquisition & Retention

Questrade Financial Group; Toronto; Hybrid; CAD 180,000 - 250,000; Full time

Benefits offered by this job

Health & wellbeing programs

Paid vacation, personal and sick days

Competitive compensation and benefits

Job summary

Questrade Financial Group is seeking a Director of Acquisition & Retention to own the revenue-driving transition from prospect to funded client. You will lead cross-functional initiatives to maximize conversion velocity through AI-enabled analytics, streamlined onboarding, and a unified hybrid inbound/outbound growth engine.

You will partner with Marketing, Product, and Engineering to optimize CRM, dialer strategies, and self-service tools, while ensuring high-account funding, retention, and

Qualifications

• University degree in Business, Finance, or Engineering; MBA or advanced certification highly preferred.
• 10+ years of leadership experience in Financial Services or Fintech with revenue responsibility.
• 5+ years in senior sales management or revenue operations leading large teams (40+).
• Expertise in Sales Effectiveness frameworks and playbooks to accelerate conversion velocity.
• Experience with Salesforce CRM, dialer systems and marketing automation.
• Proven ability to translate funnels and churn data into actionable insights.

Responsibilities

• Own the Growth Infrastructure roadmap and CRM lead logic optimization.
• Lead cross-functional design with Marketing, Product, and Engineering to align funnel and capacity.
• Drive AI adoption for predictive analytics like churn modelling and lead nurturing.
• Establish and enforce retention protocols and conversion velocity metrics.
• Bridge Marketing/Sales channels to ensure zero funnel leakage and funded accounts.

Skills

Sales leadership

Financial services

CRM Salesforce

Leadership experience

Hybrid inbound/outbound

AI in sales

Data analytics

Executive presence

Power BI/Tableau

Education

Bachelor's degree in Business/Finance/Engineering

MBA preferred

Tools

Salesforce (CRM)

Dialer management (Genesys)

Marketing automation tools

Job description

Questrade Financial Group (QFG), through its companies - Questrade, Questbank, Questrade Wealth Management, Community Trust Company, Zolo, and Flexiti, provides securities and foreign currency investment, professionally managed investment portfolios, mortgages, real estate services, financial services and more. We use cutting-edge technology to help Canadians become much more financially successful and secure.

At QFG, we combine human-centric collaboration with AI-driven innovation to redefine financial services. The ideal candidate will be a catalyst for change, using AI to transform and deliver unparalleled customer experiences and shaping a future where AI empowers our teams to do their best work.

Join our diverse, inclusive, and hybrid workplace to unleash your creativity and nurture your curiosity without limits. If you share this sense of infinite possibility, come shape your future at QFG.

What’s in it for you as an employee of QFG?

• Health & wellbeing resources and programs
• Paid vacation, personal, and sick days for work-life balance
• Competitive compensation and benefits packages
• Work-life balance in a hybrid environment with at least 3 days in office
• Career growth and development opportunities
• Opportunities to contribute to community causes
• Work with diverse team members in an inclusive and collaborative environment

This job posting is for an existing vacancy.

We’re looking for our next Director, Acquisition & Retention. Could It Be You?

The Director, Acquisition & Retention is the executive business owner for the most critical revenue-generating phase of the client lifecycle: the transition from prospect to funded, active client. This role is responsible for maximizing "Conversion Velocity" by eliminating operational and psychological friction during the onboarding and funding process.

Leveraging a sophisticated background in Sales Effectiveness and Strategic Planning, this leader is the architect of the firm's Growth Infrastructure. You are responsible for integrating the specialist-led "Save" teams and acquisition squads into a unified "Hybrid Inbound/Outbound" engine. You own the Scale Paradox for the growth vertical: ensuring that as marketing lead volume increases, the conversion efficiency and client "save" rates improve through superior lead-logic, systemic automation, and a culture of "Extreme Ownership."

Need more details? Keep reading…

In this role, responsibilities include but are not limited to:

Service Delivery & Growth Velocity

• Conversion Command Center: Orchestrate a specialist-driven "Growth Middle Office" that manages the complex transition from lead to funded account. Direct the strategic evolution of Multi-Channel Engagement, ensuring that dialer strategies, SMS, and voice interactions are optimized for maximum conversion and retention.
• Strategic Capacity Partnership: Collaborate with the centralized Workforce Management (WFM) team to optimize the deployment of resources. Ensure peak conversion service levels during high-intensity periods (e.g., RRSP Season) by translating marketing spend and lead-gen forecasts into actionable pod scheduling requirements.
• Culture of Extreme Ownership: Foster a culture where specialists act as "Journey Owners," ensuring they possess the deep product expertise (Options, Registered Plans, Precious Metals) required to provide high-fidelity technical guidance that builds immediate trust and funds accounts.
• Growth Scorecard Management: Own the aggregate pod performance metrics, including Funding TAT, Lead-to-Funded conversion ratios, Propensity-to-Attrite "Save" Success Rates, and NPS for new clients.

Product Strategy & Growth Infrastructure

• Growth Infrastructure Roadmap: Serve as the primary executive stakeholder for the "Acquisition & Retention" technology roadmap. Prioritize the optimization of CRM (Salesforce) Lead Logic, automated dialer management, and self-service "Save" tools.
• Friction Economics: Quantify the "Cost of Friction" in the onboarding journey; prepare board-ready business cases to secure Product/Engineering investment for Straight-Through Onboarding and automated account funding.
• AI-Enabled Transformation & Scaling: Champion the strategic adoption of AI and Predictive Analytics within the pod; collaborate with AI Engineering to deploy solutions such as Propensity-to-Churn Modeling and automated lead nurturing to enhance retention before clients take action to leave.
• Cross-Functional Design: Collaborate with Marketing, Product, and Engineering to ensure that top-of-funnel marketing initiatives are perfectly aligned with downstream operational capacity and execution capabilities.

Strategic Sales-Ops Integration & Governance

• Sales-to-Ops Hybridization: Act as the primary executive bridge between Marketing/Sales channels and the back-office. Ensure that growth initiatives are operationally supported and that sales-driven leads are transitioned into funded accounts with zero "funnel leakage."
• Retention Governance & Protocol: Establish and enforce the enterprise-wide "Save" protocols, ensuring that specialized retention competencies are embedded into the service model to protect the firm’s AUM.

Leadership Attributes

• Entrepreneurial Boldness: Drives a culture of urgency; views every "stalled" account as a lost opportunity for the client and the firm.
• Passion for Customers: Deeply understands the client's perspective during the high-anxiety phase of moving their first dollar to Questrade.
• Talent Mastery: Invests time in inspiring and developing a team capable of balancing high-volume processing with high-touch relationship management.

So are YOU our next Director, Acquisition & Retention? You are if you…

• Have a University degree in Business, Finance, or Engineering. An MBA or advanced professional certification in Strategic Sales (e.g., Korn Ferry/Miller Heiman) is highly preferred.
• Have 10+ years of progressive leadership experience in Financial Services or Fintech, specifically senior sales leadership and financial accountability with a proven track record of delivering bottom-line commercial results against a substantial sales budget and driving scalable growth.
• Have 5+ years’ experience in a senior sales management or revenue operations role, with demonstrated success leading large, high-performance teams (40+ people capacity) within a high-volume, hybrid inbound/outbound contact center environment.
• Have authoritative expertise in Sales Effectiveness frameworks, with a clear history of translating these methodologies into high-impact digital/voice "playbooks" that directly accelerate conversion velocity and maximize revenue.
• Have advanced experience with Salesforce (CRM) architecture, dialer management systems (e.g., Genesys), and marketing automation tools.
• Have product ownership & ROI expertise, with a proven ability to build compelling business cases for tech investment by quantifying the impact of conversion friction on top-line revenue.
• Have exceptional skills in translating complex conversion funnels and churn data into actionable insights. Familiarity with SQL, Power BI, or Tableau is a significant asset.
• Have strong executive presence with exceptional presentation skills; strong ability to influence Marketing and Product executives to align roadmaps with operational realities.
• Are creative, adaptable, and a team player with an infectious positive attitude and a drive to lead the industry in "Conversion-to-AUM" metrics.

At Questrade Financial Group of Companies, with multiple office locations around the world, we are committed to fostering a diverse, inclusive and accessible work environment. This is an environment where individuals are treated with dignity and respect. Here, the unique skills and experience you bring will be valued. You will be supported and motivated, so that you can harness your unlimited potential. Our team reflects the diversity of the communities we serve and operate in. Having a collaborative and diverse team helps us push boundaries to bring the future of fintech into existence -not only for the benefit of our customers, but for those who build their career with us.

Questrade Financial Group of companies Applicant Tracking System utilizes artificial intelligence (AI) for application screening. The AI system operates on predetermined criteria, with final decisions subject to human review.

Candidates selected for an interview will be contacted directly. If you require accommodation during the recruitment/selection process, please let us know and we will work with you to meet your needs.