Director, Acquisition & Retention

Questrade Financial Group

$120K — $150K *
Finance & Insurance
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • University degree in Business, Finance, or Engineering; MBA or advanced certification preferred.
  • 10+ years of leadership experience in Financial Services or Fintech with proven commercial results.
  • 5+ years in senior sales management or revenue operations roles leading large teams (40+ members).
  • Expertise in Sales Effectiveness frameworks, translating to impactful digital/voice 'playbooks'.
  • Advanced experience with Salesforce CRM and dialer management systems.
  • Product ownership and ROI expertise with ability to build investment business cases.
  • Exceptional skills in converting data analytics into actionable insights.

Responsibilities

  • Orchestrate a 'Growth Middle Office' to streamline lead-to-fund transitions.
  • Collaborate with Workforce Management to optimize staffing based on lead forecasts.
  • Foster a culture of 'Extreme Ownership' among specialists for enhanced client trust.
  • Manage performance metrics like Funding TAT and Lead-to-Funded ratios.
  • Serve as executive stakeholder for the 'Acquisition & Retention' tech roadmap, prioritizing optimization initiatives.
  • Quantify 'Cost of Friction' in onboarding for resource investment.
  • Champion AI adoption for retention solutions and predictive analytics.

Benefits

  • Hybrid work model offering flexibility for remote and in-office work.
  • Opportunities for professional development and growth within the organization.
  • Access to advanced tools and technology to enhance job performance.
  • Collaborative work culture emphasizing cross-departmental teamwork.
  • Focus on employee well-being with support systems in place.
Full Job Description
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.


Sounds like you? Click below to apply!

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