Outbound Associate Jobs in Whitby, ON (NOW HIRING)

Strategic Leadership 

• Define and execute the Direct-to-Consumer growth strategy, including annual sales, marketing, and P&L objectives working collaboratively with the leaders of each of these functions. 

• Translate corporate goals into actionable plans for marketing, sales, and service execution. 

• Partner with Strategy and Marketing to optimize the value proposition, pricing, and go-to-market strategies for D2C offerings. 

Customer Acquisition & Sales Performance 

• Oversee the lead generation strategy and execution between Marketing and Product optimizing for CAC, quality of customers and number of customers.   

• Oversee the team managing all inbound leads, ensuring exceptional customer experience, rapid response times, and strong conversion metrics. 

• Define the overall strategy to manage inbound leads and outbound communications for the channel.  

• Continuously optimize the sales funnel from awareness through application to funding, identifying friction points and opportunities for improvement. 

• Work with marketing to define the nurture strategy and oversee execution. Optimize the direct-to-consumer journey including marketing support.  

• Implement and monitor KPIs that measure lead quality, conversion, cost per acquisition, and customer satisfaction. 

Operational Excellence & Enablement 

• Build and refine processes, tools, and training to enable efficient and consistent execution across the D2C funnel. 

• Lead CRM and digital tool strategy and implementation to support scalability and performance. 

• Ensure data quality, compliance, and regulatory adherence across all customer touchpoints. 

Technology & Innovation 

• Champion digital transformation within the D2C business - leveraging automation, analytics, and new technologies (e.g., chatbots, AI lead scoring) to enhance efficiency and customer experience. 

• Partner with Technology and Data teams to evolve the sales and marketing tech stack, enabling real-time insights and streamlined workflows. 

People Leadership 

• Lead, coach, and develop a high-performing team across sales operations, customer engagement, and marketing enablement. 

• Foster a culture of accountability, collaboration, and continuous improvement. 

• Champion the voice of the customer and frontline teams across the organization. 

Cross-Functional Collaboration 

• Work closely with Legal & Compliance, Credit, Product, and Marketing to ensure alignment on programs, policies, and brand standards. 

• Serve as the business owner for all D2C initiatives, driving alignment and decision-making across multiple stakeholders. 

Job Complexities/Thinking Challenges:  

• Requires a balance of strategic thinking and hands-on execution, driving both growth and operational discipline. 

• Must quickly understand the product, market, and customer base to make informed decisions that drive revenue and customer satisfaction. 

• Operates in a dynamic, high-growth environment requiring adaptability, creativity, and a test-and-learn mindset. 

• Involves collaboration across multiple departments with competing priorities - requiring strong relationship-building and influence skills. 

• Must maintain a start-up mentality within a larger organization, combining entrepreneurial drive with structure and accountability. 

Accountability:  

• The incumbent will directly manage the Customer Experience Sales Team (4 individuals today) and have dotted line accountability of marketing, technology, contact centre, underwriting and servicing responsibilities.  

• The individual will be responsible for making decisions that drive the key metrics for this role - prospects, leads, applications and funding. 

Internal/External Contacts: 

• The individual will manage and interact with marketing and technology suppliers including our record agency, SEO provider, POS provider etc.  

• This will involve helping set the strategy, managing execution and key metrics related to these external contacts. Additionally, this individual will help negotiate key contracts for approval by the VP, Decumulation.  

• Internally, key contacts include: marketing, technology, contact centre, underwriting and servicing.  

Physical Demands/Working Conditions: 

• The job will require the individual to be in office 1-5 days a week with a few meetings a month with suppliers / vendors a quarter that will take place around Toronto. No travel is expected outside Ontario.  

• This role is not physically demanding and will require the individual to spend most of the day at a desk.