Senior Manager, Sales Performance and Enablement

Sienna Senior Living; Markham; On-site; CAD 97,000 - 121,000; Full time

Benefits offered by this job

Competitive compensation

Health & Dental Benefits

RRSP with Company Match

SOAR (Share Ownership & Reward)

Employee Share Purchase Plan

Continuous learning

Diversity and inclusion

Job summary

Sienna Senior Living is seeking a Senior Manager, Sales Performance and Enablement to drive data-driven insights and scalable performance across the Aspira Retirement Division. You will partner with cross-functional teams to improve occupancy, lead conversion, and move-in funnels, translating data into executable strategies.

Highlighting your experience in sales analytics, dashboards, and enablement, you will shape training programs and standardized processes to boost sales effectiveness across

Qualifications

• Bachelor's degree in Business, Sales, Marketing, Analytics, Operations or related field.
• 7+ years of progressive experience in sales performance, sales operations, sales enablement, business analytics, commercial operations, or related.
• Experience translating sales data and BI into actionable recommendations.
• Experience designing and implementing sales training, enablement programs, playbooks, or performance improvement initiatives.
• Strong understanding of sales funnel metrics, performance management, and conversion optimization.

Responsibilities

• Analyze sales performance trends across key metrics (occupancy, lead conversion, tours, move-ins).
• Develop and maintain dashboards, scorecards, and performance reporting for leadership.
• Translate data into actionable insights and recommendations for sales leaders.
• Partner with Data & Analytics to enhance reporting capabilities and KPIs.
• Identify gaps and recommend training, coaching, tools, or process improvements.
• Lead or support strategic projects to improve sales effectiveness and portfolio performance.

Skills

Sales analytics

Sales enablement

Performance management

Cross-functional collaboration

Education

Bachelor's degree in Business, Sales, Marketing, Analytics, Operations

Tools

CRM platforms

Dashboards

Job description

At Sienna, we empower our team members across Ontario, British Columbia, Saskatchewan and Alberta to help our residents live the life they desire and deserve. Our purpose is simple: to cultivate happiness in daily life!

What Sienna Offers: We aspire to cultivate an environment and culture where team members feel valued, heard and empowered to do meaningful work. We offer a number of programs and benefits that support team members’ financial, personal and professional needs:

• A competitive compensation and vacation package
• Employer Paid Health & Dental Benefits
• RRSP with Company Match
• Share Ownership and Reward Program (SOAR)
• Employee Share Purchase Plan with Company Match
• Continuous learning and growth so you have the skillset needed to succeed and take on new challenges
• A welcoming culture that values diversity and differing perspectives, experiences and beliefs

What You’ll Be Doing:

Reporting to Senior Director, Sales Strategy & Support, the Senior Manager, Sales Performance and Enablement drives sales performance across the Aspira Retirement Division through data-driven insights, operational improvement, sales enablement and consistent execution. This role serves as a critical partner, translating performance data into actionable strategies, identifying emerging risks and opportunities, and equipping sales teams with the tools, capabilities, and best practices needed to improve results.

The Senior Manager, Sales Performance and Enablement will work closely with cross-functional teams to strengthen sales effectiveness and establish scalable, standardized approaches to performance management and enablement.

How You’ll Succeed:

• Analyze sales performance trends across key metrics, including occupancy, lead conversion, inquiry-to-tour, tour-to-move-in, move-in volume, and related funnel performance.
• Develop and maintain executive-level dashboards, scorecards, and performance reporting that provide clear visibility into results, trends, and emerging risks and opportunities.
• Translate complex data into actionable insights and recommendations for sales leadership and Regional Sales Partners.
• Partner with Data & Analytics to enhance reporting capabilities, establish meaningful performance indicators, and develop predictive insights.
• Identify performance gaps and root causes, distinguishing between capability, process, market, and execution-related opportunities.
• Monitor the effectiveness of sales strategies and initiatives and recommend adjustments based on measurable outcomes.
• Identify capability and performance gaps and recommend targeted training, coaching, tools, or process improvements.
• Design, develop, and implement sales training and enablement programs aligned to business priorities and performance needs.
• Establish consistent sales processes and standards across the portfolio.
• Partner with Regional Sales Partners and field leadership to reinforce adoption, execution, and accountability.
• Identify opportunities to improve sales processes, operating rhythms, systems, and workflows.
• Lead or support strategic projects that improve sales effectiveness, productivity, and portfolio performance.
• Support the adoption of new sales technologies, tools, and systems, including change management, communication, training, and measurement of adoption.
• Serve as a strategic thought partner to Regional Sales Partners, helping translate performance data into practical actions and measurable improvement plans.
• Collaborate with cross-functional partners to align sales performance, operations, analytics, technology, and enablement priorities.

Who you are:

• Bachelor’s degree in Business, Sales, Marketing, Analytics, Operations, or a related field preferred.
• 7+ years of progressive experience in sales performance, sales operations, sales enablement, business analytics, commercial operations, or a related discipline.
• Experience translating sales data and business intelligence into actionable recommendations.
• Demonstrated experience designing and implementing sales training, enablement programs, playbooks, or performance improvement initiatives.
• Strong understanding of sales funnel metrics, performance management, and conversion optimization.
• Experience partnering with senior leaders and field-based sales teams in a complex, multi-location or multi-region environment.
• Excellent written and verbal communication skills, with the ability to communicate effectively at all organizational levels.
• Experience with dashboards, reporting tools, CRM platforms, and data analytics preferred.
• Demonstrated project leadership and change-management experience.
• Ability to manage competing priorities and deliver results in a fast-paced, complex environment.
• Experience working with Microsoft Suite (Word, Outlook, Excel, PowerPoint, etc.)

What you need to know:

• The salary range for this position is: $96,655.00-$120.818.50
• This is an on-site position at our Shared Support office in Markham
• Any offer of employment will be conditional upon a criminal background and references check.
• This posting is for a new position
• Sienna Senior Living may utilize artificial Intelligence to screen or assess applicants for this position.

Sienna Senior Living is committed to employment equity, diversity, and inclusion in the workplace. In accordance with provincial regulations, upon request, support will be provided for accommodations throughout the recruitment, selection, and assessment process.