Director, Commercial Strategy

Own the commercial performance strategy for pre-open, lease-up and occupancy-challenged residences, with clear occupancy, sales, pipeline and conversion objectives.

Diagnose the commercial drivers of underperformance and translate them into focused residence-level action plans with clear priorities, owners, timelines and expected outcomes.

Establish and lead a rigorous performance cadence for priority residences, including regular business reviews, action tracking, escalation of barriers and executive reporting.

Partner closely with Regional Operations, residence leaders, Sales and Marketing to strengthen lead generation, pipeline health, conversion, pricing and promotional strategy, referral development and local market execution.

Provide hands-on commercial leadership to challenged residences, including direct coaching and challenge of frontline sales teams, targeted field support and decisive intervention where performance is off plan.

Own pre-open and lease-up commercial readiness and execution, ensuring each residence has the demand generation, sales capability, pipeline and market activation required to achieve occupancy milestones.

Identify emerging occupancy risk early and mobilize targeted interventions before performance materially deteriorates.

Develop and drive 30/60/90-day recovery plans for occupancy-challenged residences, ensuring actions are practical, measurable and executed with urgency.

Challenge existing go-to-market approaches where results are not materializing. Recommend and, with the COO and functional leaders, drive decisive changes to sales resources, pricing, promotions, marketing investment, lead generation, referral strategy and local commercial execution when performance remains off plan.

Coordinate cross-functional support around priority residences and ensure teams remain focused on the few actions most likely to change occupancy trajectory.

Capture and scale successful practices from high-performing pre-open, lease-up and recovery situations across the portfolio.

Commercial Effectiveness & Field Enablement

Support sales force deployment, structure and resourcing decisions based on portfolio priorities and residence needs. Lead sales incentive compensation strategy and execution, ensuring incentives reinforce enterprise occupancy and commercial objectives. Partner with Sales and Marketing leaders on CRD capability, sales training and targeted development needs identified through residence performance. Support CRM and sales process effectiveness, with a focus on field adoption, disciplined lead management and consistent execution. Assess the effectiveness of key commercial initiatives and recommend where to continue, adjust or redirect investment.

Support sales force deployment, structure and resourcing decisions based on portfolio priorities and residence needs.

Lead sales incentive compensation strategy and execution, ensuring incentives reinforce enterprise occupancy and commercial objectives.

Partner with Sales and Marketing leaders on CRD capability, sales training and targeted development needs identified through residence performance.

Support CRM and sales process effectiveness, with a focus on field adoption, disciplined lead management and consistent execution.

Assess the effectiveness of key commercial initiatives and recommend where to continue, adjust or redirect investment.

Education & Experience

Bachelor’s degree in Business, Commerce, Marketing, Hospitality, or a related discipline; equivalent relevant experience will also be considered.

8–10+ years of progressive commercial, sales, operations, or revenue leadership experience, ideally in a multi-site consumer, hospitality, seniors living, real estate, or service-based organization.

Demonstrated track record of personally driving measurable revenue, sales and/or occupancy improvement, with clear examples of materially changing the trajectory of underperforming businesses or locations.

Significant experience directly leading, coaching and challenging frontline sales teams; equally comfortable working alongside teams in the field and operating in the executive room.

Experience developing and executing turnaround or performance recovery plans for underperforming locations, including diagnosing root causes and translating them into decisive commercial action.

Experience supporting new openings, market launches, lease-up or other high-growth environments is strongly preferred.

Skills & Capabilities

Commercial operator: Strong instinct for what drives occupancy and revenue, with the ability to quickly identify where performance is breaking down and what needs to change.

Execution-oriented: Moves readily from strategy to action and maintains urgency, accountability and follow-through until performance improves.

Sales leadership: Strong understanding of the full sales funnel, lead management, conversion, referral development, relationship selling, closing and sales leadership.

Performance turnaround: Able to assess an occupancy-challenged residence, establish a focused 30/60/90-day recovery plan, mobilize the right resources and drive measurable improvement.

Market and pricing acumen: Comfortable assessing competitive positioning, pricing, promotions, customer demand, local market dynamics and barriers to purchase.

Cross-functional leadership: Able to bring Operations, Sales, Marketing and other partners together around a clear commercial plan without relying solely on positional authority.

Field orientation: Willing and able to spend meaningful time in residences, working directly with GMs, CRDs and regional leaders rather than managing performance primarily from the corporate office.

Judgment and decisiveness: Knows when incremental improvement is insufficient and can recommend and drive more significant changes to sales resources, pricing, promotions, marketing investment or local execution.

Performance literacy: Comfortable using funnel, conversion, occupancy and financial information to diagnose performance and make decisions; does not need to be an analytics specialist.

Executive communication: Strong presence and ability to communicate performance, risks, actions and recommendations clearly and succinctly to senior leadership.

Working Conditions

Primarily office-based role

Regular interaction with senior leadership, operational leaders, and cross-functional stakeholders across the organization.

Ability to work effectively in a fast-paced, highly collaborative environment.

May require travel to residences, or off-site business meetings and planning sessions.

May be required to work additional hours during peak business periods, including annual operating plan development, forecast cycles, and board reporting periods.

Operates in a dynamic, fast-paced environment requiring adaptability, responsiveness, and sound decision-making under pressure.

What you can expect from us

A diverse and inclusive environment where individual differences are celebrated, and you’re encouraged to be your best self

Collaborative environment where we work together to succeed as a team

Learning and development opportunities to help you grow

Comprehensive benefit package including RRSP matching

Office is centrally located in the financial district, on the PATH and the TTC subway line, and provides easy access to downtown amenities

Some travel required (< 5%)

Hybrid work model, in office 3 times a week

At Amica Senior Lifestyles we are passionate about working together in a supportive and inclusive environment that fosters innovation and turns ideas into action. We remain committed to creating workplaces that reflect the communities in which we operate. We are actively seeking applicants from all religions and ethnicities, LGBTQ2s+, Black, Indigenous, racialized people, and persons with disabilities and encourage people from all backgrounds to apply for our positions.

Requests for accommodation can be made at any stage of the recruitment process providing the applicant has met the Bona-fide requirements for the open position. Applicants need to make their requirements known when contacted.

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