Managing Director - Employer Health and Insurance Greater Toronto, Canada Area

Bayshore HealthCare is one of the Canada’s leading providers of home and community health care services and is a privately owned company. Bayshore HealthCare is proud to showcase its achievement as a Platinum member of Canada’s Best Managed Companies Program every year since 2006. In 2015, Bayshore achieved the designation for Best Practice Spotlight Organization from the Registered Nurses’ Association of Ontario. Bayshore Healthcare is also recognized as Canada’s Best Employers in Forbes 2023 list.

The Managing Director, Employer Health & Insurance is a national senior leader who will build Bayshore's competitive play in the employer health and insurance space. This is not a role to run an existing business line as-is — it is a mandate to create a category-defining value proposition that changes how employers and insurers buy and experience employee health and well-being.

Preventing sick days, reducing short- and long-term disability incidence and duration, lowering workplace injury, and returning employees to work quickly — whether the health challenge is personal or work-related — are all bought by the same person: an employer's HR and benefits leadership, or an insurer's group-benefits team, trying to reduce the human and financial cost of employee ill health. Today they buy these as fragmented point solutions. The opportunity is to assemble Bayshore's existing services and products into one coherent, outcome-based proposition for that buyer.

The competitive context. The incumbents have set the current expectation yet solutions in this space are still emerging and increasingly customer-focused. This role is accountable for a proposition that goes up against those plays and wins on the outcomes buyers actually pay for: fewer lost days, lower claims cost and duration, and faster, healthier return-to-work.

DUTIES AND RESPONSIBILITIES

Strategy & value proposition

• Own the category strategy. Define where Bayshore competes in the employer/insurer space and how it differentiates — with the depth and breadth of domain knowledge to make defensible strategic calls against sophisticated incumbents.
• Build the shared-buyer value proposition. Frame prevention, disability, workplace injury, and return-to-work as one outcome the buyer purchases, rather than a set of disconnected services — and articulate the measurable value (reduced absence, lower STD/LTD cost and duration, faster RTW) that beats the current market.
• Learn from the industry. Bring a clear read of competitor models, market shifts, and buyer expectations, and translate those learnings into Bayshore's positioning and roadmap.

Product innovation & development

• Innovate the offering. Drive product innovation and development that assembles current and new services into solutions configured to what buyers actually need and demand — not to how Bayshore is organized internally.
• Work collaboratively across the organization. Partner with businesses such as BSRx and OEMS, as well as support functions: clinical, therapy, insurance, data, and delivery teams to bring an array of existing services and products to market as a single, coherent proposition — orchestrating internally so the buyer experiences one Bayshore, not many.

Go-to-market & sales

• Own go-to-market. Define segmentation, positioning, pricing, and the route to market for employer and insurer buyers, and build the commercial motion to win against established competitors.
• Lead sales. Own the national sales strategy and pipeline for the category — building the relationships, proposals, and partnerships that convert the value proposition into signed business.

Operating model & P&L

• Configure the operating model. Stand up an operating model tuned to current buyer needs and demands — with the structure, capabilities, and delivery approach to serve employer and insurer clients at national scale.
• Own the P&L. Carry accountability for the growth, profitability, and performance of the employer and insurer category.

Leadership & Organizational Impact

• The National Directors of Workplace Safety & Compensation Insurance, Bayshore Therapy & Rehab, and Carepath will report directly to this role, with accountability for aligning business priorities, growth strategies, and performance outcomes across the portfolio.
• Establish a shared vision, performance expectations, and governance framework that drives cross-functional collaboration, integrated service delivery, and enterprise growth.
• Act as the senior leader and advocate for the Employer Health & Insurance segment, influencing executive stakeholders and ensuring alignment with Bayshore's broader strategic priorities.

What success looks like

• Bayshore has a clearly differentiated, outcome-based proposition for the employer/insurer buyer that competes credibly with existing employer health and wellbeing solutions and EAPs— and wins.
• Fragmented services are assembled into solutions the buyer recognizes as one offering, sold through one relationship.
• Measurable buyer outcomes — reduced absence, lower STD/LTD cost and duration, faster return-to-work — become the proof points that drive growth.
• The operating model scales nationally without reverting to fragmented, internally-organized delivery.
• The category grows in revenue and margin, and Bayshore is recognized as a serious challenger in workplace health.

Candidate profile

• Deep breadth and depth in the workplace insurance / workplace health space — disability management, group benefits, occupational health, EAP, or return-to-work — with credible fluency in how employers and insurers buy.
• A commercial, entrepreneurial leader who has built or substantially grown a business, category, or new value proposition — not only run an established one.
• Proven span across strategy, product, go-to-market, and sales — comfortable owning all of them, and a P&L, rather than a single function.
• A strong outside-in, customer-focused instinct, with a demonstrated read of competitors and the ability to turn market learning into differentiated positioning.
• Skilled at collaborating and orchestrating across internal teams to assemble a unified offering from distributed capabilities.
• National-scale leadership experience, ideally in health, benefits, insurance, or care services.

Attributes we are looking for

• Strategic. Sees the category, the buyer, and the competitive landscape whole — and makes deliberate, defensible bets.
• Entrepreneurial. Builds; comfortable creating a proposition and an operating model where one does not yet exist.
• Customer-obsessed. Configures everything to the buyer's needs, not to internal convenience.
• Collaborative. Earns the partnership of clinical, delivery, and product teams to bring one offering to market.
• Commercially sharp. Owns the number, and knows what drives it.

Experience

5+ years in workplace health and insurance

10+ years in leadership roles

Deep domain fluency in workplace health and insurance. Understand how the money actually flows in this space — how employers and insurers think about absence cost, STD/LTD reserves and duration, workers' comp and occupational health, EAP, and return-to-work.

A commercial P&L track record. Owned revenue, margin, growth — and be accountable for it, not just contributed to it.

Experience across strategy, product, go-to-market, and sales. This role owns all four.

Deep provider/solutions knowledge: i.e. knows the employer health and insurance playbook inside and out.

Outside-in instinct. Instinctively configure the business and offerings to the buyer/customer rather than to internal structure.

Orchestration skill. Because the value proposition is assembled from Bayshore's existing distributed capabilities, need to be the kind of leader who earns the partnership of internal stakeholders.

National-scale leadership. Multi-region, ideally in health, benefits and insurance services.

Credentials

Master’s degree in a health-related discipline or post graduate training in business or a Master’s degree in Business Administration.

“At Bayshore Healthcare, our commitment to Equity, Diversity & Inclusion is our strength. This is how we bring our vision of being the difference in the lives of those we care for, work with and in our communities. We have a great sense of pride in creating a culture of belonging, where individual differences are embraced and celebrated, through programs, resources and policies that support each individuals purpose, potential and wellbeing.”

At Bayshore Healthcare Ltd., and its subsidiaries, we are committed to fostering an inclusive workplace and operate in full compliance with all Provincial and Territorial legislation pertaining to Human Rights Codes and Accessibility requirements. To ensure continued compliance throughout the recruitment and selection process, we encourage candidates to disclose any accommodation needs they may have.