Executive assistant Jobs in Milton, ON

Who we are

ClinicLine is a technology-enabled professional services company transforming how clinics solve one of their most persistent and disruptive challenges : recruiting, training, and retaining dependable administrative staff. Our founders understand how staffing issues create administrative burdens for healthcare professionals who are trained to provide care and lack the time and resources to manage administrative staffing.

In response, ClinicLine was established as a comprehensive, end-to-end staffing and support solution, creating contract-free access to administrative staff for short or long-term coverage. We combine offshore talent, a proprietary training platform, and AI-powered tools to provide high-quality, PHIPPA- and HIPAA-compliant administrative support to clinics across Canada. Our services allow clinics to operate more efficiently and sustainably, improving both the provider and patient experience.

Who we need

Working directly with our co-founder, we are looking for an ambitious and driven Sales Executive, HealthTech. You will play a critical role in introducing our services to clinics that urgently need a better way forward. You will build trusted relationships with clinic leaders, gain insight into their operations, present the measurable value of ClinicLine’s solutions, and close deals that make a real difference in how clinics operate.

From pursuing incoming warm leads 70% of the time to persistently knocking on doors in medical buildings and adjacent business areas, you will create engagement and interest in our business model and value proposition. This is a full sales role with strong demand, short sales cycles, and clear ROI for clients. You will be empowered to grow your territory, exceed targets, and earn uncapped commissions.

This is a remote-first role with the ability to travel to in person meetings across Ontario.

Who you are

You are a hunter who thrives in entrepreneurial environments. You know how to execute a sales strategy, find and follow leads, secure meetings, and close deals. You are looking for a meaningful opportunity where the solutions you sell solve real problems and deliver tangible benefits to clients. You are resilient, results-oriented, and motivated by purpose, performance, and professional growth. You are ready for the kind of growth that only comes from joining a high-impact company early in its scale-up.

What’s in it for you

Impact. You want to sell a solution that makes an impact. Every client you bring on enables better care and greater efficiency by solving a real operational challenge for clinic owners and staff. You are energized by consultative sales, where listening carefully and building trust leads to long-term partnerships.

Rewards. This is a high-earning potential role and a short sales cycle. You will receive a competitive base salary, an annual car allowance, a flat rate commission for every clinic you onboard and performance-based bonuses.

Career development. ClinicLine is scaling quickly in Ontario and Western Canada with plans to expand nationally. We are established in the healthcare space and are gaining traction in the dental, and allied health markets. We are committed to investing in your success through mentorship, coaching, and opportunities to expand your scope. As we continue to grow, you will have the opportunity to grow into a Sales Manager role, lead a team, and shape the future of sales across Canada.

Here’s what you bring :

• The experience . You have the hustle and persistence that come with full-cycle sales experience in B2B sales, including prospecting, discovery, demo, proposal, and closing. You are motivated to find opportunities, pursue warm leads, nurture interest, and sign the deal. You want to bring your sales skills to a growing industry with strong product-market fit and meaningful outcomes. Experience selling to clinics, practitioners, or healthcare-related businesses is an asset.
• The track record. You consistently meet or exceed quotas. You know how to identify needs, present relevant solutions, and create a compelling case for action. You are process-oriented but adaptive when needed. You can present clearly, handle objections professionally, and build trust quickly. You are comfortable using a CRM and can learn new tools quickly.
• The relationship building. You are a persuasive communicator who understands how to tailor messaging to diverse stakeholders. You have professional verbal and written skills, the confidence to make presentations, the adaptability to connect with clinic staff and gain access to decision-makers, and the ability to influence.
• The mindset. You have the hustle to succeed and you are goal-oriented. You are agile, adaptable, and calm under pressure. You stay organized and focused in a dynamic sales environment and thrive when given ownership. You are a driven self-starter with excellent time management and planning skills.
• The flexibility. You have a valid driver’s licence and a reliable vehicle. You are willing to travel to client sites, trade shows, and in-person meetings.

Why join us?

ClinicLine is disrupting how clinics across Canada manage administrative staffing and operations. Our solution eliminates recruitment bottlenecks, reduces staff turnover, improves front-desk efficiency, and allows clinicians to focus more on patient care. We support a wide range of healthcare verticals, including medical, dental, physiotherapy, and veterinary practices, and we are growing quickly and looking to expand our reach and bring our impactful services to even more clinics across Ontario.

If you meet 70% of the qualifications, we encourage you to apply. Express your interest here.

Here’s what you can expect from our interview process :

ClinicLine is committed to supporting a diverse, inclusive, and accessible workplace. We welcome and celebrate the diversity of applicants and team members across ability, race, gender identity, sexual orientation, and perspective. Accommodations are available on request for candidates participating in all aspects of the selection process.

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