District Sales Manager

📍 Location: Toronto, Canada

About Us

At Wellbytes, we are revolutionizing healthcare and financial wellbeing with innovative solutions.We have delivered 130+ technology solutions from machine learning and CRM platforms to enterprise applications and cybersecurity systems. Our flagship products - Health Spending Accounts (HSA) and Wellness Spending Accounts (WSA) - are transforming the way individuals and businesses handle healthcare benefits, retirement planning, and personal finance.

As a visionary technology group, we believe that innovative technology can solve some of the greatest problems of our time while creating the greatest value for those we serve. At Wellbytes, you’ll have the chance to shape solutions that impact real people’s lives and redefine the future of personal finance and healthcare.

Role Overview

The District Sales Manager at Wellbytes is a remote role combining Sales Development, Account Executive, and Customer Success responsibilities. This position is designed for a lean, high-impact environment where one skilled professional manages the full customer lifecycle - from inbound lead qualification to closing and onboarding - ensuring a seamless experience for every new Wellbytes client.

Key Responsibilities

Manage the full sales cycle — from prospecting and lead qualification, through demos and closing, to onboarding and activation of new accounts.
Respond promptly to inbound leads generated from digital campaigns, website forms and referrals, and proactively build your own pipeline via outbound outreach.
Sell our HSA/WSA SaaS platform to Canadian small businesses, independent professionals, or self-employed clients.
Qualify prospects by assessing their business structure, employee count and spending needs; conduct discovery calls and product demos to clearly demonstrate the financial and tax benefits of our solutions.
Ensure smooth client onboarding - assist new clients with setup, platform navigation and initial training.
Monitor ongoing account health, drive renewals, identify upsell or referral opportunities to maximise lifetime value.
Maintain accurate internal CRM records and contribute weekly reports on leads generated, conversion rates, user growth and other key metrics.
Collaborate closely with content, marketing and product teams to refine campaign strategies, optimise messaging and feed market-feedback into product road-map.
Consistently meet or exceed monthly and quarterly sales targets (MRR, client acquisition) while leveraging tools such as HubSpot, LinkedIn Sales Navigator and Google Workspace to stay organised and efficient.

Skill Requirements

Must Have

3-5 years of experience in B2B SaaS, fintech, or HR/benefits sales, ideally targeting small business or SMB markets in Canada.
Proven success in full-cycle sales - from prospecting and demoing to negotiating and closing.
Strong communication and relationship-building skills; able to explain financial and technical concepts clearly.
Customer-focused and consultative approach with commercial awareness and accountability for targets.
Maintains exceptional organization and discipline, ensuring CRM accuracy and prompt engagement with leads and clients.
Tech-savvy; proficient with HubSpot, LinkedIn Sales Navigator, Google Workspace, or similar CRM and automation tools.
Self-starter who thrives in a fast-paced startup environment, demonstrating ownership and adaptability.
Passion for helping clients make smarter financial and health-related decisions.

Nice to Have

Experience in healthtech, fintech, or benefits/insurance sales.
Knowledge of CRA rules on HSAs and small business deductions.
Skilled negotiator with strong commercial acumen: you understand partner business models and structuring win-win deals.
A well-developed network of contacts or prospective clients with potential SaaS product needs will be viewed as a strong advantage.

Why Join Us?

Remote working
Opportunity to shape sales strategy and grow with the company
Collaborative, innovative, and growth-driven environment
Competitive salary and performance-based incentives
A chance to make a real impact in shaping the future of personal finance and retirement solutions

👉 Join us on this journey - send your CV to hr@wellbytes.ca

Wellbytes

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District Sales Manager