Technical Support Strategist

Job Description: 

Business Title 
Technical Support Strategist 

Company 
Youbill Inc. dba Member Solutions 

Location 
Remote-first 

Reports To 
Client Success Manager 

POSITION SUMMARY 

The Technical Support Strategist is a high-impact, systems-minded individual contributor role that blends training, technical support, and continuous improvement. You’ll be at the center of the client enablement journey—leading live implementation sessions, resolving support tickets, and turning recurring challenges into scalable solutions. 

At Member Solutions, we're committed to continuous improvement. This role isn’t about putting out fires all day. It’s about solving problems once and solving them well—using tools like HubSpot, UserPilot, CustomGPTs, and AI-assisted documentation to create elegant, self-serve experiences for our clients. You'll collaborate cross-functionally to build better systems, reduce client friction, and make support smarter over time. 

This role is an exciting opportunity for someone with a semi-technical background in onboarding, training, or support. It offers a mix of autonomy and complexity and, most importantly, a clear path for future growth into leadership for the right candidate. 

While not a leadership role today, this position offers clear growth potential for candidates who demonstrate ownership, insight, and initiative. 

KEY RESPONSIBILITIES 

Implementation & Training 

• Lead engaging, outcome-focused training sessions for new clients as part of their implementation journey. 

• Guide clients through best practices that accelerate the adoption of Member Solutions' software tools. 

• Continuously improve training flows in partnership with the Client Success Manager using performance data, client feedback, and automation tools. 

• Hosting regular product training for colleagues will ensure all team members provide the correct information to clients and members. 

Technical Support via HubSpot 

• Resolve technical support tickets with clarity, efficiency, and empathy—owning both the resolution and the insight gained. 

• Identify root causes behind recurring issues and proactively propose scalable solutions (e.g., new help articles, guided flows, product tweaks). 

• Triage billing-related questions to our Financial Services team while documenting technical trends that require wider visibility. 

Documentation, Enablement & Continuous Improvement 

• Turn client issues into assets: create clear, searchable knowledge base content and internal playbooks to reduce repeat friction. Regular, proactive knowledge base maintenance is just as important as producing new assets.   

• Use modern tools like HubSpot, UserPilot, CustomGPTs, and AI-assisted content generation to deliver just-in-time support and training. 

• Champion a “solve once, scale forever” approach—transforming ad-hoc answers into reusable solutions for clients and teammates. 

• Participate in product and process discussions, bringing forward data-informed suggestions to enhance onboarding, ticketing, and client empowerment. 

QUALIFICATIONS 

• 2+ years of experience in technical support, client onboarding, enablement, or training within a SaaS or tech-enabled environment. 

• Demonstrated experience delivering real-time virtual training and supporting software adoption for a non-technical audience. 

• Proficiency with support tools like HubSpot, UserPilot, or ticketing/knowledge base systems; comfort learning and integrating new AI or automation tools (e.g., ChatGPT, CustomGPTs, Loom). 

• Strong written and verbal communication skills, with the ability to create polished client-facing documentation. 

• A systems thinker who identifies root causes, sees patterns, and builds scalable solutions that reduce manual effort. 

• Demonstrated ability to work independently, self-prioritize, and improve processes without needing micromanagement. 

• Bonus: Exposure to implementation process design, product feedback cycles, or self-service strategy. 

#LI-PP1

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More About Jonas Software:

Jonas Software is the leading provider of enterprise management software solutions to the Country and Golf Clubs, Foodservice, Construction, Fitness & Sports, Attractions, Salon & Spa, Education, Radiology/Laboratory Information Systems, and Product Licensing industries. Within these vertical markets, Jonas is made up of over 65 distinct brands, which are respected and leaders within their own domain.

Jonas’ vision is to be the branded global leader across the aforementioned vertical markets and to be recognized by customers and respective industry stakeholders as the trusted provider of ‘Software for Life’ and as an ambassador for technology, product innovation, quality, and customer service.

Jonas Software is the valued technology partner of over 60,000 customers worldwide in more than 30 countries. Jonas employs over 2,000 skilled individuals consisting of a cross-section of industry experts and technology professionals.  Jonas is headquartered in Canada and also operates offices throughout North America, the United Kingdom, Europe, Australia New Zealand and Africa.  Jonas is a 100% owned subsidiary of Constellation Software Inc., headquartered in Toronto and traded on the S&P/TSX 60.