Technical Support Strategist

Jonas Software; United States; Remote; USD 60,000 - 80,000; Full time

Job summary

A leading company in the tech sector seeks a Technical Support Strategist to enhance client enablement through training and technical support. This role involves leading implementation sessions, resolving support tickets, and improving processes using advanced tools. Ideal for candidates with a semi-technical background, it offers growth opportunities into leadership.

Qualifications

• 2+ years in technical support, onboarding, or training in SaaS environments.
• Experience with virtual training and software adoption.
• Strong written and verbal communication skills.

Responsibilities

• Lead training sessions for new clients during implementation.
• Resolve support tickets and identify root causes of issues.
• Transform client issues into knowledge base content.

Skills

Technical support

Client onboarding

Training

Communication

Problem-solving

Tools

HubSpot

UserPilot

CustomGPTs

Job description

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 will be at the center of the client enablement journey—leading live implementation sessions, resolving support tickets, and transforming recurring challenges into scalable solutions.

At Member Solutions, we are committed to continuous improvement. This role focuses on solving problems effectively using tools like HubSpot, UserPilot, CustomGPTs, and AI-assisted documentation to create self-serve experiences for clients. You will collaborate cross-functionally to enhance systems, reduce client friction, and improve support processes over time.

This position is ideal for someone with a semi-technical background in onboarding, training, or support. It offers autonomy, complexity, and clear growth opportunities into leadership for the right candidate.

While not a leadership role today, it provides a pathway for candidates demonstrating ownership, insight, and initiative.

Key Responsibilities

1. Implementation & Training

• Lead engaging, outcome-focused training sessions for new clients during their implementation process.
• Guide clients through best practices to accelerate adoption of Member Solutions' software tools.
• Continuously improve training flows with the Client Success Manager, leveraging performance data, client feedback, and automation tools.
• Host regular product training for colleagues to ensure consistent and accurate client communication.

Technical Support via HubSpot

• Resolve support tickets efficiently, clearly, and empathetically, owning both the resolution and insights gained.
• Identify root causes of recurring issues and propose scalable solutions, such as new help articles, guided flows, or product tweaks.
• Triages billing-related questions to the Financial Services team and documents technical trends for broader visibility.

Documentation, Enablement & Continuous Improvement

• Transform client issues into searchable knowledge base content and internal playbooks to reduce repeat issues.
• Use tools like HubSpot, UserPilot, CustomGPTs, and AI-assisted content generation to provide timely support and training.
• Promote a “solve once, scale forever” mindset by turning ad-hoc answers into reusable solutions.
• Participate in product and process discussions, offering data-informed suggestions to improve onboarding, ticketing, and client empowerment.

Qualifications

• 2+ years of experience in technical support, client onboarding, enablement, or training within SaaS or tech-enabled environments.
• Experience delivering real-time virtual training and supporting software adoption for non-technical audiences.
• Proficiency with support tools like HubSpot, UserPilot, or ticketing/knowledge base systems; comfort with AI and automation tools (e.g., ChatGPT, CustomGPTs, Loom).
• Strong written and verbal communication skills, with the ability to produce polished client-facing documentation.
• Systems thinker with the ability to identify root causes, recognize patterns, and develop scalable solutions reducing manual effort.
• Ability to work independently, prioritize tasks, and improve processes without micromanagement.

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