Training and Implementation Specialist

Full-time, permanent position. The role is based in Canada, and applicants must live in Ontario, Quebec, New Brunswick, Nova Scotia, or Prince Edward Island, and the company works remotely. 

Salary: $75,000 to $90,000 (depending on experience) plus profit share.

Why this role exists

Our customers rely on the risr/ platform to deliver high-stakes and workplace-based assessments that really matter to institutions, professionals, and ultimately patient care. For our software to have the impact it’s designed for, customers need to be onboarded smoothly, configured well, and confident using it independently or as part of a managed service.

This role exists to make that happen not just through great training, but by designing clear, scalable learning and implementation experiences that enable customers to get up and running quickly, with minimal friction and minimal reliance on one-to-one support.

The role at a glance

As a Training & Implementation Specialist, you’ll guide customers through the onboarding and implementation of our assessment solutions.

You’ll work closely with customers to understand their goals and processes, support them through change, configure the platform to meet their needs, and ensure their users are ready to launch with confidence.

Crucially, you’ll also help us move away from repeated, manual training by creating clear, solution-focused documentation and learning resources that make onboarding easier, faster, and more consistent for everyone.

What you’ll be doing

Customer onboarding & implementation

• Lead customers through onboarding and implementation, from early discovery through to launch.
• Build on early discovery carried out with our solution specialists, capturing functional requirements and existing processes, so customers experience a seamless transition into onboarding
• Configure systems to support customer needs, working calmly through complexity where required.
• Support customers through change, recognising that new systems and processes can feel daunting.

Learning, enablement & documentation

• Design and maintain clear, practical learning and implementation resources (guides, walkthroughs, solution definitions, SOPs).
• Turn recurring customer questions and challenges into reusable documentation, learning collateral and system improvements.
• Reduce reliance on live granular training by enabling customers to self-serve confidently, freeing up more time to focus on more complex areas of the implementation.
• Continuously improve onboarding materials based on customer feedback, usage patterns, and evolving product capabilities.

Training & support

• Deliver tailored training sessions where they add the most value, focusing on outcomes, not just features.
• Provide thoughtful support during critical moments, using good judgment to resolve, escalate, or enable as appropriate.
• Work alongside the wider Customer Success Team to triage and respond to support requests, always aiming to empower customers rather than create dependency.

Collaboration & improvement

• Work closely with internal teams, including business analysis, engineering and product, to surface trends, risks, and opportunities for improvement.
• Translate customer experience into clear insights that help improve our products, processes, and learning materials.
• Contribute to a calm, collaborative team culture that values ownership, clarity, and continuous improvement.

What success looks like

• Customers onboard smoothly and feel supported, not overwhelmed.
• Users understand how to use the platform confidently without needing repeated one-to-one training.
• Clear documentation and learning resources reduce friction, support tickets, and time to value.
• Customers feel trusted, capable, and well cared for throughout their journey with risr/ .

We’re more interested in how you think and work than ticking every box, but experience that will help you succeed includes:

Essential

• Experience delivering software system training or onboarding for end users.
• The ability to explain complex concepts clearly and adapt your approach for different audiences.
• The ability to communicate clearly and confidently in written and spoken English, including when delivering training and producing documentation for customers.
• A natural curiosity about customer goals, challenges, and motivations.
• Confidence in learning new systems and navigating technical details.
• Strong problem-solving skills and a calm, structured approach to troubleshooting.
• Experience creating clear, user-focused learning or implementation materials.
• Comfort handling sensitive information in line with GDPR and quality standards.
• The ability to work autonomously while collaborating openly with others.
• A curious, experimental relationship with AI. You try things, reflect on what works, and embed it into how you actually work, not just how you think about working.

Desirable

• Experience working with SaaS products and customer implementations.
• Exposure to education, training, or assessment environments.
• Experience supporting customers through change management.
• Familiarity with agile or digital transformation projects.
• Experience using tools such as Zendesk, Monday.com, or similar platforms.

Working at risr/

We’re a flat-structured, forward-thinking organisation built on trust, transparency, and autonomy, with a focus on digital self-management. We keep things simple, collaborate openly, and focus on doing the right thing, even when it’s harder.

We work remotely, and while there may occasionally be out-of-hours or on-site work (particularly around exams), we’re thoughtful about balance and flexibility.

• Fully remote working
• Freedom to choose your equipment and learning
• A high-trust, low-bureaucracy environment
• Open-book finances and full salary transparency
• Generous salary, enhanced parental leave, and profit share
• £1,200 (local currency equivalent) annual health and wellbeing allowance
• Confidential mental health support
• CanadaLife Health Insurance
• Paid for internet and mobile phone
• Truly flexible working hours
• No set annual leave limit. You are expected to take at least 28 days.
• 25% of the company's profits are shared equally across the global team

How we hire

We want to make sure we're a great fit for each other! Here is a breakdown of our application and interview process:

• Step 1: Application Review: Our team will review your application. If we believe you have what we're looking for, we'll invite you to the next stage.
• Stage 1: The Intro (Remote): A quick video submission answering a few questions on your own time.
• Stage 2: The Group Collaboration (Remote): A practical team interview with other candidates. Save the date: This will happen on July 7th at 9am ET.
• Stage 3: The Deep Dive (Remote): An interview with some of the team you will work alongside to discuss more about your skills and goals.
• Stage 4: The Final Meetup (In-Person): A face-to-face meeting with some of our Canadian team members.

If you believe this is the role for you, please continue to fill out the application form. Please note that we want to hear from you as an individual when you apply to work at risr/ , and that all content in your application should be original and your own. Applications without a cover letter will be unsuccessful.

Come and join us, we promise you won’t have worked for a company quite like it!

risr/ is an equal opportunities employer, and we do not exclude people on the grounds of sex, gender preference or reassignment, pregnancy, parental status, race, marital / relationship status, disability, age, religion, belief or sexual orientation.