Training Manager

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Training Manager

Caseware is seeking an experienced Training Manager to lead our training initiatives. In this role, you will be responsible for devising and implementing a comprehensive Caseware training strategy that aligns with our business objectives. Your primary focus will be identifying Caseware training needs across the organisation, designing targeted programs, and assessing their impact on employee and client performance, efficiency, and engagement with our software. This role is one of integration across the current services teams; from conducting a training needs analysis, to selecting or creating the most appropriate training methods and materials, to evaluating the effectiveness and outcomes of the training.

If you want to:

Training Program
Development & Delivery
Develop comprehensive training curricula for Caseware’s software solutions, tailored to different user levels (beginner, intermediate, advanced).
Ensure all training materials (manuals, online courses, video tutorials, etc.) are up-to-date, clear, and aligned with software updates and new product features.
Create training modules for both in-person and virtual delivery.
Lead training sessions and workshops for clients and employees to ensure effective adoption and usage of the software.
Continuously improve training offerings based on feedback from participants, product updates and issues arising from support calls.
Employee Development & Internal Training
Train internal staff (Sales, Consulting, Support, and Product teams) on new software features, customer service best practices, and troubleshooting techniques.
Organise continuous professional development initiatives to ensure that all staff members have the knowledge and tools to perform effectively in their roles.
Conduct assessments to measure the effectiveness of training programs, identifying gaps and providing follow-up learning opportunities.
Manage the accreditation process to ensure all staff are accredited and their skills are assessed on a regular basis.
Customer Training & Adoption
Collaborate with customer success and account management teams to design and deliver training for clients, ensuring they are able to fully leverage the Caseware solutions.
Analyse customer feedback and training outcomes to continuously refine and tailor training sessions to the specific needs of clients.
Develop customised training solutions for large or strategic clients to enhance adoption and user proficiency.
Track and report on customer training outcomes, including engagement rates and product usage statistics.
Partner with the sales and admin teams to ensure the full utilisation of purchased products, as well as significantly improve the overall client experience with our software.
Training Metrics & Reporting
Manage the training budget and deliverables, staff, and vendors, to ensure that the training meets the requirements of both internal and external users of our software.
Manage the training projects and resources efficiently and effectively to support the optimal delivery the training.
Stay abreast of the changing needs and expectations of learners and the organisation while balancing the quality and quantity of the training.
Demonstrate the return on investment and business impact of training offered, while leveraging the latest trends and innovations in the learning field.
Enhance the performance and potential of employees in the organisation by creating a learning environment that promotes growth, engagement, and excellence through planning, implementing, and evaluating learning programs that are in line with organisational goals.
Create and manage training dashboards that track participation, completion rates, user feedback, and learning outcomes.
Use metrics to evaluate the success of training initiatives, making data-driven recommendations for improvements.
Regularly report training progress to senior management, including impact on customer satisfaction, employee performance, and product usage.
Identify best practices and improvements by evaluating existing processes, products, and procedures.
Provide recommendations to improve the overall strategy of the Training function.
Stakeholder Engagement & Collaboration
Work closely with product managers, software developers, and business leaders to understand new product features and ensure training programs reflect those updates.
Engage with customers and prospects to gather insights into their training needs and preferences.
Collaborate with the marketing team to promote available training programs and encourage participation.
Maintain a high level of collaboration with other teams to ensure a consistent, positive user experience across all touchpoints.

And you have:

Experience in a training or learning development role within the financial software or technology industry.
Strong communication and presentation skills, with the ability to engage both technical and non-technical audiences.
Proven ability to design, implement, and evaluate training programs.
Familiarity with Learning Management Systems (LMS) and other training tools.
Excellent project management skills with a track record of delivering training on time and within budget.
Knowledge of financial software solutions is a plus.
Completed Matric
Bachelor’s Degree (or higher) in a relevant field, such as Business, Information Technology, Finance, Education, or Communication.
3-5 years of experience in a training or learning and development role, preferably within the financial software or tech industry.
Experience in software training or support—specifically in training clients or internal staff on complex software systems.
Desirable Requirements
Experience with Learning Management Systems (LMS) and e-learning tools.
Proven track record in developing and delivering training programs that drive product adoption and customer satisfaction.
Experience in managing training projects, from content creation to delivery and evaluation.
Familiarity with adult learning principles and instructional design methodologies (e.g., ADDIE model).

And these essential skills:

Organised, focused and deadline driven.
Positive attitude.
High level of professionalism.
Well-developed problem-solving skills.
Self-starter who is highly motivated.
Proven ability to excel under pressure in a very busy environment.
Mature individual with high level of emotional intelligence.
Analytical skills to assess training needs and gaps.
Creativity skills to aid in the design of engaging learning solutions.
Ability to create engaging and effective training materials.
Problem-solving and analytical skills to assess training needs and outcomes.
Customer-focused with experience in delivering training for diverse audiences.

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