About the role
We are expanding our worksite distribution footprint across South Africa and are looking for a Senior
Worksite Development Manager to open payroll deduction opportunities with large employers. This
role focuses exclusively on opening new worksites and does not involve managing an existing book of
business.
As a strategic hunter within our worksite channel, you will play a critical role in securing employer agreements that allow our distribution teams and
broker partners to offer individual insurance products to employees via salary deduction (stop
order). Success in this role is measured by the number of employees made available to sell to
through newly opened worksites.
What you'll be doing
You’ll work closely with the Head of Direct Distribution & Partnerships to identify, secure and
activate large employer worksites across South Africa. This includes negotiating payroll deduction
arrangements, securing physical access to employees, and navigating complex employer approval
structures.
Key responsibilities include:
- Identifying and securing new worksite opportunities with large private employers, municipalities, national government departments (PERSAL), and state-owned entities
- Negotiating payroll deduction (stop order) arrangements and employer administration agreements
- Securing physical access to employer premises so that our sales teams and approved broker partners can engage employees on-site
- Building relationships with key decision makers including HR leaders, payroll managers, treasury stakeholders, and union representative
- Navigating employer approval processes within municipal, corporate, and unionised environments
- Leveraging our existing PERSAL deduction code by securing physical access to government departments
- Prioritising large-scale opportunities, typically 1,000+ employees, to maximise distribution impact
- Maintaining a pipeline of high-value worksite opportunities across major metros nationally.
- Coordinating with internal teams to transition newly secured worksites into operational sales environments
What we're looking for
Experience and qualifications
- 10+ years’ experience in insurance or employee benefits distribution.
- Demonstrated success opening payroll deduction worksites with large employers (1,000+ employees)
- Extensive experience working within payroll deduction and stop order environments
- Proven track record opening new employer groups, not simply maintaining existing relationships. Candidates must have personally led the process of securing employer approval and opening the worksite.
- Nice to haves: Experience in worksite insurance distribution, corporate employee benefits, and/or payroll deduction scheme environments
Candidates should be able to provide examples of worksites they personally helped open, including employer size, the stakeholders involved, and the process followed to secure payroll deduction approval.
Sales and tech skills
- Strong relationship-building ability with senior stakeholders
- Negotiation and commercial structuring skills
- Deep understanding of payroll deduction systems
- Ability to navigate complex organisational structure
Work style
- Self-driven and highly proactive
- Comfortable operating independently in a national role
- Strategic thinker with strong commercial judgement
- Focused on opening high-impact opportunities
- Based in Cape Town and willing to travel
Must Have
- At least 10 years of experience in insurance or employee benefits distribution
- A proven track record of personally leading the process to secure employer approval and opening new worksites.
- Demonstrated success opening payroll deduction worksites with large employers
- Extensive experience and a deep understanding of payroll deduction systems and stop-order environments
-
Based in Cape Town with the willingness to travel nationally
Nice to Have
- Previous experience specifically in worksite insurance distribution or corporate employee benefits
- Experience navigating payroll deduction scheme environments
Responsibilities
- New business acquisition
-
Stakeholder negotiation
- Manage physical access to employer premises
- Building and maintaining a high-value pipeline
- Developing and implementing securement strategies
- Transition secured worksites into active, operational sales environments
Why join Simply?
Joining Simply means becoming a vital part of a purpose-driven fintech that is actively reshaping the South African insurance industry. In our flexible and entrepreneurial environment, you will collaborate with smart, driven teams and own high-impact projects from initial strategy through to final execution.
What we offer
We offer a supportive and dynamic culture that prioritizes psychological safety and a desirable work-life balance. Here, every employee has the opportunity to see the real-time impact of their work and make a meaningful contribution to our collective success as we scale.
Salary
Competitive, market related
Security, peace of mind
Life, disability & family funeral cover
Employee wellness
Great culture
Supportive & dynamic environment
Psychological safety
Leave
20 days annual leave
A note on diversity
Preference will be given to candidates from previously disadvantaged groups, particularly to meet our employment equity targets in alignment with our commitment to BEE objectives.