Senior Project Manager

Johannesburg-Based | Scale-Up | Full-time Role | Engineering Machine | Hiring Manager: Thamsanqa Moyo

Jem is hiring a Senior Project Manager to own enterprise integration and customisation projects end to end.

Jem is a fast-growing HR tech scale-up building payroll, HR and benefits tools for frontline teams. We currently support just under 200,000 frontline employees across South Africa.

As we scale into larger enterprise clients, the quality of our integration and customisation delivery is now the single biggest lever on growth and gross margin. We need a project manager who treats delivery as a craft, leads technical conversations with client IT teams, and uses AI agents every day to do the work of a larger team.

If you've felt the frustration of integration projects that slip silently, scope that keeps expanding and status reports that don't tell you the truth, this role is for you.

⭐️ Your Mission

• Own the enterprise integration and customisation portfolio end to end, from scoping through go-live and into early support
• Hold the line on scope, surface risk early, and protect gross margin on every integrated client
• Use AI agents and automations daily to multiply your output and remove repetitive coordination work
  
  

⭐️ What Success Looks Like

• Every enterprise integration ships with a standalone plan, an explicit scope agreement and a live risk register before any date is committed
• A mandatory weekly technical standup runs with every client's IT gatekeeper, their technical lead and our customer success manager
• Days lost, days recovered and net delay are tracked and visible across the portfolio every week
• Total integration cost per client is known, gross margin per integrated client is tracked, and an ROI test runs before new asks are accepted
• Status reports, client updates, risk registers and follow-up tracking run on automations you've built yourself
  
  

⭐️ What You'll Do

Scope, Plan and Lead Client Engagement

• Write a standalone integration plan for every project, separate from the commercial contract, with in-scope and out-of-scope defined explicitly
• Identify deal breakers up front (access, gatekeepers, environments, third parties) and refuse to start until they're confirmed
• Translate client requirements into technical work packages engineering can estimate against
• Run a mandatory weekly technical standup with the client's IT gatekeeper, their technical lead and our customer success manager
• Lead on-site discovery and go-live sprints at client offices and build trusted relationships with technical sponsors at the executive level
• Present technical progress and risk to client stakeholders in their language

Make Risk, Cost and ROI Visible

• Track days lost, days recovered and net delay every week
• Maintain a live risk register tied to real consequences and escalate on defined triggers, not when panic sets in
• Track total integration cost per client (vendor fees, middleware, internal engineering hours, shared platform costs)
• Apply a clear ROI test before committing to new integrations or customisation requests, and reopen commercials when scope grows
• Work with finance to measure gross margin per integrated client and feed this into future go or no-go decisions
• Run post-go-live reviews and feed learnings back into the playbook

Use AI to Scale Yourself

• Automate weekly status reports by pulling from Linear, Slack, Gmail and project management tools
• Build dashboards and live artifacts that surface the portfolio state without manual effort
• Use meeting transcription and summary tools to generate action items and chase them automatically
• Draft scoping documents, client-facing updates and escalation memos with AI, then edit for voice and accuracy
• Write your own small skills, prompts or agents to remove repetitive coordination work, rather than waiting for engineering to build PM tools for you
  
  

⭐️ You'll Thrive Here If You

• Have owned enterprise delivery projects where the cost of a missed deadline was real
• Have said no to a client and made it stick
• Are comfortable in the room with a client's IT director and on Slack with an engineer at 10pm
• Believe AI is changing how project management works and want to be in front of that change
• Care about gross margin as much as go-live dates
• Would rather build a small tool than file another status update by hand
• Can read an API spec and smell a bad estimate
• Stay calm under pressure, including during post-go-live incidents
  
  

⭐️ Requirements

Minimum:

• 5+ years running complex delivery projects in a software or SaaS context
• Track record of owning enterprise projects end to end, from scoping through go-live and into early support
• Demonstrated ability to hold the line on scope and timeline under commercial pressure
• Comfort with formal escalation, risk management and structured weekly cadences
• Can read an API spec, understand the difference between cloud-hosted and on-premise systems, and smell a bad estimate
• Familiarity with ERP, HRIS and payroll systems (examples: Sage, PaySpace, SAP, Dynamics, Workday)
• Understanding of integration middleware and iPaaS platforms (examples: Flowgear, MuleSoft, Workato)
• Daily use of AI assistants in your workflow (examples: Claude, ChatGPT, Gemini)
• Experience using AI coding tools or agents (examples: Claude Code, Cursor, Codex) to build small automations even if you're not a developer
• Ability to lead technical discussions with enterprise IT teams and excellent written and verbal communication with non-technical executive stakeholders
• Comfortable travelling to client sites for discovery and implementation sprints

Nice to have:

• Experience in HR, payroll or financial services domains
• Direct experience with iPaaS platforms
• PMP, Prince2 or equivalent formal certification
• Background that blends technical project management with commercial or pre-sales exposure
• Experience building internal tools in low-code or scripting environments
  
  

⭐️ What You Can Expect From Us

• Hybrid work environment with a 3-day office policy in our newly renovated Johannesburg office.
• Competitive salary (R100,000 to R120,000 monthly base salary depending on experience and fit).
• Great benefits (lunch 4 times a week, medical aid contribution, retirement annuity contribution, etc.) and 22 days of annual leave.
• Real ownership of the portfolio that determines whether Jem hits its gross margin targets. This is not a coordination role.
• Frontier AI tooling and a team that expects you to use it, plus direct client impact with the teams that run their businesses on Jem.
• We respond to all applications. You can expect feedback on your application, even if we decide not to move forward.
  
  

When our customers thrive, thousands of South African employees get access to the benefits and security they deserve. If you're ready to help build the future of how companies care for their people, we'd love to have you apply.