Careers
Lead, Employee Success
June 2, 2026

Lead, Employee Success

Location
Cape Town
,
Johannesburg
Employment:
Full-time
Location Type:
Hybrid
Department
Operations
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About Playroll

Playroll was built to power a borderless economy. We help businesses and their people thrive, no matter where they're based. Since opening our doors in 2022, we've grown alongside the world of distributed work. What started with our Employer of Record solution has expanded into an integrated suite of HR solutions for companies of every size, covering contractor management, global employment, payroll, benefits and compliance. We're looking for talented people to help shape the future of work, today.

We're driven by a constant pursuit of excellence – building better products, better problem-solving, better ways to work across borders. If you thrive in fast-moving environments and want to help build what comes next, join our team to drive meaningful change.

About the Role

What Being A Lead, Employee Success At Playroll Entails

Playroll is looking for an Employee Success Lead to take ownership of one of the most important stages of the customer journey: employee onboarding. As an Employer of Record (EOR), onboarding sits at the centre of our business, ensuring employees are hired compliantly, contracts are completed accurately, and customers experience a seamless transition from hire to go-live.In this role, you'll lead and develop a team of onboarding specialists while continuously improving processes, systems, and customer outcomes. You'll work closely with teams across Sales, Legal, Operations, Product, and Customer Success to create an efficient, scalable onboarding experience that supports Playroll's growth and commitment to service excellence.

Responsibilities

What You'll Do

  • Lead, mentor, and develop a team of onboarding specialists, ensuring high performance, strong compliance standards, and exceptional employee and customer experiences.
  • Design and improve onboarding workflows within CRM systems to increase efficiency, reduce onboarding timelines, and support scalable operations.
  • Ensure global onboarding processes comply with employment regulations, internal policies, and operational requirements across multiple jurisdictions.
  • Collaborate with Sales, Legal, Operations, Product, and Customer Success teams to deliver seamless transitions from signed customer to active employee.
  • Develop initiatives that improve employee satisfaction, engagement, and overall onboarding experience throughout the early stages of employment.
  • Monitor onboarding performance through KPIs, identifying trends, opportunities, and operational improvements that drive measurable outcomes.
  • Implement technology, automation, and process enhancements to streamline document collection, contract generation, and onboarding administration.
  • Assess onboarding risks proactively and implement controls that support compliance, due diligence, and operational integrity.
  • Oversee the complete onboarding documentation lifecycle, ensuring accuracy, completeness, timely contract drafting, and signature collection.
  • Drive a culture of continuous improvement, accountability, and service excellence aligned with Playroll's values and growth objectives.
Skills & Experience

What You'll Bring

  • Experience managing customer service teams, including leading multiple direct reports and developing high-performing, engaged team members.
  • Strong leadership and coaching capabilities with a proven track record of building successful teams and improving operational performance.
  • Experience identifying process inefficiencies and implementing workflow improvements that increase productivity, quality, and scalability.
  • Excellent stakeholder management skills with the ability to build trust and collaborate effectively across multiple business functions.
  • Experience working with CRM platforms and driving system enhancements that improve workflows, visibility, and operational outcomes.
  • A data-driven approach with the ability to analyse performance metrics, identify trends, and implement meaningful improvements.
  • Strong organisational skills and the ability to manage competing priorities in a fast-paced, high-growth environment.
  • Experience balancing operational execution with strategic thinking to deliver both immediate results and long-term improvements.
BENEFICIAL

Bonus Points For

  • Experience using Salesforce or similar CRM platforms to manage workflows, reporting, and operational processes.
  • Experience working within technology, internet, SaaS, or other fast-paced high-growth business environments.
  • Ability to influence and build strong relationships with internal stakeholders while using data to solve complex operational challenges.
  • Experience driving cross-functional initiatives that improve customer experiences, operational efficiency, and business performance.
Life at Playroll

Hybrid & Flexible Working

Office or remote, we're a hybrid company! Our current model: 3 days in office, 2 days remote.

Office Perks

Stocked snacks, fresh popcorn, and good coffee. Great work needs great fuel!

Continuous Growth

We invest in your growth through courses, mentorships, and a supportive environment designed to help you grow.

Health & Wellbeing

We contribute to your health insurance so you can stay well and do your best work.

Share Incentives

Through our share incentive plan, you grow as Playroll grows with real ownership in the business you're helping build.

Generous Time Off

Alongside our generous PTO policy, we offer 4 weeks ‘work from anywhere’ every year.

Offsite & Get-Togethers

From annual company offsites to regular team events throughout the year, there's no shortage of moments to connect and celebrate.

Six smiling women posing for a photo at a Playroll event with a purple banner in the background.
Interview Process
1
Introductory Screening Call
2
Hiring Manager Interview
3
Case Study
4
Value Fit Interview
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