People Business Partner

Job DescriptionSyspro is looking for a People Business Partner to own HR across the US and Canada. Based in Chicago, you'll be the go-to HR presence for our North American team, partnering directly with business leaders, running the full employee lifecycle, and making sure our global people programmes land well on the ground.  You'll work as part of a small, close-knit global People team spanning South Africa, the UK, and North America. Collaboration is central to how we work: together, you'll embed consistent global HR processes that hold up across geographies while still feeling relevant locally.  To thrive here, you'll need to be as comfortable reviewing payroll and navigating multi-state compliance as you are coaching a manager through a difficult conversation or handling a complex employee relations case. A true generalist role — broad in scope, grounded in the detail, with a key focus on strengthening employee trust and building lasting manager capability. Job RequirementsMinimum Level of Education Bachelor’s degree in Human Resources, Business Administration, Industrial Psychology, or a related field.Beneficial Qualifications SHRM-CP or PHR certification.CPHR designation ordemonstratedfamiliarity with Canadian HR practice.Minimum Experience 5+ years’ experience as a sole or senior HR generalist owning the full employee lifecycle for a defined US region or multi-state geography, without a local HR team.Demonstratedtrack recordas a credible business partner to Sales, Marketing, or Operations leaders.Hands-on experience reviewing and signing off US payroll, with genuine payroll literacy across deductions, multi-state compliance, and error identification.Deep, practical experience administering US employee benefits (health, dental, vision, life) and 401(k) plans including open enrolment, plan audits, and 5500 filings.Solid working knowledge of US federal and multi-state employment law; working awareness of Canadian federal and provincial employment legislation.End-to-end recruitment experience: intakes, pipeline management, structured interviewing, and onboarding.Experience running performance cycles and engagement programmes, from communication through calibration to action planning.Experience working as part of a distributed or global HR team, collaborating across time zones.Beneficial Experience Prior HR experience supporting Canadian employees or familiarity with provincial employment law.Background in a tech, ERP, or B2B software business — understanding sales cycles, technical roles, and channel dynamics.Exposure to post-integration or scaling environments, particularly where employee trust needed rebuilding.Experience with HRIS platforms such as HiBob, Deel, or similar tools.Coaching or facilitation skills that go beyond advice-giving to actively develop manager capability.Change management experience in environments where buy-in is not guaranteed.Special Skills & Knowledge Payroll literacy across multi-state and cross-border (US/Canada) environments.Strong interpersonal and communication skills — able to hold difficult conversations with fairness, composure, and empathy.Influencing skills: able to challenge, advise, and shape decisions without formal authority.Analytical approach to people data — able to identify trends, surface insights, and recommend action.Proficiency with HRIS and payroll systems; comfort with Excel or similar tools for reporting.High level of personal organisation and follow-through in a remote, globally distributed team environment.Cultural awareness and the ability to adapt communication style across diverse employee populations and time zones.Bilingual capability in French an advantage for Canadian employee support.Job ResponsibilitiesBusiness Partnering & Manager Capability Act as a genuine HR partneracross the US and Canada, building credibility and trust at all levels.Coach and support managers through performance conversations, difficult employee situations, and day-to-day people decisions.Proactively develop manager capability over time, enabling managers to lead their people with confidence and reducing reliance on HR for routine decisions.Employee Relations & Trust Building Serve as a visible, accessible point of contact for employees across the region,listening actively, following through consistently, andrepresentingemployee and business interests fairly.Lead employee relations matters including investigations, grievances, and performance improvement plans, ensuring legally compliant and consistent outcomes.Drive initiatives to rebuild and strengthen employee trust, using data and direct feedback toidentifypriorities and inform action.Payroll, Benefits & Compliance Review and sign off US and Canadian payroll with a high degree of accuracy — understanding deductions, catching errors, andmaintainingcompliance across multiple states and provinces.Own US employee benefits administration (health, dental, vision, life) and 401(k) plans, including employer matching, open enrolment, plan audits, and 5500 filings.Apply working knowledge of US federal and multi-state employment law and Canadian federal and provincial employment legislation; escalate to legal counsel whereappropriate.Recruiting, Onboarding & Offboarding Manage end-to-end recruitment for North America: intake meetings, pipeline management, structured interviewing, offer management, and hiring manager partnership.Design and deliver structured onboarding programmes that accelerate new hire integration and reduce early attrition.Conduct thorough, respectful offboarding processes that capture insight and maintain Syspro’s employer brand.Performance & Engagement Roll out performance review cycles and engagement programmes across the region — communicating the ‘why’ clearly and supporting managers through calibration.Analyse engagement and performance data to surface themes and translate findings into targeted, time-bound action plans.Global People Team Collaboration Work as a coordinated member of the three-person global People Business Partner team, aligning with SA and UK counterparts on shared processes and standards.Adapt global frameworks for the North American context whilemaintainingconsistency and fairness across countries.Contribute to cross-functional people projects as the functional owner for Sales, Marketing & Operations globally.Job Benefits13 paid company holidays in 202620 vacation days6 wellness days401k from day one of hireHealth/Dental/Vision Insurance the first of the month after hireLife insuranceBonusMaternity and Paternity Leave