Head of People & Operations (Full-Time, Milan)

Gemmo AI Ltd.; Lombardia; Hybrid; EUR 27,000 - 37,000; Full time

Benefits offered by this job

Meal vouchers

Public transport reimbursement

MacBook Pro (M5)

Job summary

Gemmo AI Ltd. in Milan, with HQ in Dublin, is hiring a Head of People & Operations to own end-to-end people operations and payroll across two entities. You will design, run and optimize processes from onboarding to payroll, manage external payroll partners, and lead organizational learnings and offsite planning.

We value proactive ownership, cross-functional collaboration, and fluency in Italian and English as we support a growing AI-focused team in regulated financial services.

Qualifications

• 2+ years of experience in HR, people operations or HR generalist roles, ideally in a startup or scale-up.
• Italian employment administration knowledge: CCNL contracts, payroll, payslips, leave, internships and convenzioni di stage
• End-to-end hiring experience, including technical and graduate recruiting
• Ownership of outcomes: payroll and onboarding deadlines
• Ability to manage external partners such as payroll consultants, accountants and labour lawyers
• Build and document processes and improve them rather than reinventing them
• Clear written and spoken communication in Italian and English; HQ in Dublin; international colleagues

Responsibilities

• Own every process that keeps Gemmo running, from candidate applications to payslips, laptops and performance reviews.
• Hire, onboard and manage onboarding programs; run performance review cycles end-to-end.
• Design and run onboarding experiences, including a 90-day plan with buddy assignments and check-ins.
• Support Agile rituals and ensure they stay useful and on schedule.
• Lead learning programs for the technical team and manage training budgets and enrollments.
• Manage leave requests and the company holiday plan to avoid conflicts with delivery.
• Run monthly payroll for the Italian entity with external payroll consultant and distribute payslips.
• Procure and distribute meal vouchers (Edenred) and manage hardware purchases for Milan office.
• Oversee office facilities, travel arrangements and offsite planning, including Dublin HQ offsite.
• Automate HR/ops tasks with AI tools and keep process guides current.

Skills

HR generalist

Payroll management

Onboarding

Italian employment law

Bilingual Italian & English

External partner management

Process design

Documentation

Stakeholder communication

Tools

Workable

TeamSystem

Dipendenti in Cloud

SharePoint

Jira

Job description

About Us

We are a boutique AI firm, founded in 2020, headquartered in Dublin, Ireland, with an AI Lab in Milan, Italy. Not a consultancy. Not a software house. An AI firm, boutique by design, with one focus: financial services.

We co-create AI agents with our clients and run them in production, inside regulated financial institutions. Today more than 50 of our AI agents are live, and our team has filed 42 AI patents.

We believe in responsible, pragmatic AI: systems that are governed by design, integrate into real workflows, provide measurable value, and remain under the client's control.

Our Team

• Forward-Deployed Engineers: 24 people, including 4 Ph.D.s
• Leadership: 3 people

We are a lean, technical-first team, and we're growing.

We plan to add 10 new Team Members in the next 6 months. Growth at that pace only works if hiring, onboarding, payroll and the day-to-day running of the company work flawlessly. That is this role.

The Role

The Head of People & Operations owns everything that makes Gemmo work as a company, as opposed to what we deliver to clients. You report directly to the CEO and own each process end to end: from designing it, to running it, to fixing it when something breaks. There's no handoff chain.

In practice, the role combines three disciplines:

• People: hiring, onboarding, leave, performance reviews, and the rituals that keep a growing team aligned.
• Payroll & Administration: monthly payroll, payslips, salary payments, benefits and purchasing, working with our payroll consultant, accountant and labour-law advisors.
• Operations: hardware, the Milan office, some support to Accountancy team (light), travel and offsites.

Nobody arrives strong in all three. We hire people who are solid in people operations and Italian employment admin, and eager to grow into the rest.

We're a small company, and we value flexibility. When a task comes up in another area, such as accounting, you'll be expected to get up to speed quickly and help out.

Who You Are

• You have at least 2+ years of experience in HR, people operations or an HR generalist role, ideally in a startup or scale-up
• You know Italian employment administration well: CCNL contracts, payroll, payslips, leave, internships and convenzioni di stage
• You have run hiring end to end, including technical and graduate recruiting
• You take ownership of outcomes, not just tasks: payroll and onboarding deadlines don't slip on your watch
• You're comfortable managing external partners such as payroll consultants, accountants and labour lawyers
• You build processes, document them and improve them, rather than reinventing them every month
• You write clearly and communicate confidently in Italian and English, both written and spoken: our HQ is in Dublin and we work in English with international colleagues

What You’ll Do

You’ll own every process that keeps Gemmo running, from a candidate's first application to their payslip, their laptop and their next performance review.

Hiring

• Create, publish and manage job announcements in Workable, from spec to offer
• Run our internship pipelines with ITS and TTS institutes, and publish openings on university career boards
• Finalise convenzioni di stage with universities and institutes

Onboarding and people management

• Onboard every new hire so their contract, laptop, email, accounts and licences are ready on day one
• Run the performance review cycle, end to end
• Deliver our "Get the basics right" course to new joiners
• Support our Agile rituals (daily standups, weekly sprints, Friday retrospectives) so they run on time and stay useful

New onboarding experience

• Redesign onboarding end to end, from the signed offer to the end of the first three months
• Build a first-weeks plan for each role, with a buddy, clear goals and check-ins at 30, 60 and 90 days
• Collect feedback from every new joiner and use it to improve the next onboarding

Learning programme for the technical team

• Design a yearly learning programme for our Forward-Deployed Engineers, built around the skills our projects need
• Select courses and certifications, and manage the training budget and enrolments
• Organise internal knowledge-sharing sessions, and track participation and progress

Leave

• Manage holiday and permessi requests
• Monitor and finalise the company holiday plan, so delivery and leave never collide

Payroll and benefits

• Run the monthly payroll for our Italian entity with our external payroll consultant
• Check and distribute payslips, and prepare salary payments
• Purchase and distribute meal vouchers (Edenred)

Purchasing, hardware and facilities

• Handle purchases with company cards for the Milan office, with every receipt reconciled
• Buy hardware and manage our laptop fleet through our device-management platform
• Manage the Milan office rent and the landlord relationship

Travel and offsites

• Organise travel and accommodation for the team
• Plan our offsites, including the annual Dublin offsite at HQ

AI is how we work here too: you'll use AI tools to automate routine admin and keep our process guides current. This is not an administrative support role: at our size, the Head of People & Operations both designs the processes and runs them, from day one.

What You Will Learn

• Building the people function of a fast-growing AI firm as it scales, rather than inheriting one
• How an Italian company inside an Irish group runs payroll, benefits and employment admin across two entities
• Using AI tools and agents to automate HR and operations work, and improving that workflow as the tools evolve
• How a business that builds AI for regulated financial services operates and makes money

Tech Stack

We use a mix of modern tools. You'll work with tools like these:

• HR & recruiting: Workable
• Payroll & attendance: TeamSystem, Dipendenti in Cloud
• Documents & processes: SharePoint, Jira
• AI: Claude (including Claude Design and Claude Skills), ChatGPT

Remote Work and Schedule

• 3 days in our Milan office (Tuesday, Wednesday, Thursday) and 2 days remote (Monday, Friday)
• Working hours: Monday to Friday, 8:30–17:30 (Italian time)
• Lunch break: 12:30–13:30

Salary and Benefits

• Gross annual salary (RAL): €27,000–37,000, CCNL Metalmeccanico, level C1 to B3 depending on experience, reviewed every year
• Contract: Tempo Determinato (6 months) and then Tempo indeterminato
• Meal vouchers: €10 for each day in the office (around €120/month)
• Public transport pass reimbursement: reimbursement of the cost of local, regional or interregional public transport passes, up to €200 per month, upon submission of proof of purchase (single tickets and carnets are not eligible)
• AI tools: high usage limits on frontier models and AI agents, with new releases available from day one
• A brand-new 15-inch MacBook Pro (M5) for your work with us

Selection Process

We keep it fast, respectful and transparent.

1. First Interview with the CEO (15 min): your motivation, background and availability.
2. Practical case with the leadership team (45 min): a realistic scenario, such as planning the onboarding of five new hires starting the same Monday, or designing our first performance review cycle. No trick questions.
3. Meet Gemmo with our Head of Engineering (30 min): once we've got to know you and want you on the team, we tell you about Gemmo and what it can mean for your career. If you reach this step, you're on our shortlist.
4. Offer: selected candidates receive an offer, which stays open for 24 hours. We're telling you now so there are no surprises.