Head of Mid-Market Sales (SaaS)

Location: Hybrid in Milan, Italy, with three days per week at the Milan Sales Hub and flexibility to work from home.

Salary: €100,000–€120,000 annual OTE, plus equity, performance bonuses, and a relevant stock option package.

Company

hirify.global is building an AI product for lawyers, law firms, and companies, focused on improving productivity and modernising legal work.

What you will do

• Lead and develop a high-performing team of Mid-Market Account Executives through regular 1:1s, pipeline reviews, structured coaching, and performance management.
• Recruit, onboard, and ramp sales talent from sourcing through the first closed deal.
• Design and operationalise the Mid-Market sales playbook, including pipeline generation, deal qualification, multi-threaded selling, and forecasting.
• Implement and optimise sales tooling and CRM workflows to improve rep efficiency and data accuracy.
• Define KPIs, build dashboards, analyse pipeline health, and use data to guide coaching and strategic decisions.
• Partner with Marketing, Product, and Customer Success on ICP alignment, feedback loops, and expansion opportunities.

Requirements

• Proven sales leadership experience in SaaS or B2B technology, including at least 2 years managing a quota-carrying team in an enterprise or mid-market segment.
• Deep familiarity with enterprise and mid-market sales methodologies, including hands-on experience with MEDDPICC, SPICED, or Challenger Sale, and the ability to coach representatives in complex deal cycles.
• Builder mindset with the ability to create sales processes, playbooks, and team rituals from scratch in ambiguous environments.
• Strong operational and analytical skills, including forecasting models, pipeline metrics, dashboards, and data-driven decision-making.

Culture & Benefits

• Work with focused, autonomous teams combining innovation, rigor, curiosity, and discipline.
• Opportunities to lead high-stakes projects and shape legal technology.
• Hybrid work with flexibility between home and the Milan Sales Hub.
• Health insurance and meal vouchers.
• Performance bonuses, equity, team retreats, and off-sites.