Bilingual Sales Coach in Milan - Freelance/Part-Time

Culture Live; Lombardia; On-site; EUR 83,000 - 124,000; Part time

Job summary

Culture Live is expanding into Italy and seeks a Sales Coach based in Milan to guide our first client-facing coaching program for B2B teams. You will shape how reps prospect, qualify, and close deals, while developing scalable playbooks and metrics.

You will report externally to clients and internally to the sales leadership, collaborating with an English- and Italian-speaking team. The role is freelance, part-time, starting in November 2026, with 2.5 days per week and growth potential.

Qualifications

• Solid B2B SaaS sales experience with non-transactional cycles.
• You have coached salespeople in-house or consulting roles.
• You communicate clearly with concrete actions and outcomes.
• Fluency in Italian and English is required.
• Nice-to-have: familiarity with MEDDIC, SPIN, Sandler, or Challenger.

Responsibilities

• Coach sales reps and managers across the full B2B cycle.
• Run reviews, workshops, and cadence rituals to improve prospecting.
• Support managers with change management, KPI tracking, and feedback.
• Build and maintain client messaging, playbooks, and scripts aligned to our platform.
• Provide clear, regular reporting on adoption, engagement, and performance.

Skills

B2B sales

Coaching & mentoring

SaaS experience

Client focus

Italian/English bilingual

Job description

Culture Live is expanding into Italy and seeks a Sales Coach based in Milan to guide our first client-facing coaching program for B2B teams. You will shape how reps prospect, qualify, and close deals, while developing scalable playbooks and metrics.

You will report externally to clients and internally to the sales leadership, collaborating with an English- and Italian-speaking team. The role is freelance, part-time, starting in November 2026, with 2.5 days per week and growth potential.