B2B Sales Coach — Milan: Build Winning Playbooks

Culture Live; Lombardia; Hybrid; EUR 83,000 - 131,000; Full time

Job summary

Culturelive is expanding into Italy and seeks its first Sales Coach based in Milan. You will combine deep B2B SaaS sales expertise with the ability to operate in both Italian and English environments.

You will coach sales reps and managers across the full cycle, run performance rituals, and help shape our sales frameworks. The role is freelance, starting November 2026, with a 2.5-day week schedule and a focus on measurable outcomes.

Qualifications

• Solid B2B sales experience in SaaS or tech.
• Experience coaching or supporting sales teams.
• Strong client focus with high standards and personal touch.
• Fluency in Italian and English required.

Responsibilities

• Coach sales reps and managers across the full B2B cycle (prospecting, discovery, follow-up, closing, account management).
• Run performance rituals (pipeline reviews, call sessions, workshops).
• Support managers with change: posture, feedback, KPI tracking.
• Structure and maintain client sales frameworks (messaging, playbooks, sequences, scripts).
• Deliver clear reporting focusing on adoption, engagement, and performance.
• Contribute to developing scalable sales/coaching methodologies.

Skills

B2B sales

SaaS experience

Coaching

Client focus

Sales analytics

English & Italian

Tools

CRM systems

Playbooks & scripts

Job description

Culturelive is expanding into Italy and seeks its first Sales Coach based in Milan. You will combine deep B2B SaaS sales expertise with the ability to operate in both Italian and English environments.

You will coach sales reps and managers across the full cycle, run performance rituals, and help shape our sales frameworks. The role is freelance, starting November 2026, with a 2.5-day week schedule and a focus on measurable outcomes.