Sales Coach — Freelance · Italie (Milano)

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

As a Sales Coach, you are at the heart of Culturelive’s mission: helping our clients perform better.

Better manage their sales teams. Better prospect. Better sell.

We are expanding into the Italian market and are looking for our first Sales Coach based in Milan — someone who combines deep B2B sales expertise with the ability to operate in both Italian and English-speaking environments.

Your main responsibilities:

• Coach sales reps and managers across the full B2B sales cycle (prospecting, discovery, follow-up, closing, account management).

• Run performance rituals (pipeline reviews, call sessions, workshops) and embed sustainable prospecting routines over time.

• Support managers through change: posture, feedback, team management, KPI tracking.

• Structure and maintain our clients’ sales frameworks (messaging, playbooks, sequences, scripts) in alignment with our platform.

• Deliver clear, regular reporting to clients — focused on adoption, engagement, and performance.

Internally, you will also contribute to:

• Formalising and improving our own sales and coaching methodology to make it actionable and scalable.

• Sharing your expertise with the team (co-development, mission debriefs, internal content).

Requirements:Solid B2B sales experience, including time in SaaS or a tech environment, on non-purely transactional sales cycles.You have already managed, coached, or supported salespeople (in-house or in a consultancy) — and you genuinely enjoy it.You are passionate about B2B sales: you care as much about skills as you do about processes and structure.You have a strong client focus, deliver with care, and know how to hold high standards without losing the human connection.You are comfortable challenging, redirecting, and encouraging — always with concrete examples and clear action plans.Fluency in both Italian and English is required — you will work with Italian -speaking clients and collaborate with a French-speaking team.

Nice to have:Familiarity with sales methodologies such as MEDDIC, SPIN, Sandler, Challenger, etc.Experience on sales transformation / sales performance projects in the Italian market.French is a plus.

Location: Milan, ItalyStart date: November 2026Schedule: 2.5 days/week to start, with the opportunity to grow as the role developsContract: freelance