Sales Coach — Freelance · Italie (Milano)

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Sales Coach — Freelance · Italie (Milano) | JobCheckPoint

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, Italy
Start date: November 2026
Schedule: 2.5 days/week to start, with the opportunity to grow as the role develops
Contract: freelance Culturelive is building a SaaS platform that amplifies the impact of sales culture on the day-to-day actions and performance of sales teams. We believe that sustainable sales performance is built on people — not on automation, AI replacements, or untargeted campaigns. We are committed to growing dynamic, motivated and resilient sales teams by focusing on the right actions, the right behaviors and the right mindsets, reinforced every week through targeted support. Our platform empowers sales teams by structuring workflows for consistent prospecting, delivering continuous, personalized skills development, and fueling motivation through gamified experiences and real-time recognition. Fully integrated with existing CRM and collaboration tools, Culturelive turns daily routines into powerful sales habits — delivering visible results within weeks.

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Sales Coach — Freelance · Italie (Milano)

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