Head of Sales

Coverflex; Milano; Remoto; EUR 60.000 - 80.000; Tempo pieno

Descrizione del lavoro

A dynamic compensation company in Italy is seeking a Head of Sales to design and implement a sales strategy that drives growth. This role involves leading multiple teams and developing high-performing sales strategies across BDR, Buoni Pasto Sales, and SMB Sales. The ideal candidate has a proven track record in B2B or SaaS environments, exceptional communication skills, and strong data analysis capabilities. You'll thrive in a fast-paced environment focused on building what doesn’t exist yet.

Servizi

Base Salary: €60,000 – €80,000

Bonus / Commissions: €25,000 – €30,000

Equity options available

Welfare: €4,000 – €8,000

Meal vouchers: €8/day

Competenze

• Proven experience in B2B or SaaS environments.
• Ability to lead teams and drive results in growth environments.
• Strong strategic planning and analytical skills.

Mansioni

• Build, scale, and lead the sales strategy.
• Own two-thirds of the revenue engine.
• Coach and develop sales reps and future leaders.

Conoscenze

Proven track record in executing and scaling growth strategies

Experience developing and leading a high-performing sales team

Solid data skills: forecasting, commission plans

Exceptional communication skills

Fluent in Italian & English

Strumenti

HubSpot

Notion

Slack

Descrizione del lavoro

Coverflex

Work changed. Pay didn’t.
Coverflex exists to make compensation work for everyone.
Pay is still rigid, fragmented, and hard to feel.
We turn compensation into choice — one platform, one card, one app — for benefits, meal allowance, insurance, and more.
Our platform is simple for HR and meaningful for employees.
We provide choice, smarter compensation tools, and empowerment.

⚙️TL;DR (The Essentials)

Role: Head of Sales
Seniority Level: Head of/ Senior
Type: Manager
Languages: English (main) & Italian (required)
Main Tools: HubSpot, Notion, Slack
Location: Remote (Italy)
Compensation:

• Base Salary: €60,000 – €80,000
• Bonus / Commissions: €25,000 – €30,000
• Equity: Yes
• Welfare: 4,000€ – 8,000€
• Buoni Pasto: 8€/day
• Benefits: Check all benefits and perks below

💥 Your Impact

This isn’t a “maintain and optimise” role , buta build, scale, and lead mandate. You’ll turn our GTM strategy into predictable, repeatable revenue and own two‑thirds of Coverflex’s revenue engine.

You’ll create momentum by designing and running the sales engine that takes Coverflex to the next stage in Italy and beyond. You’ll lead 15–20 people across our three core teams — BDR, Buoni Pasto Sales, and SMB Sales — and drive the pipeline forward with consistency, clarity, and ambition.

Your work will shape how we discover real customer pain, run world‑class demos, and close deals that move the market. You’ll coach and develop both reps and future leaders, set the bar for excellence, and use data to forecast accurately, identify bottlenecks, and accelerate growth.

Across Sales, Marketing, Product, and CS, you’ll be the connector that helps us learn fast, iterate even faster, and scale what works. Your leadership will define how we win new markets, new segments, and new categories.

This role exists because we’re entering a new stage and we need someone who can move the market, not just respond to it.

How we’ll measure success:

• Main KPI 1: New ARR generated by the team.
• Main KPI 2: Number of new Buoni Pasto users.

⚡ Reality Check - What Makes This Role Hard

If you’re looking for a stable, polished machine, this is not it.

We’re scaling fast, entering new verticals, and rewriting the way compensation works and that requires someone who thrives in ambiguity, speed, experimentation, and ownership.

You’ll need to:

• Make decisions with imperfect data.
• Build processes while executing them.
• Recalibrate strategy as the market moves.
• Be hands‑on when needed, and high‑level when it matters.
• Lead teams through change, not just through comfort zones.

This role is for someone who gets energy from building what doesn’t exist yet, and who understands that impact and discomfort often live in the same place.

👤 You

Must-haves (evidence, not years)

• Proven track record in executing and scaling growth strategies, particularly in B2B or SaaS environments.
• Experience developing and leading a high‑performing sales team in a growth environment (inside & outside sales; inbound & outbound).
• Solid data skills: forecasting, commission plans, reporting.
• Strong aptitude for sales supported by quantitative analysis, planning and strategic thinking.
• Pragmatic, open to change, and comfortable dealing with unexpected challenges.
• Willing to go outside your comfort zone, whilst having the emotional maturity to know when to ask for help. You love to give and receive feedback.
• Exceptional in‑person/digital, verbal and written communication skills.
• Fluent in Italian & English.
• Integrity: you do the right thing even when it’s hard, communicate transparently, and build trust through actions, not words.

Nice-to-have

• Experience in the benefits, fintech, or welfare market.
• Familiarity with Saas.
• Experience in remote selling and multi‑channel communication.
• HubSpot CRM mastery.

🧬 Your DNA

• Sales: you love it!
• Curiosity: you ask why before how.
• Ownership: you take initiative and act like a founder.
• Energy: you bring enthusiasm and perseverance to high‑volume or repetitive tasks.
• Clarity: you communicate simply and effectively.
• Collaboration: you share learnings and help teammates grow.

You’ll probably find this role frustrating if you:

• Need constant reassurance or close supervision.
• Avoid owning business results.
• Struggle with pressure and challenging targets - yes, we are a scale up!
• Prefer rigid processes over flexibility.

👥 Manager & Team

Meet your Manager

Hiring Manager: Andrea Guffanti Scotti - General Manager, Coverflex Italy
Location: Italy
LinkedIn Profile: https://www.linkedin.com/in/andreaguffantiscotti/
Profile Snapshot:

• Energy: high‑intent, pragmatic, and positive — calm under pressure, fast when needed, always focused on outcomes and numbers
• Communication: direct and clear, transparent on context, informal when helpful
• Feedback Style: honest, practical, and fast

How to work with me - in the Manager's own words:

I’m a manager who works with you, not above you. My job is to give you context, clarity, and space, and then get out of your way when you’re executing well.

I expect ownership, discipline, and a genuine desire to grow every day. In return, I give you real support, full transparency, and zero micromanagement.

I move fast, make informed but pragmatic decisions, and stay focused on outcomes without losing integrity or calm. I value people who bring solutions, not problems; who prepare, follow through, and stay steady even when things get messy.

Your Team

You’ll work day‑to‑day with:

• BDR Team: Tommaso, Giorgia, Andrée, Ivan & Andrea
• Buoni Pasto team: Simone, Beatrice & Alessandra
• SMB team: Francesco, Michele, Antonio & Andrea B.

Key Stakeholders:

• Federica Felicetti, Head of Marketing https://www.linkedin.com/in/federica-felicetti-marketing/
• Francesca Pedroni, Head of Customer Success & Networks https://www.linkedin.com/in/francesca-pedroni/
• Marco Nari, Head of Indirect Sales & Strategic Partnerships https://www.linkedin.com/in/marco-nari/
• Stefano Molteni, Enterprise Director https://www.linkedin.com/in/stefano-molteni/

💜 Access & Belonging (Equal Opportunity)

We hire for impact and potential, not pedigree.

We welcome applications from people with non-linear careers, career breaks, caregiving gaps, and those changing fields.

No discrimination on the basis of age, disability, gender identity/expression, marital or family status, pregnancy, neurodivergence, race/ethnicity, religion/belief, gender, sexual orientation, or any other protected ground.

Assessment fairness:

We anchor on evidence of outcomes (what you shipped, moved, or influenced).

We actively de‑bias by using structured rubrics, multiple assessors, and blind screening most of the time (we won’t know your name, gender, or personal info until the interview stage).

📬 Application Clarity

No cover letter required.
Apply with your CV.
You may be asked a few short, relevant questions.

Total candidate time investment: ~3 hours end-to-end.

🧩 Hiring Stages (What to Expect, Why & How Long)

1. CV Screening — Signal check vs must-haves

• Done by People + Hiring Manager.
• You’ll hear from us within 8 business days.

2. Role-Fit Questionnaire (async)

Purpose: capture signals your CV can’t and calibrate seniority.

Format: multiple choice and/or short answers, possibly a short video.

3. Quick Interview with the Hiring Manager (Intro Call) - Mutual fit & context • 30 min

With Andrea Guffanti. Covers role scope, salary, location, and timeline.

4. People Interview - Allow us to know you! • 45 min

With Marisa Mercês. Stress‑free virtual coffee, focused on getting to know you as a person. We talk about culture, beliefs, and purpose.

5. Business case - Let’s peak into this role’s challenges • 60 min

With CRO and Andrea, deep‑diving into the business case you’ll receive in advance. Expect a mix of strategy, execution, and practical reasoning.

6. Final Conversation with CEO — Values, strategy, and your growth • 30 min

⏱️ Speed & Communication

• Decision: within 6 weeks of your application.
• Updates: weekly if the process runs longer.
• Scheduling: interviews between 10:00–16:00 CET (flexible across Europe).
• Feedback: from the Case stage onwards, you’ll always receive written or verbal feedback - what went well, and what to strengthen next time.

#LI-Remote