Head of Sales

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 SalesSeniority Level: Head of/ SeniorType: ManagerLanguages: English (main) & Italian (required)Main Tools: HubSpot, Notion, SlackLocation: 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 ItalyLocation : ItalyLinkedIn Profile : />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 Francesca Pedroni, Head of Customer Success & Networks Marco Nari, Head of Indirect Sales & Strategic Partnerships Stefano Molteni, Enterprise Director 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 #J-18808-Ljbffr