Head of Sales

Coverflex

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.

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

• Base Salary: €60,000 – €80,000
• Bonus / Commissions: €25,000 – €30,000
• Equity: Stock options under our Equity Incentive Plan
• Welfare: €4,000 – €8,000
• Buoni Pasto: 8€ per day

This isn’t a “maintain and optimise” role, but a 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—driving 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.

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

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.

• 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.

• 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, while having 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.

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

• 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.

• Need constant reassurance or close supervision.
• Avoid owning business results.
• Struggle with pressure and challenging targets.
• Prefer rigid processes over flexibility.