Chief Of Staff

About The Company
At Smartness, we are building the future of hospitality tech. Our SaaS helps lodging providers boost revenues by 30%+ and get more direct bookings.
We are the fastest-growing B2B SaaS in the industry, trusted by 4,000+ clients across 40+ countries, with billions of euros in bookings processed. Backed by top international investors and named one of Italy's Top 10 LinkedIn Startups, we are on a mission to scale globally.
Want to grow with us? Let's go!
What Will You Do?
You will report directly to the CEO and play a key role in turning strategy, performance, and execution into tangible results.
Performance & Talent Management

• Lead and continuously improve the company’s performance review processes
• Align individual and team goals with Smartness’ strategic objectives
• Measure performance and outcomes consistently using a data-driven approach
• Provide strategic insights on performance, talent development, and capability gaps
• Ensure performance reviews are fair, consistent, and analytically rigorous
• Act decisively on underperformance

Strategy Execution & Accountability

• Translate strategic objectives into clear initiatives with defined owners and timelines
• Track cross-functional execution (Product, Ops, Risk, Growth, etc.)
• Push teams to make decisions quickly and close every open loop
• Ensure clear ownership, deadlines, and real follow-through

Executive Enablement

• Prepare executive meetings, board decks, and weekly business reviews
• Cut through the noise and focus attention on what truly matters
• Challenge assumptions and narratives with data and critical thinking
• Represent the CEO in selected meetings when required

Strategic & Special Projects

• Lead or support organizational design initiatives
• Manage major operational changes and new strategic initiatives

What Are We Looking For?
We are looking for an extremely solid, autonomous, and impact-driven individual.

• Strong analytical skills: ability to turn data and KPIs into concrete decisions
• Strong business acumen (SaaS economics, growth levers, organizational dynamics)
• Ability to break down ambiguous goals into executable plans
• Extreme ownership, strong bias for action, and zero tolerance for open loops
• Ability to drive initiatives without formal authority
• Excellent executive-level written and verbal communication
• Comfort challenging assumptions and narratives with facts and data
• High judgment under pressure, discretion, and the ability to quickly recognize misleading information, weak narratives, or poorly grounded justifications

Background

• 2+ years of experience in top-tier strategy consulting (McKinsey / BCG / Bain) or in roles such as ex-founder, business analyst, or performance manager within high-growth companies
• Experience in hypergrowth environments (plus: M&A or international expansion exposure)
• Fluent in Italian and English

What Do We Offer?

• Work in a small and top-performing team that moves extremely fast where you are extremely important.
• Work without having to deal with jerks and ego-maniacs.
• The opportunity to join one of the best travel-tech sales teams in Europe.
• A place where your talent can blossom.
• An environment where mistakes are allowed – we make bold choices to achieve ambitious goals, learn from mistakes, and move forward.
• A place where your voice matters – meetings provide space for new ideas and projects, regardless of your role or seniority.
• Continuous growth – we challenge the status quo, renewing our sales processes and approaches to meet challenging goals.
• We have fun while working! We are easygoing people.
• Work with the best software out there to automate repetitive tasks and let you focus on customers and targets.
• Remote working with frequent opportunities to meet up.
• Fun and enriching experiences – unforgettable team-building events that go beyond the usual outings.
• Competitive salaries and bonuses – as a meritocratic team, we recognize talent and hard work, rewarding them appropriately.

Before you apply
If you're reading this, it means you're genuinely interested, and that excites us! Here's what you need to know:

• We're highly driven and set our goals higher than most, pushing boundaries others may deem impossible.
• We work much harder than most companies out there.
• Every day, we step out of our comfort zones, fueling rapid growth and learning, even though it might come with its stress.
• We hold ourselves and our team to the highest standards of excellence and culture.
• Should we feel that this role isn't the right match for you, for the benefit of both parties, we may need to part ways.

We hope this sheds light on whether this could be your next adventure. If you believe it is, we warmly invite you to apply. Discover your full potential with us!