Giulio Castiglioni: Finding a Dream in Your Job

Welcome to Escalations, a series where I’ll be sharing stories of some amazing careers that started in Customer Support. While many of these will be compiled into a book, I will also be regularly sharing stories here, too. If you like this content, please consider subscribing or sharing. 

Introduction: The Starting Point

Giulio began his professional life coaching youth football in Italy. Although he once hoped to earn a full living through sports, he quickly recognized the challenges of making that dream a reality. Still, he remained driven by the satisfaction he found in guiding others to grow—a passion that took on new life when he discovered an opportunity to blend sports and technology.

His first meaningful contact with frontline support happened at PrenotaUnCampo, an Italian startup building a SaaS solution for sports clubs. Initially hired in sales, Giulio soon realized his real talent lay in working with customers after the sale—helping them troubleshoot issues, understand the product, and achieve success.

The Growth Path

After PrenotaUnCampo merged with Playtomic, Giulio’s role quickly expanded. Despite having no formal background in customer support systems, he proactively taught himself to configure tools like HubSpot and set up effective live chat solutions. Though the pandemic cut short his coaching, it opened a new door: honing his customer-care skills on a global stage.

He realized that simply taking on tasks wouldn’t suffice for Playtomic’s rapid growth, so he focused on building scalable processes from the ground up. Whether recruiting new teammates, leading onboarding sessions, or creating knowledge bases, Giulio designed each step to be repeatable and future-proof. Meanwhile, the communication tactics he’d perfected on the football field proved critical as he coordinated with team members and customers across Europe and the Americas.

Key obstacles Giulio had to overcome included:

• Moving from an individual contributor to a more visible role in record time

• Navigating international hiring processes (without a dedicated HR team)

• Demonstrating that strong customer care drives positive changes in product development

Despite these barriers, Giulio’s “solve it before they ask” mindset helped him advance to become Customer Care Director. If you’re aiming for similar progress, consider how his experiences can guide your own path.

Implementing This in Your Own Career

• Focus on knowledge transfer early (build self-service resources)
  Even if you’re not a manager, advocate for documentation and self-service tools. Volunteering to create or update FAQs shows initiative and highlights your expertise.

• Lean on existing talents (communication, leadership) to guide personal growth
  Use the strengths you already have—like cross-team communication or organization—to stand out for new opportunities or roles.

• Find ways to do more with less (automation, thoughtful collaboration, cross-training)
  Offer solutions that streamline workflows. By reducing manual tasks for everyone, you position yourself as a resourceful problem-solver.

Breaking Through: Lessons & Key Decisions

1. Embrace Unexpected Opportunities

Giulio jumped into PrenotaUnCampo because it blended sports and tech. When Playtomic acquired the startup, he tackled broader responsibilities rather than waiting to be handed a formal “growth plan.” Proactively leaning into change can accelerate your own career.

How You Can Apply It

• Offer your help when you see big organizational changes, rather than waiting to be told what to do

• Jump on cross-functional projects that expose you to new roles and skills

• Frame challenges (e.g., sudden mergers or restructuring) as chances to prove adaptability

2. Learn by Doing, Then Share What You Learn

Without formal support training, Giulio taught himself how to use CRMs and build customer-facing systems. Then, he documented everything so others could benefit—raising his profile as the go-to resource.

How You Can Apply It

• Dive into tools, courses, or tutorials on your own initiative—even if it’s not your manager’s idea

• Keep notes or guides you can share with coworkers, making you the resident expert

• Look for feedback loops: refine processes based on real-world results, then repeat

3. Promote Talents from Within (Starting with Yourself)

Giulio recognized that leadership potential isn’t limited to top performers. Individuals who excel in organization, empathy, or cross-team relationships often rise faster. If you have these abilities, showcase them—don’t wait for a specific “leader” label.

How You Can Apply It

• Identify your personal strengths (e.g., project management, relationship-building) and use them in volunteer projects or side tasks

• Ask your manager or peers about ways to demonstrate leadership without a formal title (e.g., training a new hire)

• Track milestones that reflect your soft skills, such as coordinating multi-departmental efforts

4. Anticipate Before You’re Asked

A major reason Giulio advanced so quickly is his habit of solving problems before being officially tasked. By spotting potential issues early and proposing fixes, he became an indispensable contributor.

How You Can Apply It

• Stay curious: research potential roadblocks (e.g., spikes in support tickets)

• Draft a simple plan or proof of concept to back up your suggestions

• Communicate your solutions confidently—step forward with constructive ideas, not just problems

5. Leadership Is an Ongoing Practice (Even for Non-Managers)

Giulio’s experience with culturally diverse teams taught him that leadership is more than a title. It involves constant learning, empathy, and the willingness to adapt—traits anyone can develop by working closely with colleagues.

How You Can Apply It

• Listen and observe how teammates communicate best (e.g., Slack vs. video calls)

• Offer consistent support or guidance, even if you’re not “in charge”

• Reflect on each day’s interactions to see how you might fine-tune your approach

Actionable Takeaways

• Build Self-Service Options Early

  • Seek opportunities to create or improve documentation (like an FAQ).

  • Pitch chatbots or other tools that address common customer pain points.
    

• Foster a Culture of Mentorship

  • Reach out to a mentor—or mentor a newer teammate—so everyone learns faster.

  • Share both victories and struggles to support collective problem-solving.
    

• Seek Cross-Functional Alignment

  • Collaborate with other departments (product, marketing) to tackle recurring customer issues at the source.

  • Present your findings in a way that clarifies the impact on overall business goals.

• Empower Yourself (and Others) to Innovate

  • Suggest “free project” hours to experiment with new ideas, even if it’s just an hour a week.

  • Recognize and celebrate small wins openly, building a case for bigger initiatives.

• Aim for Internal Growth

  • Volunteer for tasks beyond your current role to learn new skill sets.

  • Keep an eye out for informal leadership roles (e.g., heading a short project) to show you can handle more responsibility.

Where They Are Now & Final Words of Advice

Today, Giulio leads a global customer care team at Playtomic, bridging data-driven insights with genuine human support. His story—evolving from a young football coach to an international director—shows that a meaningful career often comes from combining your fundamental passions with the agility to embrace change.

Do you have a story to tell or insights to share? Consider having a conversation with me so I can share something like this about you!