Coaching & Advisory
Strategic Guidance for Senior Technical Leaders
I help VPs of Engineering, CTOs, and technical co-founders scale their teams and sharpen their leadership, drawing on 15+ years building and leading engineering organizations at Google and beyond.
Why I Coach
Early in my career, I didn't have access to mentorship. It wasn't until my time at Google that I discovered how much of a difference it made to have someone who could be a guide, a sounding board, and help me question my assumptions. My growth accelerated considerably, and I couldn't believe I'd missed out on that for so long.
That experience inspired me to start actively coaching others. I've since worked with dozens of professionals — from ambitious early-career engineers to seasoned leaders navigating organizational complexity. There's a George R.R. Martin quote I come back to often:
"I have lived a thousand lives and I have loved a thousand loves. I've walked on distant worlds and seen the end of time. Because I read."
I mentor for similar reasons. Each conversation lets me deeply empathize with someone in a different situation and think about how we can solve their challenges together. It makes me more introspective, a stronger leader, and a better professional.
Who I Work With
Leaders from Google, Meta, Microsoft, Anthropic, and venture-backed startups across 17 countries
I work best with leaders who've been in the trenches and are now grappling with organizational complexity, team scaling, or the shift from technical excellence to strategic impact.
Read my writing on engineering leadership to get a sense of how I think.
VPs and Directors of Engineering
Scaling organizations and navigating the transition from hands-on to strategic leadership.
First-time CTOs and Technical Co-founders
Building engineering orgs from the ground up while balancing technical and business demands.
Senior ICs Transitioning to Executive Roles
Developing executive presence, stakeholder management, and organizational thinking.
Leaders at Inflection Points
Navigating re-orgs, rapid growth, career transitions, or high-stakes organizational change.
How I Can Help
Drawing on my experience leading engineering at Google and as VP at a climate-tech startup
Deep-dive conversations on your most pressing leadership challenges, with concrete takeaways.
Team structures, reporting lines, and processes that scale with your organization.
How to stay technical enough to earn trust while operating at the strategic level your role demands.
Framing technical decisions for the board, navigating difficult conversations with your C-suite peers, and getting buy-in across functions.
Designing interview loops that actually work, making calibrated hiring decisions, and shaping the culture you want as you grow.
Ongoing strategic advisory for startups that need experienced engineering leadership on a flexible basis.
How It Works
Discovery Conversation
We start with a no-commitment conversation to understand your situation, goals, and whether we're a good fit.
Tailored Engagement
Based on your needs, we design an engagement: ongoing coaching, a focused sprint, or advisory arrangement.
Ongoing Partnership
Regular sessions with async support between calls. I invest in understanding your context deeply so every conversation counts.
What Clients Say
★★★★★ 5.0/5 from 20+ reviews
“His style is very personal, he patiently listened to my questions and dove into clarification before answering. He really tries to make his answers clear and as close to the core of the question asked regardless of the subject. His experience is very extensive too, allowing us to discuss a wide range of subjects, so I feel like I got more than one mentor in one.”
Fernando
Engineering Manager
“Alessandro pushes me to think like a Director, not just an EM. He doesn't give surface-level advice – he asks probing questions to understand root causes, then provides concrete, actionable strategies. Most importantly, he creates a safe space for growth. Since working with Alessandro, I've made significant progress overcoming impostor syndrome, achieved strong success in hiring negotiations, and gained frameworks for accountability and strategic planning that I use daily.”
Roman
Engineering Leader
“I met with Alessandro to discuss some soft skills topics, the session was great and more than I anticipated! Alessandro not only addressed my concerns but also deduced additional underlying aspects from it, and provided multiple valuable advice — all in the short time of the meeting.”
Eyal
Frequently Asked Questions
What happens in a discovery conversation?
It's a free, no-commitment conversation where we discuss your current situation, goals, and challenges. I'll share how I might be able to help, and we'll both decide if it's a good fit.
How is this different from generic career coaching?
I'm not a career coach — I'm an engineering leader who has built and scaled teams at Google and startups. My coaching is grounded in first-hand experience with the exact challenges you're facing: org design, technical strategy, stakeholder management, and executive leadership.
Can my company pay for this?
Yes. Many clients expense coaching through their company's professional development or L&D budget. I can provide invoices and documentation to support this.
How does pricing work?
Every engagement is tailored to your situation and goals. After our discovery conversation, I'll propose an arrangement that covers scope, cadence, and pricing. There are no lock-in contracts.
Ready to Level Up Your Leadership?
Let's start with a conversation. No commitment, no pressure, just an honest discussion about where you are and where you want to go.