Individual focus
Executive Coaching
- 1:1 sessions with C-level executives
- Leadership development focus
- Scaling challenges navigation
- Decision-making support
Accepting 1 new advisory client for Q1 2027
Ready to scale. Not sure what’s holding you back.
Decisions slow down. Strategy fragments. Teams work hard but impact plateaus. You know you need to change something, but what?
I help growth-stage companies navigate the 20 to 200+ employee transition by identifying what’s blocking them and building the systems that unlock scale.
Luca Cipriani
Former CIO at Arduino and VP of Engineering at Jimdo
The scaling challenge
Growing from 20 to 200+ people changes everything. What worked before starts breaking.
Slower decisions
Alignment meetings multiply. Decisions that took hours now take weeks. Leaders become bottlenecks instead of accelerators.
The fix
Clear decision-making processes that put velocity back in your hands.
Lost focus
Teams work hard on different priorities. Effort increases but impact plateaus. Strategy fragments across departments.
The fix
Strategic alignment frameworks (OKRs) that keep everyone rowing in the same direction.
Execution drift
Projects take longer. Quality slips. The startup agility that fueled growth becomes a memory.
The fix
Execution systems that preserve agility at any scale.
How AI-ready is your team?
Free 3-minute check: your readiness score, a skills breakdown, and a concrete roadmap — works with any AI stack.
I’m not a theorist
I’ve lived the scaleup struggle and built the systems that solved it.
As VP of Engineering at Jimdo, I scaled teams through rapid growth and built systems that maintained execution speed. As CIO at Arduino, I oversaw product, engineering, and operations while navigating the chaos of scaleup dynamics.
I’ve driven AI and digital transformation, built management teams, and delivered multi-year industrial plans. Now I help other leaders do the same.
Methodologies I draw from: OKRs, Shape Up, RAPID decision frameworks, and custom approaches designed for your context.
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Arduino
Chief Information OfficerRan global tech operations. Oversaw product, engineering, and operations. Implemented frameworks that actually worked.
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Jimdo
VP of EngineeringLed 100+ person engineering organizations. Scaled teams through rapid growth. Managed cross-functional alignment at scale.
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Prestiter
Chief of StrategyBuilt management team. Drove AI and digital transformation. Built execution engine for 5-year industrial plan.
Arduino
Chief Information Officer
I launched the Arduino Cloud business line, transforming Arduino from a hardware company to a cloud-first IoT platform.
Key contributions
Jimdo
VP of Engineering
I led a team of 100+ engineers, achieving 100% uptime for customer sites in 2024 and delivering 1.5M in cloud spending savings through FinOps initiatives.
Key contributions
AgileLab
OKR Coach
I introduced and implemented the OKR framework across the organization, building internal expertise and sustainable processes.
“For all people looking forward to leverage OKR I can recommend Luca Cipriani as OKR Coach. He helped us a lot to learn OKR the right way and still providing shadowing to refine our practice.”
Paolo Platter
Co-Founder & CTO, AgileLab
Key contributions
OGR Torino
Startup Mentor & AI Readiness Assessment
I mentor startups in the ReAction program and run the AI Readiness Assessment for OGR Startup Booster, helping founders define strategy, scale teams and put effective execution frameworks in place.
Key contributions
Feat Ventures
OKR Trainer & VECTAR Mentor (Aerospace & Robotics)
I launched an OKR Training program for portfolio startups, equipping founding teams with the tools to scale with focus and alignment. As a VECTAR mentor, run with Fondazione Links, I hold workshops and 1:1 office hours for research teams in space, drones and robotics.
Key contributions
Prestiter
Chief of Strategy
I built the management team, led digital and AI transformation, and created the execution engine for the five-year industrial plan.
“Meeting Luca was providential. He enabled us to immediately apply the OKR methodology effectively and reach full adoption in just a few quarters. We also greatly improved information sharing, time management, and our decision-making processes.”
Andrea Di Vincenzo
CEO, Prestiter
Key contributions
Bikeroom
Fractional CTO
As Fractional CTO, I lead technology strategy and engineering for Bikeroom, the marketplace for new and certified used premium bikes.
Key contributions
Guidoio
Tech Coach & AI Instructor
I coach and mentor the tech department, and I train the team on how to use AI in their daily engineering work.
Key contributions
Italia Non Profit
Chief of Strategy
I introduced Nora, the AI for social project design, transforming how non-profit organizations access grants and funding opportunities.
Key contributions
Proven results
Measurable outcomes from my advisory and leadership work.
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100+
Engineers scaled at Jimdo.
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0 to A
From 1 engineer to Series A at Arduino.
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2×
Conversion rate at Prestiter.
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200+
OKR trainees across multiple clients.
What clients say
Leaders I’ve worked with share their experience.
“For all people looking forward to leverage OKR I can recommend Luca Cipriani as OKR Coach. He helped us a lot to learn OKR the right way and still providing shadowing to refine our practice.”
Paolo Platter
Co-Founder & CTO, AgileLab
“Meeting Luca was providential. He enabled us to immediately apply the OKR methodology effectively and reach full adoption in just a few quarters. We also greatly improved information sharing, time management, and our decision-making processes.”
Andrea Di Vincenzo
CEO, Prestiter
Strategic partner, not consultant.
I don’t deliver slide decks and disappear. I work alongside your leadership team as a peer—someone who’s sat in your chair, managed your problems, and built the systems that solved them.
At Jimdo, I scaled engineering through rapid growth. At Arduino, I oversaw product, engineering, and operations during the messiest phase of scaleup. I’ve built management teams, led AI adoption, and delivered multi-year transformation plans.
I take on a small number of retained advisory clients at a time. If we work together, you get direct access to my thinking, not a junior associate.
Speaking & press
Sharing insights on scaling, OKRs, and technology leadership.
- Il Sole 24 Ore Il metodo OKR per le PMI: ecco perché può favorire crescita e innovazione
- YouTube Why Engineers Hate OKRs — and How Leaders Can Change That
- Spotify I developer devono saper progettare user experience?
- Spotify Il ruolo dell’Engineering Manager e talent retention
- LinkedIn Live Guidance Counselor 2.0 + Tips to Hiring Managers
Strategic advisory areas
I work alongside your leadership team as a strategic peer, not as an external implementer.
Organizational scaling
Restructuring teams, decision rights, and communication patterns to maintain velocity as you grow from 20 to 200+ people.
Strategic alignment
Creating clarity from strategy to execution. Ensuring every team understands priorities and how their work contributes to outcomes.
Digital & AI transformation
Technology strategy and organizational change for companies modernizing operations. Practical AI adoption roadmaps, high-impact use cases, and integrating new capabilities into workflows.
How I work
Strategic partnership, not consulting. I accelerate your thinking and build lasting organizational capability.
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01
Diagnose
Deep dive into current operating model, decision flows, and strategic blockers. Identify highest-leverage interventions.
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02
Design
Co-create the organizational architecture, goal frameworks, and communication rhythms that fit your culture.
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03
Embed
Hands-on support through first cycles. Coach leaders, facilitate sessions, and iterate until systems run independently.
Focus on independence
“I build internal expertise so you own the process end-to-end. My goal is to make myself unnecessary.”
Luca Cipriani
Strategic advisor
Ways to work together
Choose the format that fits your needs. All engagements start with a discovery call to understand your context.
Ongoing partnership
Strategic Advisory
- Monthly strategic sessions with leadership
- On-demand access for critical decisions
- Quarterly planning facilitation
- Ongoing organizational coaching
Intensive engagement
Transformation Project
- Full diagnostic and design phase
- Implementation support (3–6 months)
- Leadership team workshops
- Change management guidance
Common questions
What you might be wondering before we talk.
Strategic advisory is designed to leverage your time, not consume it. Expect 2–4 hours per month for our sessions, plus async support. I adapt to your calendar and decision rhythms.
Most clients see improved clarity and decision speed within the first month. Structural changes typically show measurable impact in 2–3 months. I focus on quick wins while building long-term capability.
My goal is to make myself unnecessary. I build internal expertise and documented processes so your team owns the systems end-to-end. Many clients transition to lighter check-in arrangements.
I maintain strict confidentiality and avoid direct conflicts. If there’s potential overlap, I’ll discuss it transparently before we start. Your strategic conversations stay private.
Consultants deliver reports and leave. I work alongside your team as a peer who’s accountable for outcomes. No junior associates, no generic frameworks — direct access to someone who’s solved these problems firsthand.
Let’s discuss your scaling challenges.
Schedule a 30-minute discovery call to explore how strategic partnership could accelerate your organization’s growth trajectory.
Pick a time that works for you. I’ll send you a calendar invite with the video call link. No pitch, no commitment. If I can’t help, I’ll tell you and point you in the right direction.
Ready to scale?
Book a call