Strategic Advisory & Executive Coaching

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.

Unlock Your Growth See the Solutions
15+
Years in Technology Leadership
100+
Engineers Managed at Scale
0-200
Employee Scaling Experience
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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.
Luca Cipriani

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.

Arduino
Chief Information Officer
Ran global tech operations. Oversaw product, engineering, and operations. Implemented frameworks that actually worked.
Jimdo
VP of Engineering
Led 100+ person engineering organizations. Scaled teams through rapid growth. Managed cross-functional alignment at scale.
Prestiter
Chief of Strategy
Built management team. Drove AI and digital transformation. Built execution engine for 5-year industrial plan.

Trusted By

From startups to scale-ups. Click to see detailed case studies.

Unlock Your Growth

Proven Results

Measurable outcomes from my advisory and leadership work.

100+
Engineers Scaled
Jimdo
0 to A
From 1 Engineer to Series A
Arduino
3x
Revenue Growth
Italia Non Profit
200+
OKR Trainees
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
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
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.

Unlock Your Growth

Speaking & Press

Sharing insights on scaling, OKRs, and technology leadership.

Il Sole 24 Ore Il metodo OKR per le PMI: ecco perche puo 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.

01

Diagnose

Deep dive into current operating model, decision flows, and strategic blockers. Identify highest-leverage interventions.

02

Design

Co-create the organizational architecture, goal frameworks, and communication rhythms that fit your culture.

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.

Ways to Work Together

Choose the format that fits your needs. All engagements start with a discovery call to understand your context.

Individual Focus

Executive Coaching

  • 1:1 sessions with C-level executives
  • Leadership development focus
  • Scaling challenges navigation
  • Decision-making support
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.

Accepting 1 new advisory client for Q2 2026

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.

Let's Scale Together
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