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Paulo André
CTO at Resquared (YC W21)
Paulo André is an engineering executive with a passion for coaching. He approaches leadership through the lenses of complexity, systems, and neuroscience.
Paulo holds a Master's degree in Computer Science from the University of Évora.
With a rich and diverse professional background, Paulo has held key positions in several prominent organizations. He has served as the Chief Technology Officer at Resquared, Fractional VP Product Engineering at Resquared, and Fractional CTO at Inflow, among others.
Paulo's experience includes roles such as VP of Engineering at Sharpist, Leadership Coach and Fractional CTO/VPE at PA Leadership Coaching, VP of Engineering & Interim VP of Product at TourRadar, Director of Engineering at HelloFresh, and various positions at HelloFresh ranging from Engineering Manager to Senior Software Engineer and Data Engineer.
His career journey also includes stints as a Software Developer at Universidade de Évora, InfluAds, and Freelance, as well as a Writer at LOUD! Magazine.
Paulo André has a holistic approach to leadership and shares his expertise through coaching and executive roles in the engineering and technology sector.
Highlights
Can you have both internal contentment and external success?
Is it a trade-off? To what extent? I believe you can have a great degree of both, but you can't maximize both. What really matters is 𝘄𝗵𝗶𝗰𝗵 𝘀𝗶𝗱𝗲 𝘆𝗼𝘂 𝗳𝗼𝗰𝘂𝘀 𝗼𝗻.
Let's use Warren Buffett's terminology: the "inner" and "outer" scorecards.
If you focus on external success—the outer scorecard—you depend on things you cannot control, like what others think and do.
This is the road to feelings of failure, unhappiness, and burnout.
If you focus on internal contentment—the inner scorecard—you focus on what you say, do, and think (inputs). You care about outcomes, but they aren't your main focus. Your contentment relies on what's within your control.
This the road to peace of mind.
For example, in a difficult work conversation, the outer scorecard focuses on the outcome, much of which is out of your control. The inner scorecard focuses on your courage to have the conversation and how well you did your part, which you can control and improve. Ironically, this increases the chances of a good outcome.
Many think not focusing on outcomes means they'll be "soft" or "unambitious."
Nothing could be further from the truth.
Caring deeply about outcomes is fine. The "aha!" moment is realizing that no matter how much you care, all you can control are your actions.
When you focus on outcomes before inputs, you set yourself up for disappointment and exhaustion. This affects your sleep, diet, exercise, and relationships, leading to you to do poorly on inputs. As Coach Wooden said, of "being at your best when your best is needed."
I have learned that there is absolutely nothing more leveraged than understanding and abiding by this deceptively simple truth.
Focus on your inner scorecard, and the outer one will take care of itself.

There's a silent disconnect in startups leading to pain, unhappiness, disengagement and burnout.
It's no one's "fault". It's just the way the deck is stacked.
VCs invest money into multiple startups expecting a multiple of their investment in return. Businesses obviously need to grow in value—the more, the faster, the better.
That's the game.
Those who take the money are then beholden, in a significant way, to their investors: there’s a commitment, codified as certain targets in a budget, mixed up as forecasts, which often find their way to the company's OKRs.
Unsurprisingly, when you’re managing to a number, you crave...
- Predictability
- Certainty
- Stability
And what do you have as a means to get there?
A bunch of humans, all quirky, each one a beautiful snowflake with their own story, issues, hopes and ambitions. Each with their own life experience, cultural background, childhood traumas, mental models and cognitive biases.
In other words, what you have is a complex system. Which is...
- Unpredictable
- Uncertain
- Variable
Do you see the conundrum?
In a complex system, behavior emerges. You can't control emergent behavior. But we sure do try. Oh boy, do we try.
Not all is lost, however. But there is a choice to be made:
🔵 𝗢𝗽𝘁𝗶𝗺𝗶𝘇𝗲 𝘁𝗵𝗲 𝗺𝗮𝗰𝗵𝗶𝗻𝗲. Manage top-down, executives do the thinking, rank & file executes, efficiency is sought, failure is avoided at all costs, learning is a nice to have. When things don't work, look for the culprit in individuals.
🔴 𝗡𝘂𝗿𝘁𝘂𝗿𝗲 𝘁𝗵𝗲 𝗹𝗶𝘃𝗶𝗻𝗴 𝘀𝘆𝘀𝘁𝗲𝗺. Manage bottom-up, executives create clarity and principles, everyone makes aligned decisions, effectiveness is sought, (fast) failure clears the path to success, learning is celebrated must-have. When things don't work, look for the culprit in the environment first.
Blue pill pretends complexity doesn't exist, it's all just complicated stuff and we are experts. Red pill acknowledges complexity, we don't know much, and we need to get smarter, faster.
What's it going to be?
#complexity #startups #leadership
