In this episode of The Breakout CEO, host Jeff Holman sits down with Phil Alves, founder of DevSquad, to unpack his journey from Brazil to leading a thriving SaaS product development agency. Phil shares how his modular “squad” model transformed DevSquad from a small shop into a 100+ person company, why scaling requires systems that outlast the founder, and how culture became his greatest lever for growth. He also reflects on his breakout moment during the pandemic, when he chose to pause new client work to protect quality — a decision that reshaped DevSquad’s future.
When the pandemic hit in 2020, demand for software exploded. DevSquad was flooded with new clients, and Phil pushed hard to meet it — hiring rapidly and stretching his team thin. But soon, cracks appeared. Playbooks weren’t holding, quality slipped, and Phil himself was working 14-hour days.
That’s when he made the bold choice to stop. For four months, DevSquad put prospective clients on a waitlist, turning away revenue to rebuild infrastructure and reinforce systems. Clients were asked to put down deposits and wait their turn. Many did — proof of DevSquad’s strong reputation. The result? 150% growth that year, but achieved sustainably and with team alignment intact.
Phil’s breakout insight: scaling isn’t about saying yes to everything. It’s about setting boundaries that protect your people, your culture, and your reputation. By prioritizing quality over unchecked growth, DevSquad created a new model — measured growth, limited client spots each quarter, and systems that keep optionality in the founder’s hands.
For scaling CEOs, the lesson is clear: sustainable growth requires discipline. True scale comes from building playbooks, empowering leaders, and knowing when to say no.
What he learned:
Phil realized that unchecked growth creates diminishing returns — overwork, quality decline, and damaged reputation. By slowing down, he discovered that clients valued predictability and quality so much that they were willing to pay deposits and wait in line. Growth could be strong and controlled, as long as systems and culture were prioritized.
Advice for scaling CEOs:
Phil’s breakout insight: scaling isn’t about saying yes to everything. It’s about setting boundaries that protect your people, your culture, and your reputation.
For scaling CEOs, the lesson is clear: sustainable growth requires discipline. Build playbooks, empower leaders, and know when to say no. True scale comes when the business thrives even in your absence.
Listen to the full episode for Phil's detailed story and insights.
Phil Alves’ story is a reminder that scaling is about more than headcount or revenue. It’s about building systems, empowering people, and protecting the culture that makes growth possible. His decision to choose quality over speed during DevSquad’s busiest year created a foundation for long-term sustainability — a path many scaling CEOs can learn from.
For SaaS, ecommerce, and tech CEOs navigating growth, Phil’s approach echoes a key principle: put the odds in your favor. Whether that means hiring a fractional general counsel for SaaS, developing a patent strategy for ecommerce, or building modular teams, sustainable scaling depends on foresight and discipline.
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Phil Alves is the CEO of DevSquad and a seasoned entrepreneur with deep experience building and scaling SaaS products. Originally from Brazil, Phil has helped dozens of founders bring their ideas to life with lean, scalable development strategies. Connect with him on LinkedIn.
LinkedIn: https://www.linkedin.com/in/philalves/
DevSquad is a SaaS product development agency that builds custom software solutions through a unique “squad” model. By combining cross-functional teams with repeatable playbooks, DevSquad helps entrepreneurs go from concept to product-market fit while ensuring quality and accountability.
Website: devsquad.com
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Jeff Holman is a CEO advisor, legal strategist, and founder of Intellectual Strategies. With years of experience guiding leaders through complex business and legal challenges, Jeff equips CEOs to scale with confidence by blending legal expertise with strategic foresight. Connect with him on LinkedIn.
Intellectual Strategies provides innovative legal solutions for CEOs and founders through its fractional legal team model. By offering proactive, integrated legal support at predictable costs, the firm helps leaders protect their businesses, manage risk, and focus on growth with confidence.
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The Breakout CEO podcast brings you inside the pivotal moments of scaling leaders. Each week, host Jeff Holman spotlights breakout stories of scaling CEOs—showing how resilience, insight, and strategy create pivotal inflection points and lasting growth.
Listen and subscribe on your favorite podcast platform:
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Want to be a guest—or know a scaling CEO with a breakout story to share? Apply directly at go.intellectualstrategies.com.
00:05 — Scaling a Service Business
Phil explains how DevSquad evolved from a 4-person startup to a 100+ person agency using the “squad” model. Each squad is a modular, cross-functional unit that can deliver end-to-end SaaS products.
08:42 — From Doer to CEO
Scaling a service business isn’t just about more clients. Phil shares why founders must transition from being the doer to becoming a true CEO who builds systems that run without them.
10:46 — Culture as a Growth Engine
At DevSquad, leaders are expected to create other leaders. Phil describes how rituals, expectations, and a “culture squad” sustain alignment as the company scales.
13:07 — The Power of Optionality
Phil explains why he optimizes his business for optionality — the ability to say yes or no to growth, clients, or strategy shifts without outside investor pressure.
31:00 — Breakout Moment: Hitting Pause in 2020
Amid skyrocketing demand, Phil slowed growth, implemented waitlists, and refocused on quality. The move safeguarded DevSquad’s reputation and created a more sustainable model.
36:08 — Building a Sustainable Future
From client deposits to capped onboarding each quarter, Phil explains how DevSquad now grows at a controlled, high-quality pace.
