I still remember that tiny startup office—the hum of one server, the click of keyboards, the aroma of strong coffee, and the creaking of the wooden floorboards as we all squeezed around a single table. We all knew exactly what was happening. A quick word across the desk solved problems instantly. It was magic.
Then came growth. We went from 12 people to 50 in six months. Suddenly, no one knew who was supposed to fix that bug or handle that angry customer email. I remember the founder, eyes red from late nights, saying, “I can’t keep all of this in my head anymore.” That’s when we knew: we needed structure.
Stage 1: The All-Hands Phase
I remember walking into a tiny Bangalore office where the walls were peeling and the coffee was always too strong. The CEO was writing backend code while arguing with a sales lead on speakerphone. A designer sat cross-legged on the floor sketching wireframes on a whiteboard. It was chaotic—but it worked. For a while.
What happens: Everyone wears every hat. Engineers test. Designers handle support. The CEO writes code and sells to customers.
The high: There was an intoxicating rush in those days—every bug fix felt like a team victory, every launch a collective adrenaline spike.
Why it works: With a 12-person team, communication is one shout away. You’re fast because you share a brain.
When it breaks: By hire #20, you’re running on chaos. Decisions that took five minutes now drag on for days.
Mini-case study: A mid-market retail app scaled from 15 to 60 employees in four months. Their release cycle went from one week to four weeks because every feature needed sign-off from three department heads. That’s 300% slower.
Quick fix: Add just enough process to cover gaps. We chose a weekly 30-minute standup for cross-team updates because it balances regular touchpoints without overwhelming calendars.
Reflection: If your team grew by 300% and your release cycle slowed by 300%, where would you start tightening up? Standups? A shared roadmap?
Stage 2: The Tween Phase
I call it the Tween Phase—that awkward middle stage where the company isn’t scrappy and small anymore, but it’s nowhere near mature. It’s grown beyond the “everyone-does-everything” chaos of the early days, but the systems, clarity, and ownership that come with scale haven’t landed yet. This is when roles start to blur, responsibilities fall through the cracks, and fingers start pointing: “I thought you owned that.” Time to choose your org shape.
| Model | Pros | Cons | Impact (per feature) |
|---|---|---|---|
| Functional | Deep expertise, consistent standards | Slow cross-team launches | +1 week of quality, –2 weeks launch speed |
| Product squads | Fast end-to-end ownership | Risk of duplication, silo mentality | –4 weeks time-to-market, +$50K in overlaps |
Mini-case study: A fintech startup formed three cross-functional squads. They cut feature time-to-market from six weeks to two (–67%), but ended up with two different billing modules, each costing $50K to maintain.
Framework: Communication Triage Matrix
Reflection: Think of your last big misfire—was it a sync issue or an escalation issue? How could this matrix have helped?
Stage 3: The Big League
There was a founder I worked with who’d built something magic. The product was flying off the shelves, the team had grown to 120, and investors were circling. But inside? It was falling apart. Decisions dragged. People kept building the same thing twice. Teams started joking about needing a map just to find who owned what. When I asked who was in charge of launching the new feature set, five people gave me five different names.
He didn’t need new hires. He needed a new org.
Hundreds or thousands of people. Now the stakes are higher.
But here’s the hidden challenge at this stage: the leadership team. You might have a clear org chart, but if your execs don’t scale with the company, structure alone won’t save you. I’ve seen it up close—a brilliant product leader at a company that grew 10x in 18 months. She was phenomenal when the team was 15 people. But as the org crossed 100, she struggled to delegate, hoarded decisions, and eventually became a bottleneck. Features stalled, team morale dipped, and the founder had to make the hard call to layer above her.
It’s what I call executive design debt—when the roles and responsibilities of your senior leaders no longer match the scale of the work. And like tech debt, the longer you wait to address it, the messier it gets.
So as you look at whether to scale functionally or divisionally, also ask: do you have the right leadership layer in place to carry the complexity? And if not—do you coach them up, layer them, or let them go?
Functional at scale:
- One massive design team. One engineering org. Decision rights by craft.
- Trade-off: They slowed feature innovation by 20% but maintained a flawless, integrated product feel.
Divisional at scale:
- Separate P&Ls. Autonomy for each business unit.
- Case in point: A SaaS leader spun into five divisions, each with its own marketing, engineering, and design. They launched features 40% faster but saw a 15% increase in redundant work.
Reorg Trigger Checklist
- 🚩 Decisions bottleneck at executives.
- 🚩 Teams duplicate core work.
- 🚩 Customer complaints about inconsistent experiences.
- 🚩 Strategy shifts (new product, market, or acquisition).
Reflection: Which of these flags is waving at your company today? How soon can you act?
Keeping Quality and Taste Alive
There was this design lead—quiet, brilliant, obsessed with typography. For years, she set the visual standard. Everything went through her. But one day, the team was too big, and the roadmap too fast. She couldn’t keep up, and the cracks showed. The product looked stitched together. Customers noticed. She broke down in a review, not because she was tired—but because she felt like she had let the company slip out of its own skin.
That’s when we realized: good taste doesn’t scale unless you teach it. Codify it. Build it into the culture. And protect it like it’s part of the product.
The founder’s eye for quality can’t scale by itself. Instead, bake it into process:
- Design review committee: A small group that vets all major releases. I once sat in on a heated debate where designers argued over button placement until the committee intervened and saved the flow from a confusing UI.
- Quality criteria in specs: Add a “brand taste” checkbox.
- Leader spot-checks: Execs spend one day a month in the design tool or support queue.
Case study: A consumer platform insisted on a monthly “editorial day” where product and design leads co-signed on every new flow. This ritual cut UI inconsistencies by 80%.
Investor note: Every hour execs spend unblocking team issues is an hour not spent on growth. Structure that reduces exec hand-holding by 50% can improve time-to-market and free leadership bandwidth for strategy.
Dangerous Patterns That Sneak Up on You
These are the silent killers—the organizational dysfunctions that don’t show up on dashboards:
- The Hero Founder Bottleneck: One person still reviewing everything at 100+ people. Speed dies in their inbox.
- The Phantom VP: They’ve got the title, the salary, the Slack channel—just not the authority.
- The Polite Delay Spiral: Endless syncs. No decisions. Everyone smiles while the roadmap gathers dust.
- The Silo Slide: Your org chart looks clean, but nobody talks to each other. Sales builds what marketing wants. Product ships what nobody asked for.
If any of these feel familiar—you’re not broken. You’re just overdue for a redesign.
My Role as Your Design Org Partner
- No structure is permanent. Revisit your org annually. For instance, when a founder I worked with adopted annual org reviews, they cut miscommunication escalations by 30%.
- Match structure to priorities. Tune for the communication paths that matter now.
- Make culture explicit. Write your values. Use them in decisions.
- Lead by example. Execs must model the behaviors and quality they expect.
- Communicate relentlessly. At scale, information is oxygen.
Final reflection for investors and founders:
- If your release cycle has doubled, what’s the cost in dollars and reputation?
- When was your last org checkup? What flags did you miss?
- How much exec time is eaten by coordination vs. innovation?
Design your org like a product: prototype, test, iterate. Get the structure right, and you’ll build faster, smarter, and keep that original spark alive—no matter how big you grow.
One founder told me, “I thought I needed a better product roadmap. But what I really needed was to stop being the roadmap.”
So here’s your challenge: what’s the next prototype your org needs to run?
Your challenge: What’s the next experiment you’ll run on your org?. Get the structure right, and you’ll build faster, smarter, and keep that original spark alive—no matter how big you grow.
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