Why big company backlogs are actually harder

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👋 Hey friend,

I have a confession.

When I joined HubSpot from a small startup, I thought managing the product backlog would be easier.

More resources. More process. More support.

Turns out… I was completely wrong.

Managing a backlog at a 20-person startup was significantly easier than managing one at a company with thousands of employees. And if you’re thinking about making the jump from small to big (or vice versa), this might change how you think about the move.

The startup wishlist: 47 items

At my startup, our product wish-list lived in Jira. It had maybe 47 items at any given time.

When a customer asked for something, I could:

• Talk to them directly within hours

• Check if it aligned with our 3-month roadmap

• Decide yes or no by end of week

• Ship it in the next sprint if it was a yes

Leadership, the entire eng team, and I could fit in one Zoom room (or meeting room in the office). Everyone knew what we were building and why.

Simple. Fast. Scrappy.

The enterprise backlog: Infinite

At HubSpot, our backlog isn’t a list. It’s an ecosystem.

There are feature requests from:

• Direct customer feedback

• Support ticket patterns

• Sales asking for deal-closers

• Customer success flagging churn risks

• Product marketing seeing market trends

• Other product teams needing integrations

• Internal teams needing their own workflows

• Leadership pushing strategic bets

Every single day, someone has a legitimate customer pain point that needs solving.

And here’s the thing: they’re almost all right.

Why bigger backlogs are actually harder

At the startup, prioritization was straightforward. Will this help us not die? Yes or no.

At a big company, prioritization is a completely different game:

1. Everyone’s customer is hurting

At the startup, we had one customer segment. At HubSpot? We have enterprise customers with completely different needs than small businesses.

A feature that delights a 50-person company might break workflows for a 5,000-person company. Both are paying customers. Both are “right.”

You can’t just solve the loudest problem anymore. You have to think about which segment you’re serving, what your strategy is, and who you might be leaving behind.

2. Stakeholder algebra is exponential

At my startup, I needed buy-in from maybe 3 people: Management, CTO and our lead engineer.

At HubSpot, a single feature decision can involve:

• My immediate team (PM, design, eng)

• Adjacent product teams whose features intersect with ours

• Go-to-market teams (sales, CS, marketing)

• Legal and privacy review

• Accessibility review

• Localization team for international markets

• Data and analytics teams

• Leadership across multiple orgs

That’s not bureaucracy for bureaucracy’s sake. It’s because when you have millions of users, a “small” change can have massive ripple effects.

Getting alignment isn’t about one meeting. It’s about building a coalition.

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3. Technical debt is a real constraint

At my startup, our codebase was 2 years old. If we wanted to rebuild something, we could.

At a company like HubSpot, some systems have been running for 10+ years. They’re supporting millions of customers who’ve built entire businesses on top of them.

That “simple” feature request? It might require refactoring a core system that 47 other features depend on.

Suddenly your 2-week project is a 6-month initiative that needs its own eng team.

You can’t just build fast and break things. You have to build sustainably.

4. The long game matters more

At my startup, if we shipped something mediocre, we could fix it next sprint. Our user base was small enough that we could iterate our way to great.

At scale, a bad launch means:

• Thousands of confused customers

• Hundreds of support tickets

• Sales teams scrambling to explain

• NPS or CSAT damage that takes quarters to repair

You can’t afford to ship half-baked solutions just to check a box. The bar for “good enough” is way higher.

This means some customer pain points sit in the backlog longer. Not because no one cares, but because solving them right takes real time.

The thing nobody tells you

Here’s what I wish someone had told me before I made the jump:

At a startup, you’re optimizing for speed. At a big company, you’re optimizing for impact at scale.

Both are hard. Just hard in completely different ways.

The startup taught me to move fast, talk to customers, and ship scrappy v1s.

The big company is teaching me to think systematically, build alliances across the org, and play the long game.

Neither approach is “better.” They’re just different problems.

What this means for you

If you’re at a startup dreaming of big company resources: yes, you’ll have more support. But you’ll also have way more constraints. That freedom to just build? You’ll miss it.

If you’re at a big company dreaming of startup speed: yes, you’ll move faster. But you’ll also have way less support. That infrastructure you take for granted? You’ll miss it.

The grass isn’t greener. It’s just different grass.

Quick Reads on Backlog Management

• Inspired by Marty Cagan: Product discovery and prioritization at scale (this is my favorite product book of all time)

• Escaping the Build Trap by Melissa Perri: Stop measuring outputs, start measuring outcomes

• The Lean Product Playbook by Dan Olsen: Systematic approach to what to build next

Challenge: Audit Your Backlog Honestly

This week, pick your top 10 backlog items and ask:

1. What’s the real constraint? (Not “it’s not prioritized” - dig deeper)

2. What would it take to actually ship this?

3. Is this truly high impact, or just high visibility?

Sometimes the honest answer is: “This would take 6 months and isn’t worth it right now.”

And that’s okay. That’s actually good prioritization.

The goal isn’t to clear the backlog. The goal is to build the right things.

Your backlog will always be infinite. Your time and resources never will be.

See you next week,
– Stef

P.S. The hardest part about big company backlogs? Learning to say no to good ideas. At a startup, you say no because you’ll die if you don’t focus. At a big company, you say no because you need to be great at a few things, not mediocre at everything.

💬 Want to talk product? I’m mentoring on ADPList! If you’re navigating startup vs big company decisions, or just need a sounding board on prioritization, you can book a free session with me right here.

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If you like Stef the PM, here are a few other reads worth checking out:

• → The Byte – Fast, punchy tech and AI news

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• → Practical Marketing – No-BS marketing tactics that work

• → Two Dads in Tech – Honest conversations about tech careers and life

• → Cooking Agile – Agile practices made practical

• → Seedradar AI – Startup and AI trends to watch

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