Lessons From Moving Upmarket

In 2024, we stepped up to work with bigger startups. Series A and B companies with real traction, real teams, and real budgets.

It’s been better in a lot of ways. More interesting experiments to run. More data to work with. More recognition in the market because the client logos carry weight.

But the assumption I had going in — that bigger companies would be easier to deliver for — turned out to be wrong. Bigger doesn’t mean easier. It means different challenges.

Here are the lessons we learned the hard way.

Even impressive companies are struggling with GTM right now

This was the most surprising thing. We started working with companies that had raised serious rounds, had hundreds of customers, and had real brand recognition in their space. I expected their GTM infrastructure to be solid.

It wasn’t.

Some of these companies had never done outbound at all — they’d grown entirely through inbound, product-led growth, or founder-led sales. When the market tightened and inbound slowed down, they needed outbound to work, but they had no infrastructure for it. No domains warmed. No list-building process. No enrichment workflows. No messaging framework beyond whatever the founder had been saying on sales calls.

Others had tried outbound and failed because they applied 2021 tactics to 2024 realities. Mass emails with generic personalization. Apollo exports with no enrichment. No deliverability hygiene.

The takeaway: company size and traction don’t correlate with GTM operational maturity. Some of the most impressive companies we worked with were starting from scratch on outbound infrastructure. That’s not a criticism — it just means the problem we solve is relevant at every stage, not just for early-stage startups figuring things out.

There are no shortcuts on buyer understanding

Every outbound team needs to know three things in great detail: WHY buyers buy, WHEN they evaluate, and WHAT motivates them to change their current process.

This sounds obvious. It’s not, in practice. Bigger companies often assume they know their buyer because they have customers. But having customers and understanding the buying trigger are different things. Your customers can tell you why they stayed. They often can’t tell you what made them look in the first place.

The teams that got results quickly from our work were the ones willing to do the hard research upfront. Talking to recent customers about what triggered their evaluation. Mapping the buying committee. Understanding the competitive alternatives, including “do nothing.” Building messaging around specific situations, not generic pain points.

The teams that wanted to skip this and go straight to “just send emails” always hit a wall. Usually around week four, when the reply rates came back flat and we had to retroactively do the research we should have done in week one.

Terrible email deliverability hides behind great products

Some companies grow to hundreds of employees with email infrastructure that would make a deliverability specialist cry. SPF records half-configured. No DMARC policy. Sending domains with no warmup history. Marketing emails and sales outreach running through the same infrastructure with no separation.

How did they get this far? Great marketing and an amazing product. When your inbound engine works and your product sells itself through word of mouth, you can get away with 2019-era email infrastructure. Nobody notices because nobody is relying on cold email to drive pipeline.

The problem surfaces the moment you try to scale outbound. You set up sequences, hit send, and watch your emails land in spam. Then you realize you need weeks of warmup, proper domain architecture, inbox placement testing, and ongoing monitoring — all things that should have been built months ago.

This was a recurring pattern across our bigger clients. The fix isn’t hard, but it takes time. And time is the one thing a company that just decided they need outbound doesn’t want to spend.

What worked six months ago might not work today

I’ve seen this at every stage, but it hits harder with bigger companies because the stakes are higher and the feedback loops are slower.

A messaging angle that crushed it in Q1 goes flat in Q3. A channel that was delivering consistent pipeline suddenly stops working. A segment that was responsive goes cold because three competitors started targeting the same people with the same approach.

Top teams accept this. They treat every campaign as an experiment with a hypothesis, not a proven playbook. They test continuously. They kill what’s not working without ego. They measure everything so they know when something shifts before it becomes a crisis.

The teams that struggle are the ones looking for The Playbook — the single strategy they can set up once and run forever. That doesn’t exist in outbound. It barely exists anywhere in GTM. The only durable advantage is the ability to test, learn, and adapt faster than everyone else.

Bigger teams mean more stakeholders

At a four-person startup, everyone has the same priority: survive. You can make a decision over lunch and execute by end of day.

At a 50-person startup with a VP of Sales, a Head of Marketing, a RevOps lead, and a CEO who all have opinions about outbound — things move differently. Not everyone agrees on ICP definition. Marketing wants messaging consistency. Sales wants volume. RevOps wants clean data. The CEO wants results yesterday.

This isn’t dysfunction. It’s the natural reality of a growing organization. But it means that delivery timelines stretch, approvals take longer, and you spend more time aligning stakeholders than you do building systems.

The adjustment we made was building alignment into our process explicitly. Shared dashboards with metrics everyone agreed on. Weekly syncs with all stakeholders in the room. Written experiment briefs that defined success criteria before we launched. This overhead felt unnecessary at first, but it eliminated the worst failure mode: building something that one stakeholder loves and another one vetoes.

Everything gets easier with a loved product and a recognized name

This is the most honest lesson, and it’s not one we can take credit for. When you’re running outbound for a company whose prospects already know the brand, everything changes.

Open rates are higher because the company name in the “from” field isn’t unknown. Reply rates are higher because the prospect has heard of the product and has some baseline curiosity. Conversion rates are higher because the sales team doesn’t have to start from zero credibility on every call.

The inverse is also true. When you’re doing outbound for a company nobody has heard of, with a product that’s hard to explain in one sentence, the entire system has to work harder. Messaging needs to be sharper. Targeting needs to be more precise. The signal that triggers outreach needs to be stronger because you don’t have brand recognition doing any of the lifting.

This doesn’t mean outbound only works for well-known companies. It means you should be honest about where you’re starting from and calibrate expectations accordingly.

The Bottom Line

Moving upmarket taught us that the fundamentals don’t change — data quality, buyer understanding, deliverability, continuous experimentation. Those matter whether you’re working with a three-person pre-seed team or a 200-person Series B.

What changes is the complexity around those fundamentals. More stakeholders, more legacy infrastructure, more assumptions to challenge, more inertia to overcome. The work itself isn’t harder. Getting the organization aligned to do the work is.

Bigger is different. Not easier.