Susan Liu
Raising a Series A in an AI-First World
Learnings from helping Uncork portfolio companies raise their Series A in the last few months.
The bar for raising a Series A has never been higher. Before joining Uncork, I spent many years investing at the Series A and B stages, so I’ve now seen this process from both sides of the table: as the investor being pitched and as the partner helping my seed stage founders prepare. Over the last year, especially in this post-LLM environment, the game has changed, so I wanted to write about what I’ve observed while helping several of our companies successfully navigate the Series A process.
The Role of Pre-Emptions
There are 2 ways companies raise a round today:
Run a process
Get pre-empted
Pre-emptions have become very common again. Many later-stage firms have explicit theses around a category they want to invest in, and they actively hunt for companies to invest in within these markets. These conversations are valuable as they often come with real intent and I would take those inbound meetings seriously.
That said, getting pre-empted isn’t something you can force and not getting inbounded doesn’t mean you’re doing something wrong. Plenty of companies still raise strong Series A’s by running a thoughtful process.
What Does It Take to Raise a Series A Today?
Simply put: growth expectations have skyrocketed.
You’ve probably seen the a16z revenue benchmark charts circulating recently. In my experience, it pretty accurately represents where investor expectations sit today. Pre-LLM, companies hitting ~$1M ARR could reasonably begin a Series A process. Now, we’re regularly seeing companies go from 0 to $3-5M ARR in a single year and that’s roughly what it takes to get a Series A done.
While traction is not the whole story, it is the first filter. To get meetings, and to stand out in a crowded AI landscape, you need to be on a genuinely compelling growth trajectory.
So what if you’re falling short of these Series A benchmarks? Raise a Seed+ (or Seed II) round. These have become increasingly common and have largely lost the stigma they once had, precisely because Series A expectations are so much higher today. Seed+ rounds are typically in the $5–10M range and are often raised from new or existing seed investors to give the company more time to hit the traction needed for a strong Series A.
How Much Should You Raise?
Most companies raise $10–20M in their Series A. Some raise more, typically if they have a high-profile team or are growing at an exceptional pace.
You should expect roughly 10–20% dilution in a Series A. As you think about how much to raise, remember that investors are doing the math to back into your valuation expectations.
For example, if you’re raising $10M and an investor assumes ~20% dilution, they’ll infer you’re targeting a $50M post-money valuation: $10M ÷ 20% = $50M post.
The takeaway: the amount you raise implicitly signals your valuation expectations. Be thoughtful about the number you pick, because it shapes how investors frame the opportunity.
When Should You Raise?
The best time to raise is at a clear inflection point.
Founders often ask, “How do I know when it’s time?” A few common triggers:
You’ve recently nailed your GTM motion and had a breakout quarter or two. Most companies decide to start a fundraise because this happens
You’ve unlocked a key distribution channel that materially accelerates the business (ex: an integration with a key distribution partner that will 10x your revenue growth next year)
You’ve hit a product milestone that significantly expands your market or value prop
Ideally you raise when something happens in the business that meaningfully changes your trajectory and the additional capital from this round will accelerate your business.
Which VCs Should You Spend Time With?
At the Series A, meeting the right partner matters just as much as meeting the right firm.
In categories where LLMs are having a very large impact, this matters even more. At a high level, many markets can look “competitive.” Therefore, it can be very easy for investors, who don’t understand your market, to pass quickly. But when you find the investor who has a real understanding of your space, that’s the person you should lean into. They’re far more likely to engage deeply and ultimately be the one who gives you a term sheet.
This is where your seed investors can be incredibly helpful. At Uncork, we spend a lot of time helping founders think through who the right person is at later-stage funds, not just which firms to talk to. We’ve been in the ecosystem for a long time and often have valuable insider context: which partners are best fits for specific markets and company profiles, what they tend to care most about (whether it’s team, traction, etc.), and how they like to engage.
And one more thing: once a partner takes the first meeting, it’s effectively their deal. You rarely get “reassigned,” even if someone else at the firm might be a better fit. Choose your partners thoughtfully because once a partner passes, the firm effectively passes, you likely won’t get another shot with that fund.
Storytelling Still Matters
Even at the Series A, you’re selling the dream, but now with initial signs of product-market fit.
The strongest pitches hit four core elements:
Team: Talk about founder-market fit and why your team will win
Market: Why your category is big and / or expanding
Product wedge: The insight that gives you a unique path into this market
Traction: Evidence that the business is working
Lean into your strengths. You won’t have everything figured out at the Series A and that’s okay. What matters most is clearly articulating what is working and having a thoughtful point of view on why you’re positioned to win.
I often encourage founders to put on their VC hat for a moment. When investors get excited about a deal, they usually have a clear thesis for why this could be a generational company that returns the fund many times over. As a founder, you have a thesis too, it’s why you started the company in the first place. Be explicit about it.
Finally, put the good stuff up front. Investors are extremely busy. Hook them early and give them a reason to lean in from the very first few minutes of your pitch.
On Competition: Figure Out Your Angle
In the AI world, “kingmaking” is very real. Certain companies are being labeled “the winner” very early (sometimes as early as the Series A!) and these companies often get pre-empted quickly as VCs look to invest before it’s too obvious / expensive. There’s a belief in venture capital that value tends to accrue to the perceived market leader over time.
That said, I believe there can be multiple winners in very large markets. The key is making a clear case for why you are one of them. Don’t pretend your competition doesn’t exist. Investors already know who they are (or can figure it out with a few minutes of research). Instead, figure out your angle and address the competition head-on.
Some common (and effective) angles I see work well:
Customer focus / GTM strategy: selling to the enterprise via a top-down sales motion vs. selling to SMBs through inside sales or PLG. A classic example is Box vs. Dropbox
Use-case depth: owning a specific, high-value workflow within a broader market (e.g., Ivo is the best AI contract review product for in-house legal teams)
Broad vs. vertical approach: horizontal platforms vs. deeply opinionated, vertical-specific products
Once you figure out your angle, you should focus on explaining:
Why your approach is different
Where your wedge is stronger
Why you still have a credible path to win
Sophisticated investors don’t expect you to have no competition. They expect you to understand the market landscape and have a sharp point of view on how you win.
Be Ready Before You Start
Once you kick off fundraising, you’ll be incredibly busy — sometimes you can have 10+ pitches a day. There won’t be time to rethink your story. Do all your prep upfront:
Practice your pitch. Your seed investors are a good source of feedback. At Uncork, we encourage founders to run a full practice pitch in front of the entire partnership to work out the kinks before officially going on the road. The goal is to strengthen the narrative and make sure it lands clearly.
Have your data ready. Know your numbers cold and be able to answer follow-ups without scrambling. Pull together your most important metrics and KPIs ahead of time. It’s much harder to do this on the fly once fundraising is underway. Side note: be very precise when presenting your numbers. One common Series A pet peeve is confusing Contracted ARR with Live ARR. Precision builds trust.
Momentum is important in your fundraise if you want to maximize your outcomes. Don’t slow down the process by not being ready.
Good Luck, Truly
Raising a Series A today is harder than ever. The rules have changed, but the fundamentals remain: build something people want, grow quickly, and tell a sharp, compelling story.
