In this edition of Cosmic Conversations, I sat down with Edward Keelan, Partner at Octopus Ventures. Octopus is one of the most active investors in Europe, a B Corp, and part of the wider Octopus Group. Edward has spent 17 years backing B2B software and AI from pre-Series A to Series B out of a ~£550m software fund that does roughly a deal a month.
You can watch the full conversation above or take in the best bits in the short summary of Q&As below.
Q: What kind of companies do you invest in at Octopus Ventures?
We invest across several funds, but my focus is B2B software and AI from pre-Series A to Series B. The software fund I sit on is about £550m. We are active across Europe and typically back companies that are starting to show real traction.
Q: What are the most important signals you look at when evaluating new investments?
Founder quality comes first. I want to know if this is someone I can work with for five years. I look for resilience, openness to change, and the ability to clearly explain the problem they solve. If a founder cannot communicate that simply, it will be hard for them to convince customers, hires, or future investors.
Q: How important is commercial acumen at seed to Series A?
At our stage we want signs of traction. As a guide, many of the companies we back are at £500k ARR or more. If the founder is not commercial, someone on the team needs to own go to market. Deep tech is an exception. For most B2B software, clear funnel ownership is non-negotiable.
Q: Where do founders overspend after a raise?
Headcount, you should be tracking burn ratio as a sense check. If you are adding £1 of ARR for each £1 of burn, you are in range. If you are burning three or four for everyone added, something is off. Once headcount runs ahead of plan, it is painful and slow to unwind.
Q: When should founders hire a VP of Sales?
Later than most teams think. Founders should hold the go to market until the funnel is understood and repeatable. The common pattern is hire a senior sales leader too soon, pipeline stalls, the team churns, the founder jumps back in, things lift, and the cycle repeats. Own the motion until you have clear inputs, conversions, and outputs.
Q: Which GTM motions get you most excited?
There is no single right motion. Outbound, PLG, partner led, marketing led can all work. What matters is repeatability and believable volume. If you can reliably create enough qualified opportunities, you can tune conversion. What worries me is a reactive mix of activities with no defined strategy and no evidence you can generate the volume your plan requires.
Q: How should founders choose a VC, and what support should they expect post investment?
Diligence the investor. Talk to portfolio founders. Look for scars as well as wins. At Octopus we have a dedicated talent team that helps with job descriptions, agency selection, and the first wave of hiring. Early hiring quality matters. A bad commercial hire does not just cost salary. It costs time, momentum, and real runway.
Key takeaways from this Cosmic Conversation:
- Founder quality and clear communication are the first filters.
- By the time you hit ~£500k ARR, someone must own the commercial motion.
- Headcount is the hidden killer. Watch burn ratio and stay disciplined.
- Hire a VP of Sales later than you think. Hold the wheel until the funnel is repeatable.
- There is no perfect GTM motion. Repeatability and lead volume win.
- Diligence your investors. Make sure they bring practical support on hiring.
- A poor early commercial hire destroys time and optionality.
If you enjoyed this conversation with Richard, check out our other recent Cosmic Conversations with leading VCs.
Connect with Edward Keelan on LinkedIn and find out more about Octopus Ventures.
