Co-host Episode Episode 01

From the Board
to the Trenches

Two ex-VCs on why they left the boardroom behind — and what nobody tells you about becoming an operator.

About This Episode

What actually happens when a venture capitalist decides to become an operator? Not the polished LinkedIn version — the real one, with the panic, the muscle memory relapses, and the exhilarating feedback loops you never got in VC.

In this debut episode of Top of the Ops, co-hosts Cecilia (former VC at Talis Capital, now Chief of Staff at Seqera) and Bea / Beatrice Aliprandi (former VC at Lakestar, now Chief of Staff at Praktika) go deep on their own transition stories. These are two investors who spent years advising startups from board seats — then chose to get their hands dirty from the inside. This conversation covers everything from the imposter syndrome that hits on both sides of the table, to the macro forces reshaping VC, to the very specific skills that transfer (and the ones that don't).

What We Cover in This Episode

The Real Imposter Syndrome — On Both Sides of the Table

Bea makes a critical distinction that many junior VCs silently live with: "Most people go through imposter syndrome and it's not right — they are actually qualified. In my case, I was an actual imposter." When it comes to deeply operational questions — org design, hiring, execution — sitting on a board without operator experience means you often just… don't speak. And knowing when to stay silent is the first honest signal that the operator path is calling.

The Push, the Pull, and the Fund That Closed

Cecilia's transition wasn't a carefully planned career pivot — it was equal parts pull (the itch to actually build) and push (the fund closing, forcing the question). Bea's story is different: six years of looking for the right startup, angel investing in Praktika, and convincing a founder three times to hire her. Both paths are different, but the gut-check moment is the same: stop cheering from the sidelines.

The Macro Case: European VC Is Under Pressure

The numbers aren't comfortable. European VC fundraising is down 69% since 2022. Active investors are down 50%. Only 19 IPOs happened across all of 2025. At the same time, a handful of AI companies are raising mega-rounds. The shift from 'everyone wants to be in VC' to 'everyone wants to be an operator or founder' isn't just cultural — it's structural. Bea's prediction: a third shift is coming, where ambitious people skip VC and operating entirely, and simply build directly, because AI has made the barrier to product creation almost negligible.

The VC Skills That Actually Transfer to Operations

Both hosts were surprised by what carried over from their investing days. Cecilia's three most transferable skills: pace and speed under pressure, critical thinking and attention to detail, and — the unexpected one — applying an investment lens to internal decisions. A new hire is an investment. A product bet is an investment. Bea's additions: the prioritisation framework (internal micro-IC), North Star vs. vanity metrics, and emotional distance. The ability to kill a project that isn't working, even when you care about it deeply.

Is VC 'Value-Add' Actually Real? Now They Know.

Both Cecilia and Bea have now sat on the receiving end of VC involvement — and the verdict is nuanced. The network genuinely works. Getting a fast introduction to an operator who solved the same problem last year? Invaluable. The promise of strategic value-add? That varies wildly. And the board member who talks just to prove they're earning their board seat? That's a pattern they both know too well — because they've been that person.

Evaluating vs. Executing: The Biggest Mindset Shift

The single biggest thing VCs get wrong when they try to operate: they keep researching instead of building. Bea's framework: ship an 80% accurate process, then iterate. Stop waiting for the perfect strategy. Cecilia's version: trust your instinct, start tinkering, and resist the perfectionism that comes from years of pattern-matching at arm's length. The best summary of the shift comes from a COO Bea spoke to before joining Praktika: "I still research things, I still have critical thinking — I just fill the missing gap. I get it done."

Resources & References

  • Scaling People by Claire Hughes Johnson (Stripe's COO) — Bea's top book recommendation for aspiring operators

Frequently Asked Questions

What skills transfer from VC to operations?

The most valuable transferable skills include: pace and speed under pressure, critical thinking and pattern recognition, applying an investment lens to internal resource allocation decisions, and the ability to prioritise ruthlessly. Perhaps most surprisingly, emotional detachment — the ability to kill a project that isn't working — is a skill operators consistently undervalue.

What is the hardest part of transitioning from VC to operator?

The biggest mindset shift is moving from evaluation to execution. VCs are trained to research, analyse, and pattern-match. Operators need to build, ship, and iterate quickly. The tendency to over-research before acting is one of the most common failure modes for former VCs joining startups.

Is a Chief of Staff role good for former VCs?

The Chief of Staff role is a particularly strong fit for former investors because it requires exactly the Swiss Army knife versatility that years of deal-making build. You're constantly switching contexts — strategy, product, GTM, investor relations, team operations — while also needing to identify and solve problems nobody assigned to you. The VC background also makes former investors better at choosing which startup to join, since they apply the same diligence to investing their time as they once did to investing capital.

How is AI changing the role of junior VCs?

AI tools are rapidly automating many of the tasks that justified junior VC roles — research, financial modelling, pattern analysis, and even early-stage due diligence. At the same time, AI has dramatically lowered the barrier to building tech products, reducing the amount of pre-seed capital founders need. Both trends are putting pressure on the traditional VC model, particularly at seed stage.

Episode Transcript

Introduction

Ceci [00:09]

Welcome to Top of the Ops, the podcast where we have real conversations about what happens behind the scenes of startups. I'm Cecilia, former VC at Talis Capital and now Chief of Staff at Seqera.

Bea [00:19]

And I'm Bea, former VC at Lakestar and now Chief of Staff at Praktika.

Ceci [00:23]

We both made the jump from VC to operators a couple of years ago. Today we're talking about what that actually looks like. The good, the bad, and the deeply uncomfortable. Let's start with you, Bea. There's a quote from a Sifted piece that really stuck with me — you said you were sitting on boards of startups and couldn't actually advise on hiring or org design. Tell me more about that feeling.

The Real Imposter Syndrome

Bea [00:47]

That feeling was somehow an imposter syndrome feeling — with one key difference. Most people go through imposter syndrome and it's not real; they are actually qualified for the job. In my case, I was an actual imposter. I was sitting on boards giving advice I had no idea about. I was probably quite diligent in the topics I could advise on — capital allocation, financial models, patterns I was seeing across businesses. But whenever it came to something deeply operational, I just shut up. I didn't want to talk about things I simply didn't know. And that gave me a hint: if you are not an operator, the so-called value-add of VCs decreases quite a lot. But switching to you, Ceci — you made the jump after thinking about it for maybe 20 minutes. Walk us through what went on in your brain.

Ceci [02:02]

I've always been more of a 'let's go with the flow' kind of person. It was the end of 2023 — a quite odd period in the VC market. Friends at startups were seeding the question: why don't you join a startup? Why are you not an operator? I was quite settled in my VC and investor identity. Then the fund I was working with closed down, and I was forced to ask myself what I really wanted. The CEO of the company I currently work at gave me a call and asked if I wanted to join as Chief of Staff. Something really resonated. I felt like I was on boards of startups I'd invested in, and I felt like a barrier — an itch I wanted to scratch by getting more involved. I was getting a lot of positive energy working with those founders but I was limited by my identity as an investor. That question made it crystal clear. It was a gut feeling and I just jumped. I'm very happy I did.

Bea [03:18]

It's very frustrating sometimes when you cheer from the sidelines and you can't actually just get things done.

Ceci [03:25]

So much. I was getting really close with founders I was working with — either through investment or proximity — and there was so much I wanted to help with. But I was also, like you, quite aware of my imposter syndrome. A lot of the advice I was giving was common sense stuff I'd read or studied, but I couldn't get my hands dirty. I also realised I enjoy building things. I'm not a coder, I don't build products, but I get a lot of satisfaction from the idea of building — something I wasn't getting from just investing and cheering from the sidelines.

Tiptoeing Around Operations for 10 Years

Ceci [04:05]

Do you think you were always going to move to operating, or were you set on being an investor?

Bea [04:20]

I joined investment banking because I really liked numbers, and I come from a very entrepreneurial family. I thought the closest thing to companies and operations was investment banking — which of course is the furthest removed. I was actually at a pretty operational bank where they'd bring juniors in front of management teams quite a lot, but those were very large companies. VC seemed to be a step closer. In essence, I've just been tiptoeing around for 10 years when I could have just joined a startup out of university. At some point you get into a bit of a golden handcuffs situation in VC. But subconsciously I always wanted to go operating — it just took me 10 years to fully realise it.

Ceci [05:33]

That's fair. And people coming from 10 years of investment banking and VC — do you think that adds something more special to the company you're joining than 10 years of pure operational background?

Bea [05:54]

It definitely brings more maturity. To be in a startup you have to be emotionally intelligent, able to prioritise, and able to push back. At 21, I wouldn't have had the same conviction to prioritise and push back. On reflection, I'm happy I went into operations in my 30s with a solid set of experience and hard skills. But I would have made the jump a couple of years sooner.

Ceci [06:32]

In VC you're forced to form your own opinions very quickly. It made me a lot more opinionated — able to take a position on a subject independently rather than just following what other people were saying. Now it's not investment decisions but product or capital allocation decisions — but having that ability to create and voice your own opinion is something I don't think I would have had without that background.

Bea [07:03]

Don't you think being an investor was also helpful for choosing which startup to join — rather than running after the first exciting idea?

Ceci [07:13]

100%. Because ultimately I'm not investing someone else's money anymore — I'm investing my time, which is my most scarce resource. Seeing so many companies pitch, seeing some fail and some succeed, you come to understand the various types of founders. For me it's always been three core criteria: what is the company building, is the industry exciting, and can I work very well with the CEO?

Bea [07:53]

The founder is very important to me too. I gel well with very ambitious, hardworking, but humble people. After six years in VC you can spot the other kind pretty quickly.

Ceci [08:09]

Exactly. You develop a founder-phenotype-reading eye very fast after working in VC. An investment is like a marriage — you're together for 10 years. Joining a startup at the level we did, close to founders, you have to gel. You have to see the world in a very similar way, have a similar work ethic, and you have to have fun together.

The Growth Ceiling in VC

Bea [08:44]

We have very similar trajectories — both VCs, both now Chiefs of Staff at completely different companies. What are the odds? At partner level, VC is incredibly rewarding and even philosophical. But at junior and mid level, I'd argue your growth is a little bit capped. There are very few examples of people who've reached partner level without going through the operating side. Bill Gurley was in investment banking, Mike Moritz was a journalist. But beyond that? If you really want to grow, you're going to have to get your hands dirty at some point.

Ceci [09:38]

Agreed. What I really lacked from being on boards — telling founders 'you should do A, B, and C' — is the understanding of what it actually takes to make the machine move. The empathy and understanding you gain from being inside a company completely changes how you talk to founders. Also, in the era of AI, the junior VC role has changed entirely.

Bea [10:06]

It takes a Chief of Staff.

Ceci [10:35]

I don't know — Claude does everything now.

Bea [10:37]

Just for the audience — Cecilia and I are both Italian and we call Claude 'Claudio.' So throughout these episodes you might hear references to our best friend Claudio, which I think is very sweet.

The Push and the Pull

Bea [10:52]

Was it a pull towards operating or a push away from VC — or both?

Ceci [11:05]

Very much both. The pull came in the last six to nine months of VC when I realised I was giving founders advice I'd heard someone else say or read somewhere — just rinse and repeat. I started to understand the power and impact my words could have, and I realised these weren't really my words. That made me quite sceptical of my own role. The push happened when the fund closed. It forced me to think about what I really wanted. I'm not sure I'd have moved when I did if the fund hadn't closed.

Ceci [11:55]

You joined a very AI-forward company at the beginning of the AI era. Was that a big part of your pull?

Bea [12:10]

Let's hypothesise that I was subconsciously always going to be an operator. The question was: which startup? Throughout six years in VC, I hadn't seen a startup where I felt compelled enough to put all my eggs in one basket — taking a salary cut and betting on stock options. When I angel invested in Praktika and saw the mission — people getting new jobs because they could speak English, relocating their lives — it felt very compelling. I wanted to be part of that story. And I volunteered myself. Famously, the founder said no to me three times before I eventually convinced him to hire me. The AI wave also made it harder to sit on the sidelines. When you see a platform shift happening in real time, you want to play a role in it.

Ceci [13:55]

There are two ways of being part of the AI wave. One is to invest — pick the companies, watch how they evolve. The other is to be inside a company right now, when every single process is changing every time Anthropic or OpenAI releases a new model. What I used to do manually a few months ago, I can now use Claudio to transform. That is learning through experience and through living. It's the better way for me.

The Macro Shift: VC, AI & The New Founder Era

Bea [14:40]

Let's go macro for a second. The European VC landscape is under serious pressure. Fundraising has collapsed 69% since 2022. Active investors are down 50%. There were only 19 IPOs across all of 2025. Does the data back up what we're feeling?

Ceci [15:03]

We're seeing these numbers, but we're also seeing a small number of companies raising massive rounds in AI. There's something very big happening, but it's hard to understand the direction from the sidelines. The best way to understand it is from the inside — in a company that works within AI every day.

Bea [15:53]

If you're not in a company, you can really only understand AI through articles written by AI.

Ceci [16:00]

Exactly. But let's talk about another generational shift. 2020 and 2021, everyone wanted to break into VC. Now everyone wants to be an operator or a founder. What flipped?

Bea [16:15]

We are in the era with the lowest barrier to entry to build a tech product. The role of VC is changing drastically. Before, you absolutely needed pre-seed funding to get a developer to code your product. Now Claudio can do it in about 10 minutes. There's probably less need for VC funding, especially at seed stage. And I think there's even going to be a third shift — where people skip VC and operating entirely and just become founders directly, because they can build a product with the vision alone. We're at the cusp of that.

Ceci [17:20]

I agree. We're also rethinking what being a founder means. We grew up with the idea that a startup founder has to build a billion or ten billion dollar company. But there are so many ideas and companies that can be built that are far less valuable than that, but still make a great business for the small team running them. I'm very excited to see where that goes.

Bea [18:07]

I can speak to this personally. We went down in headcount and doubled revenue. The capital we should have spent on hiring, we didn't. The investment criteria for VCs have to change too — before it was all about technological moat. But what is the technological moat when Claude can code everything for you? The moat could be brand, could still be technology, but we're moving towards a sector with increasingly lower technological barriers. I'd be seriously confused if I were in VC right now.

Imposter Syndrome: Inside the Trenches

Bea [19:10]

Going back to your imposter syndrome — you wrote in your Medium article that the imposter syndrome hits harder than your morning coffee. What was the worst moment in your first few months as an operator?

Ceci [19:26]

I joined and started doing things across different areas as a Chief of Staff does. Then I had this sudden realisation that every single thing I was doing — except maybe helping with a pitch deck — was something I'd never done before. Coming up with a marketing campaign. Preparing a product release keynote. Organising a company retreat. None of those things. And not only that, I was working shoulder to shoulder with people who'd done those things for many years. I was asking myself: why am I here? What am I bringing? Big panic. Then I calmed down and worked inwards — understanding what I could bring from my experience that was different from the classical operator. And I got to it.

Bea [20:44]

My biggest shock was the first week: the founders inundated me with everything that was in the backlog — all the post-Series A clauses at once. I felt immediately overwhelmed. But after the first week I realised: take one thing at a time, prioritise, build a framework, execute. And the biggest thing that gave me energy was the feedback loop. I could understand whether things were working almost daily. If something didn't work, you iterate. That is very different from VC, where you make an investment and wait years to know if you were right. Having immediate feedback loops — that gave me the most energy. I would never swap it back.

Ceci [21:56]

What gave me energy relates directly to what shook me at the beginning. I've always been a solo worker — independent, doing things on my own. And then I was parachuted into a team of over 60 people. You need to communicate constantly, wait on others, remind people of things, be reminded yourself. That was all foreign to me. Then I got used to it. I started managing a small biz ops team at Seqera and seeing the bigger projects we could build together, the impact they had for the whole company — it made me realise the power of a team and what you can achieve beyond just yourself. I love having a team.

VC Skills That Transfer (and Ones That Don't)

Bea [22:51]

What VC skills surprised you by being very helpful on the operating side?

Ceci [22:59]

Number one: pace and speed. In VC, when you meet a company on a Wednesday and it's a hot round, you're working fast to get the term sheet and IC approval. Having that instinct for when to push hard on the accelerator definitely helped. Then the attention to detail and critical thinking VC gives you. And the third was something I didn't realise was transferable: looking at internal decisions as investments. A new hire is an investment. Doubling down on a product is an investment. Allocating a team to market A vs B — all investments. If you take the same VC mindset of asking the right questions, it works incredibly well. I always say: I may not know the market or product deeply, but I can ask questions that make you question whether you're making the right choice.

Bea [24:11]

For me it was the prioritisation mechanism — running a micro internal IC in your head. Does this have ROI? Is it actually worth pursuing? Then condensing the business into healthy North Star metrics, not vanity metrics. And emotional distance. It's really hard when you're in ops and all your eggs are in one basket. But sometimes you have to be emotionally detached — if the A/B test doesn't work, you kill the project. That's painful, but necessary.

Ceci [25:04]

I never thought about it, but I am like a cold machine — and that is sometimes really, really helpful. Just take a step back.

Bea [25:09]

I'm terrible at it. I care so much about what I pursue that I want to make it work. But I try to remind myself: emotional detachment is the move. You also wrote about the 'Swiss Army knife muscle' — what does that mean in practice?

Ceci [25:44]

Being a Swiss Army knife means being able to melt into different situations and problems. One moment you're talking to a founder about consumer strategy, the next about legal, then the financial model — a different problem every 30 minutes. It's a massive context switch, which I love. In the Chief of Staff role especially, you're not just constantly switching context between GTM, product, investor relations, team presentations — you also have to find your own problems to solve. You look at the company, identify what needs fixing or improving, and without anyone telling you, you go fix it. You have to tap into your own Swiss Army knife and figure out what ammunition you have.

Is VC 'Value-Add' Actually Real?

Ceci [27:00]

VCs really pride themselves on the value they add and the networks they open for founders. Now we've been on the reverse side, working with our own investors. Is it real? Is it overrated?

Bea [27:21]

I've been fortunate to work with very involved investors — constantly on WhatsApp, constantly sending business opportunities, hiring leads, help. Their involvement has been amazing. But I've also seen the network of so-called value-add VCs who really shouldn't say much. The currency of VCs is their network, and that has translated very well into ops. When I needed to figure things out quickly, I could go to the network, get introduced to operators who could answer my question.

Ceci [28:34]

When you're inside a company, you can really tell who is genuinely value-add — who has the right person for the right problem at the right moment, who asks the tough questions that change the trajectory of your business for the better — and who is perhaps sitting on the sidelines, which is still much better than being a negative force.

Bea [28:58]

We always had the emotional intelligence not to talk when we didn't know what to say. But there is a type of investor imposter syndrome — where you feel you have to speak because you're on the board. You don't. Just don't speak if you have no value to add. Sometimes certain investors feel the need to say something when they actually have no idea what's happening in the business.

What VCs Get Wrong When They Think They're Ready to Operate

Ceci [29:37]

What's the biggest thing VCs get wrong when they think they're ready to operate?

Bea [29:49]

I'd condense it to two things. First: evaluating versus executing. Stop philosophising, stop researching every little thing, and start executing. You want an 80% accurate product — whether that's a process, workflow, or strategy — and then iterate from there. In VC it's the opposite: lots of research, very little execution. The second is going deep versus broad. In ops, even as a Chief of Staff, you have to go more in depth versus floating across everything.

Ceci [30:49]

On the research point — at the beginning at Seqera I had the habit of going to see how other companies did A, B, C, D. That's a good framework and good indicator, but what worked for someone 10 or 20 years ago may not work for your company. There's always a ceiling to where your learning ends. A lot of the time, you need to trust your instinct and common sense and just start tinkering. Sometimes perfectionism — not wanting to start before you've created the perfect process in your head — is the enemy. Just start building.

Bea [31:43]

Before joining Praktika, I had a chat with a COO who'd also made the jump from VC to operator. She said: 'I still research things, I still have critical thinking and form opinions. I just fill the missing gap — I get it done.' That is very empowering.

Rapid Fire

Ceci [32:11]

One thing you wish someone had told you before you made the jump.

Bea [32:22]

Do it sooner. — Ceci, first week as operator: what was your worst moment?

Ceci [32:30]

I was on LinkedIn scrolling, someone posted about a pre-seed company, it looked really cool. I went into autopilot and I was about to press send on a cold message to the founder. Then I caught myself — I have no money to invest. This is not my job anymore.

Bea [32:45]

That's your old muscle. — Best book recommendation for aspiring operators?

Bea [32:51]

Scaling People by Stripe's COO Claire Hughes Johnson. It's such a gem — packed with great information. — Best piece of advice for someone in VC thinking about making the jump?

Bea [33:09]

Just do it.

Ceci [33:09]

Think about what kind of VC you want to be. What is your personal edge with founders — what do you give them that nobody else does? Is it insight? Industry knowledge? And how do you feel about rolling up your sleeves and actually bringing something to life?

Bea [33:28]

Last one — now that you've experienced the Top of the Ops, would you ever want to be a founder?

Ceci [33:36]

I scratched that itch when I was 17 and I haven't had a good idea since. So it's not for me.

Bea [33:40]

I wouldn't exclude it, but right now I'm more conscious than ever of the sacrifice you have to make as a founder. I wish I didn't know it, but now I do — and I'm a little more sceptical.

Ceci [33:58]

There's so much glorification of the founder figure. But when you're actually inside the trenches, you see the grit, the sacrifices, the personal toll that founding a generational company takes. That's a lot.

Bea [34:20]

It's really hard. You have to work the hardest of anyone in the company, do the longest hours, and it takes a lot of consideration. It's not a jump I'd make lightly.

Ceci [34:36]

Thank you for listening! See you next time.

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