Reflections on 3 years of finding a product/market fit inside a venture fund

Andrea Di Pietrantonio
8 min readOct 29, 2020

It’s already been well over 3 years that I’ve worked at Inventure honing our Portfolio Operations, and today marks a special day. I’m now officially a Portfolio Operations Director at Inventure, which is not only an exciting validation of the work done so far, but a strong indicator of where we will be pushing in the future to make a difference for our founders.

All of it has me in a reflective mood, which is why I’ve tried to gather some of my learnings in this article, such as:

  • Portfolio Operations is still a terribly misunderstood term. For me, it signals our commitment to giving our all to help our hyper-growth portfolio companies like Swappie and Insurello, by having a structured function, team and a product, that is separated from our day-to-day investment activities. That way we can remain laser-focused on helping the portfolio companies with solving meaningful problems in the most efficient and enjoyable way. Our daily work consists mostly of giving strategic advice and sparring, sharing more practical know-how, or connecting our entrepreneurs to the best people we have in our network.
  • My first 3 years of doing Portfolio Operations has had awfully a lot in common with finding product/market fit and trying to get to the intersection of what our entrepreneurs need the most and where we can genuinely make the most impact for them.
  • That just like in startups, saying ‘no’ and being relentless about focusing on just selected things (for us, mostly things related to expansion and talent), makes all the difference when it comes to delivering just the right things at just the right time.
  • Portfolio Operations should probably take a page or two from the playbooks of Customer Success Management, because that’s what we’re ultimately trying to do: make our customers — the very best Nordic and Baltic entrepreneurs — succeed in the crazy hard and ambitious mission they’ve taken upon.

Let’s get started. So just as we advise our startups, we try to eat our own dog food by being relentless on focusing only on the things that matter the most, and being almost as relentless in saying ‘no’ to all of the rest. But that’s the truth of it in my mind: in order to help our entrepreneurs in just the rights things at just the right time, we can’t for a minute be focused on throwing pizza & beer events or writing insightful Medium po… — ahem, let me have my yearly guilty pleasure, will you?! (See parts “One year into VC Platform” & “Two years into VC Platform”)

We’ve put ourselves in the mindset of a tech company: we know our core customer group is the very best Nordic and Baltic entrepreneurs, but what are their most meaningful problems that we can help solve better than anyone else in the market? What are the playbooks, models and frameworks we want to use to build a product and a service that does that in the most efficient and enjoyable way without bringing any extra annoyance into their already stressful enough lives? (And in some cases, we’ve found the best playbook to be the one which we call “shutting our mouths, getting out of the way and letting the ones actually doing the work, do the work”)

In addition to helping us better empathise and put ourselves in the shoes of the entrepreneurs, we’ve come up with higher-level operating principles as well as more day-to-day practices that help us help our entrepreneurs the best. I won’t go into too many details here, but try to offer something to structure one’s thinking around. What’s important to remember is that there is no “one-size-fit-all” model or playbook when it comes to startups but there are clear principles and actions that can help designing the path. Each firm going through this journey would most likely achieve a different outcome based on individual preferences, skillsets and partnership dynamics. Building alignment within the firm is key to succeed in portfolio operations. Weekly one-on-ones with senior partnership (kiitos Timo!) helped shape up the function as it is today, as it is not a person’s effort but a full team exercise to put portfolio operations front-and-center in our offering.

What follows is not a perfected, complete, one-size-fits-all set of best practices that all VCs could or even should follow, but a rather humble tale of one Italian early-stage-startup-employee-turned-VC striving to build a function, a team and a product to help entrepreneurs better make the world of difference they desire to.

I’m an operator at heart, and a very data-driven one at that. I love reading and studying the best sales strategies, operating models, and I love whipping up ones myself based on all the things I’ve seen at our portfolio companies and in the Nordic venture ecosystem in general. Which is why I’ve found that the easiest way to present my three years of learnings in the most concise way, is to describe them through the terminology and operating models of Customer Success Management. Because as said, at the end of the day, that’s what I and our team are trying to do: manage and make our customers — the very best Nordic and Baltic early-stage entrepreneurs — succeed in the crazy hard and ambitious missions they’ve taken upon.

So without further ado, let’s get into the different stages of the VC version of Customer Success Management, that I’ll use to simplify and model the complex mess sometimes called ‘Portfolio Operations’. I’ve formalized it here as a 3-step-process of “Onboarding”, “Execution and expansion”, and “Fundraising and renewal”.

1. Onboarding (the startup into our portfolio)

I’ll start the process with this step, but truth be told, Portfolio Operations at Inventure often starts even before the companies decide to join the portfolio. We think it’s only fair that the entrepreneurs considering partnering with us have a good understanding of what it will mean to work together and where they can expect our help and support. It’s crazy to think VC used to operate without a structured sell process and a general selling point of “take our money and this person on your board”. I believe no modern top-level entrepreneur would or should settle for that.

Back to onboarding! Onboarding usually begins with an onboarding session between us, the company and the co-investors. The session is a pure prioritisation exercise where we go through the goals for the next funding round and the short term plan to get there. This is the time when we align on how the founders want to run the show and what they expect from us.

The outcome is no more than 1–3 clear action points we need to deliver on in the short-medium term to support the founders’ plan. We usually want those action points to be as big yet as concrete as possible, because while ‘provide support in fundraising’ is extremely vague and hard to track, items such as ‘set up and follow a recruitment process to hire a CPO before March’, ’10 intros to companies having expanded to France’ and ‘organise biweekly business model sparring sessions’ are quite clear and easy for our entrepreneurs to keep us accountable for.

The onboarding sessions are of course also extremely helpful in the sense that we make a coordinated plan that all relevant parties fully commit to. It’s not just for us to be accountable with certain actions, but the other investors as well. And that it’s all clear and in the open what are the most important things we all want the startup to achieve and execute in the coming months, which creates the foundation for thinking about where we can help the most.

2. Execution and expansion

This is the most important part, yet the hardest one to describe if you don’t go into the nitty gritty. This is where planning stops and talking turns into walking, which we’ve seen to be surprisingly hard for parties and people mostly geared towards high-level planning. But as an ex-operator myself, I know and appreciate the reality that actually happens in startups after all the fancy strategic buzzwords are thrown around sufficiently in big board room meetings. That’s why I believe an ok plan executed to perfection is still light years ahead of a perfect plan barely executed at all. The more concrete and trackable the actions to be taken are, the easier it is to gently remind people to focus more on walking, and less on talking. This is usually also the part where the best individuals and teams separate from the rest.

While focus and prioritisation are extremely important in themselves, they also allow speed. If our entrepreneurs ask for help in an area that’s not in our scope, we can quickly and openly state the fact and direct them somewhere else. And when they do have a problem related to our expertise, say expansion or fundraising, we can deliver the ultimate top know-how and contacts in less than 24 hours, which we’ve set as an internal time limit for how quickly we want to deliver.

3. Fundraising and renewal

During the final stage of the process, if all has gone as planned, we again sit down with all of the relevant parties. We take a look at the journey thus far, both before the last round and after it, and start building the narrative for the next round. I’ve written a separate article on Soaked by Slush on how to run a fundraising process, so feel free to check that out for my more in-depth thoughts on the matter. To summarise the gist of it, we 1) build a long list of all semi-potential investors 2) make initial contact with some just for the sake of having practice rounds 3) we focus the follow-up discussions with the most relevant ones and iterate based on the feedback 4) we secure a couple of pending term sheets from which to help choose the one to continue to DD. If the plan we made after the last funding round has been executed to perfection and showing clear signs of growth, it’s much easier to present a new plan and a narrative for the next round.

What’s next for Inventure, our portfolio and our Portfolio Operations?

I am not ready to bet on 2021 being easier than 2020, but what I am sure about is that we are witnessing technological change at unprecedented speed due to our old way of living being turned upside down. 2021 will come with many challenges but, hopefully, new major opportunities for our portfolio companies.

From our side, the code words will continue being “less noise, more action”. It has not been an easy year for our entrepreneurs, but we believe it’s made the responsibility of VCs even clearer. Building a hyper-growth company to tackle hard, meaningful real-world problems is one of the most difficult things an individual can decide to do, so let’s at least try our best to not make it any harder than it already is. It’s up for each venture fund to choose their strategy and operating models, but after three years of living and breathing ‘Portfolio Operations’, I know I’m rooting for a more active, structured, and laser-focused approach.

Reach out:

Finally, I do believe that the way VC work is changing and we at Inventure would rather be at the forefront of this trend. I would be happy to spar with fellow VCs and hear your feedback on what we are building.

If you are interested in a chat feel free to reach out to

PS: Big thanks to Linus and, most of all, Aapo for sparring with me on this article and helping drafting it!



Andrea Di Pietrantonio

European of Italian nationality. VC at @inventureVC @a_adp