How many years have you been in your current role as Chief of Staff at Greyparrot?

I've been in my current role for 3 months but I've worked in the startup ecosystem, across accelerators and CVC, since 2015.

What's your backstory. How did you come to be where you are today?

I started my career within innovation at Telefonica, whereby, through a number of pivots, I stumbled upon CVC and the corporate acceleration space through Wayra. Posed against the bureaucracy of such a large company, startups felt like such unbridled freedom to go and build something unconstrained, positive and ambitious; it was infectious. ‘Luck’ played a part, which has turned me into an advocate for increasing visibility of tech startups/VC at a much younger age; I wish I’d known far more about this world years ago!

What has been the highlight of your career so far?

Aside from the odd, overnight success, patience is a virtue in this game. What most gives me joy is to see all of the hard work and grit pay off for founders and teams I worked with during my earlier career. One recently raised a series B last month and it’s simply astonishing to see all they’ve achieved in that time; I couldn’t be happier for them!

What has been the lowlight of your career so far?

The imposter syndrome!

How did you come across Landscape?

I remember being in a discussion where a founder had fallen foul of some especially onerous terms. Somebody commented that there ought to be better ways for founders to share these experiences before others needlessly go through the same pain. Of course, somebody then flagged that it already existed and it was called Landscape!

Biggest challenge right now/thing you need help on?

When working with deep tech startups in previous programmes I ran, I used to see a unique growth trajectory that was often poorly understood by all but a relatively small subset of VC. Now navigating that journey on the other side of the table, I’d be keen to hear experiences of any deep tech teams who have scaled into series A and beyond.


What's the biggest mistake you’ve made so far and what did you learn from it?

Burning out earlier in my career, an experience I wouldn’t wish upon my worst enemy. I learned an obvious lesson the hard way: that time is the one resource you can never get back. Yes, be extremely ambitious. But play the long-game, look after yourself, make time for the relationships in your life that matter and build a foundation such that, whatever the outcome, there’s more to life than your startup alone.

What piece of advice would you give to others who are in a similar role as to you?

In a Chief of Staff role, set expectations across the team early on as to your portfolio of responsibility. The CoS role has unbeatable breadth, but in its ambiguity it can subsequently mean very different things to others across the team. Setting clear expectations and boundaries will help others better understand the overlaps and allow you to focus.

What is the most frustrating thing you find about the startup fundraising ecosystem?

The somewhat loose alignment of VC with solutions to the great challenges of our time. VC isn’t a charity of course - IRR is king - but it does get frustrating when so many last-mile grocery startups become ‘hot stuff’ whereas, say, a promising AI company developing a breakthrough cancer drug struggles along with a fraction of the funding. How might we speed up, say, radical solutions to climate change if we took faster, bigger, bolder bets on the stuff that really matters?

What you would like to see change in the startup fundraising ecosystem within the next 5 years?:

For me, it’s all about how we make the ecosystem as meritocratic and transparent as we possibly can. As it stands, the world of fundraising and VC is still cliquey and to impenetrable for so many across the country. We have a talent and information gap that we would do well to solve if we want to attract the most talented, ambitious people into our sector and fund them in such a way that sets them up for success at scale.

Harry is  Chief of Staff at Greyparrot. His LinkedIn profile can be found here & his Twitter here.

His email address is also harry@greyparrot.ai and he is happy to be contacted.