The Mindset Shift Needed for a Mid-career Pivot to Startup Life.

Why candidates should embrace Product/Market Fit, and why startup employers should mid-career candidates.

I often meet mid-career professionals that want to switch from a corporate/enterprise career, to a career in startups. I don’t mean students or grads, I mean people with 5–10 or more years experience working in the corporate or agency world, with established skills in marketing, product development, technical development and more.

It’s not just the dream of holding equity at the point of exit, or the lure of fewer corporate policies and processes. Startups offer the chance to do really exciting work!

This applies not just to the specific problem an individual startup’s solution may seek to solve, if you are interested in say, experimenting with the latest best practices in growth engine automation, it’s easier to do this start-up side, than at a mature company or their agency. And this is also in the interests of the startup, too…

Mid-career talent represents a wonderful opportunity for startups

Given that almost every startup aspires to grow and become a big brand, it could benefit your startup to hire people that have experience of operating at scale. Furthermore, within their previous careers lie gems of knowledge and experience that could benefit your startup in unexpected ways.

Consider for example Sebastian, who chose to invest in pivoting his career from that as a due diligence analyst at a Venture Capital firm, by taking a Product Management course at General Assembly. Why would you NOT want to hire a Product Manager that knows exactly how to appraise the real market viability of a product as a VC would?

Mid-career professionals often have no lack of useful talent, just a problem ticking the boxes on a recruiter’s checklist.

I.E, How do you get experience in such a role, when winning that role often requires you to have that experience already?

But arguably it is harder for mid-career professionals to overcome that chicken and egg problem, because taking a step backwards in order to move forwards is extra tough when you may have mid-life responsibilities and constraints.

It seems to me, that in an industry that constantly bemoans the shortage of talent, this is a problem worth solving.

One organization that is seeking to help professionals make this change is Tradecraft in San Francisco. Tradecraft specializes in “training smart people to succeed in traction roles at high-growth startups.

Ellen Wilson is one recent graduate from Tradecraft that successfully made the switch from corporate to startup.

Young companies can really benefit from seasoned professionals who know how to assess the competitive landscape, engage senior stakeholders such as clients and investors, position brands, coach junior team members, manage cash flow etc. But these more senior hires also need a mindset shift to embrace scrappiness, failing fast and learning fast to help figure out the new business and capitalize on the opportunity.
-Ellen Wilson

The most important difference in mindset

Earlier this year I had the opportunity to give a mentor’s presentation to students of the Product Management and Growth faculties at Tradecraft.

And as someone that made the switch from global agency to startup myself, I thought it was a great opportunity to share what I believe to be the most important mindset shift to make when switching from enterprise to startup. And that is; understanding and optimizing for Product/Market Fit.

Product/Market Fit is the no.1 difference between how Startups act, and how other companies act. It is the most important thing a startup needs to get right in order to succeed, and I believe it is therefore the most important thing you should take into your next job in Startups.

In it, I introduce:

  • How to deconstruct the notion of Product/Market Fit into a number of achievable stages
  • Why it is so important for professionals that wish to lead startups to optimize their decisions
  • Why and how to beware the dangers of “Expert Opinion”

Of course, as I have written about before, I believe that all businesses should optimize for Product/Market Fit, particularly if they aspire to create innovations that survive beyond the initial launch, and grow into the becoming the future of their business.

But specific to the point of switching career, if I think that it is not the list of roles and employers on your CV that indicates whether you will succeed in a startup, as much as the mindset that you approach the role with. And I believe that the most important way to ensure you add value is to make every decision regarding a new product or feature in the context of achieving, or retaining Product/Market Fit.

Interested in switching yourself? Act now!

I’m delighted to have recently started as Head of Marketing and Growth for Topology Eyewear. Right now we are working hard on crafting the future of the eyewear industry, by making glasses that are custom tailored for each individual person’s fit and style preferences.

We are currently hiring in all areas of the business, especially technology and UX. If you believe your experience and capabilities are relevant to our mission, write to us and tell us why. We know how to look at your work, not your previous employers.

  • If you are interested in learning more about Tradecraft and their programs, check out and get in touch
  • I’ll post separately with a shortened edit of the rest of the presentation, which walks through my process to achieve Product/Market Fit. Or in the meantime, you can watch the full-length version here.

As always, I’m happy to hear your thoughts and feedback, and I’m grateful for your help spreading the ideas within the post by recommending and sharing below.

Chief Marketing &Growth Officer at Topology Eyewear :: @guesto

Chief Marketing &Growth Officer at Topology Eyewear :: @guesto