Joining A Founder-Led Start-Up: 4 Key Focus Areas For Execs Coming From Large Companies

Brent Lowe
5 min readMay 21, 2021


Photo by Amy Hirschi on Unsplash

As a seasoned executive, you’ve been yearning for something different. Joining an early-stage start-up after years in a stifling corporate environment can be exhilarating. You’re buzzing, because you know your experience will impact and propel the organization to new heights.

The idea of getting involved in a start-up has tremendous allure. It provides an opportunity to get your hands dirty, fulfil your entrepreneurial urges and make a real difference. You’re energized by the idea of playing a part in disrupting an industry. You dream of realizing untapped market opportunities and mushrooming prospect lists. Limitless possibilities, clear of senseless bureaucracy and toxic hierarchy, are at your fingertips.

At first, you think the transition will be a piece of cake. You’re surrounded by an innovative team moving at warp-speed in what appears to be perpetual chaos. Everywhere you look, there are opportunities for improvement. Underdeveloped systems. Lack of structure. Operational inefficiencies. No clear policies. You can fix this stuff quickly, right?

I’ve had hundreds of conversations with successful and talented executives as they’ve planned to jump on board with an entrepreneur. I’ve helped hired many of them into their roles. CXOs. VPs. Leaders. Super-talented industry specialists. Unfortunately, I’ve also been a shoulder to cry on when their dream became a nightmare, and they exited the business.

For most seasoned executives, starting with an early-stage company feels like falling into the proverbial cookie jar. You’re filled with excitement and anticipation. Energy and ideas abound. You get straight to work because you want to prove your worth. While this approach is understandable, it paves the well-intentioned path to failure.

If you’re considering taking the leap from corporate to start-up, here are a few helpful focus areas:

Avoid “Saviour Syndrome”

If this is your first time in a founder-led organization, seeing yourself as the hero can be disastrous. You’ve done this work before and succeeded. You’re skilled and intelligent. You’ve got this covered. The truth is, the company isn’t in need of a saviour.

In reality, you’re more likely to be the horse with blinders. You don’t know what you don’t know. Sure, you have a lot to offer, but you probably have more to learn from your new colleagues.

Quick wins present a real danger. Areas calling out “fix me first” can be distractions that cause you to veer off course.

In fast-growing companies, tasks are plentiful and time is limited. Significant or urgent issues that don’t have a rapid or easy solution can be tempting to neglect in favour of a quick win. The absence of systems, processes, and guidelines can be frustrating for the seasoned executive. Closing these gaps seems logical but often yields little benefit.

Entrepreneurs abandon low-hanging fruit. They focus on the hard stuff that makes an impact and delivers results. Their focus is on scaling the business, and tackling problems worth solving.

So how do you avoid the temptation to be a saviour? See your first 3 to 4 weeks through the lens of curiosity. Keep your team in the loop, so they know you’re prioritizing asking questions over making decisions. Find out why there’s untouched low-hanging fruit. Take time to understand what the team has tried in the past. Gain clarity on why certain things rank higher than others.

Pursue recognition and appreciation over ‘constructive criticism’

When you’re coming in fresh from classic corporate into a start-up, you’ll see glaring gaps. Noticing everything that’s wrong in those early days is easy. You’re accustomed to smoother running operations. You may believe your previous company did things better.

No matter how well-intended, criticism and condemnation rarely provide a great foundation for thriving relationships. The founder and their team have been in the trenches together, fighting side by side long before you joined. They made mistakes and learned lessons. Recognizing and appreciating what they have achieved so far is a much stronger starting point than picking apart their efforts.

Instead of launching into a fault-finding mission, identify and recognize the hard work that created the company. Get curious about the early successes and painful hurdles. Recognize grit and applaud the team for enduring through those tough times. Find an opportunity to sincerely acknowledge the learning that the team has gone through.

Invest the time to understand the founder

Entrepreneurs are wired differently, with a deep desire to be successful and the drive to make it happen. While they share common traits, each individual has a unique spark that sets them apart. Without their boundary-challenging divergent thinking, the world would be devoid of outstanding achievements. The initial success and ongoing survival of their companies are anchored by their critical talents.

What makes them different can be invisible or even frustrating to newcomers joining the entrepreneurial world.

Entrepreneurs are innate and fast learners. They are decisive. They’re not easily swayed. They don’t fit into neat little boxes, and they couldn’t be more different from the leaders you worked with in larger companies.

So how do you get to know the founder better? Be intentional and set aside more time than you think is necessary to build rapport. Want to know how you are annoying or frustrating them? Ask. Observe who they connect with, who they clash with and why. Above all, embrace the realization that the founder is not going to change, despite your best efforts — so learn to roll with it.

Enjoy the ride

Entrepreneurial companies can be a wild ride, full of fun. As a senior leader, you have knowledge and experience that can bring great benefit to a growing start-up. The key to your success will be expecting and overcoming the pitfalls of the switchover from classic corporate. Buckle up and enjoy!

I help Founder CEOs of companies between 5 & 40 people who are experiencing early stage success and ready to scale — especially those wanting to build shared responsibility and accountability within their team. Click here to get your free copy of the 5 principles and 6 leadership roles for scaling a sustainable, prosperous company.



Brent Lowe

The Scale Coach for Founder CEOs and co-author of Lead Together: The bold, brave, intentional path to scaling your business