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Established company or start-up? Where should you look for your next sales role?

Antonio Ciarleglio

When searching for a new sales role, one of the biggest questions many will face is whether you should consider a new role with an established company or start-up?  No doubt you will probably be aware of some of the basic differences between both; large traditional companies have fixed office hours, whereas start-ups tend to be flexible, large companies offer benefits; medical, dental, pension, etc. Start-ups offer free lunch, in some cases free travel, working from home, free concierge services, office pets and games during downtimes; table tennis, table football, darts, etc. 

When considering the above, what is not often talked about or taken into serious consideration is whether a corporate role is better that a start-up job for your career in the longer term. A start-up may offer flexible hours and the option of working from home at the beginning, will it however, give you the prospect of moving into a senior management position in the future, participate in the decision-making process for future growth of the business, or benefit from stock options? On the other hand, a role in a large organisation may be the perfect place to receive structured training, but will it offer you the environment and creative thinking skills you need to potentially start-up your own business in a few years?

Having worked in large organisations and several start-ups, I have been exposed to the advantages and disadvantages of both. If you are undecided about which option to take, take a few minutes to consider the following questions to help you make maximise your talent and career potential, both in the short term and in the future.

Your Dream Job. What is it? Are You Still Deciding?

When I worked at a start-up, I had to wear many hats and cover a lot of roles. I managed a sales team, created training manuals, designed corporate and product brochures, answered the phone, interviewed potential employees, cold called, pitched to prospects and closed deals. And that was only at the beginning! We had a small team of twenty people and we were all expected to roll up our sleeves and pitch in wherever needed. At the time it was a great challenge, and enjoyable, as I was not certain what I was looking for in a long term career.

When I moved, I moved to a large corporate organisation. I was more confident in my capabilities and what I really enjoyed doing, I was able to focus on my role and without having to wear several hats! 

Overall, in larger organisations, positions will tend to have narrower roles. If you are a sales manager, you will be responsible for managing a sales team and driving revenues, if you are a sales specialist, you will be responsible for selling and increasing revenues. If you know the role you want or the direction you want your career to develop, a large corporate environment will help you grow and develop those skills, without the distractions of wearing too many hats and having other responsibilities which will distract you from your core role. 

Alternatively, a sales specialist role with a start-up can help you further develop your entrepreneurial skills, gain insight into multiple positions and how to manage a business, and work in a flat management structure alongside the Founders and CEO. You may also decide that a start-up is exactly what you are looking for in your career, a dynamic job in a highly energetic environment, with a many different responsibilities.

Support. What Type Do You Need to Reach Your Career Aspirations?

In my early career, I did not quite know what I wanted to do and what I was doing, and when I landed my first leadership role, I felt very insecure and lacked confidence. It was in a start-up under a CEO who did not have much more experience than I did. My mentoring came from management books, sporting and political heroes and great achievers. I did not have a company mentor.

When I entered a corporate position, I suddenly found more resources at my disposal, co-workers had a wealth of knowledge and experience, my Sales Director was inspirational and had several years of experience and took me under his wing, mentoring me and bringing out the best in me. The company also provided training guides and product manuals both hard copy and online.

Here is where the big difference needs to be seriously considered. What do you need personally to succeed? If you are entrepreneurial, thrive in taking risks, take initiative to get the resources you need, and are comfortable learning from trial and error, you may not need the resources in a corporate position of the support of an in-house mentor to reach your career goals.

If however, you prefer vault of knowledge and experience close at hand, and to advance your career to a position within a specific timeframe, you might feel that an established company will best suit your talents and personality. It will all depend on how you work, learn and which environment will help you perform to your very best.

Influence. What Kind Do You Need? How Quickly?

When I first entered an established company, I was very naïve. I knew I was entering the company at the bottom of the career ladder and I did not expect to get so frustrated so quickly my lack of influence and input into the business. The reality was that I really had no say when it came to decisions that were made about me, the team I worked with or our sales objective and strategy. This move happened after I had left a very good position at a start-up, where I had authority, influence and visibility into business decisions which affected my role and the sales team. 

Generally speaking you are going to have to accept that you will have less influence in an established company than you will have in a start-up or smaller company. If you should have a Sales Leadership or a Senior C-level Sales position as your career objective, it will possibly take you much longer to achieve your career aspirations. 

Alternatively, you will gain much more insight into how a start-up company operates on a daily basis, and accelerate your sales career, combined with the ability to have your opinions heard and influence the business sales objectives and strategy. Moving up the ladder however could look a lot different. If the position above you is the MD or CEO, they may not open up for some time or ever. You will have to expand your role accordingly in other ways, making the route to your eventual career goal, less straight ward to achieve. 

Environment. What Will Help You to Succeed?

To summarise, you must consider all the elements which will be essential to help you perform at your best and achieve your goals. Will you work better with; a constantly changing, “creative thinking’’, ‘’outside of the box” distributive start-up environment, or an established organisation where you can work to a structured process with proven sales methodology toward your career goals? Both environments are very different and neither is better than the other. The decision to consider a role with an established company or start-up, will depend on your personality, work style, talents and your individual career goals. These will help you decide which environment you will better fit into, bring the best out of you, and achieve your career ambition. Consulting your family and friends, and a respected recruitment consultant, will also help you make the right choice!

If you have any questions or would like to comment, I will be happy to chat. I would also welcome your thoughts at:

For more information about Harrington Starr, our services, new career opportunities in FinTech, or a career as a Recruitment Consultant with Harrington Starr Group, please contact me at: or