Working for a technology startup can be a positive career and life-changing experience – if you make the right choice

As a restless recruiter during this lockdown, I’ve spent some time discussing hiring, recruitment and talent acquisition with our stakeholders at technology startups and tech-driven early-stage firms. The founders and owners of these firms were generally receptive to new ‘How-to’ ideas and hiring strategies. There was a lack of 'group think' or 'hive mind' or the 'we have always done it this way' attitude. I didn’t encounter resistance to trying new things that I sometimes meet when working with in-house or human resources teams that are part of mature or large corporate businesses. Those kinds of businesses often have an established corporate framework that decides what can and can’t be done; for better or worse.


Those startup recruitment conversations led me to think: what if I were a Software Developer, Product Manager or Sales guy etc. considering joining a startup? What would I look for? How might I spot the next Unicorn? Or, if not the next Unicorn, how can I avoid joining a business that is going to bomb and I find myself unemployed in a few months? There isn't a cookie-cutter answer.


Part of life is about risk and managing risk. If you’re considering an early-stage firm as an employer, I hope you find these thoughts useful when thinking about that critical career move.



The first thing to consider is culture – if the culture isn’t right it isn’t going to work for you. It doesn’t matter what the tech is or what the product or service is.

If you come from a corporate technology background or a large consulting firm or systems integrator, you will be used to having access to teams to support the work you do. For example: if you work in Sales, you may be supported by an Inside Sales team for lead generation, a Digital & Social Media marketing team and perhaps, even, Appointment Setters. If you’re a Technical Software Architect, you may be supported by Software Engineers, Application Developers and Business Analysts.

At a startup, in most cases, you can say good-bye to that support. At a startup still trying to prove it has a viable and scalable business model, you can expect to wear many hats every single day. Expect to multi-task a matter of course and never, ever, ever say, “That isn’t my job”.

If it is a long time since you’ve written basic Java or C# code, how are you going to feel about being ‘back on the tools’? How do you feel about grinding out line after line of code and then running the testing environment – be honest? Sales professional? Can you still motivate yourself to do 50 cold calls on a wet February morning? Are you prepared to write your own marketing content on the train on the way home because during office time you’re glued to the phone selling? “Marketing? Hey! I’m a sales guy. That’s not my job!”.

If you join a startup, you will truly find out what self-starter, motivated, rainmaker and Ms. Super-flexible really mean. 9-5 with a full hour for lunch kind of person? Don’t join a startup. Risk averse with an albatross of a mortgage, school fees and a pension pot to feed? Think carefully and discuss it with your stakeholders e.g. your partner and/or the kids. It is a different kind of working experience and it can change everything in your life.


1.      Product, Service & Widgets

What’s the product and how is it made? It could be software, it could be a new game, or Something As A Service, an industry-specific platform, or a physical device (e.g. wearable technology).

Most people will look at the product or service and ask themselves if it excites them. Do you believe there is a market for it? If so, why, and how and where? And look beyond whether farming software or an IoT-ready oil refinery widget enthuses you: look at the back-end. What is the technology? Does the firm use the latest development languages and tools? Are they building UIP (Unique Intellectual Property)? Are they working with older, legacy technologies? If so, why? There could be a good reason for it (robust, proof of concept and so on). These are some of the questions to ask your recruiter (they should know) and at interview.


2.      Investigate the market

You don’t need a meerkat to compare the market; just a few hours with a search engine to map the space.

Who is already in that market? Are they shifting product? Who and what is unique and disruptive? Are there new entrants on the horizon? If there are, does that suggest there is a genuine demand for your prospective employer’s widget? What are the barriers to successfully launching a new product or service? Who else looks good? Should you be sending them a CV as well?


3.      Funding

You probably won’t find out much about this in the public domain and most (not all) recruiters won’t have a clue about their clients’ financial health. At Identify HR, we brief our candidates on the financial status of the firms they are interviewing at.

By all means run the company through Companies House and look at the directors, persons with significant control and any accounts that may have been submitted. Most startups will claim small company exemption from submitting full accounts. If they're in a Venture Capital or Private Equity incubator it gets murkier. Perhaps you have a friend who works in an accounts or finance function somewhere? Can run a credit report using a tool like Creditsafe or Dun & Bradstreet?

If you’re considering joining an early-stage outfit It is quite acceptable to ask at interview how the firm is funded; who funds it, shareholder activism and what cash is at hand to grow the business, develop the product and pay the staff (that’s you).


4.      Team

You could be working at the next Facebook, Twitter or Skyscanner, but if you don’t like the people (and the people become the culture), then this is a red flag.

If you’re a pinstripe suit kind of girl or guy, sitting with a team of Developers who are wearing headphones, hoodies, and Metallica t-shirts, it may not be right for you. It may be. But you need to think carefully about your style, your personality and work experiences to date.

If you’re a salesperson pitching to corporates, it may not matter that the Developers in the office are wearing flip-flops and combat trousers. But then again, it might. Ask to meet as many of the team as is practically possible as part of the hiring process. Don’t be shy. People matter as much as product (for our purposes).


5.      Founders, Owners and Management

I’m not a corporate kind of person. Give me a rule book or company handbook and I’ll bottom-drawer it unread and chuck it in the bin on the day I leave. Not maverick; just me. I’ve mostly been attracted to similar personality types to mine when choosing my next boss. This has been a rip-roaring success on occasion. Once or twice it has been a car crash. Messy, tangled metal and blood on the highway. What are you? Do you need rules? Do you always follow rules? Or are you a bit of mad-genius who can roll without an org chart and HR’s mantra of “Thou shall not”?

Are your new bosses off-the-wall types with a great idea, a vision and a plan who thrive on chaos? How will you build and manage that relationship? If you’re of the Husker Du t-shirt wearing persuasion and your new boss is trying to build a mini Accenture or Oracle or other successful but very corporate-type firm, how will that work for you? Do you want to drop £750+ on a decent suit and a couple of hundred beer tokens at Churches on sensible shoes your mother would approve of? Or does that Dead Kennedy's t-shirt still have another summer left in it and, damn it, it’s your lucky t-shirt for testing day or when you do the cut over?

What part does the founder or owner have in the business on a day-to-day basis? Do they contribute? Are they managing? Can they delegate some of their baby? Or, as I have fallen foul of once or twice, are they control freaks? Someone who can’t let go, won’t let go and always seems to know better even though they’re paying you a decent salary for your expert input and opinion?

You get the idea.


6.      Owning A Slice of What You Build & Exit Stage Left

Is there an opportunity to earn or be given shares, share options or other instruments of ownership in the business you are helping build? Have you been asked to sacrifice salary today for jam tomorrow (shares)? If so, why? See (3) again.

If you end up working for the next Uber and become insanely wealthy off the back of your shares – fantastic. If they can’t pay market rate today on salary, why not? See (3) again.

Is there a road-mapped journey for the firm, the product(s) and key, early-stage people? Will that include you? You need to know and you’re entitled to ask.

These points may seem fairly obvious, but it is easy to fall in love with a new (potential) boss, firm, brand or product. If they’re using the latest technology and you’re a tech-head, it can blind you to the wider business and career considerations. I’ve done it. I fell in love with a new boss. I got excited about what I thought was going to be our journey together. I didn’t ask the right questions before signing on the line. Doh! I’ve been through that pain so you don’t have to.

Joining a startup or an early-stage firm can be a career highlight. If it doesn’t work out, that’s okay if you went into it with eyes wide open and you can justify your decision making process. If it bombs, it isn’t the end of your career.


Last Thoughts

Risk. Reward. Cover the basics. Take off the rose-tinted spectacles. Be objective. Ask the right questions and keep asking until you are satisfied you have enough data and information to make the right decision for your career. Perhaps I’ll see your Ferrari parked on George Street one day. Good luck!

I work for Identify HR. We recruit experienced Technical, Developer, Functional and Sales & Marketing hires for Enterprise Software and SaaS firms, as well as niche vendors and consulting firms. And, of course, well-funded startups.

You can reach me at or 07743978179. You can connect with me on LinkedIn at Kenny McAllister. Follow me on Twitter at @kennyrecruiter. I don’t do Instagram. I’m 53.