Setting Yourself up for Success at an Early Stage Start-up

By Nina Lobo and Sanjna Malpani

So you’ve taken the plunge and signed an offer to work at a startup — congratulations! You’re on an extremely exciting path that’s going to be full of adventure and learning opportunities: get ready to dive in headfirst. Before you find yourself completely free-falling off a cliff as you navigate your responsibilities, here are some reminders that will help you remain grounded and focused right from Day 1.

“Startup” is a broad term — even mammoth companies like Credit Karma and ZenDesk called themselves “startups” until very recently. However, we’re focusing our advice more on early stage startups (~30 people or less) since working for such a small company looks vastly different than a “startup” at their Series D. To begin with, internalize right from the get-go that 9/10 startups fail. We know, we know — it’s certainly not what you want to hear as you prepare to head into your first day of work and we don’t want to dampen your mood. But, you have to keep this stat in mind — since the truth is, all the due diligence in the world (like the methods we outlined in the last article) might not help you see failure coming. Andy Rachleff of Benchmark Capital put it this way :

“When a great team meets a lousy market, the market wins. When a lousy team meets a great market, the market wins . When a great team meets a great market, something special happens.”

You can’t always predict when the market will be lousy — and we’re seeing this in real time as a global pandemic has taken several industries by storm and sent shockwaves through the market as a whole (though they seem to be bouncing back a bit). Now while this is an extreme and completely unprecedented scenario, smaller shockwaves happen all the time and there’s only so much you can do to stay on top of the market. So, that brings us to the bigger question:

How can you set yourself up for success whilst working at a startup (especially if it goes belly-up)?

To begin with — make a clear list of what you’re optimizing for at this stage in your career, and clearly put yourself first. Say you emerge from this role a couple of years later: what would you ideally like to put on your resume in terms of skills learned and opportunities fulfilled? Focus on the value additions this role is going to add to your current profile and start working backwards from there.

• Sit down with your manager or your team to ensure that your job profile and tasks include some aspect of these. If not, you may want to volunteer early on to take on side projects that can include the skills you’ve identified you want to learn and walk away with. This can evolve over time, but make sure you keep revisiting this list from time to time (we suggest once a month if possible).
• Keep track of tasks and accomplishments that you have, even if they strike you as atypical or unimportant. This helps to keep track of valuable projects and experience that get lost in your memory over time. It’ll also help you make the case for a promotion or new role over time!
• Developing a system of organization early is key to staying afloat and thriving, especially when you’re starting out. You will likely wear many hats even in a seemingly niche role, and a system of organization will help you keep track of everything going on-including your changing role as the company evolves. Whether you use Excel sheets, sticky notes, Trello boards (a personal favorite) or a combination of tools, be sure to track your key projects, relationships and contacts, and develop a set of metrics for measuring your success. Build the habit of updating your notes at a certain time each day or each week: the future you will definitely thank the current you.
• Finally, find a mentor or a champion in the organization who you can speak with honestly, learn from and run ideas by! This is much easier said than done and will likely take the first six months of your role to do — but keep it in the back of your mind. I can’t stress enough how important it is to have someone that can not only be a sanity check (for all the crazy things that will inevitably come your way) but who will also vouch for you when it comes to promotion time.

Remember that you might need to take your professional development into your own hands!

To bring order to the creative chaos of a startup environment, develop your own metrics for professional development. Keep your professional development milestones in a specific place and revisit them every six months (more often is good too!). Take notes on what’s working and what isn’t, and what may have changed. If you were assured an outcome that hasn’t manifested, or you’ve been asked to take on much more responsibility at work than you signed up for, you don’t have to rely just on your feelings: you can trust your gut and your notes.

You may have to take initiative to set up regular meetings with your managers for professional development. This is especially crucial if your organization doesn’t have a clear process for promotions. In our experience, working with your manager to develop a list of clear developmental outcomes helps you to maintain concrete goals. Much of the grunt work will come from you, but it can pay off as a more graceful way to regularly share your achievements and growth.

It’s also highly likely that your startup has not yet carved out a specific budget for professional development — but remember that doesn’t necessarily mean they’re not willing to support you. Keep your eye out for certifications or training courses that might boost your growth — if you’re not sure what resources you need, try to leverage your professional networks and ask around for suggestions. Once you have a clear thesis on why the training/certification might help you succeed in your role, start involving your manager so they can support you to ask the organization to cover any associated costs or effectively carve out time for you to pursue the training.

Finally, remember that in your 20’s, working at a startup can be an exciting opportunity to dive headfirst into the realities of starting a business without being pinned down to a specific career track.

You’ll experience multiple aspects of project development and business growth (finance, technical development, community partnerships, sales, etc.) that you’re unlikely to experience in larger organizations where the processes and roles are far more established — so you want to ensure that you make the most of it!

If you’ve been offered a role at a startup, at the core, you’ve been hired to help grow the business. Understand that the role you agree to on paper is just the baseline for the responsibilities you may actually take on over time as the business grows, expands its product lines and markets, or even shifts direction. This mindset will empower you to grow both as a trusted member of your current team and as a professional in the longer term!

Stay tuned for our follow-up piece on how best to cut your losses if things start going south at the startup you’re working for! As always, please leave your own learnings, advice and comments below — we’d love to hear what’s worked/not worked for you and any feedback you might have.