Choosing the Right Startup for You

Lee Lubner, Tim Atkins (COO, CancerAid), Rhiannon White (Chief Product Officer, Vend), Kanav Bhama (Business Operations, Dovetail), Ellen Dinsmoor (Head of Operations, Vow), Will Dennis (APAC Commercial Finance Director, Afterpay), Tom Bass (Growth Product Manager, Atlassian), Chris Quirk (Investment Manager, rampersand), Emer McCann (Manager, Talent & People Operations, Simply Wall St), Tim Rossanis (GM, Head of Growth - Retail & New Verticals A/NZ, Uber), Jess Rogers (Strategy and Operations Manager, Snap Send Solve), Amelia Crawford (Legal Counsel, TikTok), Amy Dobbin (Chief of Staff, Sonder)

Firstly, I would ask yourself the questions below to help guide your thinking. Then I would do some research to figure out where a start-up sits on the start-up lifecycle (Tim Atkins, COO, CancerAid).

  1. Knowing what you don't enjoy doing is just as important and one could argue more important if you have not nailed down the specifics of what you do like (Lee Lubner)
  2. What do you want to learn? (Lee Lubner)
  3. What is your risk appetite & how does that correlate to the stage of tech business you join? When going to Uber right before the IPO, I had a level of stability which much earlier businesses couldn't give me. With a young family to support, that variable was just as important as passionately believing in the mission. (Tim Rossanis, GM, Head of Growth - Retail & New Verticals A/NZ, Uber)
  4. Do you find the industry interesting? (Chris Quirk, Investment Manager, rampersand)
  5. Just one. Does the problem/opportunity space interest you? If it isn’t a HELL YES, it is a no. Keep moving (Tom Bass, Growth Product Manager, Atlassian)
  6. What’s important to you in life? Is it work-life balance? Is it learning? Is it building a network? Is it having a stable financial situation to pay down your mortgage? (Tim Atkins, COO, CancerAid)
  7. Does the mission drive you? That will make a difference when things get tough. Don’t go to a fin-tech if finance doesn’t interest you.
  8. ‘Is working at an early stage startup the RIGHT move for me and what I want in life?’ (Tom Bass, Growth Product Manager, Atlassian)
  9. Startups are not for everyone and that’s ok. Understand what you value in a role and company before making the leap (Emer McCann, Manager, Talent & People Operations, Simply Wall St)
  10. What problems, challenges, and “missions” are important to you? You don’t have to work somewhere that you think is going to “save the world,” but given how much time you’ll spend on this mission, it’s important to have some alignment with its mission. (Ellen Dinsmoor, Head of Operations, Vow)
  11. What type of people do you like to work with, and do you see this replicated in the founders of a company you may be considering? Do they have values that align with yours, and do they treat others in a way that you’d want to see replicated across the company?   (Ellen Dinsmoor, Head of Operations, Vow)

There’s an amazing article by Hanna Neep on whether a start-up is the right move for you. Check it out here.

Kanav Bharma (Business Operations, Dovetail)

Joining a startup can be taking a big punt on its vision, rallying behind that vision, and also understanding how you can do your best to contribute to that startup achieving success, whatever that may be defined as. 

With that in mind, there were the questions I asked myself before joining Dovetail: 

  • Am I going to work on things which would accelerate my exposure and contribution to helping a business grow? Am I going to stretch myself here? 
  • Do I believe the product(s) are solving real customer pain points? At the time as a Consultant, I could draw links to how Dovetail would’ve helped me do my job better. 
  • Do I feel on the same wave-length of ambition to the Founders and team? 
  • And lastly, is this my escape from pulling together pretty PowerPoint slides barely anyone reads? F*^k yeah.  

Jess Rogers (Strategy and Operations Manager, Snap Send Solve)

I really think anyone can work in a start-up - it’s about finding a mission, funding stage and team that you’re happy to work with. And that depends on your interests, skills and risk appetite. 

Questions I’d think about include:

Role and skills 

  • What level of structure do I like to have in my work? What certainty do I like to have in my role and responsibilities? Later-stage, larger start-ups are more likely to have structured teams and responsibilities and a more well-established way of doing things. In early-stage companies, roles will be broader and less-defined. 
  • What skills do I want to build? If you’re making a career change, have a think about what skills you want to build and find an environment that will foster your learning and development. There’s a lot of learning by doing and trial and error in start-ups, but zeroing in on what you’re hoping to learn in the next phase of your career will help you find a start-up that suits you. 


Team

  • What kind of people do you want to work with? This one’s key. The people you work with will have a big impact on your everyday. Think about whether you want to work with people who have a track record of building companies or if you’re happy to work with people running a company for the first time. Do you like to have autonomy or do you want to work in a team that’s high-touch and more collaborative? Visualise what environment you work best in and work backwards from there.


Funding

  • What runway does the start-up need to have for me to feel comfortable? Some people are naturally more risk-averse (whether it’s for personal, financial or other reasons). And that’s okay. It doesn’t mean start-ups aren’t for you. But you’ll probably be better served going to a later-stage start-up that’s found product market fit, has established customers and a clearer trajectory. The way forward is often less clear in an earlier-stage company. On the financial side, there’ll also likely be less money around to pay you when a start-up is new (although an ESOP can provide good upside if things go well). You can command a larger salary at a well-funded, established start-up. 


On a practical level, Michael Batko has written an article on questions to ask to assess cultural fit when you’re getting to know a company. 

Will Dennis (APAC Commercial Finance Director, Afterpay)

The decision to join a start-up should be viewed like an investment decision, meaning it is important to conduct proper due diligence. The investment you make in joining a start-up is not only financial but involves the more valuable commodity of your time.

It is important to ask yourself whether you support the purpose and mission of the start-up, as the connection of working towards something greater than oneself is a paramount to the success of your experience and only

Rhiannon White (Chief Product Officer, Vend)

Alignment with mission, values, problem looking to solve and customers seeking to serve. Appetite for risk and need for clarity (or not). And above all - ‘can I work with these people when under pressure?’ As you will be! And it all comes down to the people you are in the trenches with.

Amelia Crawford (Legal Counsel, TikTok)

I’d start by looking at industries and brainstorm from there. Yes - grab a paper and pen and draw as many circles and lines as you can! What industries interest you: sport, music, fashion, tech, agriculture? Or are you more drawn by a cross-industry sector such as sustainability? If you’re working in an industry or field that interests you, that's a great foundation as it’s more likely that you will be working for a product that you believe in. Having an honest belief in what the company does will foster a sense of purpose. 

Amy Dobbin (Chief of Staff, Sonder)

Picking the right start-up can be overwhelming - the best advice I’ve received from seasoned operators is to focus on the company, not the role. Pick the stage, not the role. Once you’ve nailed the right company and stage, the rest can fall into place.  Put another way, to verbal Sherly Sandberg’s sentiment, “If you’re offered a seat on a rocket ship, don’t ask what seat. Just get on.”. Practically- the hard part is working out whether the start-up is actually a rocket ship or not!!  The most helpful checklist that guided me when assessing numerous start-ups was a mix of values, key financials, fundraising plans and performance: Specifically, keep a check on: 

  • Ethical founders and purpose
  • Competition 
  • User-related metrics 
  • Financials 
  • Unit economics 
  • Cash balance 
  • Fundraising plans 
  • Investor base
  • Last round’s share price 
  • Comparable compensation packages 
  • Performance review process 


It's not always possible to have these all ticked off before you're in the door- but doing your research (through formal and informal channels) will go a long way to ensuring you're joining the right start-up!

What have we missed? Please hit 'Contribute to the Guide' to give your perspective and help others into their first role.

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