Lessons learned from leading start-up operations

Stephanie von Staa Toledo
4 min readOct 25, 2020

Twice in my life, I was put in a leadership position at start-up operations.

In an attempt to organize the learnings, I sat down with (former) team members and summarized them in 5 big topics: people management, cash management, culture, strategy, and leadership outlined below.

Please note that these are not supposed to be a ‘bible’ for every situation, but rather a summary of the key learnings based on my experience that I hope is relevant for you!

For people management:

  • Hire smart and driven people. People are the heart, soul, and engine of any organization, but especially for one just starting its journey. It is key that the first hires are not only smart and driven people that will challenge the status-quo but are also open to feedback and willing to have their minds changed.
  • Consider first hires your founding-team. These profiles usually do not need, nor want to be micro-managed. They do, however, need to feel co-responsible, empowered and engaged. The best thing you can do is involve these team members in the building the strategy and making key decisions.
  • Choose first hires with relevant past experiences. This will help increase efficiency and reduce errors. Although this may seem obvious, it is often forgotten in a start-up environment. For example, a person that has spearheaded the launch of a new brand before (even if in a big corp.), is likely to have a better idea of where to start and be able to move more quickly.
  • Hire carefully: better slowly, but surely. Biggest mistakes here were: over hiring too soon, combined with no clear reporting structure. This is especially dangerous after a successful fundraising round. Do not let the availability of cash put pressure on building a big team quickly. This is especially important in jurisdictions where letting people go is not that simple/ cheap, for example in Brazil or most European countries.

For cash management:

  • Cash is king. Manage it. Every penny. Also, try to predict future cash requirements. Pro-tip: there is a plethora of affordable software available to help you with this super important, yet frequently mundane task. Think of it as a ‘not pleasant but necessary habit’, like brushing your teeth.
  • Start by knowing your contribution margin. Seems basic, but I have often seen businesses start operating without an accurate idea of their costs! Ergo, not knowing how to find the balance between what to charge customers and how to cover expenses. For a long-term financially sustainable business, it is imperative to crack this code, before scaling your team and operations.
  • Bootstrap to test and learn. This wildly proven concept is often ignored by previously successful (read overconfident) and/or passionate entrepreneurs and leaders. Just to reiterate, before spending millions on production and marketing, test and learn within a budget.
  • Do not become dependent on expensive marketing campaigns. Figure out who buys regardless of spend on Google and Facebook. Then sync with their needs, desires, and emotions so that the rest will follow.

For strategy:

  • Dream big, sure. But crack the code before… Yes, ‘Start with Why?’ (Reference to Simon Sinek’s book) and ‘Dream BIG’ (reference to 3G’s strategy)… but just before you do — figure out a few key things — what is your unique selling proposition (USP) e.g. why is your company different, who is your target market, and how badly do they want your product? Lastly, check if the price they are willing to pay covers your cost and expenses.
  • Plan. Once you have established a long-term goal, the next logical thing to do is to break this down into smaller pieces to tackle in the short-term. When building a 1- to 2-year plan for a non-existent business, only one thing is certain — the future will be different than what you expect now. Although constant change can be frustrating, planning for what comes next is extremely necessary. This exercise helps organize thought processes, receive feedback, and prioritize important tasks.
  • Markets are local. A winning go-to-market strategies in one cultural environment will not necessarily be the same in another. Here is a simple example: flip flops are bought in department stores in Spain, boutique shops in Italy, and shoe-chains in Germany.

For culture:

  • Have fun… I do not know, listen to music? Go hiking? Talk about your family and friends? Whatever it is, let moments of flow and fun happen. Once you find them, actively try to repeat them.
  • …but do not over-anchor on positivity. The worse thing I have seen happen to a culture, was enforcing a ‘dictatorship of positivity’. To promote a positive environment, always, leaders actually intimidated team members and made them less likely to share bad news or real concerns.
  • Be open to listen and adapt. Coincidence or not, the leaders I have worked with who have dictated positivity, were also those that were least likely to hear other arguments and change their minds. For the type of challenges that a young business has, and the type of people it needs to attract and retain — this is a suicidal move.

For leadership, I have combined this specific experience with others — summarized in another article. To come 😉

Good articles that cover similar topics:

https://hbr.org/2017/10/contribution-margin-what-it-is-how-to-calculate-it-and-why-you-need-it?utm_source=linkedin&utm_medium=social&utm_campaign=hbr

https://hbr.org/2017/11/how-to-excel-at-both-strategy-and-execution?utm_campaign=hbr&utm_medium=social&utm_source=facebook

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