Growing pains beyond Series A – a perspective from Outward’s founders

  • Author

    D'Arcy Whelan

  • Category

    Fintech

  • Date

    May 30, 2022

Growing pains beyond Series A – a perspective from Outward’s founders

We recently hosted our inaugural Founder “Supper Club” where seven of Outward’s early portfolio founders were joined by two of our later stage founders - Anand Sambasivan (CEO and Founder of PrimaryBid) and Norris Koppel (CEO and Founder of Monese).

We organised and moderated the dinner as we wanted our founders to hear first hand about life at and beyond Series A – the highs and the lows, the growing pains of scale up and what to watch out for.

Norris and Anand were exceptionally generous with their time – 4 hours to be exact – both were kind enough to provide some valuable insights, all accompanied with some entertaining anecdotes. As with all our events, Chatham House Rules applied but we thought it would be useful to share some of the general (less juicy) key takeaways of the night.

Culture is fragile in the scale-up phase and what was once obvious can be quickly misplaced

1. How to protect and foster culture when the business grows beyond 50 people

  • Retain as much of the founding team as possible
  • The Founder CEO has the biggest voice and must use it to build a compelling narrative that brings every team member into the mission
  • Remember, culture is fragile in the scale-up phase and what was once obvious can be quickly misplaced – the values, mission and what you stand for needs to be communicated to the team constantly

2. Getting the most from your Board

  • Board meetings are not the forum to spring surprises. Create a constant flow of communication with your board so that everyone is up-to-date beforehand. Board meetings are for decision making and setting a clear direction 

3. Bringing on a co-founder later in the company’s journey

  • Whilst you need to choose carefully, the benefit of bringing a co-founder on is that you have someone who can share the burden of making the business a long term success – someone who has as much to lose as you do

The Series A fundraise (your first round with institutional VC funds) will likely be the hardest round you ever do

4. Tips for raising your series A

  • The Series A fundraise (your first round with institutional VC funds) will likely be the hardest round you ever do
  • Expect to get a lot of nos (maybe hundreds). Do not give up. More importantly, make sure you understand why and use it as an opportunity to be sharper about your business   
  • When pitching, use data and numbers as much as you can – show you are not selling hot air and if there is ambiguity, deal with it hard and fast
  • Leverage your current investor rolodex, they want your company to raise as much as you do

5. How transparent should you be with your team when fundraising?

  • If you are too transparent and the fundraising drags, the team may question the mission. This is where it is beneficial to have multiple founders to share the fundraising burden and insulate the wider team from the fundraising stresses
  • At all times, the team needs to feel the founder(s) has everything under control

6. Fundraising in today’s bear market  

  • Funding rounds will take longer and the later the stage, the more scrutiny you’re likely to face. Raise as much as you can and do what is necessary to extend the runway

At Outward, we believe that the best skill of founders and investors is knowing what you don’t know. Accessing an experienced and generous community can make all the difference. Our founders can look forward to more Supper Clubs!