Working as the Head of Sales in an early stage startup is both exciting and challenging. One of the biggest challenges is reporting to the founder, who can sometimes be a control freak due to their lack of understanding of sales. This can lead to a lack of autonomy and difficulty in bringing new ideas to the table.

Another challenge is when the founder is validated by receiving millions of dollars in VC funding, which can lead to reckless decision-making. Lack of clear expectations and boundaries can also be a challenge in early stage startups, as founders may not have the bandwidth to communicate effectively, leading to confusion and lack of progress.

Moreover, founders who flew by the seat of their pants early on often didn't create processes, making it challenging to scale. However, this is where the Head of Sales comes in - to create processes and help the company scale.

Reporting to the founder of an early stage startup can be an awesome experience, as it offers the opportunity to work closely with someone who is passionate, driven, and has a clear vision for the company. But it can also be rough at times, and it's important to be aware of the challenges and pitfalls so you can navigate them effectively.

To overcome these challenges, it's essential to establish a clear line of communication with the founder and set expectations and boundaries. Make sure to have regular check-ins and be transparent about the progress and challenges of the sales team.

Additionally, be proactive in creating and implementing processes and systems that will help the company scale. This will help to establish structure and ensure that the sales team has the tools and resources they need to succeed.

In conclusion, being the Head of Sales in an early stage startup reporting to the founder can be a challenging but rewarding experience. By being aware of the challenges and taking proactive steps to address them, sales leaders can help their company grow and succeed.