Learning How to Sell: From Sales Rep to CRO to Startup Co-Founder

The Reflect: Episode 3

?? In Episode 3 of The Sales People Podcast, we sat down with, co-founder of tiller ?? to explore his journey from a sales rep to building his own tech startup. Alistair shared invaluable insights on scaling sales teams, facing startup challenges, and keeping resilience alive when the going gets tough.

What I Loved: Alistair’s dedication to persistence really stood out. Even when faced with setbacks, he kept pushing forward. His focus on building Tiller to solve real problems, like improving CRM usage for sales teams, shows a deep understanding of both sales challenges and effective solutions.

What Challenged Me: Alistair’s experience with rejection as a founder was eye-opening. He mentioned how different it feels when you’re building your own product—every “no” feels personal. It reminded me of the mental resilience needed to keep going, especially when you’re emotionally invested.

Top 5 Takeaways:

1?? Persistence is Key, But Happiness Fuels It Alistair highlighted that being persistent doesn’t mean burning out. He advised staying persistent while also finding joy outside of work to maintain a balanced life. “You can’t just grind non-stop—you need to recharge,” he shared.

2?? Structure is Essential in a Sales Pipeline When building a pipeline, Alistair emphasizes the need for accuracy and structure, moving beyond vague categories. This ensures accountability and helps teams keep track of progress.

3?? The Evolution of Communication in Sales Alistair’s experiences showed that adapting to clients’ preferred modes of communication can make a significant difference. With the expansion of tools like WhatsApp and Zoom, sales strategies must be versatile.

4?? Building a Data-Driven Sales Function Tiller’s core feature is automating CRM updates and analyzing sales conversations to identify effective pitches. This data-driven approach not only saves time but boosts the overall accuracy and performance of sales teams.

5?? Scaling Sales Teams Requires a Cultural Fit Alistair highlighted the challenge of maintaining a startup’s culture as the team grows. He believes that fostering a hustle culture, especially in places like the UAE, aligns well with Tiller’s growth objectives.

Final Thought: Alistair’s journey is a testament to the importance of resilience, structure, and data-driven insights in scaling a sales team. For anyone looking to grow their own business, his story offers a valuable look at the ups and downs of the entrepreneurial path.

?? Check out the full episode of The Sales People Podcast to hear more of Alistair's insights and his journey with Tiller.