Key Lessons from Three Serial Entrepreneurs, The Value of Being Assertive with Customers- Tactician #0038

18/01/2024

KEY LESSONS FROM THREE SERIAL ENTREPRENEURS

Todd Jackson, Partner at First Round Capital, highlights the unique journey of Jessica McKellar, Waseem Daher, and Jeff Arnold, founders at Pilot, who built and exited two previous companies together, providing insights into their approach to identifying market needs, building product, and maintaining a strong co-founder relationship in “Pilot’s Path to Product-Market Fit — Three-Peat Founders on Picking the Right Team and the Right Market”

• Journey from Concept to Pilot's Formation:

  • “Reflecting on our journey, we remember how we couldn't afford a back office team back in our early days, leading us to get a copy of ‘QuickBooks for Dummies’ and QuickBooks Desktop software to manage our finances ourselves. [...] This early experience of grappling with our financial management was a problem we had lived through, a decade prior. The realization that this was an unsolved problem for many others became apparent. Eventually, we reached a point where we just had to make a decision. We stopped deliberating on ideas and took the plunge to see if we could get someone to pay for our solution. Payment, in our eyes, was the true proof of concept."

• Acquiring the First Paying Customers:

  • "By January 2017, even without engineers, software, or bookkeepers, we didn't see these as barriers. We approached fellow founders, confirmed that bookkeeping was indeed a pain point, and then boldly asked, 'Would you pay us $100 to take care of your bookkeeping?' If they hesitated, we delved deeper to understand their reservations. But if they agreed, we were ready to take their ACH details and start our journey as their bookkeeper."

• Launching and Finding Product-Market Fit:

  • “Our focus at Pilot has always been on delivering a service that people genuinely love, appreciate, and recommend. This customer satisfaction has been the driving force behind our growth. The most significant turning point for us came when, almost effortlessly, we began attracting customers from broader markets and various verticals. This natural expansion was a strong indication that we were not only meeting but exceeding the expectations of our customers, suggesting a clear sign of product-market fit.”

• Expanding the Product Suite:

  • “Once we found our initial product-market fit, it instilled the confidence we needed to start broadening our services and exploring new customer segments. Our goal has always been to provide comprehensive financial back office support to a wide range of businesses. Maintaining high customer satisfaction (CSAT) has been pivotal in this expansion. Every decision, every new service introduction is weighed against its impact on customer satisfaction.”

• Key Lessons from Serial Entrepreneurs:

  • "Reflecting on our journey, there are a few key lessons we’ve learned: First, choosing a large market is critical if you aim to build a long-standing, independent company. The market size is one of the few things you can't change later. Secondly, it's vital to ensure that the problem you're solving is actually the one your customers want you to solve. There's a danger in overfitting to your own experiences and missing the broader market needs. Lastly, building a product that naturally extends into other areas is crucial. This approach has allowed us to expand our offerings organically, in response to our customers' evolving needs.”

THE VALUE OF BEING ASSERTIVE WITH CUSTOMERS

Wes Kao, Founder at Maven, encourages founders and customer facing teams to not shy away from being assertive and proactive in their interactions with customers in “Be more assertive with customers”

• Recognizing Opportunities for Assertiveness:

  • "There are dozens of moments when you’re talking to prospects, customers, or partners, where you can choose to (a) be more assertive or (b) take a step back. In those moments, I hope you’ll decide to speak up, knowing this proactive posture will serve the customer and you."

• Serving Customers, Not Pestering Them:

  • "It’s important to remind yourself that you are serving your customers, not bothering them. You are not asking them for a personal favor. And they are not doing you a personal favor when they comply with your requests."

• The Consequences of Holding Back:

  • "When you hold back, you’re harming your customer... Your customer benefits when you are brave enough to speak up, respectfully disagree, and share information that may be at odds with their current knowledge."

• Engaging in Productive Conflict:

  • "It takes courage to engage in productive conflict. Your customer benefits when you are brave enough to speak up, respectfully disagree, and share information that may be at odds with their current knowledge."

• Empowering the Team for Assertiveness:

  • "If you want to see more boldness, you need to reward attempts to be assertive, not only the outcomes of being assertive."

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