Jenny Lefcourt - The Go-to-Market Motion

Principles & Lessons:

• Understanding the customer is fundamental to success: Jenny underscores that a deep, authentic comprehension of who the customer is and what they truly need is non-negotiable; as she puts it, "I love working with founders who really understand their customer. Who are they? What does their future look like?" and later emphasizes that go-to-market strategies must start with obsessing on the customer—"the only way to do it is to absolutely obsess on the customer"—which shows that insights derived from real customer behavior, rather than abstract market trends, drive sustainable business decisions.
• Balancing idealism with market reality is essential: She illustrates the tension between idealistic business models and real consumer behavior by recalling her early wedding registry pitch, where critics argued, "You don't have to work with retailers," yet she countered that "brides are not ready to register at random.com" because they trusted and preferred familiar retailers; this teaches that even if a model looks great on paper, it must align with how customers actually behave and the context in which they make decisions.
• Vision, team, and market size are core investment criteria: Jenny explains that her framework begins with evaluating the founder’s vision—"Do I believe in the future the way that they see it?"—and then assessing if the team is capable and adaptable, with a "growth mindset" and the ability to recruit and serve their market, while also considering whether the market, even if nascent today, can grow into a lucrative opportunity; this multi-pronged evaluation ensures that investments are grounded in both potential and practicality.
• Designing products for specific demographics requires simplicity and empathy: When building for older consumers, Jenny advises keeping user interfaces straightforward—"big buttons, big text, black text on white background"—to accommodate those who may not adapt easily to rapidly changing apps, thereby highlighting that product design must be tailored to the user's capabilities and preferences to reduce friction and enhance adoption.
• Effective go-to-market strategies solve today’s pain while opening up a better future: Jenny describes what she calls the "one-two punch" approach, where a product must immediately address a current problem (for instance, reducing excessive customer service calls as with Narvar) and simultaneously educate the customer on future benefits—“you have to solve a need that they have yesterday and paint them a future that they're going to need you even more in the future”—demonstrating that a compelling market entry requires both immediate ROI and visionary value.
• Adaptability in work practices is key amid evolving work environments: In discussing the future of work, Jenny notes that while remote work offers efficiency, it lacks the serendipity and energy of in-person collaboration, remarking, "I don't think I'll be doing this job really well if I just stayed in front of my computer all day long," which suggests that future organizational models must balance efficiency with structured opportunities for genuine human connection and spontaneous collaboration.
• New market themes, like aging and low-code/no-code, open overlooked opportunities: Jenny is drawn to sectors that have been traditionally neglected—such as technology solutions for an aging population—and she stresses the need to "understand who they are, what they need, what exists, and what doesn't," while also being excited about low-code/no-code because it empowers non-developers to build solutions, effectively broadening the pool of potential innovators and addressing market gaps that more conventional tools may miss.
• Building and leveraging authentic networks drives long-term progress: Reflecting on her experiences with initiatives like All Raise, Jenny illustrates how collaborative relationships can significantly enhance deal flow, due diligence, and overall success, noting that working closely with a network of peers—"an amazing network of women who have my back"—not only fosters mutual support but also challenges conventional biases, which she identifies as a major barrier to diversity and progress in the tech industry.

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