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Welcome to another episode of Category Visionaries — the show that explores GTM stories from tech’s most innovative B2B founders. In today’s episode, we’re speaking with Dennis Thankachan, CEO and co-founder of Lightyear, a telecom operating system platform that has raised over $18 million in funding.

  • Dennis’s journey from tinkerer and student entrepreneur to investment banker at Goldman Sachs to hedge fund analyst covering the telecom and enterprise software sectors, and how his diverse experiences led him to start Lightyear.
  • The problem of enterprises lacking a digital means to buy, manage, and renew mission-critical telecom services, leading to costly inefficiencies and limited data-driven decision making.
  • Lightyear’s approach to solving this problem by providing a software platform that enables enterprises to procure and manage telecom services with transparency, automation, and data-driven insights.
  • The advantages and challenges of being an “outsider” in the telecom industry, and how Dennis’s background in data and software enabled him to identify opportunities for disruption.
  • The journey of finding product-market fit, from initially targeting SMBs with an incomplete product to discovering the key features and value proposition that resonated with enterprise buyers.
  • The transition from founder-led sales to building a scalable, metrics-driven sales machine, and the importance of productizing and constraining the sales motion.


Unlearn the Conformist Mindset of Corporate Environments:

Dennis emphasizes the need for founders to shed the pressure to conform that often pervades large organizations like Goldman Sachs. To build something unique and impactful, founders must embrace their quirks, cultivate diverse interests, and bring their full authentic selves to their work. Muting the qualities that make you special in pursuit of fitting in will only hinder your ability to innovate and lead.

Exploit Pricing Inefficiencies to Bootstrap Your Data Moat:

In the early days of Lightyear, Dennis and his team identified long-tail keywords with high purchasing intent and wrote content to rank for those terms, generating a steady stream of inbound leads. By focusing on highly specific, technical queries that competitors had overlooked, they were able to capture valuable data on buyer behavior and preferences, which they used to refine their product and GTM. Founders should seek out similar untapped opportunities to accumulate proprietary data assets.

Ruthlessly Prioritize Depth Over Breadth in Large Markets:

While the sheer size of the telecom market can tempt founders to expand horizontally into adjacent categories, Dennis remains laser-focused on building the most comprehensive solution for his core use case. By going deep rather than wide, Lightyear can capture more value from each customer relationship and establish itself as the definitive platform for telecom procurement. Founders should resist the urge to prematurely broaden their scope and instead strive to dominate their initial niche.

Reintroduce Constraints to Maintain Discipline Amidst Abundance:

Reflecting on the frothy funding environment of 2021, Dennis observes that the pressure of scarcity breeds a level of rigor and efficiency that can be lost when capital is plentiful. Despite Lightyear's strong balance sheet, he has deliberately reintroduced constraints to ensure that every decision is scrutinized and every dollar is deployed productively. Founders should maintain a constraint mindset even in periods of abundance to build resilient, enduring businesses.

Cultivate a Process-Oriented Approach to Optimize for Scale:

As a self-described "ruthless SaaS investor type," Dennis leans heavily on metrics, systems, and processes to drive predictable growth. Rather than relying solely on the charisma of natural-born salespeople, he has invested in productizing Lightyear's sales motion, instrumenting each stage of the funnel, and building a machine that can scale beyond founder-led efforts. Founders should embrace a similarly process-oriented approach to create a foundation for sustainable growth.