For Kunwar Asheesh Saxena, Angel Investor and Technology & Growth Advisor, evaluating a startup goes beyond assessing its product or the technology behind it. It requires understanding the commercial opportunity, the strength of the founding team and the ability to build a business that can sustain growth over time.
Having worked across technology leadership, entrepreneurship, investment and advisory roles, Asheesh brings the perspective of someone who has experienced the challenges of building and scaling businesses firsthand. His experience includes technology leadership at MakeMyTrip and co-founding Singapore-based Commeasure, which subsequently launched RedDoorz. As Co-Founder and CTO of RedDoorz, he built and led technology organisations supporting the company’s growth across Southeast Asia.
His experience at Commeasure, which helped independent hotels strengthen their digital presence and generate direct bookings, also shaped his understanding of how market opportunities evolve. The business grew to more than 500 hotel customers, primarily in India, with a presence in Bali. However, the larger opportunity extended beyond helping individual hotels sell online. It involved creating a recognisable brand across budget accommodation properties with consistent guest experiences and technology-enabled operations. This thinking eventually led to RedDoorz, which expanded across Southeast Asia.
Reflecting on this journey, Asheesh believes that a startup’s ability to recognise when its original business model needs to evolve is just as important as the initial idea. A product may demonstrate traction, but founders must also recognise where the larger commercial opportunity lies.
Looking Beyond the Product to Evaluate a Startup
For Asheesh, a compelling product is only one part of a successful startup. What matters more is the problem it solves, the customers it serves and whether the business can create lasting value.
He looks at whether a startup has identified an unmet need, an underserved customer segment or an inefficient process that can be improved. Customer willingness to pay, retention, distribution and the economics of reaching the market are equally important considerations.
He also believes founders must understand whether their business becomes stronger as it grows. Scale should ideally improve customer insight, service quality, distribution or operating economics rather than simply increase costs and complexity.
From an investor’s perspective, he evaluates the market opportunity, evidence of demand, unit economics and the founder’s ability to execute. He also examines whether the technology strategy is appropriate for the company’s stage and whether technology investments are improving customer value or operational efficiency.
His investment and advisory experience with DOCO, an operations-intensive distribution business, reflects this approach. The business demonstrates why a startup cannot be evaluated on its application alone. Distribution economics, partner relationships, operational discipline and technology must work together.
The Transition from an Early-Stage Product to a Scalable Business
According to Asheesh, the capabilities that help establish a startup are not always the ones required to scale it. In the early stages, founders often manage almost every aspect of the business, from product decisions and customer relationships to technology and daily operations. However, this dependence can eventually become a bottleneck.
He believes founders should first establish a repeatable and sustainable economic model. Revenue growth alone does not indicate business health. Customer acquisition costs, retention, contribution margins and the capital required to support expansion must be understood clearly.
The next priority is building organisational capability. Teams need defined responsibilities and the authority to make decisions without depending on the founder for every operational issue.
Technology is another important foundation, but Asheesh cautions against preparing for a scale that has not yet arrived. Startups need systems that support visibility, consistency and reliable execution, without investing prematurely in unnecessary complexity.
For him, the most important shift is often in the founder’s own role: moving from personally driving every activity to building an organisation that can deliver consistently.
Why Technology Leadership Matters in the Growth Journey
Having held technology leadership responsibilities across MakeMyTrip’s hotels, B2B and partner businesses, Asheesh understands the difference between teams that simply deliver software and those that actively enable business growth.
He believes a strong technology team should understand not only what it is building but also why it is being built, how customers will use it and what operational impact its decisions may have.
When assessing a company’s technology readiness, he looks at architectural decisions, incident management, system dependencies and collaboration between engineering, product and commercial teams. The ability of technology leaders to develop other leaders is equally important.
He also identifies two common mistakes startups make while scaling: building elaborate systems before they are needed and allowing temporary technical solutions to become permanent dependencies. Both can create unnecessary costs and slow down future development.
Technical debt, he explains, is not automatically a failure. Startups often make compromises while growing. The real concern arises when those compromises are no longer visible or actively managed.
The objective should not be perfect architecture, but a technology organisation that understands its dependencies, controls complexity and can adapt without making every change expensive.
Balancing Product Development with Reliability and Security
For Asheesh, speed and engineering discipline should not be treated as competing priorities. A technology organisation must be designed in a way that allows teams to move quickly while maintaining reliability as the business becomes more complex.
His experience at RedDoorz offered an important lesson in this regard. A booking at a RedDoorz property involved several interconnected functions, including inventory availability, pricing, reservations, payments and property operations. An inconsistency in one area could affect the entire customer experience.
Managing such systems required clear system boundaries, reliable data flows and an understanding of how the platform would respond when something failed.
He favours faster development where decisions are reversible, while maintaining stronger controls around core transactions, data integrity, security and critical integrations. Automated testing, observability, controlled deployments and clear system ownership should be part of everyday engineering practices.
He also emphasises that architecture should respond to actual business requirements rather than assumptions about future scale. The long-term cost of technology depends not only on how much it takes to build but also on how easily it can be changed.
Expanding Across Markets Requires More Than Technology
RedDoorz’s expansion across Southeast Asia, including Indonesia, the Philippines, Vietnam and Singapore, gave Asheesh first-hand experience of the challenges involved in building a multi-market business.
He points out that a business model may be scalable without being identical across markets. Customer behaviour, payment preferences, accommodation supply, competition and operational expectations can differ significantly from one country to another.
While a common technology platform can support reservations, inventory, pricing and payments, local market understanding and operational capabilities remain essential.
At RedDoorz, the proposition involved making affordable accommodation more predictable through brand standards, digital distribution and operational support. Delivering this consistently required strong relationships with local property partners and teams that understood the realities of each market.
He believes founders should identify which parts of their business model can be repeated and which need to adapt. Central teams can help maintain consistency, but local leaders must have enough authority to respond to market conditions.
For him, international expansion should not be measured by the number of countries entered, but by the ability to build competitive and sustainable businesses in different operating environments.
Using Technology and AI to Improve Business Efficiency
Asheesh believes technology creates the most value when it addresses a clearly defined business problem. His experience at RedDoorz provides an example through RedFox, the company’s in-house revenue-management platform.
As the network of budget accommodation properties expanded, pricing and inventory decisions became increasingly complex. Demand varied by geography, season, occupancy and booking patterns, making manual management difficult.
To address this, the company developed data-driven capabilities, including machine-learning-supported forecasting and dynamic pricing. RedFox received the Singapore Business Review Technology Excellence Award in 2019 in the Big Data – Hospitality & Leisure category.
For Asheesh, the significance of the platform was not simply the technology involved, but its connection to a specific operational challenge and measurable business outcomes.
He applies a similar approach when assessing AI adoption. Startups should first identify where decisions are delayed, information is fragmented or manual work creates unnecessary effort. In some cases, AI and advanced analytics may be appropriate; in others, cleaner data, better integrations or simpler workflows can deliver better results at a lower cost.
He also believes that AI is changing the economics of software development and creating opportunities to rethink entire workflows. In his recent LegalTech consulting work, he designed and developed an internal legal-operations analytics platform using AI-assisted software development methods, focused on workflow visibility, data architecture and performance reporting.
However, he cautions against treating AI integration as a competitive advantage in itself. More durable differentiation is likely to come from domain expertise, proprietary workflows, trusted distribution, useful data and dependable customer outcomes. Accuracy, security, privacy, integration and ongoing usage costs must also be considered.
The Role of Technology Advisors in Helping Founders Grow
Through DeepLayer Technology Consulting, Asheesh works with founders and leadership teams on technology strategy, platform evolution, organisational capability and business growth.
He sees an advisor’s role as helping founders connect their business ambitions with the capabilities required to execute them. For instance, a company preparing for institutional funding must understand whether its technology platform can support its growth plans, what additional investments may be required and where partnerships could be more efficient than building everything internally.
These considerations matter because raising capital is not just about funding a business plan; it is also about ensuring that the organisation has the ability to deliver it.
He believes good advisory support requires independence. Sometimes the right recommendation is to invest in a new capability, while at other times it may be to simplify an existing system, delay an initiative or reconsider an assumption.
An advisor should not replace founder judgement or become another layer of management. The objective is to help leadership teams make better decisions and build capabilities that remain within the organisation.
Building Globally Competitive Technology Businesses from India
Asheesh is optimistic about India’s ability to build technology companies that compete globally. However, he believes the country must move beyond positioning lower development costs as its primary advantage.
The greater opportunity lies in creating original products, intellectual property and businesses that compete on quality, customer experience and execution.
Drawing on his experience with technology teams across India and Southeast Asia, as well as advisory engagements with businesses in the US and UK, he emphasises that technical competence alone does not guarantee global competitiveness. Founders must understand how customers in their target markets buy, what they expect from suppliers and how regulation, data protection and local business practices influence the business model.
He also encourages startups to involve international customers earlier in product development rather than waiting until after launch to adapt their offerings. Strong leadership, dependable operations, technology governance and the ability to work across cultures and time zones are equally important.
His advice to founders is to build from India while benchmarking against the best companies globally from the beginning. The goal should be to create businesses that international customers choose because they offer some of the best solutions available.
India’s Startup Ecosystem: The Next Phase of Growth
Looking ahead, Asheesh expects India’s startup ecosystem to be judged increasingly by the depth and sustainability of the businesses it creates rather than the number of new companies or headline valuations.
He believes the next phase will require differentiated intellectual property, stronger governance, capital efficiency and credible routes to liquidity for founders and investors.
AI is likely to lower the cost of experimenting with software-based ideas and enable smaller teams to pursue opportunities that previously required significant capital. At the same time, easier access to technology will intensify competition, making customer access, distribution, domain expertise and reliable execution even more important.
He also sees considerable opportunities in sectors beyond visible consumer categories, including enterprise workflows, healthcare, financial services, manufacturing and logistics, where complex operational problems remain.
Another development he hopes to see is a stronger cycle of experienced founders becoming angel investors, mentors and strategic advisors. Having moved from building companies to investing and advisory work, he believes the experience gained through technology decisions, market transitions and fundraising can help younger businesses avoid costly mistakes.
For Asheesh, the real measure of a mature startup ecosystem will be the number of companies that remain competitive through successive technology and economic cycles. While more unicorns would be welcome, building enduring businesses with global relevance would be a greater achievement.
-By: Aakriti Jaiswal
