Closing Big: Unlocking Secrets to Landing Larger Deal Sizes for Tech Startups

Are you a tech startup looking to scale and make a significant impact in the market? If so, you know that landing larger deal sizes is crucial for your growth and success. As a growth leader and serial entrepreneur, I have personally sold over $265 MM of complex enterprise tech to 850 companies and 5,000 senior executives, and today, I want to share with you the secrets to closing big deals.

When it comes to selling to enterprise-level customers, it's not just about the size of the deal but also the long-term impact it can have on both theirs and your business. In this article, I will reveal the strategies and techniques that have helped me unlock opportunities for landing larger deal sizes, and I'll even share some personal anecdotes along the way to illustrate key points.

So, let's dive in and discover how you can take your sales to the next level by closing big!

Understanding the Value Proposition

To land larger deal sizes (elephants, whales...), you must have a compelling value proposition that resonates with your target customers; from the mid-managers up to the CEO and sometimes, the Board level. More than 70% of vendors fail to achieve this. Why? Because Marketing writes the company's product value proportions. They are fine people. But they usually are not classically trained in Sales, most often never built a startup and spent years selling in difficult markets, and do not have the value skills to incorporate calculated business outcomes and hard results in the Value propositions.

Again, it's not the total responsibility of Marketing. The burden rests on the startup to prioritize having business outcomes and measurable, impactful value as part of what Sales and Marketing will do.

One of my personal experiences involved a tech startup that developed an AI-based SaaS platform. We realized that to capture the attention of enterprise customers, especially at the executive level, we needed to clearly articulate the unique value not just in improved KPIs like revenue or costs, but physically align it to their priorities or initiates. Otherwise, we have a generic value statement without the connectivity to what the clients want and will pay more for help based on these conditions.

Additionally, we conducted extensive market research and understood the pain points of our target audience, and were able to tailor our value proposition specifically to address their challenges. This customized, business outcomes approach helped us win larger deals, as decision-makers saw the direct impact our solution could have on their business in dollars and cents.

Building Strong Relationships

In the world of enterprise sales, building strong relationships is paramount. One memorable encounter I had was during an account sales meeting with a Fortune 100 SVP of Customer Growth. Instead of jumping straight into a sales pitch, I took the time to listen attentively and understand their objectives, challenges, and aspirations.

By showing genuine interest and empathy, I built trust and rapport with the executive. Then I revealed a customized Business Dossier, in essence, a one-page Business Case, that was aligned to what they said, and how I learned this.

This mechanism throttled the building of a business relationship based upon mutually beneficial and agreed-upon drivers or KPIs that govern their business. It actually gave us a better basis to start a relationship and was invaluable as we navigated the complexities of their decision-making process. Ultimately, our partnership resulted in a significant deal hitting $750,000 ACV that not only benefited their company but also positioned us as a trusted long-term partner.

Customizing Solutions for Enterprise-Level Impact

Enterprise-level customers have unique requirements and expect solutions that can scale and integrate seamlessly within their existing infrastructure. In one instance, we were approached by a mid-sized company looking to expand by 20% into the next two quarters. To secure a larger deal, we customized our sales approach, POCs, and SaaS costs in Year One, to align with their specific needs and growth metrics.

By putting "skin in the game", and then demonstrating how our tailored solution would streamline their operations, increase efficiency, and drive revenue growth with specific benchmarks and deliverables, we convinced them of the significant value we could bring to their organization. The ability to provide a solution that catered to their enterprise-level impact requirements became a key differentiator, helping us close a deal that exceeded our initial expectations. Then we used this on 75% of similar-type accounts.

ROI, Business Outcomes, and Measurable Results

When it comes to selling to enterprise customers, showcasing the return on investment (ROI) is a start, but does not go far enough. It will not incorporate tangible AND intangible business impact. In fact, from 2020, 65% of large accounts are crucial. To illustrate this point, let me share the truth. A three-year-old tech startup that we worked with, developed a newer version of a self-learning cybersecurity platform, which only gave them a twelve-month window to be differentiated, was already in an overcrowded market space.

In order to open doors, secure access to CISOs, and win over 2-3 critical clients so they could gain some market entropy, they led with a one-page value hypothesis of why them, why now, how much, and what results would ensue. Then they followed it with a free, comprehensive analysis of an account's latent and under-served security vulnerabilities, and estimated the potential financial losses they could incur without their platform.

In essence, they took an extremely complex technology and distilled it down into simple, executive sound bites that in 2 minutes their story was told.

By presenting these findings and demonstrating how their solution could mitigate tangible AND intangible asset risks, saving tens of millions of exposure and cost-recovery efforts; they showcased the business outcomes (which had an ROI on one of the line items).

Our approach helped them secure a larger deal, as CISO, CIOs, CFOs, and the CEO recognized the clear and transparent value they brought to the table.

Effective Negotiation Strategies

Negotiations can make or break a deal, especially when it comes to landing larger deal sizes; from $500,000 to $5 MM. In a memorable negotiation experience, we were working with a Fortune 200 company's procurement team. We recognized the importance of understanding their negotiation style and objectives. Plus their aggressiveness was topical, and as they thought, impregnable.

By leveraging our knowledge of their priorities, the RFP, our financial alignment to the CFO, and our quantification of value + risk+ competitive advantage with our solution, we not only found common ground, we turned the table.

We were able to negotiate a win-win agreement that not only addressed their requirements but also maximized the value for both parties involved. The result? A mutually beneficial deal that exceeded our initial expectations AND made procurement look good in front of the organization!

Conclusion

Landing larger deal sizes for tech startups is both a challenge and an opportunity. By understanding the value proposition, building strong relationships, customizing solutions, showcasing ROI and business impact, and employing effective negotiation strategies, you can unlock the secrets to closing big.

Remember, success in landing larger deals requires a strategic and tailored approach. By implementing these strategies and techniques, you can elevate your sales efforts and position your tech startup for remarkable growth.

Now, go out there and start closing those big deals that will propel your business to new heights!

Stay tuned for more insights and strategies to accelerate your sales and drive revenue growth.

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