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Mar 11, 2025
A lot of startups tend to pursue Fortune 500 customers way too early in their journey. It seems like the right thing to do—big names, big contracts, credibility—but the reality is a bit different than what you would think. If you’re not careful, you can waste months—sometimes years—without closing a deal.
Before we get started, for those of you who are reading my blog for the first time, this is Part III of the startups series, where I try to break down the lessons I have learned during my time in Silicon Valley, working alongside some of the most inspiring minds in robotics and the startup world.
Whether you're a founder, team member, or investor, my goal is simple: help you navigate the capital, operational, and psychological crevasses of building a startup with fewer scars than we did.
If you haven’t read Part I and Part II, you can read them here:
Building on those foundations now we will start Part III. The focus of Part III here will be specifically on dealing with different types of customers without draining your resources. We’ll keep it simple: prospects fall into two buckets—Fortune 500 Giants and fast-moving mid-sized companies that value your services.
Fortune 500 Giants – Big logos, long sales cycles, and a ton of stakeholders.
Mid-Sized Heroes – Fast-moving companies that are agile and eager to adopt new solutions, tighter budgets and much shorter sales cycles.
How you handle these two from Day 1—whether it’s a demo, a sales pitch, or six months of chasing your seventh meeting with the same prospect—will determine your startup’s survival.
In this post we will focus on Fortune 500 Giants and specifically lessons we learned through our meeting with Apple.
Before our meeting with Apple
Oct 16 and 17, 2019, and months preceding this meeting with Apple, have been crucial in our journey as a startup. For they taught us some hard lessons around evaluating prospects, understanding their real needs early-on in the process, and being deliberate about where we invest time and resources.
At the time, we had a few paying clients, mostly from the technology space, but our product had yet to find a solid product-market fit. Our product worked—it did exactly what it was designed to do: autonomously patrol office spaces, warehouses, and other facilities while delivering real-time safety and security insights to the security and executive teams.
The challenge?
Finding a consistent product-market fit—a steady stream of clients in one or two core domains like healthcare, technology, warehouses, or pharmaceuticals. Instead, our clients were spread across diverse industries—a food delivery startup, a financial company, an e-commerce brand, a technology firm, and more.
This was both good and bad.
Good, because it validated demand across multiple industries. Bad, because it meant an endless cycle of customizations and diverse standard operating protocols (SOPs) for each client, straining our engineering, operations, and sales teams—significantly throttling down our ability to scale.
It was during this time, fall of 2019, that our paths crossed with Apple.
The Apple Meeting : How It Happened
So around this time, fall of 2019, after months of persistence—navigating a long chain of internal champions and a maze of intros—one of our sales team members, secured an in-person meeting with the decision makers at Apple at their headquarters.
As someone responsible for leading the demo, I had a sense of what was at stake here.
Success meant objective validation from a high-caliber Fortune 500 giant.
Failure meant valuable lessons—but at the extreme cost of capital, time, and effort.
That reality drove a series of risk-focused exercises—rigorous product testing, strategic briefings with engineering, sales, and operations teams, and the intensified adrenaline rush that comes with a high-stakes deal.
We spent a reasonable amount of time preparing for this meeting. It took place on October 17, 2019 at the Apple HQ in Silicon Valley. To be clear, all this while, despite our best efforts, we were only able to speak probably half a dozen times with a below-the-line contact—someone close to the decision-maker but not the final authority. They seemed deeply interested and helped us secure this meeting.
Over months prior to this meeting, we had a sense that they were looking to augment their existing security systems with robotics, and eventually, this person got us in front of the real decision-maker.
We had a one-shot. We were ready—or at least, that’s what we thought.
On October 16, the day before the big meeting, we arrived at Apple’s Main Campus. We met our internal champion, reviewed their needs—at least, what we thought were their needs. Then we spent hours, ensuring we are all set for the meeting – product testing, understanding the problem statement, rehearsing our approach, etc. Then came the big day—October 17.
On the day of meeting–October 17
On the day of the meeting, we rolled the robot into Apple’s office, brought it to the meeting room, and greeted the five or six people from their team who had joined. The meeting started, and we reiterated our understanding of the problem they were trying to solve before moving into the demo.
We then helped them understand how we can help them solve those challenges and demonstrated our robotic-enabled security service to their team. The robot performed flawlessly—the video-calling service, the badge identification system, and the safety and security anomaly detection system, all operated without a hitch. By this point, we had built enough trust to educate them that our product had the potential to address their needs and deliver long-term value. Then came the deal-breaker.
The Deal-Breaker
There are days when you know exactly where your product stands—its strengths and weaknesses, the things it does exceptionally well and the things it still struggles with. We knew that we had one of the best autonomous navigation systems available, meticulously tuned for precision. Our hardware was resilient, with sensor redundancy at all levels. Our security compliance was solid, and our anomaly detection system was fine-tuned with some of the best machine learning models available. Even Joseph Redmon, the creator of YOLO, might have appreciated how precisely we fine-tuned it for object detection.
But there was one thing we knew we couldn’t do and that one thing defined the outcome of this meeting.
Where It Fell Apart
At this point in the conversation, one of the Apple executives asked:
"How many floors can one of these robots cover?"
Apple didn’t want one robot per floor. They wanted one robot per building, capable of navigating multiple floors autonomously. That meant integrating every single robot with elevators. Placing one robot on each floor was not an option since that would mean transforming a campus into a dystopian city with 100+ robots per campus, one per floor. The robot had to handle elevators.
Our reality?
At the time, our robots weren’t integrated with elevators—certainly not with the ones Apple had installed. Our 2WD, 5’4”, 120 lb robot couldn’t climb stairs or use escalators either.
This was not a minor feature request. This was a deal-breaker for Apple.
We had two choices:
Commit to building elevator integration—knowing it would take months, drain resources, and delay existing deployments.
Be honest that we couldn’t deliver within the required timeframe and walk away from the deal.
The decision was clear. We had to walk away.
This is how startups die. We think we understand what a customer needs, only to realize—too late—that more often than not we don’t.
Enterprise sales cycles are brutally slow and the process can burn months of your most valuable resources especially if you are an early-stage startup—your time, your team, and your capital. Still, even knowing this, when you're in the arena, the temptation to engage with industry giants is strong. We felt it too during this engagement.
The Hardest Lesson in Selling to Fortune 500s
Walking out of Apple’s headquarters that day, as I was driving back to our startup HQ with a robot in a big van, it was painful to digest this outcome, not because it led to a failure, but because of the amount of time and effort we had put into preparing for this one meeting.
It was an important one for us and yet it hadn't worked out.
The failure wasn’t in our product—it worked flawlessly. It wasn’t in our pitch—we built trust and engaged the room. The failure was in not investing enough time to understand the real needs of our prospect with an extremely high degree of objectivity and clarity.
This was a hard blow for me and my team.
If we had been able to make this work, it would have changed the trajectory of our company. Our product could have been deployed across campuses nationwide. But in hindsight, the real lesson wasn’t about the technology—it was about understanding what customers truly need before you invest time and resources chasing them.
We spent months navigating Apple’s internal decision-makers, preparing for every possible objection, and fine-tuning our demo. But in the end, we weren’t solving the problem they actually needed solved. Had we known from the outset that Apple’s non-negotiable requirement was multi-floor navigation with elevator integration, we wouldn’t have wasted time chasing a deal we could never win.
While there are tons of lessons we can learn from this engagement and probably more insights to this event, at the risk of not boring you with all the details, here are some of the most valuable lessons that we learned from this engagement.
Whether you're a founder, investor, or engineer building a startup, I hope these lessons save you time, capital, and most importantly—your health and overall well-being.
1) Landing a Fortune 500 Meeting Is Easier Than You Think
Many founders believe getting a meeting with a Fortune 500 company is the hardest part. That might be true in some cases but the reality is that if you understand the core problem of your client with extreme depth and clarity, landing a meeting with Apple, Amazon, Toyota is not that hard.
Who doesn't want to buy a solution that solves their problem? If your product is compelling and solves a real high-stakes problem, decision-makers will listen and make time for you. The real challenge isn’t getting in the room—it’s knowing what to do before you enter the room and once you’re there.
That brings us to Lesson #2: Committing yourself to deeply understanding the needs of your client.
2) What They Say They Want ≠ What They Actually Need
Enterprise clients operate with layers of priorities, budgets, and internal constraints. What they say they want and what they actually need may not always be the same.We spent months chasing Apple, yet despite our best efforts, we never got on a call with key decision-makers before the demo to truly understand their core needs.
In hindsight, it would have been better to say NO to a demo and instead chase a YES for a short but focused meeting directly with the top-level decision-makers.
We assumed Apple wanted a robotic-enabled security system to elevate their security operations. What they really wanted was a scalable system to elevate their security operations—not an operationally heavy one. Specifically, in our context, they were looking for a single security robot per building—not one per floor. That meant elevator integration was non-negotiable. They didn't want to convert the Apple campus into a dystopian robotic city.
We didn’t realize that until it was too late. Had we understood this from the start, we wouldn’t have invested months preparing for a deal that was never viable. We didn’t ask the right questions early enough—and that cost us months.
3) Fortune 500 Interest ≠ Fortune 500 Deal
Just because a Fortune 500 company expresses interest doesn’t mean they’ll buy.
Interest is cheap—conversion is expensive.
Apple’s team was engaged. They asked great questions. We thought we had momentum.
We didn’t.
The moment they asked, “How many floors can this robot cover?” we knew we had lost the deal.
The mistake we made wasn’t failing to close the deal. The mistake was thinking we knew what they needed before engaging with the decision makers. We until this point had only engaged within the folks close to the decision makers but not the decision makers. We assumed they wanted our security robots to replace or augment their current system.
But what they really wanted was more than that – a single security robot per building. One robot per building that could patrol all floors autonomously without manual intervention, something we couldn’t deliver at the time.
The real lesson? You don’t know what a customer actually needs until you’re deep in the conversation. And if you don’t figure that out early, you’ll waste months working toward something that was never possible.
4) Misreading These Needs Can Drain Your Startup Fast
We spent months optimizing security features—anomaly detection, badge scanning—features that some of our other clients cared about.
For Apple? Most of these weren’t deal-breakers.
The deal was dead the second we realized a one-floor robot wasn’t an option.
A startup’s biggest risk isn’t rejection. It’s unintentional ignorance towards deeply understanding the needs of the client early-on in the process.
A Fortune 500 deal sounds great—until it burns months of your most valuable resources: time, talent, and capital. If you’re chasing big clients without clarity, you're running towards a cliff.
5) Most Fortune 500 Demos Don’t Convert—Here’s Why
A great demo doesn’t guarantee a sale.
We demonstrated how we can help amplify safety and security services on their campus through our autonomous mobile robots and the software systems that came with it.
Our robot worked flawlessly during the demo. Every element of our product and service functioned as designed. But Fortune 500s don’t buy because a product works—they buy because it fits into their existing world–it's compatible with their needs and their infrastructure.
Apple wasn’t evaluating our tech. They were evaluating whether we fit into their infrastructure.
We didn’t.
Enterprise deals have low conversion rates because buying decisions aren’t just about the best technology. Internal alignment, budget cycles, and—most importantly—infrastructure compatibility all play a bigger role than most startups realize.
6) It’s Not the Product or the Pitch—It’s the Depth of Insight
Fortune 500s don’t have time for discovery calls.
You need to walk in with a level of understanding that makes them feel like you’re already an insider. Mid-market clients will give you room to figure things out. They’re not looking for a sales pitch—they’re looking for proof that you understand their operations at a deep level. They want to see that you’ve done your homework—that you have studied their pain points and infrastructure constraints with extreme clarity before you step into the room.
That means:
Understanding their infrastructure constraints before they tell you
Understanding how your solution can be integrated into their existing workflows
Anticipating and addressing deal-breakers before they bring them up
Mid-market clients will give you room to figure things out—you can iterate with them, adjust, and refine your offering as you go. Fortune 500s won’t offer that pathway in most cases. That’s why our biggest mistake wasn’t in our product or our pitch—it was in assuming that, no matter what the prospect needed, our product could accommodate it in its current state. And worse—assuming the prospect would tell us upfront.
They won’t.
You either walk in already knowing—or you lose. If you don't do your homework there is no second chance here.
7) If You Don’t Already Know the Deal-Breaker, You’re Too Late
Meeting with Fortune 500 executives is brutally time-constrained.
You’re not just presenting—you’re fighting for attention in a room full of high-stakes decision-makers with packed calendars. If your insights don’t immediately resonate, you’re already forgotten. The worst time to discover a deal-breaker is during the meeting. This is especially true if you are dealing with a F500 giant.
By the time Apple asked about elevator integration, it was already over.
These meetings with top-level decision makers are not a discovery session. They are a test to see how well you understand their world. If you have to ask during the meeting, you’ve already failed. No exceptions here. This was a hard and yet important lesson for me and my team.
8) Be Strategic About Your Sales Pipeline – A Slow ‘No’ Is More Dangerous Than a Fast One
You really want to be strategic about your sales pipeline because that will define the type of clients your team will chase.
Chasing enterprise clients is a high-risk, high-reward game.
It often comes with a slow "NO". And slow ‘no’ is more dangerous than a fast one.
Why? Because you have a limited supply of talent, capital, and—most importantly—time. If more than 20% of your sales pipeline is dependent on Fortune 500 clients, you have a big problem.
Define upfront: What percentage of your revenue should come from Fortune 500s vs. mid-market clients? If too much of your sales efforts are riding on F500s, your startup becomes hostage to slow-moving deals—deals that could stretch months or even years without a clear outcome.
Startups move fast. Fortune 500s don’t. We spent months getting in the door. Then months prepping for the demo. Only to realize—too late—that we were never close to closing. Had we prioritized mid-sized, fast-moving, and high-fit clients in our pipeline, we could have closed more deals and thrived.
9) Fortune 500s Buy Based on Fit, Not Features
It’s not about having the best product—it’s about understanding their world better than they do. If you can’t articulate their real, hard-core challenges with clarity, you won’t close the deal.
Enterprise customers don’t buy the best product. They buy the one that fits best into their ecosystem.
Apple didn’t pass because our robot wasn’t good.
They passed because it wasn’t designed for their infrastructure, their requirements, their reality—their operational scale. Had we known what we know now, we wouldn’t have spent months preparing for a deal we couldn’t win.
Instead, we would have:
Validated their real needs upfront
Realized we couldn’t meet them
Walked away faster
The lesson? Enterprise sales aren’t won on features.
It’s not just a technology challenge—it’s a people and process challenge. If your product doesn’t align with how they already operate—or if adopting it feels like a disruption—you won’t win the deal.
10) The Real Lesson? Ask the Right Questions Early.
The mistake wasn’t losing the deal. The mistake was thinking we knew what Apple needed before asking the right questions. Want to avoid this trap?
Ask at least these three questions before you spend a single minute on an enterprise deal:
What’s their absolute must-have requirement?
Does your product in its current state meet those requirements?
If not, how much time and effort would it take to get there?
If the answers aren’t clear, steer away from that deal and take time to reflect on the deal-breakers both for you and your prospects.
A slow “no” drains more resources than a fast one.
Not every Fortune 500 deal ends like this. In fact, a different enterprise customer—a top U.S. pharmaceutical company—turned out to be one of our biggest wins. More on that in the future posts.
What’s been your hardest lesson in enterprise sales? Drop it in the comments section—we’d love to hear.
Cheers,
Prathamesh
Disclaimer: This blog is for educational purposes only and does not constitute financial, business, or legal advice. The experiences shared are based on past events. All opinions expressed are those of the author and do not represent the views of any mentioned companies. Readers are solely responsible for conducting their own due diligence and should seek professional legal or financial advice tailored to their specific circumstances. The author and publisher make no representations or warranties regarding the accuracy of the content and expressly disclaim any liability for decisions made or actions taken based on this blog.
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