My Startup Scored a Multimillion-Dollar Contract With a Fortune 100 Client in Just 3 Years. Here’s What We Learned.

There’s no perfect litmus test to gauge if you’re ready to go after big business or not — but if you don’t take the risk, you’ll never realize the reward.

When starting a business, it’s natural to go after small clients: It generates revenue, sharpens your offering and lets you make mistakes on a lesser scale. But it’s not the only way to grow.

My company was three years old when we landed our first multi-million dollar contract with a U.S. telecommunications company — at the time, we had fewer than 10 employees. Landing a Fortune 100 client may seem a far reach when you’re a startup, but it can be done.

The total market cap of Fortune 100 companies reached an all-time high of $33.2 trillion in 2023 — a 48% increase in just one year — for a combined profit of $1.8 trillion. Winning even a small percentage of that business can bring major rewards to any startup; however, doing so requires strategic planning and grit.

Here are four key lessons I’ve learned in landing business with some of the biggest companies on Earth.

1. Create an irresistible value proposition

In the wireless industry, companies compete solely on product and price. Landing a big contract meant going up against global tech giants, who heavily subsidize their products or merge the costs into other service models. We were never going to win on those selling points alone.

To even be considered, we knew we had to create an irresistible value proposition, one that would solve pain points our competitors weren’t attuned to. To do this, we went to the source: the client. At every major company we targeted, we asked their support team what their customers’ most common paint points were.

It turned out, at the time, a customer would be cut off by their service provider if they hadn’t used a certain amount of minutes within a specified time frame. Another common problem involved battery installation: back then it was illegal to ship devices with batteries pre-installed. So they would arrive separately, causing end-user confusion.

Once we knew what our prospects’ biggest customer issues were, we were able to customize a solution that fixed the whole problem: a quick-start guide that addressed setup issues and automated reminders to use minutes before the cutoff date.

We were no longer competing against incumbents on product and price, we were offering a solution no one else had — one that not only met the stipulated requirements but also reduced call center costs and customer churn.

When you’re a startup, finding creative ways to compete on value can not only give you the confidence you need to pitch big clients; it can differentiate you from competitors with long-standing relationships.

2. Identify your inner champion

Selling to big companies is time-consuming. Outdated policies and bloated org charts perpetuate inefficiencies and change happens slowly, particularly when it comes to onboarding new partners.

Not only is it hard to get all the necessary decision-makers in one room, but you then need to get them aligned: Internal politics become a major factor in this process. I’ve seen billion-dollar projects go south due to one executive not wanting to be outshined, at the expense of the company.

For this reason, it’s critical you build strategic relationships with company insiders who have the power to champion your proposition and guide you through office politics.

Look for the people who ask logical questions in the first meeting — this hints that they’re engaged, understand strategy and may be willing to support you. if you can convince these people your company can provide significant value, they may become strategic partners and help you close the deal. Even if you miss out on the first one, maintaining these internal relationships can lead to deal flow down the road.

3. Offer white glove service

Large companies often have bad customer service and that’s where startups have an advantage.

At a large corporation, it can take days just to identify the specific person responsible for fixing a customer problem and once they are found, they may not be empowered or incentivized to act on it. When you’re a 10-person team, this is a challenge you don’t have to navigate.

If an issue arises for one of our clients, we get to the heart of it quickly while maintaining exceptional communication with the strategic partners we’ve built inside. If a request is out of scope, we let it be known, but often we’ll still help troubleshoot it if it means maintaining the longevity of the relationship.

As a startup, it’s in our DNA to hustle and beat client expectations. Offering a level of service that our larger industry peers can’t compete with has enabled us to achieve a 100% retention rate — a near-impossible achievement when servicing smaller companies.

4. Solidify deal terms upfront

I often say I’ve learned more from the 1,000 things I’ve done wrong in business, than the 100 I’ve done right. One of these key lessons is the importance of having deal terms clearly laid out in an ironclad contract, upfront.

When working with SMEs, deal terms are generally well understood between the key decision-makers. Paperwork is important, but there’s less risk of a deal falling through because a standard operating procedure wasn’t approved by a nameless stakeholder.

Multinational corporations can have dozens of stakeholders involved in the closing of any one deal and if each one doesn’t sign off, all the time you spent building relationships and negotiating the contract may have been in vain.

C-level executives leave companies and projects get canceled when leadership changes hands. That’s why it’s critical you don’t engage in any speculative work. The good news is, once you do sign off on a big contract, a large corporation’s slow-to-change culture works to your advantage, resulting in less churn and higher revenues.

There’s no perfect litmus test to gauge if you’re ready to go after big business or not, but if you don’t take the risk, you’ll never realize the reward. If you view every mistake as a learning opportunity and don’t give up on the prospect, you can compete for world-class clients and your company will emerge stronger for it.

Content from this post was originally featured in Entrepreneur.


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