So, your small team has built a solid product. Maybe it solved a nagging problem for early adopters, and now bigger companies are calling. Sounds great. But pitching to enterprises isn’t the same as selling to early users or startups.
For small companies, a single enterprise contract can transform the business. Those big logos mean revenue, reach, and often influence with future prospects. But let’s be real: landing those contracts is tough when you’re a team of five, not fifty.
Many small teams get stuck in long buying cycles, or lost in complicated procurement. Sometimes, people at big companies just never reply. But others have done it—and learned a lot along the way. Here’s what usually works.
What Makes a Company an “Enterprise”?
We throw around the word “enterprise,” but it usually means large organizations with 500 or more employees and complex operations. Think Fortune 1000 or big regional giants.
They have departments for everything: security, legal, IT, procurement, and so on. Decisions take longer and often involve multiple people.
Their priorities usually focus on reducing risk, controlling costs, and improving efficiency at scale. It’s about predictability more than speed.
Understanding Enterprise Needs
Enterprises often ask: will this solution reduce risk, save money, or make things more efficient? Can it work with our other systems? What does support look like?
They like proven solutions, stable providers, and products that won’t disrupt existing workflows. Many are looking ahead two or three years, not just rushing to fix tomorrow’s problem.
To connect with them, you need to show how your offering fits these needs—and sometimes, how it fits their company specifically.
Making a Solid Business Case
With bigger prospects, just explaining features usually isn’t enough. You’ll want to highlight clear benefits tied to dollars, hours saved, or mistakes avoided.
Try to show exactly how your product helps their business—ideally with numbers or evidence. “We reduce average processing times by 30%” is better than “we help teams work faster.”
Slide decks with numbers, customer stories, and potential ROI help. Avoid sweeping promises; stick to what you can actually deliver and prove.
Building a Value Proposition That Matters
Start by mapping out the main worries and goals of your customer. Maybe they need to secure sensitive data, or maybe their workers waste too much time on manual processes.
Frame your product as a solution to those problems, not as a laundry list of features.
If you’re small, make a point out of your responsiveness or focus. Sometimes you’re nimbler, or your product is less bloated than a big vendor’s. Don’t bash the competition—just spell out what you do differently and why it helps.
Comparisons or charts can work, but stay focused on real differences that matter to that enterprise—not just generic “we care more.”
Proving You’re Legit: Trust and Credibility
Big companies don’t like taking risks on vendors they haven’t heard of. That’s where testimonials, customer logos, and case studies come in.
If you have a recognizable client, even a small department at a major brand, put that front and center. Quotes help. If you don’t yet, see if you can run a paid pilot or trial with a reference-able customer.
A professional website, clear documentation, and fast support responses also matter more than you think. A little polish here pays off, because enterprise buyers check these details.
Getting Conversations with the Right People
Finding decision-makers in big companies isn’t always simple. Sometimes LinkedIn works. Sometimes you need a warm introduction, or maybe you meet someone at a conference.
It’s usually better to aim for champions—people inside the company who care about solving the problem and can help push things forward.
Once you’re in, listen. Ask what’s hard in their current process. Follow up. Don’t spam out generic emails; if you can mention something specific to them, you’ll get noticed.
Over time, keeping in touch helps. Even if you don’t close a deal fast, check in with useful updates or new features. Some deals take more than a year—but the relationship matters for the long haul.
Changing Your Sales Pitch for Big Companies
The sales pitch you use for startups or tiny businesses might not fly with an enterprise client. Larger organizations often have more stakeholders—IT, security, finance, and a business lead—all with separate worries.
So, you’ll want to edit your pitch as you go. For technical teams, talk about your integration and reliability. For finance, point out cost savings and value over time. The legal team? They’ll want to know about compliance and contracts.
If you’re meeting with new people each time, tweak your emails and presentations to speak their language. Using their industry terms, or mentioning examples from similar companies, helps you stand out.
Smart Tools for Small Teams
No one remembers every contact, meeting, or email. That’s why a good CRM system—like HubSpot, Salesforce, or even simple ones like Pipedrive—can keep you organized.
Record who you spoke with, what they care about, and what’s next on your to-do list. This keeps you from missing follow-ups, and helps keep the conversation warm.
Tools for e-signatures (like DocuSign) or proposal software save time. Analytics tools can show who’s opening your emails or reviewing proposals, so you’re not guessing what matters.
Staying Calm Through Objections and Slowdowns
Almost every enterprise sale comes with objections. Maybe they think your team is too small. Perhaps a competitor is already embedded. Sometimes, a new boss arrives and the project stalls.
When someone says you’re too small, turn it into a positive: “That means you’ll have direct access to our founders.” If they’re worried about support, explain who handles issues, and show what you’ve done for other customers.
Deals get slow, or sometimes lost, for reasons you can’t control. That part’s normal. Many successful teams just keep polite, no-pressure contact—with periodic updates or a quick hello. Don’t take silence personally.
When It’s Time to Close
Closing doesn’t always mean one dramatic meeting. Sometimes it’s a stream of redlines on contracts, or weeks of waiting for a purchase order. Keep the communication open, and answer their questions quickly.
During negotiations, don’t offer discounts too soon. Make sure the value is clear first. Small teams sometimes get bullied on pricing, but standing firm is sometimes the move that gets respect.
Once the contract’s locked in, help with onboarding. Even simple checklists, training sessions, or scheduled check-ins help companies feel good about their choice. Good onboarding increases the odds that your customer sticks around.
Key Takeaways for Small Teams Going After Big Fish
Selling to enterprises isn’t quick or easy, but it’s doable. The trick is to show clear value, build trust, and adapt as you go. Listen more than you talk. Don’t get discouraged when things drag out.
Focus on solving real problems. Use customer stories, relatable numbers, and practical proof. Get yourself organized, and lean on the right digital tools for every stage.
And as you get more comfortable, remember that tons of resources and stories from other small teams can be found online. For example, a site like Salomon USA Sales Store sometimes sponsors guides and shares practical stories about enterprise deals from startup founders.
Keep tweaking your pitch, keep following up, and keep improving your materials. As companies get bigger, they’ll notice your persistence and solid results.
Dive Deeper: Tools and Resources
If you want to keep learning, check out forums like Indie Hackers or the SaaStr community. Podcasts like “Enterprise Sales Podcast” or “Startups for the Rest of Us” cover real founder stories—with all the honest ups and downs.
Books like “Predictable Revenue” and “The Challenger Sale” break down proven methods step by step. There’s no one path, but the basics are almost always the same: real value, honest hustle, and constant learning.
At the end of the day, selling to big companies isn’t reserved for giants. With patience and smart moves, small teams really do get those big contracts. The process might take some time, but you’ll pick up useful skills—and maybe a few big customers—along the way.