What It Actually Takes to Close Enterprise Deals As a Startup, With Ryan Laverty, President of Arist

Enterprise sales is the holy grail for startups, massive contracts, high ACV, and long-term growth. But landing your first enterprise deal? That’s where things get hard. Fortune 100 companies want enterprise-grade products, social proof from other enterprises, and have long procurement processes.

Ryan Laverty, President of Arist, has cracked the code on breaking into enterprise as an early-stage startup. Arist, which started as a tool to deliver learning via SMS, now serves some of the largest companies in the world. In our conversation, he shared how they navigated the enterprise sales landscape, refined their go-to-market strategy, and built a sales culture that wins. Here’s what I took away.

Solving the Chicken-and-Egg Problem in Enterprise Sales

Startups face a harsh reality: big companies won’t buy unless you’re “enterprise-ready,” but you’re typically not deemed enterprise-ready without big customers. Ryan’s solution? Get creative with pilots before full-scale deployments.

The Arist Approach:

• Instead of immediately pushing for full contracts, Arist ran low-risk pilots using SMS and WhatsApp, where employees could opt-in with personal phone numbers, no security or compliance red tape.
• These early pilots resulted in soft LOIs and commitments, enough traction to raise funding and build an enterprise-ready product.
• Companies often require SOC 2 compliance before signing major contracts, but many will accept proof that you’re actively working toward certification.

For founders trying to break into enterprise, the takeaway is clear: Find a way to get your product into users’ hands, even in a limited capacity, before trying to sell the full vision.

Enterprise Isn’t One Buyer, It’s 100 Smaller Ones

A mistake founders often make? Thinking they need to “sell to Pfizer” or “close a deal with Amazon.” In reality, enterprise isn’t one monolithic buyer, it’s a hundred different teams with different needs and budgets.

Ryan’s playbook for breaking in:

• Find an entry point – Instead of targeting the entire company, zero in on one department or team that has a problem you can solve today.
• Swarm the org on LinkedIn – Arist targeted 15-20 decision-makers per company, increasing their odds of finding someone who would champion the product.
• Leverage warm intros & advisor networks – Enterprise trust is hard to earn. Working with trusted advisors who already have relationships with key decision-makers unlocked doors Arist couldn’t open alone.

The lesson? You don’t need to “sell to Pfizer.” You need to sell to one team at Pfizer, deliver results, and expand from there.

Why Message-Market Fit Matters More Than Mass Outbound

A lot of founders believe that scaling outbound is a numbers game, more emails, more LinkedIn DMs, more calls. Ryan takes a different approach: Hone the message first, then scale.

One of Arist’s most effective hooks? “People check their LMS every six weeks. They check Slack & Teams every six minutes.”

That single sentence immediately shifted how buyers thought about learning and made Arist’s value proposition click.

Before you scale outbound, ask yourself:

• Does my message spark curiosity?
• Is it different from what buyers have heard before?
• Does it make them stop and think, ‘I need to learn more’?

If the answer is no, doubling your outreach won’t help. Fix the messaging first.

Building a Sales Culture That Wins

Hiring and enabling a sales team is where many startups struggle. Ryan’s approach? Set reps up for success early.

How Arist onboards new reps:

• Get them into mid-stage deals early – Instead of making new hires start from scratch, Arist brings them into existing deals so they can gain momentum early.
• Position them as experts – When transitioning a deal from a founder to a rep, Ryan makes sure to introduce them as the real expert in the conversation, building credibility from day one.
• Foster a winning culture – The best sales orgs want their reps to make as much money as possible. That attitude is felt by the team, and it drives motivation.

Too many companies set reps up to fail by handing them zero pipeline and telling them to “go build.” Instead, Ryan’s team ensures reps start fast, which leads to long-term success.

Final Thoughts

Enterprise sales isn’t about convincing one giant company to buy, it’s about breaking in through the right entry point, proving value, and expanding.

Whether you’re a founder trying to land your first enterprise deal or a sales leader refining your GTM motion, Ryan’s playbook is a masterclass in enterprise strategy:

• Get creative with pilots before pushing for full contracts
• Think of enterprise as a collection of smaller teams, not one big buyer
• Fix your messaging before scaling outbound
• Build a sales culture that sets reps up for early success

‍