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Designing Contracts People Actually Want to Read: How Outlaw Uses Buyer-Centric SaaS Design to Win in a Crowded CLM Market

Contract Lifecycle Management (CLM) isn’t exactly a “sexy” SaaS category — until you’ve seen it done right. Evan Schneyer, co-founder and CEO of Outlaw, has built a contract platform that companies enjoy using.

That’s not a typo. In a space dominated by bloated enterprise systems and clunky workflows, Outlaw wins by focusing relentlessly on buyer intelligence, intuitive design, and user experience that serves every stakeholder — not just the paying customer.

Lesson 1: Build for the Recipient, Not Just the Sender

Most CLM vendors design for the legal team or contract originator. Outlaw took a different approach:

  • Create a clean, readable experience for the recipient.

  • Offer an optional “overview layer” — a plain-English summary that explains the agreement without replacing it.

  • Make redlining, approvals, and collaboration as simple as commenting in Google Docs.

“Even if the recipient isn’t paying us, they’re part of the buying journey,” Evan says. “If their experience is bad, deals stall.”

Agency parallel: In SaaS web design, the “recipient” is your prospective buyer. If their first interaction with your brand feels like homework, you’ve already lost momentum.

Lesson 2: Let Buyer Intelligence Shape the Roadmap

Evan and co-founder Dan started with a bold product vision — a fully proprietary contract system. But once real customers came in, they realized adoption required a bridge from the current messy workflows to their ideal future state.

That meant:

  • Listening closely to what mid-market buyers (50–500 employees) actually needed.

  • Prioritizing features that solved today’s pains before selling tomorrow’s vision.

  • Removing ego from product decisions.

Web & marketing takeaway: Your roadmap — whether for product, content, or site design — should reflect the patterns you hear repeatedly from qualified buyers, not just your original idea.

Lesson 3: Define “Big Deal” by Buyer Fit, Not Contract Size

In the early days, $240/year contracts with freelancers felt like a big win. Today, Outlaw’s sweet spot is mid-market organizations with complex contract workflows — worth $10K–$25K annually — and they’re edging into enterprise territory.

By tightening their ICP, they’ve made sales cycles shorter, retention stronger, and product adoption faster.

Positioning insight: A clear, niche-aligned ICP makes your marketing sharper, your web experience more persuasive, and your sales team more confident.

Lesson 4: Make Sales Enablement Buyer-Friendly

Outlaw’s sales process mirrors its product philosophy:

  • Speak in the buyer’s language (not just legal jargon).

  • Demo in the context of their workflows.

  • Save the “cool” features for later if they distract from solving the immediate problem.

This approach doesn’t just close deals — it ensures smoother onboarding and faster time-to-value.

Lesson 5: Culture Drives Product Quality

Evan credits Outlaw’s growth to building a team with high EQ and low ego. The hiring priority isn’t just skills — it’s attitude, adaptability, and willingness to learn from feedback.

That openness to change keeps Outlaw’s product, marketing, and sales strategy aligned with what buyers actually want.

The Buyer-Centric CLM Playbook from Outlaw

  1. Design for all stakeholders — including the non-paying recipients.

  2. Let real buyer feedback shape your product, marketing, and onboarding.

  3. Focus your ICP to increase sales velocity and retention.

  4. Structure demos to solve today’s pain before introducing future-state features.

  5. Hire for adaptability to keep evolving with your market.

Why this matters for SaaS founders & tech companies: Outlaw’s growth shows that even in a mature, competitive market, you can win by delivering a buyer-intelligent, user-first experience — and that starts with positioning, messaging, and design that match your buyer’s reality.

That’s exactly where our agency helps SaaS brands:

  • Crafting web experiences that speak to every stage of the buying journey.

  • Using buyer intelligence to align product, marketing, and sales.

  • Building sales enablement that turns demos into deals — and deals into loyal customers.