Designing a Two-Sided Marketplace That Actually Works: How SkillSetz Turns Buyer Intelligence into SaaS Growth

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Two-sided marketplaces are notoriously difficult to build. Most fail because they can’t grow both sides—buyers and sellers—at the same pace. Without enough sellers, buyers see no value. Without enough buyers, sellers disengage.

Matt McCarrick, founder and CEO of SkillSetz, knows this challenge well. His platform is a B2B services marketplace that blends the searchability and structure of Amazon with the professional talent network of LinkedIn—built specifically for enterprises and SMBs buying professional services.

Lesson 1: Build Around the Buyer’s Reality, Not the Startup’s Obsession

Matt’s 20+ years in enterprise procurement taught him a hard truth: professional services spend in large companies is a massive black hole. Contracts are scattered across business units, rates vary wildly, and there’s little visibility into volume discounts or supplier performance.

SkillSetz solves this by:

  • Structuring talent and capabilities into a taxonomy enterprises can search instantly.

  • Allowing both sides of the marketplace—buyers and providers—to onboard themselves.

  • Integrating directly with enterprise systems via REST APIs for Oracle, PeopleSoft, and Microsoft Dynamics.

Agency takeaway: Whether you’re building a SaaS product or a marketing campaign, buyer intelligence means mapping to how your customers actually operate today, not just how you wish they would.

Lesson 2: Web Experience Is a Sales Tool

SkillSetz isn’t Fiverr. The platform’s UX and messaging are designed to signal credibility to enterprise buyers from the first click:

  • Clear navigation by business function.

  • Transparent onboarding workflows.

  • A curated initial provider base to set the quality bar.

Matt’s insight: in B2B, your web design and onboarding process are part of your sales enablement. They have to build trust before a sales call even happens.

Lesson 3: Sequence Your Marketplace Growth

Rather than launch to everyone at once, SkillSetz started with:

  1. Curated providers — experienced consultants and firms Matt knew personally from his network.

  2. Enterprise buyer pilots — offering the platform free to select procurement leaders to prove value and generate case studies.

By seeding one side with trusted sellers before ramping buyer outreach, SkillSetz avoided the “empty room” problem that kills most marketplaces.

Sales strategy insight: In a two-sided SaaS model, you need a growth choreography—deliberately controlling who comes in when, so each side sees immediate value.

Lesson 4: Marketing in a Niche Requires Precision

SkillSetz is going after two distinct buyer groups:

  • SMBs who can’t hire full-time but need expert help for specific problems.

  • Enterprise procurement teams who want to consolidate and manage services spend.

Each requires a tailored go-to-market approach:

  • SMBs are reached through SEO, digital ads, and nurturing workflows integrated with HubSpot.

  • Enterprises are won through Matt’s procurement network, direct outreach, and a focus on ROI from spend visibility and process efficiency.

Agency takeaway: SaaS marketing strategy isn’t just about “generating leads”—it’s about building separate buyer journeys for each persona and aligning touchpoints to their buying context.

Lesson 5: Retention Comes from Being in the Workflow

For enterprise buyers, retention won’t come from novelty—it comes from SkillSetz becoming the default procurement channel for services. Once the platform is integrated into their systems and their providers are onboard, switching costs become high and the value compounds.

For providers, retention comes from the ability to find repeat, high-value projects without the overhead of sales and marketing.

Retention insight: In SaaS, your product should aim to become invisible—embedded in the daily workflow so deeply that leaving feels impossible.

The Buyer-Centric Marketplace Playbook from SkillSetz

  1. Map to the buyer’s current reality, not just your ideal.

  2. Design your web and onboarding experience as part of sales enablement.

  3. Sequence marketplace growth so both sides see immediate value.

  4. Tailor GTM for each buyer persona with distinct channels and messaging.

  5. Embed into workflows so retention happens by default.

Why this matters for SaaS founders & tech companies: SkillSetz’s launch shows that successful marketplaces aren’t built on hype—they’re built on buyer intelligence, sequencing, and design choices that enable sales before the sales team even speaks to a lead. These same principles can be applied to any SaaS go-to-market or retention strategy.