How to run outbound for a two-sided marketplace

Cormac Repman
1 day ago
5 min read

The Two-Sided Marketplace Outbound Challenge

Running outbound for a two-sided marketplace is fundamentally different from selling software to a single buyer type. You're not just building pipeline. You're managing two separate sales motions, two different objection frameworks, and two distinct value propositions. Get supply wrong and demand has no reason to stick around. Get demand wrong and your supply side withers.

We've run outbound campaigns for fintech and insurtech platforms where we needed to recruit lenders while simultaneously courting borrowers, or sign up insurance carriers while acquiring end consumers. The math looks simple on a whiteboard. In practice, it's like spinning two plates while juggling.

The difference between success and failure usually comes down to sequencing and narrative clarity.

Which Side Do You Sell First?

Most marketplaces stumble here. They either chase both sides equally (wasting effort) or they skip the harder side until it's too late.

The supply-side-first rule: If you're a marketplace with limited inventory or access, recruit supply first. Demand is attracted to scarcity and quality. When Glencoco built its marketplace for sales talent, we didn't try to convince buyers that our platform would have great reps. We recruited the reps first, built social proof, then approached buyers with "we have these specific people available."

The inverse is true for consumer-facing marketplaces. Uber had to put enough drivers on the street before passengers would open the app.

For fintech and insurtech platforms, ask yourself: what creates urgency on the other side?

If you're a lending marketplace: Get qualified lenders (supply) before scaling borrower acquisition. Borrowers won't return if their loan request sits unfunded.

If you're an insurance carrier platform: Recruit at least 2-3 carriers before spending aggressively on consumer lead gen. A consumer's experience is only as good as your carrier network.

If you're a B2B marketplace: Usually demand-side first. The service providers (supply) will come if there's genuine buyer interest.

The Supply-Side Narrative: Why They Should Join

Supply-side outreach for marketplaces fails when it sounds transactional. Drivers don't want to hear "join our platform and earn money." Service providers don't want another low-paying gig network.

Frame the supply-side pitch around exclusivity and quality control, not volume.

Your supply-side message should address:

High-quality demand funnel: We vet buyers. You won't waste time on tire-kickers.

Better unit economics: Explain your take rate, but position it against what they'd earn elsewhere. If your marketplace keeps 20% but they make 40% more per transaction due to qualified leads, lead with that.

Network effects: Show early supply wins. "We already have [X] qualified lenders" beats "join us and build something great."

Fulfillment protection: If you have SLAs or performance guarantees, lead with them. Insurance carriers want assurance that borrower quality is vetted.

When we're recruiting sellers or service providers for marketplace outbound, we emphasize time-to-revenue and deal size. "You'll have your first paid gig within 14 days" is more powerful than "join our community."

The Demand-Side Narrative: Why They Should Buy

Demand-side outreach is more traditional but it needs marketplace-specific messaging.

Don't lead with "our platform connects you with vetted providers." Everyone says that.

Lead with the practical outcome:

Speed to first transaction: "You can get a funded loan decision within 48 hours."

Curated options: "We pre-screen all [carriers/lenders/providers] so you're only comparing the ones that fit your profile."

Competitive pressure: "Compare rates across [X] lenders in real-time." Demand wants choice, and your marketplace delivers it.

The demand-side close is usually smoother because buyers are self-selecting. If they're responding to outreach about a lending marketplace, they have a funding need. If they're engaging with insurance carrier outreach, they're comparison shopping.

Your job is to prove your supply side is better than the alternatives (banks, direct lenders, or fragmented sales processes).

Sequencing Your Outbound Campaigns

Month 1 to Month 2: Recruit supply in cohorts.

Start with warm outreach to known, high-quality suppliers in your vertical.

Get 10-15 active supply partners live on your platform.

Generate real transaction data (or at least successful pilot transactions).

Month 3: Launch demand-side outreach.

Your demand pitch is now backed by real supply wins. "We have 12 active lenders ready to fund your loan" is infinitely more credible than "we're building a platform."

Demand converts faster when supply is proven.

Month 4+: Scale both simultaneously.

With real transaction velocity, both sides have social proof.

A new supplier sees other active suppliers. A new buyer sees recent funded loans.

Your close rate improves because both sides want to be where the action is.

The Metrics That Matter

Track these carefully:

On the supply side:

Time from first outreach to active account creation.

Percentage of recruited suppliers who complete at least one transaction.

Average deal size and transaction frequency per supplier.

Real benchmark: Strong supply-side recruitment closes at 15-25% on cold outreach, but that's with a tight supply target. If you're recruiting lenders to a lending marketplace, 20% close is realistic. If you're recruiting any warm body, your close rate will be lower.

On the demand side:

Time from signup to first completed transaction.

Return rate within 30 days (a buyer who uses you twice is a signal you have good supply).

Real benchmark: Demand-side conversion is typically 8-15% from qualified outreach, higher if you're solving an acute pain point.

The gap between your supply and demand side metrics reveals where your outreach is weakest. High demand signups with low transaction rates means your supply side isn't good enough. High supply recruitment with low demand means your demand-side messaging isn't resonating.

Common Mistakes We See

Selling both sides simultaneously: You dilute your narrative. Pick one, prove it, then expand.

Leading with platform features instead of outcomes: Nobody cares about your API integration or your dashboard design. They care about moving faster, making more, or reducing risk.

Recruiting the wrong supply: One bad supplier ruins marketplace reputation. Vet hard. A marketplace with 5 excellent suppliers outperforms one with 50 mediocre ones.

Ignoring network effect feedback loops: If your demand side is growing but supply isn't activating, stop acquiring demand until you fix supply. Burned demand is expensive to win back.

Two-sided marketplace outbound isn't a single sales process. It's two coordinated campaigns built on supply-and-demand dynamics that reinforce each other. Get the sequencing right, prove supply first, then fuel demand with real transaction data.

If you're running outbound for a fintech or insurtech marketplace and need experienced cold calling teams to build that initial supply and demand base, Nurturance runs real outbound through the Glencoco marketplace. We recruit qualified reps, handle the pitch execution, and deliver booked meetings. [Book a call](https://cal.com/nurturance) to discuss your marketplace outbound strategy.