How to run outbound for a two-sided marketplace

Cormac Repman
15 hours ago
5 min read

The Two-Sided Marketplace Outbound Problem

When we work with fintech and insurtech companies building two-sided marketplaces, we see the same fundamental challenge: you can't grow one side without the other. You need lending partners to attract borrowers. You need agents to attract customers. You need liquidity providers to attract traders. The marketplace that solves this asymmetry first wins. Most teams trying to do outbound for two-sided models fail because they treat both sides with identical messaging and tactics. That's backwards.

We've run outbound campaigns for twelve marketplace companies over the past two years. The ones that scaled fastest segmented their go-to-market by supply and demand, ran parallel sales processes with different teams, and solved the bootstrap problem with asymmetric resource allocation. Here's how.

Identify Your Constraint Side First

Before you pick up the phone, figure out which side is actually constraining growth. For most marketplaces, it's supply. Borrowers and customers show up naturally. Partners and operators need to be convinced to join an unproven platform.

Ask yourself: If you had unlimited supply tomorrow, would demand fill the slots? If the answer is yes, your constraint is supply. If you have plenty of suppliers sitting idle, your constraint is demand. This decision shapes everything downstream. Your first 100 outbound conversations should all target the constraint side.

For a lending marketplace, if your banks can fill 10x more loans than your borrowers generate, you're demand-constrained. Your outbound effort goes toward borrowers. If your borrowers are queuing and you only have two lenders, you're supply-constrained. Your entire team calls lenders until the problem inverts.

Structure Outbound for Supply-Side Partners

Supply-side outreach is consultative selling with longer cycles. Your partners are evaluating integration risk, competitive threats, and channel cannibalisation.

Build a partner deck that answers these questions first:

What volume will we generate? (specificity matters; don't say "thousands," say "we'll deliver 50-200 qualified monthly")

What's your KPI? (for insurance agents, it might be average premium per policy; for lenders, it's approval rate)

What's the integration effort? (weeks, not months; show a real technical roadmap)

How do you handle disputes and chargebacks? (partners need to trust your operations)

Are we cannibalizing your direct channel? (address this head-on; you're not)

When we cold call VPs of Partnerships at insurance companies, the first 20 seconds matter. "Hi [name], I'm reaching out because you approved 40% more policies through partners last year, and we've built a distribution channel that moves policies at half your cost. Do you have 15 minutes Wednesday?" beats any generic opener.

Partner sales moves:

Identify the partner first, then the buyer. The buyer is usually VP of Partnerships or VP of Business Development, not the CEO.

Lead with volume you've already generated (even if it's small). "We're doing $2M in annual volume through 15 marketplace partners" signals traction.

Offer a test pilot: 30 days, no contract, you pay for volume delivered. This removes their risk.

Get the trial contract written and signed before you send any traffic. Too many teams send traffic on a handshake.

Structure Outbound for Demand-Side Customers

Demand-side is faster, higher-volume, and more straightforward. Your prospects know they have a problem. They're ready to buy. The sales cycle is weeks, not months.

Your messaging focuses on speed and reliability, not partnership or scale. "You can get a loan decision in 48 hours through us" or "Book an insurance quote in 3 minutes" works. "We're a growing marketplace with 12 partners" doesn't.

Demand-side outreach plays:

Segment by use case, not by title. Call small business owners, not "CFOs." Call gig workers, not "freelancers."

Use case specificity crushes generic targeting. "Are you a delivery driver looking for a second income stream?" works. "Do you work?" doesn't.

Lead with outcome, not product. "Get insured in under 5 minutes" beats "We're a digital insurance platform."

Provide pricing or timeline upfront. Demand-side prospects are price-sensitive and time-sensitive. Hiding numbers kills connect rates.

The demand-side motion is often not traditional cold calling. Paid digital, SMS, email, and affiliate partners often outperform cold calling here. But if you're running outbound, parallel track email and phone. Email open rates on specific segmentation (gig workers, small business owners) can hit 35% if you lead with outcome.

Solve the Chicken-and-Egg Problem

This is where most two-sided marketplaces fail. You need both sides to grow, but you can only afford to recruit one side initially. Here's the workaround we've seen work:

Bootstrap with supply-side guarantees. Tell your first partners: "We're building a customer base and guaranteeing you a minimum of $10K in monthly volume by month three, or we'll pay the difference." This costs you money on paper. In reality, the partners move faster when you de-risk their bet, and you hit the volume target anyway.

Or bootstrap with hand-selected demand. Focus your first 30 days of outbound on recruiting 50 high-LTV customers manually, then use that proof point to recruit 10 partners. One lending partner with $500K in monthly funding capacity beats 50 random partners with no commitment.

We ran this play for a fintech platform. Month 1: 60 outbound calls to borrowers, 12 customers, $280K lifetime value cohort. Month 2: These borrowers' success stories landed us 8 lending partners. Month 3: With supply in place, we scaled demand-side outbound 5x.

Messaging Bifurcation

Your supply-side and demand-side messaging should sound like different companies.

Supply-side: "We have access to a vetted pool of [borrowers/customers/agents] and we're looking to expand our partner network. We take care of servicing, compliance, and disputes. You focus on underwriting and fulfillment."

Demand-side: "You can get a [loan/quote/service] in [timeframe] through us. No paperwork. Here's what it costs and how fast it works."

The supply-side prospect wants risk reduction and predictable volume. The demand-side prospect wants speed and cost. Use different teams if you can. If not, at minimum, use different scripts. We've measured 40% higher connect rates on demand-side when the messaging is streamlined versus when reps are using partnership-focused language on borrowers.

Track the Right Metrics

Two-sided marketplace outbound requires different KPIs than traditional sales.

Supply-side metrics:

Partner acquisition cost (CAC per partner)

Time from first call to contract signed

Monthly volume delivered per partner

Partner retention rate (are they still active after 6 months?)

Demand-side metrics:

Cost per customer acquisition

First-call conversion rate

Average customer LTV

Repeat usage rate

Don't mix them. A demand-side rep converting at 8% on calls is performing differently than a supply-side rep converting at 3% on calls. Both might be excellent. You're measuring different motions.

We've seen scalable demand-side outbound hit 6-12% conversion rates on cold calls when messaging is specific and pricing is clear. Supply-side conversion sits around 2-4% because cycles are longer and you're losing deals at contract stage, not at initial call.

Running Outbound for Marketplace Growth

Two-sided marketplace outbound works when you segment ruthlessly, allocate resources asymmetrically toward your constraint, and accept that supply-side and demand-side are fundamentally different sales motions.

We've helped 12 fintech and insurtech companies scale outbound marketplace growth. The fast ones moved in this order: identify constraint, recruit supply or demand accordingly, bootstrap the other side once the first side has traction, then scale both in parallel.

If you're building a two-sided marketplace and need to move fast, [Nurturance runs specialized outbound campaigns for fintech and insurtech companies](https://cal.com/nurturance/intro). We handle the entire motion: strategy, team, dialing, close. Get results in 30 days or your first month is free.