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How deskbird Scaled to $10M+ ARR by Testing 10 Markets in 6 Months

Most B2B founders obsess over market penetration before geographic expansion. Ivan Cossu ignored that playbook—and scaled past $10 million ARR faster because of it.

In a recent episode of BUILDERS, Ivan Cossu, Co-Founder and CEO of deskbird, shared how his flexible workplace management platform broke through conventional wisdom on international scaling, founder sales involvement, and outbound effectiveness in the AI era.

But the journey started with a near-death experience just months after founding.

The July 2020 Pivot: Months Before Running Out of Cash

Founded in April 2020 during COVID’s peak uncertainty, deskbird initially built an Airbnb for co-working spaces. The thesis: companies would provide employees flexible workspace access across cities—San Francisco one day, New York the next.

The co-working spaces signed up. The users didn’t.

“We got traction on the co-working spaces but not on the user side,” Ivan explains. “Companies didn’t really want—what they really wanted is a very user friendly tool to manage their own space.”

The pattern was unmistakable: customers loved the app’s UX but had no use for the marketplace. They needed the booking interface for their own offices as hybrid work emerged.

A few months before running out of capital, the team executed a complete pivot in July 2020. They rebuilt the product, salvaging reusable components, and focused exclusively on workplace management—desk booking, parking, meeting rooms, and space optimization.

Their first customer came from a demo built mostly on clickable prototypes. “I still remember as my co-founder is doing product so he was still talking to developers, we had an onboarding meeting at 3pm Friday afternoon,” Ivan recalls. “At 2:58 he was writing me that there were still bugs in the product… three or two minutes after three he joined the meeting and it went well.”

Traction hit immediately after the pivot.

Testing 10 Markets in Six Months: The Anti-Penetration Strategy

Within six months of their July 2020 pivot, deskbird had closed customers in 10 markets. This wasn’t the plan—it was the result of aggressive testing that revealed opportunity.

“We realized okay this is a huge opportunity and there is so much greenfield,” Ivan says. Their approach was surgical: launch landing pages in the UK and US, measure demand signals, then commit based on data rather than intuition.

“We saw oh traction is there, we’re getting the leads, we’re having good conversations,” Ivan explains. The decision crystallized: “If we have those kind of conversations with that budget and with that kind of still simple product, then we need to go all in and we need to go multiple markets from the get go.”

This violates the traditional “dominate then expand” approach, but Ivan’s reasoning is grounded in feedback loop economics. Channel selection in early stages should optimize for learning velocity, not ultimate market size.

“You need to avoid channels that have too long sales cycles,” he emphasizes. “For outbound I would never have gone for outbound enterprise where you need 18 months to even know if you have a chance to close a customer.”

By targeting paid search and lower mid-market segments initially, deskbird generated sample sizes large enough to validate positioning and messaging within weeks, not quarters. “You get a good sample size quite fast and that’s what we did.”

The core insight: if your funnel converts reliably, geographic expansion is lower risk than assumed. “We were way too scared of going international because it always worked out way better than we thought,” Ivan reflects. “We could have gone to the US way earlier.”

Founder-Led Sales as Permanent Infrastructure

At over $10 million ARR, Ivan still joins sales calls regularly. This isn’t founder nostalgia—it’s deliberate strategy.

“Even today I’m still going into sales calls,” he says. “One of the most successful entrepreneurs I know, one of his rules is sales is always a final topic.”

The transition from founder-led sales wasn’t binary. deskbird hired their first AE nine months post-MVP, but founder involvement never ceased—it evolved.

“The first were kind of more generalists, the hard workers,” Ivan describes. “They were not the most disciplined ones but they were the ones being able to tell a compelling story and also selling the vision.”

As the company crossed $10 million, the AE profile shifted toward execution discipline as repeatable sales motions emerged. But the founder’s role remained essential for strategic deals, competitive situations, and maintaining direct customer insight loops.

Even Marc Benioff at Salesforce still engages in deals, Ivan notes—a data point suggesting founder sales involvement scales with company size rather than phases out entirely.

The Strategic Advantage of Underfunded Categories

When deskbird mapped their competitive landscape, they identified 50-60 European competitors. What they didn’t find: the massive funding rounds that saturate some B2B categories.

“The space was never overfunded by VCs,” Ivan observes. “There’s a downside, it’s harder to get VC money, but once you get it you don’t have the problem that some spaces are overfunded and it’s crazily driving up the CAC.”

In capital-saturated categories, customer acquisition costs inflate as competitors outbid each other for the same channels and accounts. The dynamic creates winner-take-most outcomes where “number two, number three, number four—it will often be a very sad consolidation place for them.”

Limited competitor funding forced deskbird to compete on product differentiation rather than marketing spend. Their approach: bring “Airbnb or Uber like UX to something boring like desk booking” while maintaining enterprise-grade customization. Traditional competitors “felt more like a database query, you needed programming skill to book a desk.”

This dual capability—consumer UX with enterprise complexity—became their defensible position in an underfunded market where better products win without requiring war-chest CAC spending.

Outbound Strategy in the AI Era: Why Email Is Inflated

As deskbird matured past $10 million, they needed secondary growth muscles beyond inbound. Their outbound strategy challenges current best practices.

“I don’t believe in emails and any kind of written communication especially not in the age of AI,” Ivan states. “It’s just inflated.”

The core issue: AI-generated outbound has saturated inboxes, making written communication nearly ineffective regardless of quality. deskbird’s alternative focuses on high-friction, hard-to-scale tactics:

Physical mail and offline media for breaking through digital noise. Cold calling infrastructure—but with operational rigor most companies can’t execute. “You need to have the machine, having all the BDRs and AEs knowing which accounts they have to call, seamlessly calling account after account, lead after lead. Just few companies manage to do that successfully these days.”

Account selection sits between hyper-targeted (1:1) and spray-and-pray (1:1000). “You should not be too specific, you should not just go for the three accounts in the world, but I think you can definitely not say okay I’m going to target all the insurance companies of the world.”

Best results emerge when marketing and sales collaborate tightly: “Marketing is heating, warming up some leads, they have some intent, they have some data, and they’re handing them over seamlessly to outbound teams and they can actually pick up already somehow warm leads.”

The US Close Rate Signal: When Disadvantages Validate Investment

deskbird’s US expansion decision came from counterintuitive data: they were closing American deals from Europe with higher success rates than any other market—despite working in mismatched time zones with non-native AEs.

“Looking at the closing rates, the US or North America including Canada had the best closing rates of all markets,” Ivan shares.

The strategic logic: “If we can close them from Europe with our European AEs, they’re not US natives, they work in different time zones, they cannot deliver the same SLAs—if we then go for the US then it should get even better.”

Winning despite structural disadvantages signals exceptional product-market fit. Rather than wait for perfect execution infrastructure, deskbird used remote close rates as the green light for local investment. They’ve since hired their first US-based team members.

This inverts traditional expansion thinking: instead of building infrastructure before testing demand, use disadvantaged selling to validate demand before infrastructure investment.

Building Category Leadership Through UX-Enterprise Balance

Ivan’s five-year vision targets clear positioning: “deskbird is the leading workplace experience and intelligence platform.”

The dual value proposition mirrors Salesforce’s category dominance strategy:

• Employee layer: “The app where employees can do whatever they want to do with their workplace”—booking desks, checking on-site yoga classes, seeing which colleagues are coming in.
• Intelligence layer: Becoming “the trusted strategic advisors for corporate real estate teams,” delivering benchmarks like “we know you are in an insurance industry, we know from other customers your benchmark in terms of square meter efficiency, this is where you can optimize, this is how much money you can save.”

“We’re trying to build what Salesforce is for CRM for workplace management,” Ivan explains. “A true category leader that on one side is very strong for the users with outstanding UX people love to use from the beginning, but on the other side also has all the advanced customization that you need.”

Workplaces vary dramatically—some companies need specific teams booking certain areas on Mondays while other teams book different areas on Tuesdays. The platform handles this granularity without sacrificing the consumer-grade experience that drives adoption.

Implementation Takeaways for B2B Founders

deskbird’s path to $10 million ARR offers tactical frameworks for founders navigating similar inflection points:

• International expansion timing: If core conversion metrics are solid, test new markets immediately rather than perfecting local penetration. Geographic risk is often overestimated when product-market fit is strong.
• Channel selection in early stages: Optimize for feedback loop speed over potential scale. Choose channels where you can iterate weekly, not annually, even if they’re not your ultimate target segment.
• Founder sales evolution: Plan for permanent involvement, not phased exit. Hire AEs to scale volume while maintaining founder involvement in strategic deals and customer insight loops.
• Category selection consideration: Evaluate competitor funding levels as seriously as market size. Underfunded categories with real demand can offer better unit economics than saturated markets with excessive capital.
• Outbound effectiveness in 2024: Written communication has been devalued by AI saturation. Winning outbound requires high-friction tactics most companies won’t operationalize—which creates opportunity for those who do.
• Expansion validation signals: Look for success despite structural disadvantages. If you’re winning with mismatched time zones and non-native sellers, you’ve de-risked the investment in proper infrastructure.

For founders building toward category leadership, deskbird demonstrates how unconventional sequencing—testing broadly before perfecting locally, maintaining founder-led sales at scale, and choosing underfunded categories strategically—can accelerate growth while maintaining sustainable unit economics.