Wingspan’s Pivot Playbook: How to Know When and How to Execute a B2C to B2B Transition

The hardest decisions in startups aren’t about what to do—they’re about when to do it. In a recent episode of Category Visionaries, Anthony Mironov shared a candid look at Wingspan’s pivot from B2C to B2B, offering rare insights into the challenges of timing and executing such a fundamental shift.

The Warning Signs

Despite building a product that freelancers loved, Wingspan’s early direct-to-consumer approach showed concerning metrics. As Anthony reflects, “We learned it was really difficult to scale that business, both from customer acquisition cost and activation.” These challenges pointed to fundamental issues with the B2C model, but like many founders, the team initially tried to optimize within their existing strategy.

The COVID Catalyst

Sometimes external events create unexpected opportunities. During the pandemic, Wingspan noticed an interesting pattern: “During COVID we saw lots of freelancers were working together in like effectively many agencies,” Anthony explains. This observation led to the development of split payment capabilities—a feature that would later prove crucial for enterprise customers.

The Pivot Decision

In summer 2022, Wingspan made their move to B2B. “We got our first B2B customer, I think it was in the summer of 2022, and we realized that model was a lot more repeatable, especially for a venture backed business,” Anthony shares. But his most telling insight comes with hindsight: “First of all, we didn’t make the change fast enough. Looking back at it, I probably would have changed the focus a little bit earlier.”

Organizational Transformation

The technical challenges of a pivot often pale in comparison to the organizational changes required. As Anthony notes, “I didn’t really understand how much of an organizational change that is going from, you know, a self-serve signup process online to, you know, learning how to do B2B sales.” The team had to rapidly develop new capabilities and processes.

Building the B2B Motion

The transition demanded more than just new sales skills. Anthony explains how they built their initial go-to-market engine: “Our early team had to basically turn customer discovery conversations to sales conversations and eventually built a sales team, kind of an initial unit of revenue production.” They started small but focused: “We had one SDR, a couple, an account manager, and were able to prove that we could build a unit of revenue production.”

Navigating the Funding Environment

Timing a pivot between funding rounds adds extra complexity. “The pivots are really hard, especially between your seed round and your series A, because you basically have to prove that the business works and it’s fundable very quickly,” Anthony explains. This pressure forced efficiency: “It made a much more resilient and efficient business because it forced us to be much more thoughtful with our resources.”

Lessons for Founders

Wingspan’s experience offers several key takeaways for founders considering a similar transition:

1. Watch for scalability metrics early – CAC and activation rates can signal the need for change before it becomes critical.
2. Build capabilities before they’re needed – Features developed for one market might become crucial differentiators in another.
3. Consider timing relative to funding cycles – Pivots between rounds require rapid proof of concept.
4. Prepare for organizational transformation – Technical changes are just the beginning; the real work is in building new organizational capabilities.

The success of their pivot is evident in their current trajectory. As Anthony shares about their enterprise customers: “We oftentimes hear some workers won’t work with a company if they’re not on wingspan.” This network effect suggests they’ve not just survived their pivot—they’ve found a more compelling market position through it.