How to Take Win Rates from 25% to 50%

Courtny Cloeter, Chief Revenue Officer at OneSource Virtual, explains how reframing growth expectations fuels accelerated success. He emphasizes the importance of continually revisiting real customer value, engaging deeply with feedback, and cultivating a culture that welcomes constructive feedback. Courtny shares how using the “so what” test prioritizes high‑impact initiatives.

In this episode of the C-Suite Sales and Marketing Perspective podcast, Courtny Cloeter, Chief Revenue Officer at OneSource Virtual, outlines how to boost win rates from 25 percent to 50 percent by setting ambitious growth targets, continuously refining value propositions with customer feedback, and fostering a culture of constructive challenge. He introduces the “So What Test” to focus on high‑impact initiatives and avoid complacency, providing a clear roadmap for sustained revenue acceleration.

“You have to build a culture within the company and leadership team to embrace challenges, friction, professionalism, and constructiveness, and to foster an attitude that always asks why these things are going to grow the company. Don’t accept that hitting your goal or 15 percent growth year over year is a good thing. Challenge it. Try to be that person you know who hits 50 percent.” – Courtny Cloeter

Key Takeaways:

Companies should challenge the status quo and set ambitious growth goals, rather than settling for moderate targets.
Understanding and continuously refining real customer value requires direct feedback and ongoing engagement.
Collaboration and alignment within leadership teams are crucial for successfully implementing growth strategies.

Listen to the full podcast or watch it on YouTube directly below.

Article: “How to Take Win Rates from 25% to 50%”

From a podcast interview with Courtny Cloeter, Chief Revenue Officer at OneSource Virtual

Reframing Growth Expectations

Many organizations set modest targets and then limit their options. Courtny argues that aiming for the status quo limits potential. He asks, “Why only 25 percent? If you do this right, we can achieve 30-40 percent revenue growth. But it takes some strategy and involvement by the board and the leadership team of the company.” By challenging the default ceiling, teams unlock new possibilities and drive toward higher goals.

Reframing starts at the top but must permeate every department. Courtny emphasizes that growth targets should be stretch goals rather than safe bets. “Don’t accept that hitting your goal or 15 percent growth year over year is a good thing. Challenge it. Try to be that person you know who hits 50 percent.” Embedding this mindset ensures every team member thinks bigger about what’s achievable.

Embedding Customer-Centric Value

Sustainable win-rate increases come from a deep understanding and continuous refinement of the value delivered to customers. Courtny explains, “A company that is constantly in touch with the customer, constantly hearing the feedback of what we’re doing well, what we need to change, constantly is changing their value proposition.” Treating value as a living concept, not shelfware, keeps organizations aligned with evolving customer needs.

Regular feedback loops are essential. Courtny recommends advisory groups, executive programs, and direct conversations to uncover the “so what” behind every initiative. “The magic is when you get the so what from the customer. They’ll tell you how you helped them improve their retention or increase efficiency.” These concrete success metrics serve as powerful proof points that fuel further growth.

Fostering Constructive Friction

High win rates require a culture that embraces healthy conflict and professional challenge. Courtny insists that without friction, organizations grow complacent. “You have to build a culture within the leadership team to embrace challenges, friction, professionalism, and constructiveness, and to foster an attitude that always asks why these things are going to grow the company.” This approach surfaces the best ideas and drives collective accountability.

To manage limited resources, Courtny advocates the “so what” test: before pursuing any initiative, ask what impact it will have. “If you can’t define how it is going to change our customers’ lives or revenue streams, then don’t do it.” By applying this filter, companies focus on high-impact projects and eliminate distractions that dilute effort and slow growth.

Conclusion

Doubling win rates demands intentional shifts in strategy, culture, and customer engagement. Courtny Cloeter’s advice underscores that organizations must first set aggressive growth targets and never settle for modest gains. Stretch goals spark new conversations about capabilities and possibilities.

Equally important is embedding continuous customer feedback and fostering a culture where constructive friction drives improvement. By applying the “so what” test to every idea, teams ensure they pursue only the initiatives that deliver real, measurable value. When these principles align, achieving a 50 percent win rate becomes a realistic goal.

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Steven MacDonald

Steven MacDonald is the founder of Content Strategies, CEO of a MarTech SaaS Company, fractional CMO consulting with leading B2B companies and former Director of Strategy and Client Service at top ten digital marketing agencies.

Follow Steve on LinkedIn.

Steven MacDonald

Follow Steve on LinkedIn.