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Case Study: How Proposify Grew Outbound Close Rates 28%

Sales Enablement
by
Chris Orlob
May 27, 2025

The Challenge: Moving from Inbound to Outbound

Proposify had built a successful business on the back of a strong inbound sales motion. Their team knew how to qualify interest, manage deals, and close efficiently when leads were already coming to them.

But as the company matured, they needed to build a reliable outbound engine to hit their next stage of growth. That meant going after prospects who weren’t already leaning in — and who needed to be educated, persuaded, and sold to from the ground up.

The skills required to succeed in an outbound motion are fundamentally different than inbound. Reps need to:

  • Create urgency instead of riding existing interest
  • Open conversations with skeptical or cold prospects
  • Build champions without a strong initial mandate
  • Multi-thread proactively to avoid dead ends

Proposify’s leadership team recognized that their reps needed help developing these capabilities. That’s when they turned to pclub.io.

Expert-led courses with built-in reinforcement

Proposify had already built a strong coaching culture, so they didn’t need generic sales training. They needed specialized, advanced enablement — frameworks, tactics, and real-world examples tailored specifically to the challenges of outbound selling.

We partnered with them to:

  • Level up outbound discovery to uncover real, quantifiable business pain
  • Teach reps how to build and activate champions from a cold start
  • Introduce proactive multi-threading techniques
  • Improve executive alignment earlier in the sales cycle

Our program blended live coaching, asynchronous lessons, and real deal application — all customized to the realities of Proposify’s market and motion.

What Changed: Outbound Motion Selling Skills

After just a few weeks, the change in the team’s approach was obvious. Reps were asking better questions, engaging new stakeholders, and navigating deals more strategically — even when starting from scratch.

They began:

  • Opening outbound deals with a clear point of view on customer pain
  • Building multi-threaded relationships early and often
  • Driving urgency instead of waiting for it
  • Running tighter, more compelling executive conversations

Sales leaders noticed the change too. Deals felt less like “happy ears” and more like real opportunities.

The Results: 28% Improvement in Outbound Win Rates

Within a quarter of completing the pclub.io training, Proposify saw:

  • 28% increase in outbound win rates
  • 4% increase in AE quota attainment
  • 11% growth in SDR-generated pipeline

This wasn’t a one-time lift. The skills stuck because they were embedded into Proposify’s existing coaching and deal review rhythm. The team didn’t just learn — they applied.

What’s Next

With outbound motion now gaining traction, Proposify is building on this momentum by:

  • Rolling out pclub.io content to other go-to-market roles
  • Using AI-based role plays to reinforce skills over time
  • Launching mutual success planning as a standard in all enterprise deals
  • Tying skill development to real-time pipeline insights using pclub.io dashboards

“We knew we had a strong inbound machine. But outbound was a different beast. pclub.io gave our team the tools and confidence to go after it — and we’re already seeing the payoff.”
— Scott Tower, Director of Sales, Proposify

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