This article comes from David Metcalfe’s insightful talk at our Sydney 2024 Sales Enablement Summit. Check out his full presentation and our wealth of OnDemand resources.


Have you ever felt like you're caught in a professional tug-of-war between product, marketing, and sales? This was my reality and a challenge that would ultimately reshape my understanding of organizational effectiveness.

My professional journey is anything but linear. I've zigzagged through marketing, sales, HR, and back again—a career path that resembles less a carefully plotted route and more an intricate maze. Each unexpected turn, however, provided more insights into the art of cross-functional collaboration.

My first year in sales was a baptism of fire. Coming from a comfortable role at LinkedIn, I suddenly found myself navigating an information ecosystem that seemed designed to overwhelm me. Product managers bombarded me with 10 to 15 daily requests. Global sales enablement pushed continuous methodology updates. Sales targets loomed large. My once-pristine "inbox zero" approach crumbled within weeks.

But within that chaos lay an opportunity. Rather than succumbing, I began investing time in understanding and improving our enablement processes. This wasn't about fixing everything—it was about creating strategic bridges between teams that seemed perpetually misaligned.

So, today I want to dive into my cross-functional collaboration approach and hopefully share some insights that’ll transform your organization. Let’s get started.

The customer-facing roadmap: A collaborative masterpiece

The roadmap emerged from a genuine business challenge: many companies building payment platforms needed insights into our product strategy to make informed decisions. Without clear communication, customers sometimes built their own solutions only to discover we were about to launch something that rendered their work redundant.

Our solution was to create a five-to-seven-page document with 70 to 90 line items, covering 25 products across all regions, segments, and industries and the creation process was a meticulously choreographed collaboration:

  • Product's role: Provide initial technical details and roadmap insights.
  • Product marketing's contribution: Refine language, making technical information customer-friendly.
  • My role: Create a unified voice, and standardize design and presentation.
  • Sales training: Develop concise video guides for sellers.
  • Feedback mechanism: Establish a continuous loop of customer insights flowing back to product teams.

The result? A game-changer. Sellers loved it because it felt more like a consultative tool than a sales pitch. Customers appreciated the transparency. Remarkably, we've been able to maintain about 80% accuracy in our roadmap predictions because of this.

Bridging product marketing and sales enablement gaps
Tension between marketing & enablement costing you deals? Get the inside track on transforming disjointed siloes into a unified revenue engine!

Tackling cross-functional collaboration challenges

Cross-functional collaboration isn’t just about keeping teams informed—it’s about creating systems that turn shared knowledge into real impact. Too often, alignment is treated as a box to check, with teams operating in parallel rather than in sync. 

But true collaboration happens when teams understand each other’s challenges, speak a common language, and build processes that remove friction instead of adding to it. Here’s how we tackled some of the trickiest collaboration gaps and turned them into opportunities for efficiency, trust, and results:

1. Working with product teams 

Product teams are often stretched thin. They juggle multiple products, countless moving parts, and tight deadlines. They’re also the ultimate decision-makers when it comes to product development, which means engagement with them needs to be structured and efficient.

One major change we introduced was the RAPID decision-making framework, developed by Bain. This framework assigns clear roles for decision-making, ensuring projects don’t stall due to last-minute confusion. 

Before any project begins, we explicitly define who makes final decisions. It might seem bureaucratic, but it prevents countless hours of miscommunication.

Another key to success? Strategic over-communication. This doesn’t mean sending endless Slack messages. It means ensuring key updates are delivered at the right time, in the right way, to the right stakeholders. I’ve never had a colleague complain about being too informed about a project’s progress.

Achieving alignment and gaining buy-in, with Brooke Coletti
Brooke Coletti joins us on the podcast to discuss enablement stakeholders, alignment, and achieving buy-in!

2. Building meaningful partnerships with product marketing

Product marketing teams thrive on frontline insights, yet many sellers hesitate to provide feedback, fearing it’s too obvious. In reality, what might seem basic to sales is often gold for product marketing. A simple insight from the field can shape messaging, refine positioning, or even influence product development.

That’s why I established a 15-minute monthly coffee chat initiative between enablement and product marketing. These short, informal conversations provide a direct line of communication, helping PMMs understand what’s really happening in the trenches. It’s a small investment with an enormous impact.

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Pro tip: Don't just communicate through documents and Slack channels. Personal, direct communication builds trust and creates more meaningful collaborations.

3. Sales enablement: The Marie Kondo approach

Sales enablement can quickly become a cluttered mess. At Stripe, we had an overwhelming number of resources, many of which were viewed by just one seller per quarter out of 500. Clearly, something needed to change.

Inspired by Marie Kondo’s decluttering philosophy, I set out to reduce our asset library by 70%. The process involved:

  • Defining clear slide background protocols (customer-facing slides vs. internal use only).
  • Creating consistent template designs to eliminate redundant customization work.
  • Ensuring resources are actually useful and user-friendly, based on direct seller feedback.

This standardization effort wasn’t just about aesthetics; it was about time efficiency and usability. When sellers don’t have to spend hours stitching together slide decks, they can focus on what truly matters: engaging with customers.

Final thoughts

The truth is, sales enablement isn't about creating perfect resources or building complex systems. It's about connection. Connection between teams, between strategies, between people.

I'm not claiming to have all the answers—far from it! But I am committed to continuing to break down barriers, to keep learning, and to help create more connected, more effective organizational ecosystems.

To my fellow enablement professionals: our work matters more than we often realize. Some days, that looks like a perfectly crafted slide deck. Other days, it’s a 15-minute coffee chat that changes everything. But every day, it’s about bringing people together.

Keep pushing. Keep connecting. Keep enabling.