Bad tire alignment causes uneven tire wear, diminishing suspension quality, and steering problems that could cause an accident. Not great for your car, if you ask us.

The same goes for bad sales and marketing alignment — metaphorically, at least.

All too often, commercial leaders ignore when two of their most important wheels — sales and marketing — veer off in completely opposite directions. Different goals. Different metrics. Little to no communication. And the longer they go without a wheel alignment, the costlier the problem becomes.

In this episode, we spoke with a world-class “mechanic” of sales and marketing alignment. Jon Perera, Chief Marketing Officer at Highspot, joins the show to share his secrets for getting sales and marketing working better together.

We discuss:

  • Achieving alignment across the “four wheels of the car”
  • Top practices that lead to better sales and marketing partnership
  • Ways to ensure marketing content is accessible to sales

Listen to “#62 Secrets to Unlocking Sales & Marketing Alignment” on Spreaker.

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Achieving alignment across all four wheels

When you’re speeding down the highway and your car starts shaking and groaning, you don’t keep puttering on your merry way, even if the problem can be traced to a single tire.

When you have a problem with one tire, you have a problem with the entire car. We can say the same for the four wheels within a company—sales, marketing, enablement, and customer success.

Though these departments may have different definitions from company to company, the importance of alignment remains the same. In fast-paced, competitive environments, we can’t afford anything less than 100% alignment 100% of the time. 

Jon’s 15 years of sales and marketing enablement efforts at Microsoft earned him many hard-won lessons, not the least of which was witnessing the result of misalignment.

“Sales could say, ‘Marketing has their message, but we don’t use it. We use a different message that works better with customers.’ And then you have this mismatch between what’s happening on the web, the press, the analysts, and the front line.” he says.

This practice can breed confusion (not to mention resentment between sales and marketing) and trigger long-standing challenges.

To avoid contention and head-off potential misalignments, Jon asks a few critical questions: 

  • Do we have common goals?
  • Can we be open and real with each other?
  • Do we have a system to operationalize behavior change at scale?
  • Do we have a shared narrative?

When we ask these questions, we unlock new levels of collaboration. Having a single source of truth across teams increases the chance of hitting goals.

That means no secret scorecards, hidden agendas or lone rangers going off on side quests. Instead, initiatives focus on unity, cohesion, and alignment.

Top practices that lead to better sales and marketing partnership 

Jon cites a quote from Brene Brown that encapsulates the idea of open and real communication throughout a company: “Being clear is kind. Being unclear is unkind.”

A transparent company-wide narrative fosters clear action items, initiatives, and follow-through. Having open conversations is fundamental to excellence.

According to Jon, consistent growth comes down to three efforts: equip, train, and coach.

“If you want consistent execution, and you want to drive things like sales productivity, you better have a shared narrative and a comprehensive system with all three legs of the stool to make that team perform at its very best,” he says.


Equipping a team can be anything from marketing content, a sales methodology in a shared approach, a world-class onboarding experience, or a repeatable set of sales plays. 


Training does not only pertain to frontline sales reps—training managers first can reveal bugs in the process, open the floor for feedback, and ensure the managers can be good coaches for their team. In sports, a good coach performs before, during, and after a game.


Sales and marketing are no different from football in the sense of learning from past experiences and leveraging dynamic strategies as tools for consistent execution.

Ways to ensure marketing content is accessible to sales

More often than not, every single marketer in the B2B space wakes up thinking about how to help their sellers hit their quota. 

Marketers will get instructions to build a deck or a graphic or any other asset and dutifully create it.

Unfortunately, sales representatives spend four to eight hours per week searching for the content they need. When they can’t find it, they create their own assets, branding and message. 

Mastering search, browse and recommendation engines is critical to close the gap of unused content.

“You better have a system in place. Like Netflix saying, ‘I know you like this TV show. I think you’re also going to like this one.’ Or, ‘by the way, you’re in a selling situation against competitor X. People have won against competitor X also use this content.” Jon says. 

Create a path to follow. Trace commonalities across different assets and build a searchable library that delivers every time.

The other side of the content library coin is analytics. Providing sales reps with data around which pieces of content are moving deals forward creates even more cohesion between sales and marketing. And, in turn, an increased chance for consistent execution.

Listen to our full conversation with Jon on the most recent episode of the Winning the Challenger Sale podcast to learn more about achieving alignment between sales and marketing within your organization to operate like a well-oiled machine.

To hear this episode, and many more like it, you can subscribe to the Winning The Challenger Sale podcast on our website, Apple Podcasts, Spotify, or just search for it in your favorite podcast player.

Andee Harris

Andee Harris is CEO of Challenger. Andee brings more than two decades of experience growing and scaling service and technology businesses. She has previously led multiple companies, both as CEO and Senior Vice President, through periods of rapid revenue growth, critical fundraising, and successful acquisition. These companies include Highground (acquired by Vista Equity Partners), TMBC (acquired by ADP), Syndio and Emerging Solutions (acquired by Emtec).