Insights from ex-CMO of Microsoft

Big company, big learnings...

I’m on the hunt for bigger ideas these days.

So I’m looking at bigger companies.

I’m in my 9th year at SmartAsset and we’ve grown from a small startup with nearly zero revenue to a not-so-small startup that’s entering a seriously awesome phase of maturity.

For this week I picked Microsoft.

Between their OpenAI partnership and badass CEO Satya Nadella, they are all the rage.

Top of mind for me are the BIG IDEAS that occupy the minds of bigtime CEOs and CMOs.

So today I’m interrogating the online interviews of Microsoft’s former CMO, Chris Capossela.

Let’s analyze the transcripts and articles and see what Chris can teach us:

Who is Chris Capossela and What Has He Done?

Chris Caposella on a nifty staircase

Chris Capossela is the former Chief Marketing Officer (CMO) of Microsoft.

He worked at Microsoft for over 30 years, joining the company right after graduating from Harvard with a degree in computer science and economics.

Over his three-decade career at Microsoft, Chris held a variety of leadership roles spanning engineering, marketing, operations and sales.

He served as head of the Microsoft Office division, leader of the global consumer channels group, and CMO before leaving the company in early 2022.

As CMO, Chris led Microsoft's global marketing including advertising, brand, research and retail stores.

He helped rebrand Microsoft under CEO Satya Nadella, shifting the company to focus more on cloud computing and AI.

Chris played a key part in the launch of Microsoft cloud tools and services like Azure, Office 365 and Microsoft Teams.

He also oversaw high-profile ad campaigns for Microsoft products like Windows, Surface and Xbox.

I asked my good friends python, Claude and ChatGPT to analyze reams of documents for Chris’s top insights.

If you have a million hours of free time, here are some Chris Capossela interviews.

My methods are secret, but I’ll freely share the results.

Some of these are bangers.


Princeton has a 6% acceptance rate.

Y-Combinator has a 2% acceptance rate.

This guy graduated #1 in computer science from Princeton…

THEN got into YC. 

Now he's building Commandbar (AI user assistance software) on a $19M Series A round and sharing stories from the startup trenches on linkedin. 

Follow James on LinkedIn for some wild startup porn and hard-earned insights. 

Now let’s dive into Chris Capossela’s top 10 insights from his time as CMO of Microsoft:

Focus on your biggest fans to understand what your brand can improve and where innovation opportunities exist

Companies should pay close attention to the feedback from their most loyal, enthusiastic customers ("fans") in order to guide business decisions and investments.

Fans can teach brands "more about what's wrong" and help "co-invent the future" together through direct feedback and dialogue.

For example, Xbox gamers provided ideas that led Microsoft to launch Xbox Game Pass, which consolidated gaming across different devices and business models.

By truly listening and engaging hardcore fans - rather than just conducting surface-level market research - brands can better understand pain points and drive more organic, customer-led innovation.

Taking action would entail identifying top fans, soliciting open-ended input, involving them early in product development, and closing feedback loops by sharing updates.

This helps turn fans into partners, leveraging their passion to propel a brand forward in meaningful ways.

Build direct connections with customers at scale by leveraging data and digital channels

It’s important for a brand to establish personal, emotional connections with its individual customers.

The goal is to emulate human relationships digitally despite massive customer volumes.

While historically many companies took a mass-market approach, direct relationships lead to greater satisfaction, loyalty and advocacy.

Chris discussed how Microsoft is now able to "connect engagement with data" - leveraging usage telemetry and analytics to delivery hyper-relevant communications at scale.

For instance, the Xbox team sent highly personalized gaming insights and recaps to over 20 million fans based on their individual gameplay data and preferences. Taking action would entail auditing a brand's current data and digital touchpoints with customers to identify personalization and relationship-building opportunities.

Specific tactics could include usage-based content recommendations, surprise offers and experiences tied to loyalty tiers, two-way messaging apps, and mechanisms to solicit ongoing feedback at an individual level.

The goal is to emulate human relationships digitally despite massive customer volumes.

Commit to accessibility and inclusive design to expand your audience and make better products

There is a business and moral imperative of building products and services that work for all people, especially those with disabilities.

Chris discussed Microsoft's creation of an adaptive kit for the Surface tablet and an accessibility testing service for Xbox game developers.

By partnering with people who have impairments and advocacy groups, companies can design offerings that resonate with traditionally underserved populations from the outset. This expands audience reach considerably.

Accommodating accessibility needs spurs creativity that often yields broadly appealing features - like live captioning of audio on Windows devices.

Taking action requires conducting ongoing focus groups, user research and co-invention sessions with differently abled customers. Their real world feedback on early concepts and prototypes leads to better, more inclusive final products.

Prioritizing disability perspectives - both among employees and users - fosters innovation and enables more consumers to participate equally.

Reveal your brand purpose through social impact initiatives and taking stands on issues

This insight encourages brands to articulate and activate around a higher purpose beyond profits.

Just selling products without deeper meaning rings hollow.

As society increasingly expects corporations to contribute solutions to global problems, those that stand for their principles and values through action inspire trust and loyalty.

For example, Chris discussed a Microsoft video campaign that challenged stereotypes by spotlighting accomplished female athletes and leaders. By boldly addressing relevant cultural issues, companies demonstrate authentic caring for societal matters their customers and employees prioritize.

Taking action entails defining a brand's raison d'être - its motivations and place in bettering people's lives.

Social impact campaigns, nonprofit partnerships and activist messaging should flow naturally from this core objective to impact society.

Failing to lead with purpose today alienates younger generations and misses opportunities to positively engage stakeholders.

Reimagine outdated experiences that customers take for granted, don't just compete on features

Reimagining outdated experiences that customers take for granted is a key brand opportunity, rather than just competing on features and functions.

Brands should regularly question assumptions, challenge sacred cows, and reinvent elements that may have been neglected simply because "they've always been that way" - surprising customers can spark renewed affinity.

As Chris discussed, even ubiquitous apps like Microsoft Paint or Notepad - which ship with Windows and date back over 30 years - can form emotional connections when redesigned and modernized for current contexts.

Though the core functionality remains, applying the latest UI standards and dark mode support to breathe new life into legacy interfaces surprises users and reinvigorates perceptions.

To take action, audit and prototype enhancements for your most dated yet beloved touchpoints through a contemporary lens.

Monitor social chatter for complaints of elements that seem decrepit or stuck in the past as cues.

Even longtime users will appreciate dusting off forgettable parts of their user experience and catching up to the present.

Create surprises and delights to reward loyal customers and turn them into advocates

Creating surprises and delights is a powerful way for brands to reward their most loyal fans while securing new advocates.

As Microsoft CMO Chris Capossela explained regarding Xbox, personalized annual recaps of individual user statistics and gaming achievements shared with over 20 million passionate fans spurred significant organic social shares.

Tap into people's affinity for feeling valued and recognized.

Orchestrating the element of surprise also earns attention and goodwill.

Brands should leverage data and analytics to surface unique consumer insights that can be packaged as unexpected, meaningful gestures.

Identify power users and high-value customer segments primed for individualized surprises, whether virtual or by mail.

Track resultant social mentions, referrals and engagement lifts to quantify the ROI of delighting key audiences amid the torrent of impersonal digital communication.

Thoughtful surprises that demonstrate a brand's personal understanding can unlock marketing outcomes unattainable via mass promotional tactics.

Continuously experiment with new technologies to prepare your brand for the next platform shift

Continuously experimenting with emerging technologies prepares brands for the next platform shift that will transform user behaviors and business models.

While not every bet will pay off, experiments that reveal real user value can be scaled once the surrounding ecosystem develops to support consumer adoption.

As Microsoft CMO Chris Capossela discussed, the company's early creation of a dual-screen Android mobile device in the Surface Duo allowed them to test multi-screen computing experiences years before foldable devices reach mainstream.

Though not immediately embraced, this type of conceptual prototype and in-market learning positions Microsoft to capitalize when user readiness and technical maturation meet.

Moreover, the company is already architecting virtual twins of factories using cloud tools to pave the way for simulation-enhanced operations.

This insight urges brands to constantly probe innovations on the fringe that solve future consumer needs.

Establish a venture framework to regularly pilot new tech-enabled experiences, services and products - both internally and with select customer cohorts.

Measure learnings rather than financial returns.

Jumping on next waves early is preferable to losing relevance when they crash.

Make space for creativity, emotion and storytelling to connect with people on a deeper level

Making space for creativity, emotion and storytelling enables brands to form deeper bonds with people instead of just touting product claims.

Track how creative risks influence consideration.

A launch video for the Surface Studio tablet highlighted the designers behind its creation while featuring their artistic passions coming to life through the product.

This documentary-style approach skipped expected executive promotions to tap user aspirations. Likewise, an NFL partnership brought fans together with players through shared Microsoft Teams video chat sessions. Rather than simply showcasing features, the company increasingly spotlights human stories and connections unlocked by their tools.

Brands should carve out dedicated marketing budgets, staff and platforms for right-brain campaigns that fill functional gaps.

Commission multimedia narratives versus status quo social posts, while measuring their qualitative reception and impact on brand affinity.

As younger generations demand corporate transparency, creativity and meaning, products alone fail to captivate.

Prioritize company culture and values to drive organic brand affinity from employees

Prioritizing a people-first company culture and values intrinsically drives brand affinity from employees who feel motivated and supported.

When workers feel psychologically safe to take risks and propelled by a higher purpose beyond profits, their passion manifests externally.

Microsoft's cultural transformation under CEO Satya Nadella - including more empathy, learning and codevelopment with users - has been integral to recent innovations.

To activate this insight, leadership should revisit foundational cultural tenets and employer value prop for relevance.

Survey staff on whether stated values manifest day-to-day.

Employee journey mapping, focus groups and consultation with culture experts can reveal friction points. Then reorient programs, communications, symbols, rituals and narratives around refreshed culture.

This seeds viral ambassadorship as satisfied staff share what makes your company great during client meetings and at industry events.

Upholding an ethical, inclusive and people-positive culture begets pride in being part of the organization’s brand story.

Develop services and tools that empower people beyond just selling products

Microsoft's mission statement promises to "empower every person and organization on the planet to achieve more."

Brands should identify customer pain points and barriers their offerings can alleviate, not just propose new features.

This lofty ambition permeates product design and go-to-market.

For instance, a major commercial cloud contract hinged on proving how Microsoft technology would specifically help a retailer's employees better service shoppers. The approach flips old assumptions of selling based on features to an ongoing value mindset.

Survey prospective users to quantify potential empowerment value when navigating roles and processes with your solution in place.

Calculate ROI uplifts across a client organization, not just departmental software costs.

When people feel elevated personally by a company's tools in achieving their goals, devotion forms to drive relationship longevity and organic advocacy.

To dive further:

Chris Capossela Interviews

Dumb Ad of the Week:

I spotted this beauty on the NYTimes homepage.

  • Would someone with the authority to buy be genuinely surprised to learn that not all vector databases are the same?

  • What kind of insane DOWNLOAD must await the lunatic who dares leap from the uppermost point in the funnel (basic common sense) to take such decisive action as to download something?

Probably like a $50 CPM too…

Enjoy your week.

I hope these insights were helpful.


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