Nearly 20 years ago (!), in 2007, I published my first and only book: Microsoft 2.0. It focused on changes I expected at the company in the “Post-Gates” era. What would remain the same and what likely would be different once co-founder and CEO Bill Gates had left the building?

CEO Satya Nadella has not exited the company (yet). But there’s no question that Microsoft and its mission have morphed considerably in the past year or two. I’m not quite ready to christen this the Microsoft 3.0 era, even though Nadella handed the reins of Microsoft’s dominant commercial business to Judson Althoff nearly a year ago.

That decision resulted in Nadella moving into more of a “founder mode” role, allowing him to focus less on the day-to-day work of running the business. (Microsoft historians may recall that Gates made a somewhat similar move back in 2000 when he became Microsoft’s chief software architect.)

While it might not yet be time for Microsoft 3.0, we arguably could be in the “Microsoft 2.5” era. Windows and Office are still around and still play a big role. Microsoft still builds and sells developer tools and databases. But there’s no question that the cloud and all things AI are at the top of the pecking order now.

I’m embarking on a series here at GeekWire that will focus on what matters to Microsoft and, by extension, to its customers, partners, investors, and employees these days. Who are some of the people shaping and leading the company? What are their opportunities and challenges right now?

Over the next few weeks, I will be profiling various Microsoft execs working on plans for Microsoft’s ongoing evolution. Some are company veterans; some are newcomers. I’ll be talking with top execs from Microsoft’s Security, Copilot, Windows + Devices, Xbox, GitHub, and more.

I’m interested in their strategies for Microsoft’s key products and technologies and how they plan to try to turn Microsoft’s ambitious vision into reality. What are their teams building? What do they see as their biggest challenges and opportunities? And where do they see the technologies in their respective areas heading?

I feel like many of us who’ve been keeping track of the biggest tech companies (myself included) have fallen into the trap of blaming or attributing everything a company does to AI. Layoffs? AI is the culprit. Price increases? It’s all thanks to AI. Changing sales strategies? Chalk it up to AI …

But upon further reflection, I believe Microsoft’s strategy is more nuanced than “AI or bust.” There’s no question that Microsoft’s AI ambitions are shaping its goals and tactics. But Microsoft, as a heavily enterprise-focused entity, can’t simply stop supporting products that aren’t built from the ground up with AI (as much as it might like to do so). Nor can it just leave behind customers who aren’t 100% onboard with its AI moves.

Couple those enterprise hurdles with some not-so-popular consumer decisions, like axing 3,200 people in the gaming unit, and Microsoft’s approach to turning the ship looks a lot trickier.

Read the first installment in the series, profiling new Microsoft Security EVP Hayete Gallot, who’s revamping the group’s leadership as the company pushes into the agentic security.

Perhaps the only downside to building a golf-focused startup is that it leaves less time to actually play golf.

Dane Renkert will take that tradeoff, for now, as he works on something that he says will change the way people play and interact around the game.

Renkert is co-founder and CEO of Barkie, a Bellingham, Wash.-based startup building an app that aims to be a true AI caddie in every golfer’s pocket — one that tracks scores by voice alone, settles betting games automatically, and rarely requires a golfer to look down at a screen.

Renkert is no slouch as an athlete and golfer. A Washington State University graduate, he played professional baseball for the Milwaukee Brewers before moving into tech and sales leadership roles at Docugami, Komiko, and Ben Kinney Companies. As a competitive golfer, he placed 13th at the 2009 World Long Drive Championship and now boasts a scratch handicap.

The name of the company is a nod to golf terminology — a “barkie” is an honest, hard-fought par saved after a golfer’s drive ricochets off a tree.

The inspiration for the startup stems from Renkert’s own frustration with existing golf mobile apps, which he argues have essentially operated as digital spreadsheets for the last decade. Incumbents like 18 Birdies, The Grint, and Golf Genius require constant manual data entry throughout a round, Renkert said.

Noting that seven out of 10 golfers still use a paper scorecard and pencil because they like the tradition or want to avoid screen distraction, Renkert set out to build a platform centered on a simple philosophy: “keep your head up and not down.”

To translate that concept into software, Renkert initially teamed up in 2025 with co-founder Zubin Wadia, an MIT grad whom he worked alongside for five years at Docugami, the Bellevue, Wash.-based AI startup. Wadia remains a strategic advisor to Barkie.

To achieve the “heads up” experience, Barkie is differentiating itself by launching a full voice user interface that eliminates manual typing entirely. Using standard gear like an Apple Watch or AirPods, golfers can simply speak the outcome of a hole to dynamically update a digital scorecard in the background.

According to Renkert, Barkie is the first to market with an AI-native, voice-first caddie that allows for natural, fluent speech on the course rather than forcing players to toggle through menus and hit arrows to log data.

“The voice thing, in particular, I believe is a massive lift technically, but it’s a big lift from a user experience side as well,” Renkert said, adding that the platform is designed to seamlessly augment the traditions of the game rather than disrupt them.

Under the hood, Barkie relies on a patent-pending dual-layer system to prevent the application from making mistakes or hallucinating numbers. A guardrailed large language model handles the conversational front end — interpreting natural voice requests, answering rules questions, or trading friendly banter.

A separate, rules-based engineering backend handles all the scoring, strokes-gained calculations, and betting math. This split ensures that while golfers can talk to the app like a human caddie, the actual bookkeeping remains completely accurate.

When the betting function comes online, that same backend will settle real-money side games — Nassau, skins, wolf, hammer bets — instantly once a round ends, sparing golfers the aggravation of hashing out who owes what on the 18th green.

Barkie’s simplest use case doesn’t require voice at all. Through a feature called ScoreShot, golfers can snap a photo of a paper scorecard. The app digitizes it and pushes the data directly to GHIN, the USGA’s official handicap system, via a partnership Renkert says gives Barkie access to course-specific data like slope rating and tee-box selection. Golfers without a club membership or GHIN account can still generate a handicap through the app, calculated according to World Handicap System guidelines.

Either way, the result is hole-by-hole performance data that Renkert says no other golf app currently offers — letting players see which holes they’re strongest and weakest on, and, he added, which holes they should be pressing their buddies on.

Barkie is available for download on iOS (optimized for iPhone, iPad, and Apple Watch companion setups) and Android devices via the App Store and Google Play Store.

The app offers a free tier that includes GPS mapping features. The premium tier unlocks unlimited hands-free voice tracking, advanced Strokes Gained analytics, the Barkie Betting Engine, and full GHIN integration. Limited-time pricing is available at $4.99 monthly or $29.99 annually.

Barkie has attracted seed funding from friends and family and notable investors, including Rob Gough, an entrepreneur and collector perhaps best known outside tech circles for his record-setting $5.2 million purchase of a 1952 Topps Mickey Mantle baseball card. According to his LinkedIn, Gough is also an investor in Jeff Bezos’ AI startup Prometheus, which raised $12 billion in Series B funding last month.

“I invested in Barkie.ai because I believe they’re building something that delivers real value to golfers, not just another AI demo,” Gough said in a statement. “Great companies have an unfair advantage, and Barkie has exactly that: a founder with deep domain expertise as a scratch golfer who genuinely understands the game, combined with a world-class AI team recruited from companies like Meta, Google, and NASA.”

Barkie’s cap table also includes former Seattle Seahawks linebacker Lofa Tatupu, who serves as an advisor to the company.

Armed with high-profile backing and a team recruited from tech giants, Renkert isn’t shy about his ambitions to disrupt the entrenched players in the space.

“I want the incumbents to know I have a lot of backing, and I’m coming for you,” Renkert said. “I’m not trying to compete with you, I’m trying to take it over.”

For now, taking over means grinding behind a desk instead of on a fairway. Renkert admits that building the startup cut heavily into his own time on the course this past year — even leading to a rough showing when he tried to qualify for the U.S. Amateur.

But the grind is the point.

“I’ve done a lot of cool things in my life, but this is the hardest I’ve ever worked for something,” Renkert said. “I believe, hopefully, this will be my mantle piece.”

Amish Patel knows his neighbors by their dogs’ names before he knows their own. It’s a pattern he noticed in his Seattle neighborhood — and one he’s now built an app around.

Patel’s newest pet project — born out of his Conduit Venture Labs startup studio, is Sniff, an iOS app that turns the everyday moment two dogs greet each other on a walk into a lasting connection between their humans.

The idea traces back to Patel’s own block in Seattle’s Madrona neighborhood, where he moved with his standard poodle, Chewie, right before the pandemic. With no kids and limited ways to meet people, the neighborhood park became the default hangout — and a group text thread became, in Patel’s words, a real sense of community. The catch: most of those contacts were saved under names like “Glory’s mom” or “Louie’s dad.”

“The five people in Madrona that I hang out with, more often I met through him,” Patel said of Chewie.

Beyond widening Patel’s own social circle, Sniff has a greater societal objective — taking on loneliness and isolation, an epidemic cited in the U.S. Surgeon General’s 2023 advisory on social connection.

“Younger people are having kids less, getting more isolated … we’re sitting on our phones, even though we’re all next to each other,” Patel said. “One out of four people don’t know their neighbors or talk to their neighbors.”

Dogs — and Sniff — could be an answer.

Sniff verifies that users are real people who actually live in the neighborhood they claim, using address and location data, and the app is geofenced so members can only discover dogs nearby. Inside the app, users see only dog profiles and photos — no human names or personal details — until a connection is made. Patel said artificial intelligence plays a role only on the trust-and-safety side — confirming identity and location — rather than in matching people up.

Once connected, neighbors can message through the app, arrange meetups, and lean on each other for help — dog walking, sitting, or just a hand when something comes up. Patel said the trust that builds from already knowing someone’s dog often translates directly into people who are willing to help.

The pilot is open in Madrona, Leschi, Madison Park, the Central District and Capitol Hill, but pet parents anywhere in Seattle can sign up today. Each neighborhood stays geofenced until it reaches enough engaged sign-ups, at which point Sniff opens it up — Madrona, the first to launch, already has about 100 people on the platform.

To help build momentum in each neighborhood, Sniff is partnering with the Seattle Chamber of Connection — where Patel sits on the board — to recruit “Pack Leaders”: local dog owners who help organize meetups and informal introductions as their neighborhood’s user base grows.

Patel is a Microsoft vet who spent eight years on projects including Xbox Kinect and Microsoft Band, before moving into the startup world with stints at fitness wearable maker Katalyst and football helmet manufacturer Vicis. He landed an entrepreneur-in-residence role at Seattle startup studio Pioneer Square Labs in 2020, and two years later co-founded Conduit Venture Labs with Susan Paley, the former first CEO of Beats by Dre.

Conduit focuses on “hard-tech” ventures that blend hardware and software. Sniff is Conduit’s fourth in-house startup, following Fluffy — a computer vision platform for doggy daycares — and an audiobook AI venture in the loneliness space that Patel said is preparing for a public seed round this fall. A fourth project, in health tech, remains under wraps for now.

The Sniff app itself was built lean: a couple of developers, a product lead, and Patel splitting his time across the studio’s other projects. Patel said the team has since shifted to AI-assisted development to move faster, and is now searching for a CEO to take the project in-house full time as it raises capital and pursues some hardware-related features.

For all the talk of trust layers, geofencing and future hardware, Sniff’s entire premise still comes down to a dog doing what dogs do. The humans get the friendships, the favors, the group texts. The dogs, Patel said, get something simpler.

“They just get to be more social,” he said, “because we don’t keep them in our house with us while we’re doom scrolling through everything.”

Nick Parker, a 26-year Microsoft veteran who led the company’s worldwide commercial sales business, is leaving to become Nvidia’s new sales chief — a high-profile talent shift between two of the biggest players in the AI boom. 

Parker will join Nvidia as executive vice president of worldwide field operations, effective Aug. 24, according to a regulatory filing. He succeeds Jay Puri, who is retiring after 21 years running Nvidia’s global sales operation and will stay on as a senior adviser. 

“Microsoft and NVIDIA are great partners and I look forward to continuing to nurture that fantastic relationship,” Parker wrote in a LinkedIn post announcing the move.

The regulatory filing by Nvidia sets Parker’s base salary in the new role at $1 million, with a $5 million signing bonus and equity grants targeted at $40 million. The bulk of that, $35 million in restricted stock units, vests over roughly four years, while the additional $5 million in shares is tied to Nvidia outperforming the S&P 500 over three years.

The new role puts him in charge of global sales and customer relationships at the center of the AI boom, reporting directly to Nvidia CEO Jensen Huang — one of the most consequential commercial roles in the industry, overseeing the operation that sells Nvidia’s chips to the world’s largest companies.

Parker, 55, rose through OEM, device and partner sales roles at Microsoft before being named president of industry and partner sales in 2022. After a promotion this year, he served most recently as executive vice president and chief business officer of Microsoft Worldwide Sales & Solutions, reporting to Judson Althoff, CEO of Microsoft’s commercial business.

Puri, 71, is credited with helping transform Nvidia from a consumer gaming brand into an AI infrastructure giant, building the enterprise sales operation Parker will now inherit.

On Thursday, Microsoft unveiled a $2.5 billion initiative called the Microsoft Frontier Company, which will embed AI engineers inside customers. It will be led by Rodrigo Kede Lima, a longtime Microsoft sales and enterprise leader, most recently president of Microsoft Asia. 

Microsoft is launching a new AI “company.” It won’t be a separate legal entity, and most of its 6,000 people already work at Microsoft. But the $2.5 billion behind it is real, and the stakes are big, given how many of its AI partners and rivals are racing to do basically the same thing. 

The tech giant on Thursday announced “The Microsoft Frontier Company,” which will embed engineers inside customers to build and run AI systems. It will be led by Rodrigo Kede Lima, a longtime Microsoft sales and enterprise leader, most recently president of Microsoft Asia.

This practice is known in the industry as forward-deployed engineering, in which a company sends its own technical employees to work inside a customer’s operations to design, build, deploy and operate AI systems on-site rather than selling a tool and walking away. 

The model was pioneered two decades ago by Palantir, but in recent months the approach has become the hot new thing in enterprise AI. Amazon committed $1 billion to its own forward-deployed engineering initiative just two days ago. (Some inside Microsoft suspect that its rival may have caught wind of what it was planning and moved to announce first.) 

Anthropic and OpenAI launched rival ventures in May to put engineers inside enterprise customers. Unlike Microsoft’s initiative, the OpenAI Deployment Company, as the ChatGPT maker’s venture is known, is an actual standalone entity — majority-owned by OpenAI but backed by more than $4 billion from a partnership led by the private-equity firm TPG. 

Similarly, Anthropic teamed with Goldman Sachs, Blackstone and Hellman & Friedman on a $1.5 billion venture — not yet named — to embed engineers inside mid-sized companies, starting with the investment firms’ own portfolio businesses.

Microsoft is attempting to one-up them all. 

“This goes beyond what has been labeled as Forward Deployed Engineering (FDE) and will be the largest, most capable, outcome-driven engineering organization in the industry,” wrote Judson Althoff, CEO of Microsoft’s commercial business, in a post announcing the new initiative Thursday morning.

Responding to questions from GeekWire, a Microsoft spokesperson called the new initiative “a purpose-built company with its own leadership and financial accountability” but stopped short of calling it a separate legal entity or standalone company.

The spokesperson said the organization “brings together more than 6,000 industry, engineering and AI professionals, drawn primarily from Microsoft’s existing engineering and forward-deployed teams,” noting that it will “grow through a combination of internal talent and external hiring across engineering, AI, and industry roles.”

Separately, some consulting roles are among those expected to be impacted by the round of layoffs anticipated next week.

Microsoft wouldn’t say whether the $2.5 billion is new spending or repurposed from existing budgets, or over what period it’s being spent. The company also hasn’t yet spelled out what the new organization means for the future of its existing consulting and services units.

Across the industry, this is happening now because the payoff from AI has proven harder to capture than many companies expected. Businesses across the economy have adopted tools like ChatGPT, Claude, Gemini and Copilot, only to find that impressive demos don’t automatically translate into results. The technology is powerful, but deploying it can be difficult inside a real company, with its own data, rules and entrenched ways of working.

So the AI providers have started sending their own engineers to work inside those companies, figuring out where the AI can actually help, then building it into their operations.

“Having the model alone doesn’t change your workflows or how you operate,” said Marc Nachmann, Goldman Sachs’ global head of asset and wealth management, in an interview with CNBC about the Anthropic partnership. “You need people who can combine the technology with what’s actually happening in the business and implement those changes.” 

The big AI providers have multiple reasons to do this. Each of them wants to get more businesses using its AI platform at higher volumes. All of them are looking to drive long-term demand for the AI capacity they’re collectively spending hundreds of billions of dollars to build.

Another big reason: AI models are becoming commodities, getting cheaper and more similar by the month. The big money for the likes of Microsoft is in selling the services needed to make AI pay off inside a company, which is a far bigger market than just selling the models themselves.

Microsoft is pitching privacy and trust as a selling point. Its promise is that a customer’s data and hard-won knowledge stay the customer’s alone. Microsoft says it won’t feed them into training its AI models in ways that would hand the same advantages to the customer’s rivals. 

It’s also promising choice: customers can run whichever AI model fits the job, from OpenAI, Anthropic, Microsoft, or open-source providers, not locked into using one.

Microsoft CEO Satya Nadella has argued that a company should be able to exchange one AI model for another without losing all the institutional knowledge it has built up. 

That’s his test, as he put it, for whether a business still controls its own future.

“The last thing any of us want is a world where every company across every sector is ceding value to a few models that eat everything they see,” Nadella wrote in a June 14 essay. “If all the value is accrued by only a few models, the political economy will simply not tolerate it. There is no societal permission for an AI future that hollows out entire industries.”

Whether that vision of swappable AI models becomes a reality remains to be seen. There’s actually a risk for customers that the opposite will happen in the forward deployed engineering approach. Even if they can theoretically swap in a competitor’s AI model, working with Microsoft’s engineers means their systems naturally end up running on Microsoft’s cloud platform and related technologies, making it very difficult to jump ship.

It’s also not clear how new all of this really is for the company. Microsoft already runs a large in-house delivery arm — Industry Solutions Delivery, the group that absorbed what used to be called Microsoft Consulting Services — with thousands of consultants and engineers building and deploying technology inside customer organizations. 

Microsoft also has programs like FastTrack to help customers roll out its software, and over the past year it has been rolling out “forward-deployed engineering” teams with partners, including a dedicated practice with Accenture and a $1 billion, five-year alliance with EY.

So ultimately the Microsoft Frontier Company is less a new company than a new push behind work the actual company was already doing, albeit bigger and better-branded than before.