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Scaling a Global Vacation Rental Software Platform | With Hostaway CEO Marcus Rader

Scaling a Global Vacation Rental Software Platform | With Hostaway CEO Marcus Rader

Hostaway CEO Marcus Rader said the best way to serve an industry with software is to come to it completely as a novice. The software as a service company is focused on vacation rental properties and the small businesses operating them. Hostaway recently raised $365 million in a round led by General Atlantic. Hostaway, which was the first property management system to integrate directly into OpenAI's ChatGPT, said it will use the money to expand globally and invest in AI.

Insights Editor in Chief Larry Dignan caught up with Hostaway CEO Marcus Rader to talk about technology. Here are the key takeaways...

Hostaway's core pitch. The company provides software for vacation rental property managers in charge of anywhere from 10 to 8,000 properties. "All of our customers are running remote operations and for that you need software to know what's going on and connect to the biggest companies in the space like Airbnb and VRBO," said Rader.

  • The advantages of being an outsider. "Most vertical software companies were started by people who are running a business in a certain industry and start building tools for that," said Rader. "We did the opposite. We're software people and had no experience whatsoever in vacation rentals when we started 10 years ago."
  • SMB challenges. Rader said Hostaway's approach is to look at what has worked and failed in other industries and then apply it to its vertical. SMBs can also be a challenge in that they may not know how to run a business. Hostaway aims to make those tasks easier.
  • The role of AI. Rader said AI has the potential to save a lot of time and money for Hostaway's customers. "AI is extremely important in our segment, because just like any hospitality business, the biggest expense is either the time you spend trying to delegate and teaching your staff, or the money that you're paying your staff," said Rader. "Every hour, every minute counts, and AI has the potential to save a lot of time and money. It's our top priority in 2025 to build out that functionality for our clients."
  • Process and efficiencies. Rader said process and efficiency plays a big role in AI. "We hate inefficiencies, especially when a company makes a decision and then two years later reverts to the old way," he said. "That's my definition of inefficiency and it's terrible. I see a lot of smaller property managers struggle with that. Their business is doing well until one day it isn't and they don't know why. And there's a ton of people more than willing to tell them that they will solve all of their problems if they give them money. Our goal is to make it easy as possible to pick the right solution when it comes to operational efficiency."

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OpenAI launches Operator, eyes AI agents without APIs

OpenAI launches Operator, eyes AI agents without APIs

OpenAI launched Operator, an AI agent that can use go to the web and perform tasks such as booking vacations, shopping for groceries and making restaurant reservations.

Operator is in research preview and the ability to interact with a webpage and use a mouse and keyboard follows a similar effort by Anthropic.

In a blog post and YouTube video, OpenAI walked through a few demonstrations. The general idea is that OpenAI's Operator can handle repetitive browser tasks using the same interface as humans. OpenAI is aiming to use agentic AI to popularize it with consumers, but the real money will be in business use cases. "Our plan is to expand to Plus, Team, and Enterprise users and integrate these capabilities into ChatGPT in the future," said the company.

For now, the Operator is available to ChatGPT Pro users.

Operator leverages GPT-4o's vision and reasoning features and a new model called Computer-Using Agent, or CUA, which interacts with graphical interfaces.

The key item here is that OpenAI Operator takes action on the web without APIs and custom integrations. If Operator gets stuck it can self-correct and hand back control to users.

Initially, Operator works with day-to-day services such as DoorDash, Instacart, OpenTable, Priceline, StubHub, Thumbtack and Uber. Over time, rest assured that OpenAI will expand to enterprise use cases.

OpenAI said it will provide an API for CUA for developers, enable Operator to handle more complex tasks and expand to enterprises.

On the safety front, Operator asks the user to takeover when it needs more information and credentials, confirm actions, decline sensitive tasks and require supervision to avoid mistakes.

 

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Hostaway CEO Marcus Rader on vacation rentals, SMBs, AI and innovation

Hostaway CEO Marcus Rader on vacation rentals, SMBs, AI and innovation


Hostaway CEO Marcus Rader said the best way to serve an industry with software is to come to it completely as a novice.

The software as a service company is focused on vacation rental properties and the small businesses operating them. Hostaway recently raised $365 million in a round led by General Atlantic. Hostaway, which was the first property management system to integrate directly into OpenAI's ChatGPT, said it will use the money to expand globally and invest in AI.

I caught up with Hostaway CEO Marcus Rader to talk about technology. Here are the takeaways.

Hostaway's core pitch. The company provides software for vacation rental property managers in charge of anywhere from 10 to 8,000 properties. "All of our customers are running remote operations and for that you need software to know what's going on and connect to the biggest companies in the space like Airbnb and VRBO," said Rader.

The advantages of being an outsider. "Most vertical software companies were started by people who are running a business in a certain industry and start building tools for that," said Rader. "We did the opposite. We're software people and had no experience whatsoever in vacation rentals when we started 10 years ago."

Rader said the first step was to learn about the industry. "What are vacation rentals all about? We started renting out properties. Just learn, in addition to talking to people. And then we started building the tools and the only global solution that's really available," said Rader, who noted Hostaway's first customer was in Portugal with an initial office in Barcelona.

A child's eye to starting a business. Rader said entering a new industry has its advantages. He said:

"One of the great things with entering a new industry is that it has preconceived notions of how things are supposed to be done, or how people think. Those truths are true, but the industry experts are often the last ones to notice when things change. That's why so many industries can be disrupted.

Taxis were not a new industry, but they were just doing the same cab rides they’d been doing for 50 years. Suddenly Uber came and took everything away. Being new in an industry you don't have opinions. You just listen to what customers want and go build it."

SMB challenges. Rader said Hostaway's approach is to look at what has worked and failed in other industries and then apply it to its vertical. SMBs can also be a challenge in that they may not know how to run a business. Hostaway aims to make those tasks easier.

The role of AI. Rader said AI has the potential to save a lot of time and money for Hostaway's customers. "AI is extremely important in our segment, because just like any hospitality business, the biggest expense is either the time you spend trying to delegate and teaching your staff, or the money that you're paying your staff," said Rader. "Every hour, every minute counts, and AI has the potential to save a lot of time and money. It's our top priority in 2025 to build out that functionality for our clients."

Process and efficiencies. Rader said process and efficiency plays a big role in AI. "We hate inefficiencies, especially when a company makes a decision and then two years later reverts to the old way," he said. "That's my definition of inefficiency and it's terrible. I see a lot of smaller property managers struggle with that. Their business is doing well until one day it isn't and they don't know why. And there's a ton of people more than willing to tell them that they will solve all of their problems if they give them money. Our goal is to make it easy as possible to pick the right solution when it comes to operational efficiency."

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Unlocking Real ROI from AI | Interviews from Davos 2025

Unlocking Real ROI from AI | Interviews from Davos 2025

🏔? LIVE FROM #Davos25: R "Ray" Wang talks with IBM's Neil Dhar on the future of #AI and consulting at the World Economic Forum (#WEF25). Here's a few key takeaways...

📌 Companies are now focused on driving real ROI from their AI investments, targeting 2-3x returns through productivity gains, increased sales, and cost reductions.
📌 Regulation and governance are critical to building trust in AI systems, especially around sensitive #data. Unlike the early days of social media, this needs to be integrated upfront.
📌 Examples of AI driving #innovation, including drug development acceleration in pharma and enhanced customer service in retail.
📌 Growth strategies are a major focus for hashtag#business leaders post-election and amid market stability.

💡Watch below to get the whole scoop, and follow R "Ray" Wang on LinkedIn and X (@rwang0) for live Davos updates!

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AI Adoption and the Future of Consulting | Interviews from Davos 2025

AI Adoption and the Future of Consulting | Interviews from Davos 2025

Tuning in from the World Economic Forum in Davos! 🌍 Constellation founder R "Ray" Wang talks with IBM's Mohamad Ali about 2025 consulting #trends... Key topics include:

📌 The critical importance of #AI adoption
📌 Overcoming cultural challenges to scaling AI
📌 Companies embracing AI will achieve 10x efficiency gains
📌Obstacles around employees adopting the new #technology

Both Ray and Mohamad agree there's more optimism in the air at Davos this year! Watch the full conversation here.

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DigitalOcean GenAI Platform now available

DigitalOcean GenAI Platform now available

DigitalOcean, a cloud provider focused on AI workloads, launched its GenAI Platform, which compiles third party foundational models to enable developers to build AI agents quickly.

The company launched the foundational model platform at its Deploy developer conference in Austin.

DigitalOcean's GenAI Platform is designed to allow customers to set up agents with their data platforms. The company said the GenAI Platform is designed to reach developers on multiple levels. To that end, DigitalOcean features services like GPU Droplets, which enables customers to spin up Nvidia H100 instances in one and eight GPU configurations.

DigitalOcean highlights the rise of boutique AI cloud providers

GenAI Platform features the following:

  • The ability to use third-party foundation models to build chat experiences with document analysis, semantic search and image generation.
  • A framework that's model agnostic.
  • Workflows to create use case specific agents with enterprise data and context.
  • The ability to integrate structured data from databases and APIs.
  • Guardrails for reliability and safety.
  • Support for private interfaces.

Bratin Saha, Chief Product and Technology Officer at DigitalOcean, said the GenAI Platform is designed to integrate with customers' existing infrastructure and cater toward multiple experience levels.

DigitalOcean said the GenAI Platform is available today. The company said it will add new features to the GenAI Platform including support for URLs as a data source, agent evaluations, auto-indexing for knowledge bases and model fine-tuning.

DigitalOcean has an annual revenue run rate approaching $800 million. Last year, DigitalOcean named Paddy Srinivasan CEO. Srinivasan had been CEO of GoTo and before that was co-founder of Opstera and an executive at Oracle and Microsoft.

Here's a look at DigitalOcean's GenAI Platform:

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OpenAI's Stargate Project diversifies its cloud infrastructure

OpenAI's Stargate Project diversifies its cloud infrastructure

OpenAI said it has launched the Stargate Project, a company that will invest $500 billion over the next four years building AI infrastructure in the US.

The company added that it is deploying $100 billion now to build an AI data center in Texas. OpenAI's investors in Stargate include SoftBank, OpenAI, Oracle, and MGX. Technology partners include Arm, Microsoft, NVIDIA, Oracle and OpenAI.

According to a joint statement, Stargate is designed to "secure American leadership in AI, create hundreds of thousands of American jobs, and generate massive economic benefit for the entire world." President Trump announced the $500 billion infrastructure effort.

With Stargate, OpenAI, which is operating the first site in Texas and the ones after it, will bring in Oracle as a cloud partner. Microsoft issued a separate statement. Both OpenAI and Microsoft said Stargate built upon a tight partnership already.

OpenAI said it will "continue to increase its consumption of Azure as OpenAI continues its work with Microsoft with this additional compute to train leading models and deliver great products and services."

Microsoft said the OpenAI terms of the partnership remain for the contract through 2030. Microsoft noted it has rights to OpenAI IP, an Azure exclusive with the OpenAI API and revenue sharing pacts.

The big change with Stargate though is this bit of text:

"This new agreement also includes changes to the exclusivity on new capacity, moving to a model where Microsoft has a right of first refusal (ROFR). To further support OpenAI, Microsoft has approved OpenAI’s ability to build additional capacity, primarily for research and training of models."

Given the partners here, it looks like OpenAI will be using Oracle Cloud Infrastructure too.

More:

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Cognizant: AI savvy consumers will drive spending, demand new experiences

Cognizant: AI savvy consumers will drive spending, demand new experiences

Cognizant said that consumers that embrace artificial intelligence are likely to drive $4.4 trillion in AI-influenced consumer spending in the US by 2030.

In a report from Cognizant and Oxford Economics, the services firm argued that US consumers who embrace AI could drive 46% of spending by 2030. In Australia, that percentage rises to 55% over the same period followed by Germany at 46% and UK at 39%.

Cognizant's report puts a customer experience spin on enterprise AI investments. Generative AI is typically seen as a way to improve efficiency, but enterprises are also looking toward agentic AI to drive revenue and experiences.

Ravi Kumar S., CEO of Cognizant, said enterprises need to examine the "full potential of how AI can reimagine the customer experience and unlock tremendous value."

According to the survey, which was based on 8,400 respondents, 75% noted that they were frustrated with the buying process. These consumers saw potential in AI when learning about products, buying them and post purchase. Cognizant grouped respondents based on their attitudes toward AI.

Cognizant argued that enterprises will have to prepare for how agentic AI will impact consumers. 

The company said:

"Businesses will also have to understand and prepare for what comes next in the AI journey: the agentic internet, an interconnected ecosystem of AI-enabled tools and agents working on behalf of consumers to autonomously locate, evaluate, purchase and maintain the products and services they rely on. With the agentic internet, consumers will gain what amounts to a personal digital concierge that works with business AI agents to orchestrate complex tasks across the purchase journey."

Key items:

  • Conversational AI was the most popular tool for consumers who embraced AI. Digital voice assistants and chatbots followed.

  • Consumers are most comfortable with AI during the learning phase. The survey found 47% of respondents were comfortable using AI to help choose products and services.
  • 75% of respondents are unlikely to allow AI to automatically reorder or pay for high-value items without direct authorization.
  • Only 16% of consumers who are older than 55 years are comfortable with AI during the decision making phase with 33% aged 18 to 44 years old comfortable.
  • 28% of consumers were comfortable using AI to reorder low priced items.

Here's a look at how Cognizant sees the AI adoption waves forming.

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Hot Take: Oracle Brings More AI to the Table for Revenue Teams

Hot Take: Oracle Brings More AI to the Table for Revenue Teams

Oracle made some significant announcements around its continuing generative and agentic AI strategy today at CloudWorld in Dubai. The new additions to the Oracle Fusion Cloud Sales portfolio includes new out of the box AI agents - aimed at streamlining key sales and CX processes to driver productivity and improve customer relationships. 

The new AI gents include:

  • Customer engagement agent: Helps sales teams save time and improve productivity by streamlining customer communication. For example, the agent can quickly generate customer-ready emails designed to bypass spam filters, while also enabling sales representatives to adjust the tone and call-to-action for their specific audience.
  • Customer records agent: Helps sales teams more efficiently maintain up-to-date account activity records. For example, the AI agent can summarize recent account activity, organize meeting notes, and automatically input them into the system for internal team access and collaboration. To meet the needs of different sales teams, the agent can also proofread and reformat meeting notes, such as incorporating bullet points or action items. 
  • Customer intelligence assistant: Helps sales teams quickly get up to speed on accounts and develop more meaningful customer connections. For example, the generative AI-powered assistant can quickly produce a summary of the account, including recent activity, current sentiment, and contract status, by leveraging end-to-end data from sales, finance, and supply chain to deliver a more holistic, personalized, and contextually relevant account overview.
  • Multilingual support: Helps sales teams seamlessly connect with global audiences. For example, embedded generative AI capabilities help sales teams to quickly translate customer engagements and interact with customers in other languages.

The agent additions bolster an already solid list of AI-powered features across the Fusion application portfolio. And these new agents seem to be smart additions as well - driving seller productivity by reducing manual, common tasks - giving time back to sellers to focus on the human element of building strong customer relationships. 

Oracle is unique in that the company has continued to deliver on a previous promise that it sees AI as just another component of building a strong CX product set. And therefore, its AI features and capabilities are not priced separately but rather included in the base fee for Fusion Sales, in this instance. Compare this to companies like Salesforce, where its Agentforce offering is adding signifiant additional costs to users, and Oracle is building a compelling case for itself as a viable CX alternative in the enterprise even outside of its solid install base. 

Oracle says that owning so much of its own infrastructure to deliver at via Oracle Cloud Infrastructure and other data and security elements allows it to keep its own costs low and thus extend the savings to users. Also, the company notes that Oracle customers tend to be achieving fast time to value with their AI tools because so much of the data, application layer, security, etc. is pre-integrated - meaning more federated data for more effective AI results, all in a more secure and guardrailed environment. 

"Sales processes have become overcomplicated and with so many administrative and complex tasks required, sales teams are struggling to find the time needed for effective and meaningful customer communication,” said Rob Tarkoff, executive vice president and general manager, Oracle Cloud CX. Said in a company statement “The new AI agents and generative AI capabilities within Oracle Cloud Sales eliminate many of these rigid and time-consuming tasks, which enables sales teams to boost productivity and create more impactful connections with customers.”

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Delta Air Lines completes cloud migration with focus on AI and data-driven customer experience

Delta Air Lines completes cloud migration with focus on AI and data-driven customer experience

Delta Air Lines has migrated most of its technology infrastructure to the cloud and is starting to leverage generative AI (GenAI) for personalized pricing, digital concierge services, and optimizing the customer experience.

The 100-year-old airline recently outlined its technology investment at its Investor Day in November, then announced partnerships and various initiatives at CES 2025 and followed up with strong fourth-quarter earnings and a bright outlook.

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Delta reported 2024 earnings of $3.46 billion with revenue of $61.6 billion, up from $58 billion in 2023. For 2025, Delta projected earnings growth of more than 10% with first-quarter revenue growth of 7% to 9%. For 2025, Delta expects free cash flow above $4 billion.

Speaking at CES 2025, Delta CEO Ed Bastian outlined Delta Concierge, which is a GenAI tool designed to personalize customer experience within the Delta app. Delta also announced partnerships with Uber, Joby (an electric air taxi service), and a partnership with YouTube.

“Together, these products and partnerships reflect our continued commitment to investing in and providing our customers with a superior travel experience,” Bastian said. “They drive greater engagement with our SkyMiles members that extend well beyond air travel, improving customer satisfaction and deepening loyalty to Delta.”

Indeed, Delta, which has sparred with CrowdStrike over the security vendor’s outage, is playing the long game with customers and is betting a more agile technology infrastructure and AI can create the personalization needed to drive lifetime value of a flier.

The airline has been investing in technology for the last three to four years. In 2022, Delta said it would migrate its infrastructure to AWS. That work is mostly complete, Bastian said, speaking during Delta’s Investor Day.

“We made some pretty healthy investments over the course of COVID to move the majority of our technology infrastructure to the cloud with AWS,” Bastian said. “And we’re just about at the end of that journey. It’s going to drive a lot of agility that’s going to drive a lot of speed, a lot of efficiency, for our ability to continue to not just provide stability to our infrastructure, but it’s also going to allow us to continue to change and move faster than others. Our platforms are modernized. Our software is continuing to get better, and it’s also allowed for the integration of many of the new AI and data analytics tools that you hear a lot about.”

Bastian said that Delta has invested about $500 million over the last three to four years moving to AWS. But that investment will pay off because it’ll enable Delta to leverage AI.

“We all know there’s a lot of hype around AI, and it’s something that we all look at and wonder if it’s going to live up to the promise,” Bastian said. “I think AI is going to be incredible in terms of its impact on our business, but it’s only going to be incredible if we’re prepared to actually harness the power. Our focus on AI is to learn, and to listen, and to make certain that we’re ready before we jump in with both feet.”

Delta is looking to apply AI to three core areas of its business. These include:

Reliability of operations. “You think about the 5,000 flights a day that operate in all kinds of weather conditions, with all kinds of variables, with staffing coming from all over the world—it’s a Rubik’s Cube every single day, and you’re trying to optimize and get the best answer,” Bastian said.

Bastian added that scheduling, prioritization, and more-efficient routing will all be key use cases for AI.

Connected experiences. Bastian said that Delta is going to leverage technology to connect with customers. At AWS re:Invent 2023, Delta said that it leveraged Amazon Bedrock to try out different models to deliver answers to customers. It’s very early, but Delta is able to hit you up during a log-in and know it’s your birthday. The free Wi-Fi and seamless log-in experience doesn’t hurt, either.

Revenue growth. Delta will leverage AI to drive pricing and revenue growth. “When you have a brand that has a 26-plus-point advantage versus your network competitors but your revenue premium is 14 points, I think there might be opportunity to do better,” Bastian said.

The framework for AI

Bastian said that Delta is early in its AI journey, but it has a framework for projects over the next three to five years. The framework is simple: Every AI project needs to fit into one of Delta’s three core priorities of reliability, experience, and revenue generation.

Delta’s operating margins are typically between 11% to 12% and the company expects those margins to grow to the mid-teens in the years ahead. Delta is also planning to grow earnings at a double-digit clip on average over the next five years.

Glen Hauenstein, President of Delta, is on the hook for delivering those metrics and said technology is critical to delivering a premium product and experience. “We saw this many years ago and went on a journey to de-commoditize the airline space,” Hauenstein said.

Hauenstein noted that everything Delta does revolves around the brand: The investment in airport facilities is brand. The network of lounges is brand. Technology partnerships is brand. The ability to expand into adjacent travel categories is brand. And the membership experience is brand.

“We’re able to describe an experience and not only create it, but sell it and retail it,” Hauenstein said. “Retail is really the frontier that we will continue to lead over the next three to five years.”

Delta also plans to use technology to segment its audience. Delta has strong ratings with millennials and baby boomers, two generations with money for travel, and is installing a digital footprint that can grow its share for future generations.

Going forward, Delta will optimize its offering through data and technology. The data will lead to experimentation, new bundles, and subcategories for seating. “We’re going to test and learn along the way, but we’re going to start from the bottom up,” Hauenstein said. “In 2025, we’re going to try some segmenting, some additional segmenting of the main cabin. You’ll see us attempting and really testing what consumers want in their bundles and what they’re willing to pay for. That’s really the way I think good retailers work and we’re going to transform ourselves over the next three to five years.”

‘Right offer, right time, and right channel’

When you listen to Bastian and Hauenstein riff, they do sound more like omnichannel retailers than an airline.

And like most omnichannel retailers, Delta will be betting on data to connect with customers.

Hauenstein said Delta is looking to connect the “right offer, right time, and right channel.”

“What we’re really trying to do is to get inside the mind of our consumer and present them something that’s relevant to them at the right time with the right price,” Hauenstein said.

Delta has partnered with an Israeli startup called Fetcherr, which uses GenAI to create optimized offers. Hauenstein said Delta has worked with Fetcherr for more than a year and about 1% of the network is being priced by the startup.

“This is a full re-engineering of how we price and how we will be pricing in the future. And if you think about it today, there are two disciplines: There is pricing, which sets the price points, and then there’s revenue management, which controls access into the inventory of those price points,” Hauenstein said, noting that over time pricing and revenue management will converge. “It’s going to really be just offer management. We will have a price that’s available on that flight, on that time to you, the individual.”

With the help of AI, Delta is betting that its systems can act like a digital analyst that can simulate real-time price points and demand.

“We’re letting the machine go ahead and price in a very controlled environment,” Hauenstein said. “It’s going to be a multiyear, multistep process as we continue to learn, innovate, teach the machine and change the business process, but the initial results show amazingly favorable unit revenues.”

Delta executives said the company will go slow even though it wants first-mover advantage and to retool its business processes as quickly as possible. Hauenstein said Delta will iterate to offer “clean choices” that aren’t overwhelming when it comes to multiple offers.

“Personalized and seamless experiences—we put a lot of effort into this, and we have a long way to go,” Hauenstein said, adding that these experiences will be priority now that the cloud migration is complete. “We can redirect to really implementing some of these changes that we have in the queue that have been kind of sitting, waiting for the cloud to be fully migrated.”

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