Matt Engfer and Adam Fleming, co-founders of Cubby, are building an AI-native operating platform designed to modernize the self-storage industry.
Matt Engfer Cubby is a founder story that started with an unexpectedly simple experience: trying to rent a storage unit. Engfer, who was working in commercial real estate technology at VTS, needed temporary space for his art business. What should have been a straightforward online transaction required a phone call and a process that felt disconnected from the modern technology he knew was possible.
That experience exposed a much larger problem. Self-storage businesses were still relying on outdated software, disconnected systems, manual processes and limited reporting tools. Engfer began speaking with storage operators, attending industry events and learning how facilities actually worked. He eventually teamed up with Adam Fleming, a software engineer whose background included Goldman Sachs and Meta Platforms, to build a modern alternative.
The result was Cubby, a New York-based software company developing an AI-native operating platform for self-storage businesses. Its technology combines facility management, tenant management, online rentals, revenue optimization, call handling and AI-powered customer communication.
On January 22, 2026, Cubby announced a $63 million Series A investment led by Growth Equity at Goldman Sachs Alternatives. The announcement represented a major milestone for a company seeking to replace legacy systems with an integrated technology platform.
Here is how the founders identified an overlooked industry problem, built a self-storage software business, developed its AI capabilities and attracted one of the world’s most recognized financial institutions.
Matt Engfer Cubby: Who Is the Founder?
Matt Engfer is the co-founder and CEO of Cubby, a software company focused on modernizing self-storage operations through integrated technology and artificial intelligence.
Before launching the company, Engfer worked at VTS, a commercial real estate technology business, as a director of client success. His professional experience gave him exposure to how software could improve the way real estate businesses manage customers, operations and information.
However, his interest in self-storage came from a personal experience rather than a conventional technology market opportunity.
While working at VTS, Engfer also operated a side business selling art. When he needed somewhere to temporarily store his artwork, he rented three self-storage units.
The rental experience surprised him. Despite working in real estate technology, he found that the process still required a phone call to book a unit.
It was an outdated customer experience in an industry that should have benefited from the digital transformation happening elsewhere in real estate.
That moment became an important starting point for the company.
Instead of assuming that one inconvenient rental experience represented an industry-wide problem, Engfer began investigating the market. He attended self-storage conferences and trade shows, speaking with operators about their software, business processes and daily challenges.
Those conversations revealed a recurring pattern: operators were managing increasingly complex businesses with technology that often created more work than it removed.
The Matt Engfer Cubby story is therefore not simply about developing another software product. It is about recognizing that an established industry had not received the same level of technology innovation as other parts of real estate.
From VTS to the Self-Storage Industry
Engfer’s transition from commercial real estate technology to self-storage was shaped by the gap between what modern software could deliver and what storage operators were actually using.
His experience at VTS provided a useful reference point. He had seen how technology could improve the management of commercial real estate relationships and operations.
But the self-storage experience was different.
A customer looking to rent a storage unit often had to navigate an inconvenient process. Facility operators, meanwhile, were dealing with outdated management systems, disconnected applications and inefficient administrative work.
Engfer saw an opportunity to bring a more modern digital experience to the industry.
He began attending industry events and talking directly with storage business owners. The more conversations he had, the clearer the opportunity became.
Operators were struggling with:
- Outdated facility management software.
- Disconnected technology systems.
- Poor online rental and checkout experiences.
- Limited visibility into business performance.
- Expensive software that did not always justify its cost.
These were not problems that could be solved simply by improving a website.
The industry needed a more comprehensive operating system that connected facility management, online rentals, pricing and customer communication.
According to an interview published by Inside Self-Storage, Engfer and Fleming also worked directly at storage facilities before building their software. They wanted to understand daily operations rather than rely entirely on assumptions about what operators needed.
That hands-on research became a defining part of the company’s product development philosophy.
Adam Fleming: The Technology Co-Founder
Matt Engfer brought commercial real estate technology and customer experience knowledge to the business. Adam Fleming brought the engineering expertise needed to build the platform.
Fleming is Cubby’s co-founder and chief technology officer.
Before joining the company, he worked at Goldman Sachs and Meta Platforms, gaining experience in technology and software development.
The two founders approached the opportunity from complementary perspectives.
Engfer understood the customer experience and the commercial problems facing storage operators. Fleming could translate those requirements into software architecture and technical capabilities.
Their first challenge was not simply creating a new interface. It was building a reliable foundation for an industry that depends on accurate financial information, occupancy data, tenant records and operational workflows.
The founders also spent time working inside storage facilities to understand how the business operated from the ground up.
This was important because self-storage management involves more than renting available units.
Operators must handle payments, tenant communication, access, maintenance, delinquency, pricing, reporting and other operational responsibilities.
A software platform that fails to understand those connections can create additional complexity instead of reducing it.
The Matt Engfer Cubby founding partnership brought together commercial insight and technical execution around a specific industry problem.
The Problem: An Industry Running on Legacy Software
Self-storage businesses operate in a competitive market where relatively small improvements in occupancy, pricing, customer conversion and operating costs can affect profitability.
Yet many operators have historically depended on software systems that were designed around older business models.
Some businesses use separate tools for facility management, online rentals, marketing, payment processing, revenue management and customer communication.
When these systems do not communicate effectively, employees must move information between applications, check multiple dashboards and manually coordinate tasks.
Consider a prospective tenant looking to rent a unit.
The customer expects to check availability, compare sizes, see pricing and complete the rental online. If the checkout experience is slow or confusing, the operator risks losing the customer before the rental is completed.
Once the tenant moves in, the business must manage recurring payments, account information, customer requests and potential delinquency.
The operational process continues long after the initial rental.
Revenue management creates another challenge. Pricing must respond to occupancy, competitor rates, demand and local market conditions. A facility with limited data visibility may struggle to identify opportunities or react quickly.
Cubby’s founders identified these problems as connected parts of a larger technology gap.
Their objective was to build a platform that could manage the entire operating process instead of asking businesses to assemble multiple disconnected products.
This industry-first perspective is central to understanding why the founders chose self-storage rather than attempting to build a general-purpose real estate software company.
Building Cubby: From Industry Research to a Unified Platform
Cubby emerged from conversations with operators and direct experience inside storage facilities.
The company was launched in 2022, according to the Inside Self-Storage founder profile. Some business databases list 2021 or 2023, so the exact founding-year description should be treated cautiously. The company’s public funding and product announcements establish its later development milestones more clearly.
The founders wanted to bring the convenience and sophistication of modern e-commerce and software to an industry that had been underserved by technology innovation.
Rather than creating a single feature, they developed a broader platform designed to support the main activities involved in running a storage business.
The product direction included:
- Facility and tenant management.
- Digital rental and checkout experiences.
- Pricing and revenue optimization.
- Customer communication.
- Call routing and performance insights.
- Reporting and operational analytics.
The company’s central idea was to give operators a unified view of their business.
This could help reduce the need to switch between separate applications and give management teams more consistent access to information.
Cubby’s approach also emphasized flexibility. Different storage businesses operate in different ways, and software should not force every operator to follow the same processes.
In a September 2026 founder-authored article, Engfer emphasized that listening to customers and understanding their individual operating models had been part of Cubby’s product development from the beginning.
That customer-feedback approach is particularly relevant in vertical SaaS, where a company’s success often depends on understanding the details of one industry better than general-purpose software providers.
Inside Cubby’s AI-Powered Technology
Cubby describes itself as an AI-native operating platform for self-storage.
The distinction matters because the company is not simply adding a chatbot to an existing facility management system.
Its AI strategy is connected to operational activities across the platform.
One important example is Comms AI, which provides configurable AI voice agents for customer communication.
These agents are designed to handle incoming sales and service calls, answer customer questions and transfer conversations to human employees when required.
The goal is to ensure that potential renters and existing tenants can receive assistance without requiring every inquiry to be handled manually by a member of the team.
Cubby’s AI approach also extends into call routing and performance analysis.
Cubby Calls can intelligently route, record and transcribe calls according to operator preferences. AI-powered call grading provides additional insights into communication quality and team performance.
Another important area is revenue optimization.
Rather than relying entirely on employees to review pricing information, Cubby’s revenue management tools use machine learning to monitor competitor rates, occupancy and demand.
The platform can recommend pricing adjustments and intelligently update tenant pricing based on market conditions.
The broader objective is to move from software that simply stores information toward systems that can help complete work and improve decisions.
However, AI capabilities should be evaluated through their actual operational results. Accuracy, customer experience, escalation procedures and human oversight remain important considerations for businesses deploying voice agents and automated pricing.
For another example of how AI is being applied to property operations, see Denote Press’s Francesco Decamilli and Uniti founder story.
Revenue Management, E-Commerce and Facility Operations
Cubby’s platform combines several major components of self-storage management.
1. Facility Management
The facility management system gives operators a unified view of facilities, units and tenants.
Instead of requiring separate logins for every property, management teams can oversee their portfolios from one system.
Built-in task management and facility walkthroughs help coordinate daily responsibilities and keep teams aligned.
Real-time analytics bring together information from marketing, pricing and operations.
2. Tenant Management
Tenant management is essential to running a storage business.
Operators need to maintain accurate customer records, manage accounts and payments, respond to inquiries and handle changes throughout the rental relationship.
Cubby brings these activities into its broader operating platform.
3. E-Commerce
Online rental experiences are increasingly important for self-storage businesses.
Cubby’s e-commerce technology allows operators to display available inventory and rental options through their websites.
Its APIs and checkout components are designed to make it easier for prospective tenants to view units and complete rentals online.
The aim is to reduce friction during the customer acquisition process and improve conversion.
4. Revenue Management
Cubby’s revenue management technology uses machine learning to monitor competitors, occupancy and demand.
The platform uses these signals to recommend pricing strategies and intelligently adjust tenant rates.
This is particularly relevant for multi-facility operators who need to manage pricing decisions across different locations.
5. Calls and Comms AI
Customer inquiries can become a significant operational burden when a business manages hundreds or thousands of storage units.
Cubby Calls provides call routing, recording, transcription and AI-powered call grading.
Comms AI adds configurable voice agents that can respond to sales and service inquiries and transfer conversations to human staff.
6. Reporting
The reporting functionality gives operators access to business information across different parts of their operation.
The goal is to make it easier to monitor performance and make decisions using connected operational data.
Together, these products position Cubby as a comprehensive self-storage operating platform rather than a narrow rental-management application.
The $63 Million Goldman Sachs Investment
One of the biggest milestones in the Matt Engfer Cubby journey came on January 22, 2026, when the company announced a $63 million Series A investment.
The round was led by Growth Equity at Goldman Sachs Alternatives, with participation from existing investors.
Cubby described the investment as support for its mission to modernize self-storage operations through AI and technology.
The company said the capital would help accelerate product development, expand its talent base and improve the products and services available to storage operators.
The announcement also highlighted the importance of building reliable infrastructure.
According to Cubby, legacy systems had prevented operators from implementing modern pricing strategies, delivering better customer experiences and making data-driven decisions.
The investment was therefore intended to support more than additional software features. It would help the company develop a stronger foundation for a broader AI-powered platform.
Goldman Sachs Alternatives also explained its investment rationale.
Kelly Wallace, an investor at Growth Equity at Goldman Sachs Alternatives, said the company was replacing legacy systems with a modern, scalable platform and described its AI-enabled workflows and customer-centric approach as important strengths.
Wallace was also expected to join Cubby’s board of directors.
The official announcement confirms the $63 million Series A and its lead investor. It does not disclose the company’s valuation, so a specific valuation should not be presented as established fact.
The Investors Behind Matt Engfer and Cubby
Goldman Sachs Alternatives led the January 2026 investment.
The investment is notable because Cubby operates in a specialized vertical software market rather than a broad consumer technology category.
Its opportunity depends on modernizing an established industry with a large base of independent operators and multi-facility businesses.
The company has also received backing from earlier investors, including Fractal Software and Third Prime, according to its earlier funding coverage.
Inside Self-Storage reported that Engfer and Fleming had raised $7 million from those venture investors before the later Goldman Sachs announcement.
The combination of earlier venture backing and the larger Series A suggests that the company has attracted interest from investors who see potential in vertical software for self-storage.
Goldman Sachs’ involvement also brings strategic support and access to a wider financial and business network.
However, investment should not be confused with proof of long-term success. The company’s ability to retain customers, expand its product adoption and deliver measurable improvements will ultimately determine the value of that backing.
Traction: Hundreds of Operators and Hundreds of Thousands of Units
Cubby’s growth story is supported by several company-reported operating figures.
In its January 2026 funding announcement, the company said its platform was trusted by more than 400 operators managing over 450,000 units across North America.
A May 2026 announcement about the appointment of Ross Levinsky as COO reported more than 400 operators managing over 600,000 units.
A September 2026 announcement about Andrew Capranos described Cubby as serving thousands of facilities across North America.
These figures reflect different reporting dates and measurement descriptions. They should not be combined into a single historical statistic.
The company’s customer testimonials also offer insight into how operators perceive the platform.
Brendan Daly of Bald Eagle Storage praised the platform’s expanding functionality.
Faraz Hemani of Iron Storage highlighted the company’s customer support and ability to deliver on expectations.
Cubby also features a case study about ClearHome, which describes how the company approached accounting accuracy and operational data.
These customer stories are useful because self-storage operators are buying software that affects everyday business processes. A platform must do more than demonstrate technical sophistication; it needs to work reliably for the people managing facilities.
The Matt Engfer Cubby growth story therefore rests on two connected factors: the scale of its customer adoption and its ability to make a complicated operating environment easier to manage.
Cubby’s Position in the Self-Storage Software Market
Self-storage software is a specialized category within property technology.
Operators need systems that support facility operations, rental management, online checkout, payment processing, revenue management and customer service.
Companies such as Storable and other established storage technology providers operate in this market, while newer vertical SaaS businesses are attempting to modernize the customer and operational experience.
Cubby’s differentiation is based on integration.
Instead of focusing on one isolated part of the business, it aims to combine multiple operational functions in one platform.
Its main competitive strengths include:
Operator-focused development: The founders researched the industry directly and built around the needs of storage operators.
Unified technology: Facility management, e-commerce, pricing and communication tools are connected within one platform.
AI integration: Voice AI and machine learning are incorporated into customer communication and revenue management.
Portfolio visibility: Operators can manage multiple facilities and access real-time information through a unified interface.
Customer feedback: The company emphasizes adapting its software to different operator workflows.
There are also competitive challenges.
Established providers may have deeper relationships with existing operators and long histories of handling industry-specific requirements.
New competitors can introduce AI features, while customers may be reluctant to migrate from software that already contains years of operational and financial records.
Cubby’s challenge is to demonstrate that its integrated platform delivers enough value to justify adoption and, where necessary, replacement of legacy systems.
Leadership, Team and Expansion
Matt Engfer leads Cubby as co-founder and CEO, while Adam Fleming serves as co-founder and CTO.
The company has also strengthened its leadership team as it has grown.
In May 2026, Cubby announced that Ross Levinsky had joined as chief operating officer. Levinsky previously worked as CTO and partner at HBK Capital Management and held technology positions at Goldman Sachs, Google, Bridgewater and D. E. Shaw.
In September 2026, the company announced that Andrew Capranos had joined as president of self-storage.
Capranos brought extensive experience in real estate and self-storage operations, adding a direct operator perspective to the company’s product and customer strategy.
These appointments indicate an effort to combine technology expertise with practical industry knowledge.
Cubby lists offices in New York City, Lehi, Utah, Toronto and Sofia, Bulgaria.
Its expansion strategy is closely tied to customer success, implementation, engineering and the continued development of AI-powered functionality.
Risks and Open Questions
A balanced assessment of Cubby should consider the challenges that come with replacing established software in an operationally demanding industry.
1. Legacy system migration
Storage businesses may have years of tenant, payment and financial information stored in existing systems. Migrating this information accurately is essential to customer trust.
2. AI reliability
Voice AI must understand customer questions, provide accurate information and transfer complex issues to employees when necessary. Errors can affect customer satisfaction and rental conversion.
3. Pricing decisions
Automated pricing must account for local demand, occupancy, competition and customer relationships. Incorrect pricing decisions can damage revenue or tenant retention.
4. Competition
Established storage software companies have existing customer relationships and industry experience. New AI-focused competitors may also challenge Cubby’s position.
5. Customer adoption
A unified platform may offer significant benefits, but operators need time, training and confidence before changing their core business software.
6. Scaling customer support
As the number of facilities grows, implementation and customer support must remain reliable. Software alone cannot guarantee a successful customer relationship.
7. Independent performance evidence
The company publishes encouraging adoption and product claims. More independently verified evidence about customer retention, revenue improvements and long-term cost savings would strengthen the picture of its commercial performance.
These are normal challenges for a growing vertical SaaS company, but they will help determine whether Cubby can become a long-term technology partner for the industry.
What’s Next for Cubby?
Cubby’s next chapter is likely to center on expanding its AI-native platform and strengthening its position among self-storage operators.
The company has already invested in facility management, online rentals, revenue optimization, customer communication and reporting.
Its AI roadmap suggests a move toward systems that can perform more operational work rather than simply display information or provide recommendations.
Voice agents that handle inquiries and rental processes are one example.
The broader opportunity is to make software a more active participant in business operations.
However, the company’s success will depend on balancing automation with accuracy, transparency and human oversight.
Engfer’s September 2026 founder-written article reinforces another part of the strategy: software should adapt to how storage operators run their businesses rather than forcing every operator into the same workflow.
That philosophy could become increasingly important as Cubby serves larger portfolios with different operating requirements.
Lessons From the Matt Engfer Cubby Journey
The Matt Engfer Cubby journey offers seven practical lessons for entrepreneurs.
1. Pay attention to ordinary customer experiences.
A frustrating storage rental experience revealed an opportunity in an established industry. Sometimes a major business idea starts with an everyday inconvenience.
2. Research the industry before building.
Engfer spoke with operators, attended industry events and learned about facility operations. That research helped validate the problem before developing the product.
3. Understand the business from the ground up.
The founders worked directly at storage facilities to understand the realities of operating the business.
4. Combine complementary skills.
Engfer brought commercial and customer experience knowledge, while Fleming brought technical expertise. Different capabilities helped build a stronger founding partnership.
5. Solve the broader workflow.
Rather than developing one isolated tool, Cubby connected facility management, pricing, e-commerce and customer communication.
6. Build around customer feedback.
Different operators have different requirements. Listening to customers can help software become more useful and adaptable.
7. Make technology produce measurable outcomes.
The purpose of AI should not simply be to make a product sound advanced. It should improve efficiency, customer experience and business performance.
Frequently Asked Questions
Who is Matt Engfer?
Matt Engfer is the co-founder and CEO of Cubby, an AI-native software platform for self-storage operators. He previously worked at VTS in commercial real estate technology.
What is the Matt Engfer Cubby story?
The Matt Engfer Cubby story follows an entrepreneur who discovered outdated technology in the self-storage industry after trying to rent storage units. He teamed up with Adam Fleming to build a unified software platform for facility management, pricing, e-commerce and AI-powered communication.
Who founded Cubby?
Cubby was co-founded by Matt Engfer and Adam Fleming. Engfer serves as CEO, while Fleming serves as CTO.
What does Cubby do?
Cubby provides AI-native management software for self-storage businesses. Its platform combines facility management, tenant management, e-commerce, revenue management, call routing, AI communication and reporting.
When was Cubby founded?
Inside Self-Storage reports that Matt Engfer and Adam Fleming launched the company in 2022. Some third-party databases report different founding years.
How much funding has Cubby raised?
Cubby announced a $63 million Series A investment in January 2026, led by Growth Equity at Goldman Sachs Alternatives. It had also raised earlier funding from venture investors.
Who invested in Cubby?
The $63 million Series A was led by Growth Equity at Goldman Sachs Alternatives, with participation from existing investors. Earlier reported investors include Fractal Software and Third Prime.
What is Cubby’s AI technology?
Cubby uses AI and machine learning for customer communication, voice agents, call analysis and revenue management. Its Comms AI product can handle customer inquiries and transfer conversations to human employees.
How many operators use Cubby?
Cubby reported more than 400 operators and 450,000 units in January 2026. A May 2026 announcement reported more than 600,000 units. These are company-reported figures from different dates.
Where is Cubby based?
Cubby is headquartered in New York City and lists additional offices in Lehi, Utah, Toronto, Canada and Sofia, Bulgaria.
Is Cubby a hospitality PMS?
No. Cubby is a self-storage management platform. It provides software for storage facilities, tenants, rental operations and revenue management rather than conventional hotel management.
What makes Cubby different from traditional self-storage software?
Cubby combines facility management, e-commerce, revenue optimization, customer communication and AI capabilities in one integrated platform. Its approach is designed to reduce dependence on disconnected legacy systems.
Conclusion
The Matt Engfer Cubby story demonstrates how an ordinary customer experience can reveal a much larger business opportunity. What began with a frustrating attempt to rent three storage units became the starting point for a technology company focused on modernizing an entire industry.
Together, Engfer and Fleming combined commercial real estate experience with software engineering to build an integrated platform for self-storage operators. Its $63 million Series A investment led by Goldman Sachs Alternatives represents a major milestone in that journey.
Cubby’s opportunity extends beyond replacing old software. By combining facility management, e-commerce, revenue optimization and AI-powered communication, it is attempting to make self-storage operations more connected and efficient.
The real test will be whether the company can maintain product reliability, deliver measurable customer outcomes and compete against established industry providers as it grows.
If it succeeds, Cubby could become an important part of the next generation of self-storage technology.
For more founder journeys in property technology and AI, explore Francesco Decamilli’s Uniti story and other articles in the DenotePress Founder Stories collection.
