Calendar icon June 28, 2023

How to Create Self-Service Tenant Onboarding Workflows

A tenant self-service onboarding workflow is a system that enables new residents to complete the onboarding process by themselves using online portals, automated communication workflows, and chatbots, with minimal involvement from property management teams.

Why automate? Automation can provide smaller property management companies with an edge by streamlining processes, improving communication with residents, and reducing manual workloads. By leveraging tech tools such as property management software, online portals, and automated workflows, smaller companies can increase efficiency, provide better customer experiences, and compete with larger players in the industry. 

Implementing tech is especially important – let’s actually say it’s imperative – in today's digital age, where residents expect instant communication and online access to property information. By embracing tech solutions, smaller property management companies can not only keep up with industry trends but also stay ahead of the competition. 

Today we are talking with a leader in property management who has also been an early adopter of some of the most innovative new AI and tech solutions for the property management industry – Wolfgang Croskey. Wolfgang shares some of the best ways to automate your resident onboarding process and how to avoid pitfalls along the way. 

Key Learning Objectives:

  • Do I need to implement self-service workflows for resident onboarding?
  • What are the greatest benefits of implementing this automated process?
  • What are the pitfalls of tech and automation in resident onboarding?
  • How do I create self-service onboarding workflows?

Meet the Expert: Wolfgang Croskey, Founder & President of How’s My Rental

Wolfgang Croskey has been working in real estate since he was a little kid. From stuffing envelopes, unclogging toilets, and serving notices to creating leases, he has touched on all aspects of property management. He is a well-respected member of NARPM, a servant leader to his community, and, to top it all off, a father of 6. Wolf has been a board member and president of the Pittsburg Chamber of Commerce, where he is currently the CEO, providing leadership and direction to the Chamber in their daily activities. He is also the Founder of How's My Rental, a site-awareness servicing California landlords as well as the founder of The Perfect Tenant, a Master Leasing Company. 

A Note on Language:

At Second Nature, we prefer the term “residents” over “tenants.” It’s our belief that focusing on the people in every interaction helps us to create better, more valuable, and more profitable business strategies in the long run. Property management is all about focusing on what residents and investors – human beings – want and need! But through this article, you’ll see us use both “tenants” and “residents” due to the fact that many parts of our industry are very technical and require accurate terminology. 


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Why should you implement tenant self-service onboarding workflows?   

Tenant, or – as we prefer to say here at Second Nature – resident onboarding is an essential aspect of property management. But as any PM will tell you, it can be time-consuming and resource-intensive. 

That's why a resident self-service onboarding workflow can be a game-changer for property managers. By providing residents with online self-service portals, automated communication workflows, and chatbots, self-service onboarding workflows can reduce the need for manual work, streamline the onboarding process, and improve tenant experiences. 

According to Croskey, property managers across the country are adopting self-service workflows and automation – but there’s still a lot of room for growth.

“There is a growing trend towards adopting self-service onboarding workflows in the property management industry, driven by the numerous benefits they provide, such as reduced manual work, faster lease execution, and improved resident experience,” Croskey says. “However, there may be some pushback from property managers who are hesitant to adopt new technology or concerned about potential security risks. Addressing these concerns through education and demonstrating the benefits of automation can help encourage wider adoption.”

As we’ve mentioned before, Croskey has called automation the “great equalizer.”

How? According to Croskey, “It allows us to compete with these nationwide companies and to provide not only the same level of service but to be able to pivot and adapt much quicker than those larger companies can. So for me, you're a smaller company, AI and Automation Tech is that equalizer that's going to allow you to shine just as well as these larger companies.”

Are there disadvantages to adopting more automation?

Croskey says there are areas of vulnerability for PMCs looking to automate their processes more deeply. 

The issue? Not having those processes right in the first place. Croskey says he’s seen many property managers assume that AI is going to fix their problems. 

“The reality is, if you don't have your policies, procedures, and processes in place, there is no tool on earth that's going to be able to save your bacon,” says Croskey. “Look at McDonald’s: At one point, some team had to roll up their sleeves and make the process of how to build the Big Mac. And it probably took quite a while to do that. But now that it's done, they haven't changed the Big Mac for at least 40 years. It's still the same nasty hamburger.” 

With a chuckle, Croskey continues: “A lot of times, myself included, we try to find technologies that can help us avoid that initial work. You’ve got to roll up your sleeves, and you’ve got to get through that.” 

How to create tenant self-service onboarding workflows 

So, let’s say you’ve accepted that building self-service workflows gives massive advantages to your PMC. And let’s say you’ve established your processes in a way you’re confident is efficient, legal, etc. Now how do you create the automation to help new residents help themselves? 

Here’s what Croskey advises, in his own words.

To create a resident self-service onboarding workflow, property managers should consider the following steps:

  1. Select Software: “To optimize your property management process, it's crucial to select software that offers robust onboarding automation features such as online applications, tenant screening, and digital lease signing.”  
  2. Integrate Workflows: “Ensure the workflow is tailored to your needs and seamlessly integrates with your existing accounting, maintenance, and communication platforms.” 
  3. Implement Data Security: “It's equally important to implement stringent data security protocols to safeguard resident information during the onboarding process.” 
  4. Equip Resident with Resources: “Finally, equip residents with the necessary resources to familiarize themselves with the self-service workflow and provide comprehensive training to your team to ensure a smooth transition.”

With those steps in place, let’s look at some of the specific aspects of the onboarding process that property managers can start with when building self-service tools.

Virtual tours 

Croskey explains that AI-powered chatbots can provide virtual property tours – answering questions, and offering additional information to potential residents in real-time.

Here’s how it works:

  • Prospective tenants can access an online customer portal or chatbot that offers virtual tours of the property. They can interact with the chatbot to select a specific unit or area of the property they want to tour.
  • The chatbot or other AI tech can then use VR or AR technology to provide a 360-degree view of the selected area. Prospective tenants can move around and explore the space as if they were physically there.
  • The chatbot can also provide additional information about the property, such as floor plans, rental rates, and amenities.

Rental application 

Nearly all automated property management solutions can provide automated rental applications. 

Here are some tips on how to ensure you’re deploying it effectively:

  • Provide residents with an online portal where they can submit their rental applications and supporting documents electronically. This can include personal information, employment history, rental history, and financial statements.
  • Use automated workflows to guide residents through the application process and send notifications when additional information or documents are required.
  • Implement electronic signature software to enable residents to sign and submit rental agreements and other legal documents online.
  • Integrate the rental application process into your property management software to streamline the process and reduce manual workloads.

Beyond that, Croskey explains that “Chatbots can guide residents through the online application process, answering questions and providing support as needed.” 


download rental inspection checklist template


Tenant verification 

Property managers can make tenant verification self-service by implementing tenant verification software into their property management system. These software solutions will help by:

  • Leveraging an online portal where residents can submit their information and documents for verification, including rental history, employment verification, and credit checks.
  • Using chatbots or automated workflows to guide residents through the process, answer questions, and provide them with updates on the status of their applications.
  • Implementing secure authentication measures to ensure only authorized individuals can access and submit sensitive information.

Lease negotiation

Here are some steps to make lease negotiation automated or self-service:

  1. Property managers can create an online lease agreement platform accessible to residents via a unique login and password.
  2. The platform can provide residents with the ability to view and select available properties and rental units, along with the associated lease terms and rental rates.
  3. Residents can submit a lease application online, which can include information such as their employment history, income, and rental history.
  4. The platform can automatically screen the application, verifying information such as credit score, employment status, and income.
  5. Once the application is approved, the resident can negotiate lease terms such as the lease duration, rental rate, and security deposit directly with the property manager via the online platform.
  6. The online platform can use AI to generate a lease agreement that reflects the negotiated terms, which can be reviewed and signed by the tenant and property manager online.

Property services onboarding 

Getting residents set up with all the services, utility connections, etc. that they need can be a hassle for everyone. You can end up answering several calls and questions, while they may spend hours on the phone trying to identify what they need and how to get it. 

Self-service onboarding can make a huge difference. One example is Second Nature’s Movie-In Concierge, part of our full-service Resident Benefits Package. In one phone call, residents find out what their best options are and can even get help simplifying setup. An experienced concierge confidently guides multiple people every day to properly set up their utilities. 

We’ve also automated filter delivery to ensure residents replace filters on time, which saves them roughly $15 per month in HVAC fees.

Document management

Property managers can make document management self-service by providing tenants with an online portal where they can access, upload, and sign documents. Here are some steps to make document management self-service:

  1. Property managers can create an online portal accessible to residents via a unique login and password.
  2. Set up permissions so residents can upload documents such as lease agreements, rental applications, and move-in checklists to the online portal.
  3. Property managers can upload documents such as rental payment receipts, notices, and lease addendums to the online portal.
  4. The online portal can provide residents with the ability to digitally sign documents, eliminating the need for paper-based signatures.
  5. Property managers can use automated workflows to track document submissions, ensure that all documents are complete, and send reminders to tenants who have outstanding documents.
  6. The online portal can be integrated with the property management software, ensuring all documents are properly filed and easily accessible.

Croskey adds that “AI can help organize, store, and retrieve documents related to the onboarding process, streamlining the experience for both property managers and residents.”

Resident communication

Here are some steps to automate resident communication and ensure residents can help themselves to the info they need.

  1. Property managers can create an online portal that can provide residents with information about their lease, rent payments, and property services, as well as the ability to submit service requests and communicate with the property manager.
  2. Chatbots or other AI tools can provide instant communication to residents during the onboarding process, answering questions and addressing concerns efficiently.
  3. Property managers can use automated workflows to send reminders to residents about rent payments, lease renewals, and move-in/move-out procedures.
  4. The portal can provide residents with the ability to report maintenance issues, request repairs, and track the status of their requests.
  5. Property managers can use automated workflows to manage and track service requests, assign tasks to maintenance staff, and ensure the timely completion of service requests.
  6. The portal can provide residents with access to a knowledge base or FAQs, where they can find answers to common questions about their lease and the property.

Maintenance coordination

AI and chatbots can help coordinate move-in inspections, maintenance requests, and repairs, ensuring a smooth transition for new residents.

The best way to do this is to implement a maintenance management system that integrates via an API with the resident communication platform.

  1. Property managers can provide new residents with access to the online portal, where they can submit maintenance requests and track the status of their requests.
  2. The portal can include a list of frequently requested maintenance tasks and allow residents to select the task and provide details about the issue.
  3. You can use an automated workflow to assign maintenance tasks to the appropriate staff member, schedule the task, and notify the resident of the scheduled date and time.
  4. The maintenance staff can update the status of the task on the portal, allowing the resident to track the progress of the repair.
  5. You can use data analytics to identify recurring maintenance issues and proactively address them before they become larger problems.
  6. Finally, you can provide residents with the ability to rate and provide feedback on the maintenance staff's performance, allowing property managers to continuously improve their service.

What are some of the best tools for implementing self-service onboarding workflows?

Several automation tools have emerged as industry leaders in resident onboarding. The best tool for your property management business will depend on your specific needs and requirements, says Croskey. 

He recommends looking into some of the more popular options online, including:

  • AppFolio: AppFolio is a comprehensive property management software that offers automated tenant onboarding, including online applications, screening, and lease signing.
  • Buildium: Buildium provides an end-to-end resident onboarding solution, including application management, tenant screening, and electronic lease signing.
  • LeadSimple: LeadSimple provides a process-oriented solution to onboarding a tenant. By using reactive templated emails, tenants have the ability to select options and then drive the process along.

What does the future of self-service onboarding look like?

We asked Croskey, and he answered:

As technology advances, self-service onboarding workflows can become even smarter by:

  • Personalized onboarding experiences: AI can analyze resident data to tailor the onboarding process based on individual preferences and requirements.
  • Integration with IoT devices: The onboarding process can be integrated with smart home devices, enabling residents to set up utilities, internet, or other services through voice assistants or other IoT interfaces.
  • Enhanced data security: Advanced encryption and AI-driven security measures can better protect resident data during the onboarding process.
  • Automated compliance checks: AI can automatically verify that leases and other documents comply with local, state, and federal regulations, reducing the risk of legal issues.

Final thoughts: Just get started!

Croskey says the key is to start learning how to use automation and AI now – and make sure you provide your team with the training and support they need. 

“My recommendation is just to get started and try these new tools,” he says. “And as you grow more confident, make sure to do your team justice by providing them training and providing them opportunities to learn how to use these tools as well. It’s not fair to say, ‘Okay, starting tomorrow, we're using this brand new tool, have a nice day.’ Really focus on some training.”

You can learn more by listening to our podcast with Wolfgang: Everything You Need to Know about Practical AI for Property Management. We’re keeping our fingers on the pulse of this space – stay tuned for more!

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10 Best Property Management Websites for Property Managers

One important approach that property managers can take to keep up to date with current industry trends and approaches is to maintain a watchlist of different property management websites. That's because these sites often reflect best design practices and website templates as well as content sharing ideas. Today we'll cover some of the top property management websites, all considered favorites and regularly featured on “Top 10” lists in the industry, with a focus on what makes each one distinctive, whether from a design optic or a content perspective. 1. Second Nature It may seem odd for us to mention ourselves first on this list, but we are genuinely proud of our brand and messaging! After all, we’re in this business for a reason – and that’s why the content of the Second Nature website is so squarely people-focused, with an emphasis on solutions that improve the lives of residents, investors, and property managers alike. There’s a robust business principle underpinning this “Triple Win” philosophy: residents want their needs proactively anticipated, and they're willing to pay (and stay) for that service. This is particularly true for a younger generation that is attuned to the convenience offered by services such as Uber and Amazon. That’s why the language used on the website reflects a humanistic approach that goes beyond transactional basics, preferring “residents” rather than “renters,” for example, or “home” rather than “rental property.” It’s also why Second Nature’s “Resident Benefits Package” is front and center, and designed to give residents, investors, and property management businesses a win. Accordingly, like all successful marketing, Second Nature’s value proposition is not only tangible – it’s personal. Visit to learn more. 2. Nest DC The Nest DC website also focuses on the families behind the doors and the people behind the investment portfolios. Although residential real estate management is associated with a certain gravitas, the language as well as the overall branding of the Nest DC website plays off of a certain “avian” riff and is designed for easy readability. Where most sites incorporate an “About Us” page, for instance, Nest DC features an “About the Birds” content piece. It’s all done with serious intent, however, and the website design is sleek, clear, and user-friendly. Visit 3. Bay Management Group As soon as you hit the homepage of the Bay Management Group website, it’s clear that its primary target audience consists of real estate investors and property owners. That said, the site does host an impressive library of instructional and advisory videos for tenants, property managers, and landlords, as well as investors. With the tagline “property management that’s a cut above the rest,” home page testimonials, and a blue-toned web design of the sort favored by financial institutions to connote trustworthiness, the focus is on differentiation through delivery of high-quality property management services to deliver reliable rental income. Beyond its primary “free property management analysis” feature, other web functionalities include a blog, owner portal, tenant portal, and various program application options. Visit 4. Rentberry Rentberry is a global rental platform describing itself as a “transparent and secure home rental platform that connects tenants and landlords.” With the tagline “Renting done right – finally,” its principal focus is on prospective tenants and landlords. Top-level navigation includes online rent payments/rent collection. It also includes tenant screening functionality as well as options to search listings for vacancies or create a property listing. Among the usual resources (blog, help center, FAQ, contact information), Rentberry also features pricing guides for both tenants and landlords to help streamline the onboarding process. Visit 5. Grace Property Management & Real Estate Based in Denver (Colorado), Grace Property Management & Real Estate focuses on both residential and commercial properties in Denver. Although the company was founded in 1978, its online presence boasts astute use of online marketing tools and property management solutions, to say nothing of search engine optimization, with numerous calculators and other resources available from the top-level menu. Like many companies with a strictly regional presence, Grace Property follows the tendency of including full social media and phone contact information in the header. Visit 6. MESA Properties MESA Properties gives its geographical focus the hero image treatment, with the tagline “Servicing the Inland Empire, Eastern San Gabriel Valley and High Desert.” Below the header, it also bills itself as “an owner-centered property management company.” Accordingly, much of the functionality on offer from the top-level navigation is focused on professional property manager services and resources for owners, but it does include resources for tenants, including maintenance request options, and portal login. Visit 7. Golden State Property Management The Golden State Property Management website presents with the tagline “Total property management of the most comfortable homes in the South Bay,” as well as two prominent feature buttons aimed at residents (“Pay Rent”) and potential residents (“Search Vacancies”). With straightforward top-level menu options, mobile-friendly design, and high-contrast navigation elements, this site is exemplary in its simplicity. Visit 8. Sleep Sound Property Management Sleep Sound Property Management takes aim at the stress of managing the rental process, and as such takes on an advisory persona in its content. With the word “guarantee” appearing over 10 times on the homepage alone, the message is clear: this is a company devoted to providing great property management services in support of maximizing investment returns. Its “Why Choose Us” page also highlights its investments in cloud-based property management software, also designed to ease the stress of managing property investments. Visit 9. Good Life Property Management The website of this San Diego-based property management company is one of the only companies in the industry to highlight customizable user elements (color and font size) in the header of every page of its website. From the marketing perspective, this sends an important signal that the company is serious about finding ways to partner effectively with its community of investors and tenants. Visit 10. Luxury Property Care Luxury Property Care bills itself as “Florida’s only full-service property management and investment concierge for residential and commercial properties.” Its focus on offering high-end services is reflected in its mission statement: “Treat yourself to the luxury you deserve and let us handle every aspect of investing in off-market real estate and building a first-class rental empire with ease.” It’s also reflected in the website design scheme, with black and gold color elements being a popular way for brands to convey notions of elegance and prestige. Visit Follow the Second Nature Website to Keep Tabs on the Property Management Industry At, you’ll find an abundance of resources designed to keep you up to date on events, analysis, and expert perspectives in the field – all geared toward helping property managers create a “Triple Win” that benefits residents, investors, and property managers alike: Triple Win Property Management Blog Triple Win Property Management Podcast Triple Win Property Management Events Learn more about Second Nature’s Resident Benefits Package, which is designed to generate revenue and establish Triple Win conditions for your residents, investors, and business.

Calendar icon February 26, 2024

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10 Best Property Management Blogs to Read and Learn From

As a property manager, one of the best ways to stay attuned to the latest trends, technologies, and strategies in the field is to read industry blogs across a range of property management websites. That's because the content of these blogs often consists of shared best practices and practical tips from peers and other experts. They also help you keep abreast of any regulatory changes and compliance requirements that may inform your business decisions and strategies. Today we'll cover some of the top property management blogs, with a focus on what each site brings to the table. 1. Second Nature The SecondNature blog provides insights on a wide range of topics related to property management, including market trends, technology, resident retention, and more. Its focus is primarily on a “Triple Win” philosophy, which expresses the idea that residents, property managers, and investors can go beyond transactional basics to create new, mutually winning experiences. In that vein, sample blog post titles include “How to Start a Resident-focused Property Management Company in 13 Steps,” “9 Ways to Improve Your Resident Experience,” and “How to Craft a Lease Renewal Letter that Wows Your Residents.” With top categories ranging from “Operational Efficiency” to “Resident Experience” and “Homeowner Insights,” the SecondNature blog is a valuable, highly readable resource for property owners and managers alike. Visit the SecondNature blog 2. Bay Management Group Blog The Bay Management Group manages over 6,000 units throughout Pennsylvania, Maryland, Northern Virginia and Washington, D.C. Its blog reflects this partially regional focus, with categories including “Owning a rental property in Maryland,” “Owning a rental property in Pennsylvania,” and the like. However, much of the content is broadly relevant to the property management business, with articles including “7 Ways to Ensure Your Potential Tenant’s References are Real,” “Tips for Successful Real Estate Partnerships” and “What is the Renter’s Bill of Rights and How Does It Protect Tenants?” This is a great blog that hosts archives going back to July 2012, making it one of the more venerable sites in this list. Visit the Bay Management Group Blog 3. Nest DC Blog Nest is a Washington management firm that focuses on homes and residents in and around Maryland, with expertise in single family homes, condos, multifamily housing, and mixed-use property in high-density, urban environments. Its clean, stripped-down design dispenses with the standard trappings of blogs such as tags and categories, and features both job listings and articles, with sample titles including “Important Factors for Real Estate Investing,” “Best Practices for Tenant Screening,” and “A Guide to the Eviction Process in Washington DC.” Visit the Nest DC Blog 4. Buildium Blog The property management software company Buildium publishes blog posts and other resources on a wide range of property management topics, from accounting & taxes to legal considerations, to marketing tips and the latest news from Buildium. Clearly, the content is aimed at a broad segment of the property management community, including rental property owners, property maintenance professionals, and real estate investors. Sample blog post titles include “The ins and outs of HOA reserve fund accounting,” “The best rent payment app in 2024: Comparing 8 online rent payment systems,” and “The 5 best multifamily property management software solutions in 2024.” Visit the Buildium Blog 5. Appfolio Blog Another software company, Santa Barbara (California)-based AppFolio focuses on SaaS for the real estate market. You do not need to be a user of the Appfolio software to find its blog relevant – in fact, much of the content focuses on issues of broad interest to property management and property investment groups, with sample blog article titles including “Three Leasing KPIs Every Property Manager Should Track to Optimize Their Business,” “4 Ways to Strengthen Vendor Relationships,” and “Your Ultimate Guide to Leasing Season: How to Maximize Occupancy and Efficiency.” Visit the Appfolio Blog 6. BiggerPockets BiggerPockets is positioned as a complete resource for anyone looking to succeed in real estate investing. Thus, its blog is squarely focused on matters relating to property investment and rental income, with titles that reflect that focus (e.g., “12 Ways To Make Passive Income From Real Estate Investing,” “High Credit Borrowers Get Punished and New Landlord Laws Put Tenants First,” and “2024 Rental Market Outlook: Is a Shift Coming Next Year?”) However, it also provides a number of articles with potentially broader interest to property management services (e.g., “Put THIS in Your Lease Agreement (So Tenants Don’t Break It!)” “9 Ways Your Property Management Tool Can Improve Your Business,” and “The Rise and Fall of the American Shopping Mall”). Visit the BiggerPockets blog 7. Rentometer Blog Rentometer provides a number of offerings around its collection and analysis of approximately 10 million rental records annually. The Rentometer blog is an extension of this capability, and aims to provide marketing insights to help manage real estate businesses. Its blog publications date back to 2018, and provide perspectives on remote property management, tools for growing real estate businesses, and more. Sample titles include “6 Tips for Communicating Rent Increases,” and “How to Use Rent Comps When Setting Your Rent Price.” Visit the Rentometer Blog 8. Propertyware Blog Like Buildium, Propertyware is an acquisition of the RealPage corporation but it continues to maintain a blog featuring news, trends and tips on single-family rental properties. Sample titles include “10 Tips For Maintaining Electrical Safety At Your Rental Homes,” “What’s Hot: Tankless Water Heaters for Rental Housing,” and “How Rental Property Software Helps in Processing Security Deposits.” The blog has also compiled different article series under various themes and topics, making it easier to navigate the wealth of information on offer. Visit the Propertyware blog 9. Rent Manager Blog The Rent Manager blog is largely focused on news about this property management software developed by London Computer Systems (LCS), and features tips and best practices for users, as well as news on feature enhancements. However, the blog also includes a dedicated category for property management trends, with articles such as “The Benefits of AI for Residential Property Management,” “Why Lowering Renewal Rents is a Smart Move for Multifamily in 2024,” and “Resident Screening: The Lost Art of the Reference Check.” Visit the Rent Manager blog 10. All Property Management Blog The All Property Management Blog reflects its identity as a marketplace of property management services, with articles aimed at real estate investors as well as property managers. Blog categories include property management tips and advice, product reviews, and content related to property taxes and finances. Sample titles include “How to Rent Out an Apartment: The Go-To Guide for New Landlords,” “Top 10 Rental Listing Syndication Websites and Time-Saving Tips,” and “5 Successful Rental Property Management Strategies.” Visit the All Property Management Blog Follow the Second Nature Blog, Podcast, and Events to Keep Tabs on the Property Management Industry At, you’ll find an abundance of resources designed to keep you up to date on events, analysis, and expert perspectives in the field – all geared toward helping property managers create a “Triple Win” that benefits residents, investors, and property managers alike: Triple Win Property Management Blog Triple Win Property Management Podcast Triple Win Property Management Events Learn more about SecondNature’s Resident Benefits Package, which is designed to generate revenue and establish Triple Win conditions for your residents, investors, and business.

Calendar icon February 21, 2024

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