31 Experts Share Advice for Buying Web-Based Software

Every day, thousands of business owners buy software. Some are moving to the cloud and purchasing Web-based (aka SaaS – software-as-a-service) and often start with a free or low-cost trial. If you’re considering doing this, here are words of wisdom from 30-plus business owners, including some insights from software creators.

the cloud

Jon Ferrara, CEO and Founder of Nimble:

Today, business has changed. With the advent of social media, email, IM, text messages and more, businesses are overwhelmed by the myriad applications needed to listen to and engage with their customers. The question is no longer how to stay connected – it is how to efficiently and cost-effectively build business relationships given all the channels of communication. The best Web apps should address all of these issues.

Mark Grilli, Director of Product Marketing at Acrobat Solutions:

SMB owners should look for services designed to meet the needs of today’s fast-paced, interconnected world; services that provide their businesses with simple-to-use solutions to help them deliver their best work, every day, with the productivity, reliability, fidelity, control and cost savings that they expect and deserve.

Pamela O’Hara, President of Batchbook:

Functionality is king! That includes customization, security, ownership, mobility and portability.

Customization – Based on the priorities and the personality of your business, look for flexibility in how you can analyze the information you are collecting, as well as in the user interface.

Security – For desktop or local applications, keep anti-virus software current and back up your data frequently. For software-as-a-service (SaaS), the company hosting the SaaS product is responsible for the security of your data, so check the security policies.

Ownership – Use a business email address when registering the account administrator to protect your business from legal ambiguity about who can access the data.

Mobility – With desktop software, make sure it can sync with your mobile device, either directly or through an application like Outlook. With an online system, see if it has a mobile-ready version or app.

Portability – Ask: What information can be exported? What formats can be used? With what other software can it share data?

Costin Tuculescu, CEO of AnyMeeting.com:

Look for:

1)  An active support site that features FAQs, a knowledge base and an active support community through their Facebook or Twitter presence, showing that they care about their users

2) Other companies or users that are using the software, and find out what their reviews are when compared to the competition

3)  A history: How long has the company been around? Have they demonstrated financial stability?

4)  A free trial that lets you experience the software as closely as possible to what you will be purchasing

Michael Pesochinsky, Cofounder of GovernmentAuctions.org:

The main thing small business owners should look for when it comes to Web-based software is the cost versus output. How much more productive will we be with this software? Will the program do the job efficiently? Can I get this product cheaper–if not for free? Asking these questions prior to selecting the software will help you make the best choice.

John McMahon, Founder and CEO of Sheetster:

Lower upfront software licensing costs combined with standards-based services mean that 90 percent of an organization’s needs can be met using off-the-shelf, open-source services yet still provide “future-proof” and interoperability with line-of-business and commercial desktop products for everything from Excel to Quickbooks to SAP.

The benefits to this approach are many.  With a cloud-based server, you no longer need to worry about hardware, networking or maintaining physical systems.  Modern cloud servers and drives are extremely reliable and redundant, typically more so than in-house systems.  And by running standards-based application server software in the cloud, you get the benefits of dedicated website and database hosting, Web spreadsheets and docs, email and messaging that works with any mail client, mobile-friendly services such as email and calendaring and more.

Sarah Belfer, Director of Public Relations at eDealya:

Rather than focus on quantity, focus on quality. Look for software that engages your fans in meaningful ways – if you listen to them, then they’ll listen to you. Reach out to them at the times that they want to hear from you and about the products that they want to hear about – keep your contact relevant, concise and personalized.

Stephen Fung, Cofounder of Inflow Inventory:

Especially when looking for Web-based software, look for companies that you can trust. If you run into a bug in the software, they should be able to fix it. You’re paying not just for the software, but also for their help and for improvements to the software over time. Look for a company with a track record of regular releases and great customer service.

Robert Landsfield, CEO of Skymira:

It is imperative that companies vetting a software solution ensure that the application can easily exchange information/data/records/etcetera with other applications.

There are cloud-based solutions available that enable companies to gain efficiencies in specific business or manufacturing processes. Think of it as a “business app” store where companies can source apps that do one or two tasks well. What’s new here is there are cloud-based companies with the expertise to tie multiple apps together so they exchange information, in essence creating in a tailored ERP system for an SMB that focus only on the processes that are important to the company. This approach enables a company to layer on additional apps as they see fit over time.


Liz Pearce, VP Sales and Marketing for LiquidPlanner:

Just as important as what to look for is what not to look for. Don’t look for a silver bullet. Forget the mile-long list of requirements and focus on finding a tool that will solve your top three problems.

Darren Levy, CEO of GatherSpace:

Choosing the wrong kind of Web-based software could be a massive waste of time. Look for the following attributes:
1) Free trial – this is a must. If a company can’t let me test drive their software, than they must be hiding something.
2) 1-800 number for customer service and sales, an intuitive website that works well and has great product information, a blog, and any similar signs that show there is customer-centric management behind the curtain.
3) Solid security policies and backup to ensure your data is safe and secure.

Marc Itzkowitz, Senior Director of Product Marketing for Support.com:

When buying Web-based software or any Web-based service, your provider should be an adherent to the Tech Support Bill of Rights, which means that they will honor my right to live support from people who understand my issue but also my culture and my language; the right to have the latest tools brought to bear on my issues so they are solved efficiently; the right to flexible packages of support that meet my financial and business needs; and a guarantee they’ll fix my problem or direct me to someone who can.

Steven Aldrich, CEO of Outright:

You should have no learning curve and get immediate value … if the software is not immediately useful to your business, you don’t have time to waste on it.

Tim Beranek, Partner at BKD:

An important consideration is that the application be device agnostic. The smartphone, notepad, etcetera, trend continues to evolve as new technology is developed. However, with this consideration come huge concerns related to security. Those concerns may depend on the ability to initiate, process, store and query data and transactions. So one must think about the level of encryption on these devices, restricted and secured access, and ability to “wipe” the device if lost or stolen. Periodically, it is important to run vulnerability scans and perform penetration testing.

Eric Peters, Marketing Communications Manager at Mendix:

Look for a balance between out-of-the-box functionality and customizability. You’ll want your application up and running fast, but with the option to make it fit your organization’s business process and integration needs.

Make sure future modifiability is built in to the software: You will want to be able to continuously receive feedback from end users and apply it to the application to maintain a good ROI.

Raj Sheth, Cofounder of Recruiterbox.com:

It should be as simple as email and cost less than your monthly Starbucks bill.

Alan Canton, Owner of Adam-Blake Publishing and Jaya123:

Make sure that the service didn’t appear yesterday. If possible see if they have been around for a few years. There is nothing worse (or more expensive later on) than hitching your business wagon to a falling star!

Craig Griffiths, AskFindBuy:


SMEs should look for software that moves customers down the sales funnel without relying on their own site–like Yelp! [does] for the restaurant business. You need a service to promote your category so all you need to do is market your position and not the category itself.

Arun Prakash, Vice President of Marketing at Thinkspeed:

No matter how great the software is, you will likely run into some issues. Make sure they provide proper support so you are not hung out to dry when those issues pop up.

Brandy Sites, Owner of BR Graphic Design LLC:

When I evaluate Web-based software for my small business, the first thing I look for is an active support community. If the forums are very present and up-to-date, it makes me feel more at ease with the new software knowing that I have the proper support when I need it. The next thing I look at is the ease of use. I wear many hats in my organization, so it’s important for the software to be straightforward and easy to use.

Joe Manna, Community Manager at Infusionsoft:

Choosing software based on features and shiny objects alone will result in disappointment down the road as a user. Instead, focus on the strategic benefits that you’re really after, and the features will follow. An example of this distinction is the ability to “stop a vehicle at high speeds” (benefits) vs. “high-temperature ceramic brake pads with drilled and slotted rotors” (features).

Shane Neman, CEO of Ez Texting:

SaaS should be more than just software. Good Web-based software should be backed up by great customer service. If you’re paying for a product you should get prompt, helpful support.

Robby Slaughter, Owner of Slaughter Development:

Most importantly, you should choose Web-based software that has a clear exit path. If you can’t easily export your data and get up and running somewhere else quickly, look elsewhere. Beware vendor lock-in. Don’t confuse “open source” with “free.” There are hidden costs to all Web-based applications, and if you’re not paying someone up front to keep the system running then you will eventually pay for it yourself.

Local options trump faceless mega-corps. If a hometown company is offering a Web-based solution that has merit, the ability get support from someone in your own community is of incredible value.

Eric Richard, Public Relations Specialist at Appointment-Plus:

Make sure the cloud-based software provider is an established and proven business, not a fly-by-night operation that may cease to exist in a year. Also, be sure the provider offers sufficient customer support–including live phone support–for you and your staff.

Grace Sales at CardWiX:

When choosing Web-based software, users must keep in mind the privacy and security of their data.

Jitka Sykora, Vice President of LeaseRunner.com:

Avoid any software that charges on a “per user” basis. Collaboration, one of the biggest advantages of Web-based tools, then gets really expensive.

Amy Bennett, Cofounder of ShopKeep.com:

Know that Web-based means you are dependent on a stable internet connection and cloud server uptime. For mission-critical applications like point of sale, consider companies that provide a native app paired with a cloud-based service. Even if the Internet or cloud servers go down, you’ll still be able to ring up sales.

Juli Klie, CEO of InfoPreserve:

Remember, the Web is just another delivery mechanism (albeit a practical, cost-effective one!) The core rationale for choosing software still needs to be:

1) What’s the problem I’m trying to solve? and

2) Who does it best for our needs today and for the near-term future? Don’t get caught up by “hot” buzzwords or solutions that are great for someone else but not a one-size-fits-all answer for you.

Michael Kaiser-Nyman, CEO and Founder of Impact Dialing:

The best way is to try it out. Most Web-based software has a free plan or at least a trial; pick a few different offerings, try them all out and then stick with the best one.

Steve Tennant, Managing Director of Tennant Consulting:

Consider the total cost of adopting a software package–most of which is the time it takes for your team to get trained to use it. Do the math on the cost of training employees: days per employee multiplied by the number of employees. You might find a more expensive-but-easy-to-use software product makes more business sense.

What’s your “Plan B”?  Walk through and test what happens if the Web-based software is no longer available due to circumstances beyond your control. Can you really get copies of your data, say each day or week as an offsite backup, and could you really use that data backup in another software program? Believe it only if you’ve done it as part of your evaluation process.

Michael Ortner, Founder and CEO of Capterra:

Five years ago the common wisdom regarding Web-based software was to be careful about things like security, data access and uptime.  But these issues have been dealt with fairly adequately by the vendors, especially as they relate to small businesses, so the main things to consider when buying Web-based (or any kind of software, for that matter) relate to functionality and usability:

1) Does it do everything we need it to do?

2) How quickly can we get our users trained?

3) How user-friendly is most of the functionality?

If you are using Web-based software to operate your company, please share your expertise and wisdom in the comments. We’d love to hear about your experiences and advice for other small business owners considering moving their software into the cloud and operating on a SaaS platform.

Image from LilKar/Shutterstock

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TJ McCue TJ McCue served as Technology/Product Review Editor for Small Business Trends for many years and now contributes on 3D technologies. He is currently traveling the USA on the 3DRV roadtrip and writes at the Refine Digital blog.

19 Reactions
  1. There’s some great advice in this thread. Thanks to all who contributed!

  2. W-wow, that’s a lot of advice! I may have to read a comment each day for the next few weeks! Very thoroughly done.

  3. These are all great comments. I’ll add three to the mix:

    1) Approach selecting web-based vendors like you would if you were buying software. Identify business requirements, do demos, etc. Don’t short-change the process just because they have low start-up fees.
    2) Make sure you have calcualated short term and long term pricing. If your staff increases by 20%, what does that look like? Does the low entry price include converting historical data and loading it to the new sytem (if you need it)?
    3) Finally, know your exit strategy. I recently heard from a business owner whose old vendor is holding data hostage. Be able to periodically download your data and make sure the contract has specifics around obtaining the data on exit.

  4. A common theme in all the above advice is that you need to look for web based software which

    1) is Cost effective
    2) has great privacy practices, security and backup
    3) has excellent customer service

    *Important* One thing which is missing is having an integrated platform with all the tools in one place. There are very few such tools. As far as I know only http://apptivo.com and http://zoho.com are truly integrated platforms. Out of this only Apptivo is absolutely free, with no limits on usage.

    I know this because I work as the product manager at Apptivo.

  5. Thanks to all the contributors for your insights on buying web-based software. I suspect SAAS solutions will continue to displace on-premises solutions as we move into the future. To make the transition, some businesses may benefit from an initial hybrid approach, retaining some existing IT infrastructure.

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