CS Considerations for SMB and Non-SaaS Organizations
By Boaz Maor & Kristen Hayer
Boaz’ Take:
I love customer success! I love engaging with customers to get to know them and help them maximize value from the solutions they acquire from the company I work for. For the past quarter century or so (yes, I am getting old…), my experience has been predominantly focused on serving large enterprise customers. It is exhilarating working at small tech startups trying to solve problems for and help large companies like Wells Fargo, AT&T, Target, Intel, The City of Richmond VA, and Starbucks.
This was one of the key reasons I took my last job working for a company that provided Point of Sale (POS) solutions to small businesses, mainly Retailers, Restaurants, Coffee Shops, and small service businesses (like photographers, clinics, nail salons, etc.). I wanted to get to know this very different segment of the economy. Over 30 million small businesses in the U.S. employ over 60 million people. They represent close to half of the private sector workforce and account for almost 45% of the U.S. GDP. Wow!
I was very excited to learn about this sector and figure out how I can leverage my experience building Customer Success teams for enterprise customers and translate it to build a CS function that can serve SMB. What I found is that Small Businesses are both very different and quite exciting!
Small Businesses are VERY different from large enterprises.
There are obviously many differences and not all small businesses are alike. But, three big AHA moments struck me fairly early on as I was engaging with customers to understand their needs and how we could best assist them. These three insights became the cornerstone of the strategy I put for my team and the way we set up to execute it.
Small Business Start with a Passion
There are No Departments in Small Businesses
Many Small Businesses Do Not Want to Grow
Small Businesses Start with a Passion: most small businesses start with an owner who likes to do something and makes it their business. It’s that passion that drives them, not the money (though most of them also want to make good money from their passion). They like to make a nice design over a cup of coffee, cut people’s hair, or cook and serve food of some type. They love their business and are heavily engaged in it - not the least as it is so small, they have to.
➡ Implications for CS: Connect to their passion. You must align with their lingo, feel their pain, and really understand their industry. While these statements are true for every CSM in every company, they are really critical in servicing SMBs. Implications: Consider hiring people from within the industries you serve or those who have worked in them before. Another implication is that since the owner is so into servicing their customers, you may find yourself (and may want to!) servicing your customers’ customers too. This is where B2B2C stems from. Your playbooks and offerings may change once you internalize this insight.
There are No Departments in Small Businesses: When servicing large enterprises you, the vendor, most commonly sell to and engage not so much with “the business” as a whole, but rather with a person in a specific department. For example, you sell to the VP of Sales or head of the RevOps team. Or you may be selling to the VP of DevOps or the CISO or the VP of Finance - all professionals who built their career getting very good in their specific functional domain.
In contrast, when servicing SMBs, you need to acknowledge that there are no departments and therefore you engage (sell, service, etc.) with the owner. This must change the way you sell and the way you service them. For once, they are probably not experts in your field and don’t know as much about it. At the same time, most likely, they don’t want to spend too much time on your service: they want to cook Indian food, engage with their customers, or design a new widget. They engage with you because you provide them with a service they need for their business, but probably they don’t really like to do it.
➡ Implications on CS: (Time Saved) > (Improved Features). Internalize that you do something for the owner that they neither know much nor care about and therefore, saving them time is their highest priority. Focus on ensuring uptime and availability of your solution as a top priority, then design your interaction with them in ways that save them as much time (think, automation, self-service, off-loading tasks, etc.). Another implication is that they are likely very busy, stressed, and constantly multi-tasking. Think carefully about the timing and method of engaging with them. Hint: most likely it is not email, not face-to-face meetings, and rarely during (their!) business hours.
Many Small Businesses Do Not Want to Grow: Growth is the lifeblood of every enterprise business. Business growth is what justifies investments, enables career and compensation growth for people, and fuels the valuation of the company. In contrast, many small businesses do not want to grow. This was the biggest aha moment for me when working intimately with owners of small coffee shops, food trucks, specialty retail stores, photo studios, home-service professionals, and the like.
Stemming from their passion for what they do, they often develop their business as a lifestyle. Growing beyond a certain size (which for many is: just them!) requires them to take on tasks they may not like: including hiring and managing people, moving to a new larger location, engaging with even more outside vendors, and so on. It is not that all small business owners want to stay small - some aspire to build larger businesses with more locations, larger product lines, and more people working for them. But, many don’t.
➡ Implications for CS: your first task is to differentiate between those. And for those who are not keen on growth, you probably need to develop very different playbooks to connect with and serve well. All of them want your help to reduce costs and eliminate waste. But, that may translate into reduced costs, not necessarily increased top line.
This is where I found Kristen’s work at The Success League so intriguing. Her work with small businesses, especially in non-SaaS areas, was so enlightening, and her insights on the specific sectors so helpful for me as I explored how to best structure my team, tech stack, and playbooks.
Kristen’s Take:
Boaz’s insights highlight how customer success must adapt when working with small businesses, particularly in industries outside the traditional SaaS model. At The Success League, we’ve worked with many companies outside of SaaS, and we’ve seen firsthand how customer success must evolve to fit different industries. Whether it’s adjusting for business cycles, regulatory requirements, or customer expectations, a one-size-fits-all approach simply doesn’t work.
Like SMBs, non-SaaS companies have structural and operational differences that require adjustments to traditional customer success strategies. Below are a few key industries we’ve worked with and the unique considerations for each.
Education: The Rhythm of the School Year Matters
In education - K-12 schools, colleges, and universities - everything revolves around the school year. This seasonality means customer success teams must align their engagement strategies accordingly. At different points in the year, CSMs should focus on securing renewals, training new users, or conducting business reviews - all at the same time for every customer.
➡ Implications for CS: Build CS playbooks that account for the school year cycle. Expect peak engagement windows where training and onboarding efforts must be highly efficient. Additionally, regulations vary by state in the U.S., making localized expertise critical. Many EdTech firms hire former educators for this reason, but these new CSMs often lack formal CS training—meaning CS leadership must invest in skill development to bridge that gap.
Building Services & Construction: Balancing Small Businesses and Large Enterprises
The building and construction industry spans a wide spectrum—from independent contractors and small firms to large, PE-led conglomerates. This creates a segmentation challenge, as customer needs vary drastically across the industry.
➡ Implications for CS: Like Boaz mentioned with SMBs, many small construction businesses are owner-operated, meaning they often do administrative work after hours and may need support at non-traditional times. At the other end of the spectrum, large firms operate more like traditional B2B companies and require structured account management. CS teams must develop clear segmentation strategies and engagement models to serve both ends of the market effectively. A potential value-add for SMB customers in this space is to help them upgrade their approach to their own customers to become more proactive (additional services, next steps) and data-driven (collecting customer feedback, providing data on customers). As Boaz mentioned above, this B2B2C approach can prove very valuable.
Healthcare: The Challenge of In-Person Relationships
Healthcare organizations—including hospitals and private practices—have traditionally relied on in-person sales and account management. Many professionals in this space are accustomed to vendor representatives dropping by rather than engaging virtually, making digital CS engagement a challenge.
➡ Implications for CS: CS teams must balance virtual engagement with the expectation of in-person relationships. Additionally, healthcare customers operate in a highly complex environment, serving multiple stakeholders—patients, families, medical staff, and insurers. This complexity means onboarding and adoption cycles tend to be longer, requiring patience and careful expectation-setting.
Finance: Navigating Regulations and Integrations
FinTech firms face two primary challenges in customer success: navigating strict industry regulations and managing complex integrations with accounting platforms.
➡ Implications for CS: CSMs must be well-versed in compliance boundaries—knowing where product guidance ends and financial advising begins. Additionally, because FinTech solutions often require deep integrations with existing accounting software, CSMs may need specialized expertise in key platforms. This specialization can make customer assignment more complex, requiring careful segmentation and resource allocation.
The Expanding Scope of Customer Success
Customer success has grown beyond its SaaS origins, but the core principles remain the same: understanding customer needs, aligning engagement strategies, and driving value. That said, whether serving SMBs, education, manufacturing, or finance, the key is recognizing that traditional CS models don’t always apply.
For SMBs as well as other non-SaaS industries, CS teams must focus on time savings, passion alignment, and differentiating between growth-oriented and lifestyle businesses. Their success hinges on adapting to industry-specific cycles, operational norms, and regulatory constraints.
As customer success continues to evolve, so must our strategies. The companies that recognize these nuances and adjust accordingly will build stronger, more impactful customer relationships—regardless of industry or business size.
Looking to unlock the full potential of your customer success initiatives? The Success League offers a CS Program Assessment offers a thorough evaluation process, recommendations, and delivers tangible benefits. Reach out to us or visit TheSuccessLeague.io to learn more.
Boaz Maor - Boaz is a serial start-up executive with a passion for Customer Success. Considered one of the early executives to help drive the development of the Customer Success function, Boaz is a frequent speaker, writer, and presenter at conferences and events. As proof points, he won the “Innovator of the Year” award at CS-100 for his Customer Maturity Index and is the one who created the original entry for Customer Success on Wikipedia. Most recently, Boaz was the Chief Customer Officer at talech, a U.S.Bank company. Before talech, he served as SVP Customer Success at OpenGov (acquired by Cox), founded and led the Customer Success team at Mashery (acquired by Intel) and held customer success executive positions at newScale (acquired by Cisco) and FreeMarkets (IPO and then Acquired by Ariba). Boaz holds an MBA with honors from Carnegie Mellon University.
Kristen Hayer - Kristen founded The Success League in 2015 and currently serves as the company's CEO. Over the past 25 years Kristen has been a success, sales, and marketing executive, primarily working with scaling tech companies, and leading several award-winning customer success teams. She has written over 100 articles on customer success, and is the host of 3 podcasts about the field. Kristen has served as a judge for the Customer Success Excellence awards, and is on the board of several early-stage tech companies. She received her MBA from the University of Washington in Seattle, and now lives in San Francisco.