Supporting Success in an Early Stage Startup

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By Steve Schwartz

I’m often asked about my transition from technical, enterprise customer support into B2B SaaS customer success. I had the amazing opportunity to experience support, implementation, and account management, all at one company, and I came to see how disjointed these customer-facing teams can be. Customers struggle when there isn't alignment between teams. I thought, there has to be a better way, which led me to customer success. Here are three strategies early stage startups should consider when starting a customer-facing team.



When I hire my first Customer Success Manager, I’m looking for a teammate who can span the breadth of roles that I expect I’ll need on my team. In my last two companies, those roles included customer onboarding, training, documentation, support, and success. I also look for a high level of empathy, a natural curiosity, and someone who questions the status quo. Starting with a generalist gives your customers a single resource that they can turn to at any stage of their lifecycle, and gives your CSMs a deeper connection to their customers. Early focus on customer success ensures that you can learn quickly whether customers will be effective in using your solutions or not. As important as your first customers are as references and case studies, they can be equally detrimental if they receive no value from your company.



A customer success generalist who juggles all of these roles will ultimately get overwhelmed by one or more areas, which can make them less effective in the rest. As an example, if your number of customers doesn’t grow significantly, but your end user count does, it can lead to a significant increase in inbound support requests. If you’re in a business where responsiveness to these issues is critical to your success, then a CSM will need to be able to drop everything to address them in a timely fashion. While this may be possible when the CSM has two or three customers, it certainly gets harder when they have more. When you can no longer deliver the quality of support that you strive to, it’s time for your first customer support hire. Likewise, when implementations start to bog down your customer success team, considering splitting the roles of CSM and Implementation Manager apart.



The best way to stay ahead of your need to specialize is to constantly measure your CSMs based on how they’re allocating their time each week. A quick way to do this is to periodically have them self report roughly the percentage of time they are spending in each area. Alternately, if you use a CRM or CS tool to track customer success activities, you can have the team bucket activities by category. If you trend this data against the increase in customers or end users, you can start to build a predictive model for when you’ll need to create the next specialist role within your team.

By starting with generalists, and using data to determine when to specialize, you'll be able to create a consistent customer experience from early through the growth stage of your company. I'd love to hear more about your startup journey, and I'm happy to share more about mine!

Need help planning your customer success team? The Success League is a customer success consulting firm that offers online training and workshops designed for success leaders. Topics include Planning a Team Structure and Hiring Top Performers. For more information on these and our other classes and workshops, please visit


Steve Schwartz - Steve is a customer success leader who enjoys starting and building high-performance teams at early-stage startups. He has worked in energy startups for the past 10+ years in a variety of customer-facing roles. By engaging with customers during the sales cycle, he ensures customer expectations are fully understood and can be exceeded. When not writing for The Success League, Steve is leading Customer Success at FreeWire Technologies. He holds a BS from Tufts University and an MS from Virginia Commonwealth University, and spends his free time with his wife and two kids exploring the Bay Area.