Building the Customer Success Team That Grows With Your Startup

At the 9th Annual Startup Boston Week, a packed room of founders and operators gathered for a candid conversation about one of the most underestimated growth levers in early-stage companies: customer success. 

The session, Building Your CS Dream Team: Hiring and Growing for Early-Stage Success, featured a deeply experienced panel moderated by Erica Ayotte Favorito (Founder, Slice Advisory), alongside Mary Migiano (Head of CX, Compt), Nehal Patel (Fractional Chief Customer Officer/ Growth Advisor) and Tim Concanon (Director of Customer Success, Sword Health) 

The full event video is embedded below if you’d like to watch the conversation start-to-finish, or keep reading for an overview.

Together, they unpacked what it really takes to build, hire, and scale a customer success organization in fast-moving startups - where roles are fluid, resources are lean and the margin for hiring mistakes is razor thin.

There’s No “Right” First CS Hire, Only the Right One for Your Stage

One of the session’s earliest takeaways challenged a common founder assumption: that your first post-sales hire must always be a traditional Customer Success Manager.

According to Patel, early-stage startups (especially those in the $0–$1M ARR range) often need a “Swiss Army knife” rather than a narrowly defined CSM. Someone who can handle onboarding, support, light project management, and customer education can buy a company time while revealing where specialization is truly needed.

As companies mature, panelists agreed, roles should become more focused. More complex products may require dedicated onboarding specialists, while higher-value customers often demand outcome-driven CSMs who can clearly tie product usage to retention and renewal.

Don’t Wait Until Burnout Forces Your Hand

Migiano emphasized that many startups wait too long to invest in customer success, hiring only after churn rises or teams burn out. Instead, founders should look for early warning signs - fragmented processes, inconsistent onboarding, or unclear ownership across renewals - and hire proactively.

Customer success, the panel stressed, isn’t just a support function. It’s a strategic investment that shapes how customers experience your company long before renewal conversations begin.

Skills Matter. But Attributes Matter More.

When it comes to hiring, the panelists were clear: experience on paper doesn’t guarantee success. Some of the strongest CS hires they’ve made came from adjacent backgrounds (support, sales, or even straight out of school) with deep domain knowledge and the right personal traits.

Curiosity, resilience, comfort with ambiguity, and emotional intelligence consistently surfaced as must-haves. Customer success teams absorb customer anxiety, frustration, and urgency every day. Without emotional resilience, even technically strong hires can struggle.

“You can teach someone how to run a call,” Favorito noted, “but you can’t teach them how to genuinely listen.”

Designing a Hiring Process That Respects Candidates

In a hiring market flooded with multi-round interviews and unpaid case studies, the panel urged restraint. If presentations are used at all, they should be reserved for final candidates, tightly scoped, and focused on understanding how a person thinks, not extracting free consulting work.

Several panelists favored situational questions and storytelling over rigid rubrics, allowing candidates to demonstrate how they handle complexity, pressure, and real-world customer scenarios.

Supporting CS Teams Is a Leadership Responsibility

As the conversation turned toward management, one theme became clear: customer success teams need just as much care internally as they give externally. Leaders play a critical role in shielding CS professionals from internal friction, aligning cross-functional teams, and turning difficult moments into growth opportunities.

Champion models, where team members own specific initiatives or cross-functional relationships, emerged as a practical way to maintain focus, prevent overload, and create leadership pathways within lean teams.

AI Won’t Replace CS, But It Will Redefine It

Unsurprisingly, AI sparked strong opinions. While automation can streamline research, reporting, and repetitive tasks, the panel agreed it won’t replace the human elements of customer success anytime soon. Relationship-building, reading between the lines, and connecting product value to a customer’s real-world challenges remain deeply human skills.

Instead, AI’s real promise lies in freeing CS teams to do more of the strategic, high-impact work that actually drives growth.

The Bottom Line

Building a customer success team isn’t about copying a playbook from a later-stage company. It’s about meeting your customers where they are, hiring for adaptability over perfection, and designing roles that evolve alongside your business.

For founders in the room, the message was clear: customer success isn’t a cost center; it’s a growth engine. And getting it right early can shape the trajectory of your startup for years to come.

The full event video is embedded above (or you can watch it directly on YouTube) to catch the complete Q&A and founder stories shared from the stage.