Manager, Customer Success Enterprise — Aspire

At Aspire, we’re building the future of the green industry—and we’re doing it with a team of innovators who care deeply about solving real problems for real contractors. We move fast, collaborate boldly, and take ownership for delivering extraordinary value. Every teammate at Aspire has the opportunity to shape our trajectory, elevate our customers, and help build something extraordinary.

About Our Customer Success Organization

Our Success team is central to how we fulfill our mission: helping landscape businesses reach new levels of efficiency, profitability, and growth through the Aspire platform. The Success organization is made up of two Corporate CSM teams and one Enterprise CSM team, each responsible for driving proactive, high-impact engagements across a diverse and growing customer base. We work intentionally to understand each customer’s goals, diagnose their barriers, and recommend the product adoption paths that will help them achieve measurable outcomes. We obsess over making our customers successful - not because it’s aspirational, but because it’s how we win. 

This role will lead our Enterprise Customer Success team, which supports Aspire’s largest, most complex Enterprise and Strategic customers. These customers rely on Aspire as a mission-critical system, and this team partners closely with executive stakeholders to ensure value realization, deep adoption, and long-term success. 

What you’ll do:

Enterprise Customer Leadership

• Own the success and performance of Aspire’s Enterprise and Strategic customer segment, ensuring customers consistently realize meaningful value from the platform.

• Lead a team of Enterprise CSMs responsible for proactive account management, executive engagement, and outcome-driven adoption strategies.

• Serve as a trusted escalation point for complex customer situations, partnering with customers and internal teams to resolve issues quickly and effectively.

Team Management & Coaching

• Hire, onboard, develop, and retain a high-performing team of Enterprise CSMs.

• Coach CSMs to operate as strategic advisors - able to understand customer business models, identify opportunities for improvement, and clearly articulate Aspire’s value.

• Set clear expectations, provide frequent and candid feedback, and hold a high bar for performance and accountability.

• Foster a culture of trust, ownership, and continuous improvement where team members feel supported and challenged to do their best work.

Operational Excellence & Execution

• Translate Customer Success strategy into clear execution for the Enterprise team, including account planning, engagement models, and success metrics.

• Own key operational KPIs for your segment (e.g., customer health, adoption, retention, executive engagement) and take action when performance deviates from expectations.

• Partner with your Director to identify trends, risks, and opportunities across the Enterprise portfolio and help shape improvements to Success processes and tooling.

Customer Advocacy & Cross-Functional Partnership

• Act as a strong advocate for Enterprise customers internally, ensuring their feedback and needs are clearly represented across Product, Sales, Support, and Implementation.

• Partner closely with Product and Engineering to surface insights from Enterprise customers that inform roadmap prioritization and product enhancements.

What you’ll bring:

Experience & Skills

• 6+ years of experience in Customer Success, Account Management, or related customer-facing roles in a B2B SaaS environment.

• Prior experience managing or mentoring customer-facing teams, ideally supporting enterprise or strategic accounts.

• Strong understanding of how customers derive value from SaaS products and how adoption, engagement, and outcomes drive retention