Customer Success Specialist - SaaS

Overview

They are now looking to grow their Sales org, and are looking for revenue-focused Customer Success Specialists to own the trial-to-paid customer journey in a fast-growing B2B SaaS environment. This is not a traditional account management role. It is a hybrid of onboarding, post-sales implementation, and customer enablement, where success is measured by activation, time-to-value, and conversion outcomes.

This role is critical to driving early customer success during the first 14–30 days of the lifecycle - the period where revenue is won or lost. The successful candidate will take full ownership of new trial accounts, guiding customers from signup through implementation, activation, and paid conversion.

The ideal candidate is commercially minded, technically fluent, and highly execution-oriented, with a strong focus on speed, clarity, and removing friction.

Trial Onboarding & Technical Implementation

• Own new trial accounts from signup through conversion
• Lead onboarding kickoffs, discovery sessions, and implementation planning
• Configure and support CRM and payment integrations (hands-on)
• Ensure customers reach key activation milestones quickly and consistently
• Troubleshoot setup issues and remove blockers in real time
• Educate customers on best practices and additional value opportunities
• Drive customers to early value and key “aha” moments tied to conversion
• Proactively monitor trial engagement, usage, and risk signals
• Deliver tailored enablement sessions, walkthroughs, and demos
• Clearly communicate business value, ROI, and expected outcomes
• Partner with Sales on closing motions when appropriate

Process, Playbooks & Scale

• Align onboarding journeys to ideal customer profiles and use cases
• Build and document repeatable onboarding and conversion playbooks
• Define activation milestones correlated with conversion
• Create templates, checklists, and workflows to reduce time-to-value
• Contribute to automated onboarding and lifecycle programs

Cross-Functional Collaboration

• Surface product friction, objections, and feature gaps to Product and GTM teams
• Share conversion insights and customer trends with Marketing and Rev Ops
• Partner with Support to ensure seamless handoffs and escalation paths

Early Lifecycle Support

• Ensure timely resolution of support tickets for accounts under management
• Leverage support interactions as opportunities to drive activation and adoption

This role is directly accountable to revenue outcomes.

• Activation Rate (CRM + Payments Connected)
• Time-to-First-Value
• Onboarding Completion Rate
• Early Product Adoption Metrics
• Onboarding CSAT / NPS

• Increase trial conversion efficiency and activation speed
• Reduce time-to-value and accelerate early customer adoption

Required

• 2+ years of experience in SaaS onboarding, implementation, post-sales, or technical customer success
• Proven experience converting trial users into paying customers
• Strong technical fluency; experience with CRM or membership management systems is a plus
• Comfortable leading customer calls, handling objections, and driving conversion conversations
• Highly organized, execution-oriented, and data-driven

Preferred

• Experience in PE-backed or high-growth B2B SaaS environments
• Experience in PLG or hybrid PLG + sales motions
• Familiarity with tools such as Hub Spot, Intercom, Notion, and analytics platforms