Digital Client Success Manager

Smokeball - Legal Software•Chicago, IL

4d•$73,000 - $80,000•Hybrid

About The Position

As a Digital Client Success Manager (Legal Billing Specialist), you will play a pivotal role in supporting the success and satisfaction of our rapidly growing client base. In this role, you will act as the Client Success partner, collaborating closely with your cross-functional team to enhance and scale a product-led approach to onboarding, adoption, training, and long-term engagement. This is a hands-on, client-facing role where you'll work closely with sales and product teams to ensure our clients realize maximum value from our platform. You’ll help shape how we scale our customer engagement model as we grow. This is a hybrid position based in our Chicago, IL office. All Chicagoland employees are required to be in the office on Wednesdays and Thursdays.

Requirements

3+ years in client success, onboarding, account management, or training role in a SaaS or PLG environment
Working knowledge of billing/trust accounting concepts (e.g. QuickBooks, legal billing), sufficient to support client billing questions
Proven success managing customer relationships, product adoption, and training initiatives
Strong presentation and facilitation skills across live, recorded, and self-paced mediums
Experience working with tools like Salesforce, ChurnZero, Intercom, HubSpot, or equivalents
Project management capability to coordinate multiple onboarding/training streams simultaneously
Ability to interpret client data (e.g., usage metrics, churn signals) and take action
Patience and a genuine love for helping people

Responsibilities

Act as the dedicated account manager for Boost clients, supporting them from post-sale through funnel progression, and stepping in when a client wants to expand beyond their initial offering.
Support billing-related client questions (e.g. reconciliation queries), acting as a billing specialist/backup where needed.
Review client health metrics and onboarding progress in the CRM or customer success platform to identify accounts that may need strategic intervention or proactive outreach.
Host onboarding calls or product walkthroughs with new client segments to optimize product-led onboarding journeys, identifying friction points, and coordinating with Product teams to improve self-serve experiences.
Deliver virtual training sessions (1:1 or group) tailored to a specific client’s use case, often using real-time product demos or walkthroughs.
Respond to escalated client questions or training needs that fall outside the scope of standard support or self-serve resources.
Conduct strategic check-ins with clients to review product usage trends, uncover blockers, and align on business goals focusing on value realization and expansion readiness.
Collaborate with Sales on expansion opportunities, providing insights into usage patterns or identifying advocates for upsell.
Partner with the Product team to relay aggregated client feedback, identify usability gaps, and advocate for improvements that enhance the product-led experience.
Contribute to scalable enablement content, such as updating help center articles, onboarding flows, or video scripts, ensuring alignment with the latest product updates.
Log key client interactions and insights in the CRM or success platform to maintain visibility across teams and support data-driven engagement strategies.