Hybrid Digital Client Success Manager – Billing & Onboarding

Smokeball - Legal Software

Chicago (IL)

Hybrid

USD 73,000 - 80,000

Full time

14 days+

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Benefits offered by this job

20 vacation days

3 reboot days

Birthday off

Volunteer time off

Medical, dental, vision

401(k) match

Wellness stipend

Office snacks

SWAG

Job summary

Smokeball - Legal Software is seeking a Digital Client Success Manager (Billing Specialist) to support onboarding, adoption, and ongoing client engagement in a hybrid Chicago office. You will serve as a client success partner, aligning with sales and product teams to scale a product-led onboarding and training journey.

The role emphasizes hands-on client interaction, billing support, and data-driven coaching to maximize client value and retention.

Qualifications

3+ years in client success, onboarding, account management, or training in a SaaS or PLG environment.
Working knowledge of billing/trust accounting concepts (e.g. QuickBooks, legal billing).
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.
50% of your day will be spent responding to emails and the other 50% will be on training calls so we’re looking for someone with the patience of a saint, 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