Digital Client Success Manager

Smokeball - Legal Software; Chicago (IL); Hybrid; USD 70,000 - 90,000; Full time

Benefits offered by this job

Vacation days

Birthday off

Medical, dental, vision insurance

401(k) match

Wellness stipend

Office snacks

Job summary

Smokeball is seeking a Digital Client Success Manager (Billing Specialist) in Chicago to own onboarding, adoption, training, and ongoing client engagement for a rapidly growing client base. You will collaborate with sales, product, and client success teams to scale a product-led onboarding and expansion model.

In this hands-on, client-facing role, you will support billing questions, review client health metrics, and deliver virtual training sessions to enhance value realization and long-term

Qualifications

• 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.

Responsibilities

• Act as the dedicated account manager for our Boost and Bill client segments, supporting them from post-sale 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 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.

Skills

Billing knowledge

Relationship management

Training delivery

Presentation skills

Product adoption

Cross-functional collaboration

Data interpretation

Email communication

Tools

Salesforce

ChurnZero

Intercom

HubSpot

Job description

Smokeball powers people-law. Our legal practice management software lightens the administrative burden, so legal professionals can serve those who need them most.

And not to brag, but we've been awarded the #1 Best Place to Work for 2026 (Medium-Sized Companies) by Great Place to Work Australia. With offices in Australia, the US, and the UK, Smokeball is the leading provider of legal practice management software, helping small and mid-sized legal practices run their best firm and live their best life.

The Role

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.

A Typical Day Involves

• Act as the dedicated account manager for our Boost and Bill client segments, supporting them from post‑sale 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 customer success platform (Churn Zero) 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 within the "Bill" client portfolio, 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 success platform to maintain visibility across teams and support data‑driven engagement strategies
• Act as a member of the Client Training team to perform billing training for the broader Smokeball client base.

What You Bring

• 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
• 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!

What's in it for you?

Work-Life Balance: 20 vacation days, 3 reboot days, birthday off, volunteer time, and more!

Benefits: Excellent medical, dental, vision coverage. 401(k) match, & monthly wellness stipend

Office lunch and loads of snacks

And of course...the SWAG!!

Want to Know More?

Why do we do what we do? Where did the name ‘Smokeball’ come from? What are our values? Learn more here!

*Smokeball values diversity & inclusion and is proud to be an Equal Employment Opportunity employer. Smokeball considers all individuals seeking employment without regard to race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, sexual orientation, or any other legally protected characteristic.