SECTION I · THE BRIEF
Brief #44101Updated 02 SEP 2026CHICAGO, ILRipplingSOFTWARE COMPANIES
Employbl Company Profile

Senior Software Support Specialist

Smokeball is the first and only cloud-based legal practice management software that automatically records time and activity for you. Whether you bill hourly, fixed fee, or on contingency, Smokeball provides you the…

Location
Chicago, IL
Company size
100–200
Posted
1w ago
Comp band
$75K–$85K
Section II · Full ProfileFree with an account
  • 01Equity package & total comp detailLocked
  • 02Seniority & experience requirementsLocked
  • 03Interview process & rubricLocked
  • 04Hiring manager & team contextLocked
  • 05Growth trajectory in this roleLocked
  • 06Offer & decision timelineLocked

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Senior Software Support Specialist

Smokeball· Chicago, ILView company profile


Job title
Senior Software Support Specialist
Job location
Chicago, IL
Job description


What We Need:

We’re looking for a senior, client-focused problem solver to become Smokeball’s go-to expert on Archie, our AI tool! 

This isn’t a management role, it’s a senior individual contributor position where you’ll be the go-to person for all things Archie support. You’ll take the lead on escalations across both the Archie functionality built into our core software and our upcoming standalone Archie offering, with support remaining a shared service across both.

Reporting to Jeff, our Software Support Manager, you’ll have the opportunity to work directly with Archie’s Product and Engineering leaders. We’re looking for someone who doesn’t just flag problems, but gets curious, digs into the root cause, suggests solutions, asks for the right support, and helps figure out how we can make things better.

No two weeks will look exactly the same, but you could find yourself:

  • Serving as the primary point of escalation for Archie tickets, both from Smokeball-integrated clients and stand-alone Archie users
  • Accurately and proactively creating, maintaining, and resolving Archie tickets through ZenDesk
  • Testing and reproducing complex Archie issues to identify root cause, including issues that other support tiers couldn’t crack
  • Partnering directly with Archie product and engineering leaders to report trends, provide feedback, and propose fixes—not just problems
  • Building and maintaining Archie-specific troubleshooting guides, workaround procedures, and internal knowledge base content
  • Helping shape support workflows and escalation criteria ahead of the stand-alone Archie launch
  • Informally guiding other support specialists on Archie-related tickets, sharing expertise without formal management authority
  • Monitoring ticket trends to spot patterns worth flagging to leadership before they become bigger problems
  • Contributing to team goals by improving response and resolution times, as well as client satisfaction ratings


Who You Are:

Company culture is the single most important ingredient to our success at Smokeball.  Our core values hang on our walls, are listed in our handbook, and are discussed regularly.  Our office thrives on positive feedback from our clients and team members alike and we really, really love small law firms.  As the resident Archie expert, you’re comfortable being the person others turn to for answers, and just as comfortable bringing problems and ideas to leadership—you can articulate an issue, propose a solution, and know when to ask for help.  It is expected that you will care for your colleagues and our clients from day one and that you will work hard to identify areas we can improve.  We expect open communication, an open mind, and mad ping-pong skills (okay, not a requirement but definitely a plus). 


What You Bring:

  • 3+ years of direct experience providing software support to clients, including experience operating as an escalation point or subject-matter expert
  • Genuine curiosity about AI tools and comfort troubleshooting AI-powered products
  • Ability to communicate technical information clearly to non-technical users, and to communicate confidently and credibly with leadership
  • Proven ability to not just identify problems but to propose solutions, ask for help, and help drive fixes to execution
  • Ability to diagnose and remotely resolve complex software and AI-related system malfunctions
  • Ability to think critically and quickly learn and adapt to new and evolving product functionality
  • Excellent written and verbal communication skills
  • Capable of managing multiple tasks and projects effectively across two connected but distinct product lines


Compensation

The pay range for this role is:
$75,000 - $85,000 per year


What's in it for you?

💵 Competitive Salary

💹 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

👪 Parental leave

🥡 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.


If you’re excited about this role, we encourage you to apply even if your experience doesn’t check every box.

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Smokeball headquarters

Chicago, IL

Company size

100200 employees

Founded

2011

Total raised

$30,000,000

View company profile ↗

Funding rounds

  • Private Equity$30M