Smokeball is a leading cloud-based legal practice management platform designed to help small and mid-sized law firms run more efficient, profitable businesses. With strong product-market fit and continued global growth, we are scaling our U.S. sales organization and investing in high-impact leadership. Our culture is rooted in accountability, ownership, and empathy. We hold a high bar for performance while supporting and developing our people to do their best work.
The Role
We are hiring a Sales Manager to lead a team of 7–10 Account Executives focused on selling into small to mid-sized law firms. This is a hands-on leadership role for a player-coach who leads from the front, actively engages in deals, and is deeply committed to developing their team.
This is a hybrid role with our office in Chicago, IL. All Chicagoland employees are in the office on Wednesdays and Thursdays.
Key Responsibilities- Lead, coach, and develop a team of 7–10 Account Executives
- Drive execution across the full sales cycle, from discovery through close
- Actively participate in deals, including joining calls and advancing key opportunities
- Manage pipeline health, forecast accuracy, and deal progression
- Coach reps on discovery, multi-threading, business case development, and negotiation
- Identify skill gaps and implement targeted coaching plans
- Motivate individuals based on their unique drivers to maximize performance
- Partner cross-functionally with Marketing, SDRs, Solutions Engineering, Customer Success, and Product
- Leverage Salesforce, Gong, Outreach, and 6sense to drive performance and insights
- Reinforce a culture of accountability, ownership, and continuous improvement
- 5+ years of frontline sales leadership experience
- Proven track record of leading teams to exceed revenue targets
- Experience selling complex SaaS solutions with longer sales cycles and multiple stakeholders
- Strong coaching and people development skills
- Comfortable being hands-on in deals and sales execution
- Data-driven with strong pipeline and forecasting discipline
- Experience with Salesforce, Gong, Outreach, 6sense or similar tools
- Ability to motivate and develop a diverse team
- Familiarity with SPICED sales methodology is a plus
- Legal tech experience is a plus, but not required
- Leads from the front and is energized by being in the details of deals
- Coach at heart who knows how to diagnose gaps and develop people to the next level
- Holds a high bar for performance while leading with empathy and respect
- Strong deal strategist who can step into complex opportunities and create a path to close
- Highly accountable with a bias for action and ownership
- Motivates individuals differently based on what drives them
- Comfortable with data, inspection, and holding teams accountable to metrics
- Thrives in a fast-paced, high-growth environment and brings positive energy to the team
- Team consistently meets or exceeds quota
- Strong pipeline discipline and forecast accuracy
- Visible rep development and internal promotions
- High-quality deal execution across the team
- Consistent energy, urgency, and accountability within the team
$140,000 - 160,000 base salary
$260,000 - 300,000 OTE (DOE)
- Great Culture: We’ve been named a 'Best Place to Work' five years in a row. For us, caring is not optional and we have an ongoing commitment to building a workplace where our people feel valued and collaboration flourishes.
- Work-Life Balance: 20 vacation days, 7 sick days, 3 reboot days, 11 paid holidays, birthday off, volunteer time, and more!
- Career Growth: Smokeball believes in investing in our own people and promoting from within. Our own President started at Smokeball as an Account Manager!
- Benefits: Excellent medical, dental, and vision coverage. 401(k) match, monthly wellness stipend, generous parental leave.
- The Office: The kitchen is stocked with breakfast items, snacks, and beverages, and we have plenty of games to help you relax (ping-pong, billiards, pinball). We also offer weekly catered lunch and free monthly massages provided by a licensed massage therapist!
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.
Skills Required
- 5+ years of frontline sales leadership experience
- Experience selling complex SaaS solutions
- Strong coaching and people development skills
- Experience with Salesforce and similar tools
Smokeball Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Smokeball and has not been reviewed or approved by Smokeball.
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Fair & Transparent Compensation — Stated salary bands on job postings and market‑aligned role snapshots indicate clear, competitive base pay across several Chicago‑based roles. Explicit ranges for sales roles with base plus commission increase visibility into how total pay is structured.
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Healthcare Strength — Comprehensive medical, dental, and vision coverage with multiple BCBS plan options is characterized as strong for the cost, with profiles calling the coverage excellent. The breadth of plan choices supports different employee needs.
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Leave & Time Off Breadth — The package combines PTO and sick time with two floating holidays, three reboot days, a birthday day off, and paid volunteer time, and time off is encouraged. This mix extends beyond standard vacation to provide additional recharge and flexibility days.
Smokeball Insights
What We Do
Smokeball is a legal practice management software for small law firms. Our mission isn’t simple, but it is straightforward: help small law firms be successful businesses so that they can better serve our communities.
Why Work With Us
Named a Best Workplace by both Crain’s and Inc. Magazine, we believe that fostering a great culture is just as important as providing a great product. We live and breathe our Core Values; they inform every strategic decision we make and guide our behavior with every person we meet.
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