Sales Manager, Commercial (Legal Tech SaaS)

About Smokeball

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

Required Qualifications

• 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

Must-Have Traits

• 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

What Success Looks Like

• 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

Compensation

$140,000 - 160,000 base salary

$260,000 - 300,000 OTE (DOE)

Life at Smokeball

• 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!

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