Sales Manager, Commercial (Legal Tech SaaS)

Smokeball • Chicago, IL

13d • $140,000 - $160,000 • Hybrid

About The Position

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.

Requirements

• 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
• 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

Nice To Haves

• Familiarity with SPICED sales methodology is a plus
• Legal tech experience is a plus, but not required

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

Benefits

• 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!

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed
• Number of Employees: 1-10 employees