Sales Development Representative

Smokeball, Inc.; Chicago (IL); Hybrid; USD 54,000 - 60,000; Full time

Benefits offered by this job

20 vacation days

Excellent medical/dental/vision coverage

Monthly wellness stipend

401(k) match

Free monthly massages

Job summary

A leading legal tech firm in Chicago is seeking a Sales Development Representative to enhance outreach and drive sales. This role demands strong communication skills and resilience for cold calling and engaging law firms effectively. With a base salary of $54K-$60K plus commission, and no cap on earnings, this position offers both challenge and reward. Join a supportive team committed to professional growth within an award-winning culture focused on work-life balance and employee well-being.

Qualifications

• Hunger to learn sales with cold-calling experience as a plus.
• Comfort with high-volume outbound calling.
• Mental resilience and persistence.
• Good communication skills, written and spoken.
• Ability to explain technical concepts to non-technical users.

Responsibilities

• Finding and qualifying new sales opportunities through outreach.
• Building relationships with leads through regular follow-ups.
• Working toward activity and performance targets.

Skills

Cold-calling experience

Self-motivation

Communication skills

Time management

Technical explanation ability

Tools

Outreach

Salesforce (CRM)

Slack

Job description

Join an award-winning legal tech company that’s transforming how law firms work by boosting their organization, productivity, and profitability with software they actually love. Smokeball is a global, community-driven company united by a love for the law and a mission to help small and midsize firms thrive. We’re passionate about what we do and our clients know it! If you’re looking for a company that truly cares about its clients and its people, you’re in the right place.

The Role

This is a high-activity, outbound-first role . Successful SDRs at Smokeball are comfortable being on the phone daily, consistently dialing, handling rejection, and driving meaningful conversations with law firm decision-makers. This role requires urgency, resilience, and the ability to ramp quickly and contribute from Day 1.

This is a hybrid role with our office in Chicago, IL. All Chicagoland SDRs are in the office on Tuesdays, Wednesdays and Thursdays.

Key Responsibilities

• F inding and qualifyingnew salesopportunities through proactive outreach like cold calls, emails, and social media.
• Identifyingand prioritizing ideal customer profiles (ICP) and key personas within law firms, including firm size, practice area, and decision-makers.
• Understanding potential clients in the legal field and positioning Smokeball’s solutions accordingly.
• Building relationshipswithleads through regular follow-up, providing info, educational content, and resources to keep them engaged and moving through the sales process.
• Consistently working toward activity and performance targets, including daily call volume, meetings booked, and qualified opportunities created.
• Keeping up with the latest trends in law and sales to improve outreach strategies.
• Making sure all interactions are logged in Salesforce and Outreach.
• Becoming a Smokeball expert and mastering our outbound approach.

Required Qualifications

• A hunger to learn sales, with cold-calling experience as a plus; knowing about law is even better.
• Comfort with high-volume outbound calling and a willingness to consistently pick up the phone as a core part of the role.
• Energy and self-motivation, both for working alone and with a team.
• Mental resilience and persistence-comfortable hearing “no,” learning from objections, and showing up each day ready to dial again.
• Good communicationskills, written and spoken.
• Reliability andgood timemanagement.
• Ability to explain technical stuff to non-techies.
• Coachable mindset witha strong desireto improve through feedback, experimentation, and collaboration with teammates.
• Familiarity with tech stack, including Outreach, Salesforce (CRM), Slack, and 6Senseideal but not a requirement.

Compensation

$54,000 - 60,000 base salary, plus a variable commission component of $36,000.

There is no cap on OTE earnings, so with dedication and strong performance, the earning potential is truly uncapped!

Your manager

Nice to meet you, I’m Blake Dunlap! I’ve spent my career in Sales Development, so I deeply understand what it takes to succeed in this role. I believe strongly in the processes we’ve put in place at Smokeball and am genuinely passionate about the impact our platform has on law firms and the people behind them. As a people-first leader, I enjoy working alongside my team day-to-day, coaching, collaborating, and scaling our Sales Development organization toward record-breaking results.

Outside of work, you’ll likely find me at the theater catching the latest release, deep into a good thriller, or taking a long walk through the city - with the end goal almost always being a great dinner or happy hour .

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.