Top Sales Jobs in Chicago, IL

Own the full sales cycle in the Chicago territory, from prospecting and pipeline development through contract negotiation and closing. Build relationships with small businesses, conduct market research, execute cold outreach, communicate product value, meet sales quotas, advocate for customer and product needs, and represent Justworks at networking events and trade shows. The role requires 25% travel within the Chicago and Greater Chicago area.

The Account Executive owns the full B2B sales cycle in Orange County, including territory development, prospecting, lead generation, relationship building, product presentations, contract negotiation, and closing. The role manages a sales pipeline, meets revenue quotas, conducts cold outreach, networks with the small-business community, represents Justworks, and provides customer insights to support product development. Travel within the territory is required for networking events, trade shows, and prospect meetings.

Manage the full B2B sales cycle in the Los Angeles territory, including prospecting, pipeline development, market research, relationship building, presentations, negotiations, and closing. The role focuses on acquiring new business, meeting sales quotas, networking with small businesses, representing Justworks’ solutions, and traveling locally for client meetings and events.

Manage the full B2B sales cycle in the San Diego territory, including prospecting, lead generation, pipeline development, relationship building, product presentations, contract negotiation, and closing. The role focuses on acquiring new business from small businesses, meeting sales quotas, networking within the local entrepreneur community, advocating for customers, and representing Justworks at events. Approximately 25% in-territory travel is required.

Manage the full B2B sales cycle for a defined Florida territory, including prospecting, pipeline development, market research, networking, relationship building, product presentations, contract negotiation, and closing. The role focuses on acquiring new business, meeting quotas, representing Justworks, gathering customer insights, and traveling up to 25% for networking events, trade shows, and client meetings.

Own the full sales cycle in the Miami territory, including pipeline development, market research, prospecting, cold calling, relationship building, product presentations, contract negotiation, and closing. The Account Executive will manage a book of business, meet sales quotas, build small-business relationships, participate in networking and trade events, provide customer insights, and represent Justworks’ solutions.

As an Account Executive, you will manage a sales pipeline, prospect new clients, negotiate contracts, and close deals, while building relationships in your territory.

Own post-sale upsell and cross-sell sales cycles end-to-end, partnering with CSMs, Support, and Product Specialists. Use Salesforce, Salesloft, AI-enabled prospecting, and quoting systems to manage pipeline, meet revenue quotas, ensure smooth handoffs to onboarding, and improve SOPs to drive product adoption and revenue expansion.

Lead and coach a high-growth Account Executive team to hit revenue targets. Own daily/weekly team rhythm, pipeline integrity, CRM hygiene, forecasting, and deal coaching. Hire, develop, and motivate reps while driving culture, DEIB initiatives, and sales process improvements.