Sales Director

ProActivate; Chicago (IL); On-site; USD 275,000 - 300,000; Full time

Benefits offered by this job

Unlimited PTO

Six-month ramp plan

Leadership growth opportunities

Autonomy with cross-functional support

Job summary

ProActivate is seeking a senior individual contributor to lead enterprise AI and contact center sales. You will own the full sales cycle—from strategic prospecting to close—targeting enterprise and upper mid‑market accounts, and you will build executive relationships to win complex deals.

You’ll drive net‑new customer acquisition against a $2M annual quota, engage senior buyers, and navigate multi‑stakeholder cycles.

Qualifications

• 3+ years of B2B technology sales in enterprise or strategic accounts.
• 3+ years selling into call centers or call center operations with proven success.
• Proven track record of winning new logos and generating own pipeline.
• Experience selling complex SaaS or technology solutions to senior buyers.
• Willingness to travel for customer meetings and industry events.

Responsibilities

• Drive net-new customer acquisition against a $2M annual quota.
• Build pipeline through self-directed prospecting, supported by marketing and an assigned BDR.
• Sell AI and contact center solutions, with deal values $100K–$1M+.
• Engage senior decision-makers and navigate complex enterprise sales cycles.
• Collaborate across teams to convert opportunities into revenue.

Skills

B2B tech sales

Enterprise sales

SaaS sales

Executive engagement

Pipeline development

Travel readiness

Job description

Join an innovative AI technology company transforming customer experience in contact centers for some of the world’s largest brands. With a growing portfolio of AI solutions and significant market opportunity, this is your chance to help shape the next phase of enterprise growth.

This senior individual contributor role is built for a proven sales hunter who thrives on opening doors, building executive relationships, and closing complex enterprise deals.

You’ll own the full sales cycle, from strategic prospecting to close, targeting enterprise and upper mid-market accounts.

What You’ll Do

• Drive net-new customer acquisition against a $2M annual quota.
• Build pipeline through self-directed prospecting, supported by marketing and an assigned BDR.
• Sell innovative AI and contact center solutions, with deal values ranging from $100K to $1M+.
• Engage senior decision-makers and navigate complex enterprise sales cycles.
• Collaborate across teams to convert opportunities into revenue.

What You Bring

• 3+ years of B2B technology sales experience in enterprise or strategic accounts.
• Approximately 3+ years of experience selling into call centers or working in call center operations. Operational candidates must also have proven sales success.
• A track record of winning new logos and generating your own pipeline.
• Experience selling complex SaaS or technology solutions to senior-level buyers.
• Willingness to travel for customer meetings and industry events.
• $275K–$300K proposed on-target earnings
• Uncapped commissions, performance multipliers, and renewal commission.
• Six-month ramp plan.
• Unlimited PTO.
• Autonomy, cross-functional support, and potential opportunities for leadership growth.

Ready to bring next-generation AI solutions to market?

If you know the contact center landscape and excel at enterprise hunting, let’s talk.