Director, Enterprise Sales - SaaS; Chicago

Director, Enterprise Sales - SaaS (Chicago-based)

Hybrid - Chicago, United States | Posted on 01/21/2026

• Salary Base Salary $103, + Bonus
• Work Experience 5+ years
• City Hybrid - Chicago
• Country United States

seo Clarity is scaling its enterprise sales engine and looking for a Director, Enterprise Sales (SaaS) (Chicago-based) who leads from inside the deal. Reporting to the COO, this is a producing leadership role where you own your number, shape the enterprise motion, and set the standard for how revenue is built and closed.

This is NOT a sidelines role. You WILL carry a quota, hunt for enterprise opportunities, and stay hands on through discovery, negotiation, and close. At the same time, you will develop Account Executives, guide deal strategy, and elevate how the entire team sells into complex, multi stakeholder environments.

If you thrive in roles where leadership is earned through execution and credibility comes from carrying the number, this role is for you!

• Competitive Compensation – annual salary range $103,000 to $127,000 per year, plus variable compensation tied to personal and team quota attainment.
• Robust Benefits Package – a well-rounded package designed to support your health, financial security, flexibility, and long-term growth, including major medical, dental, and vision coverage, company-sponsored life insurance, a 401(k) with company matching, commuter benefits, generous PTO, paid sick time, and company holidays.
• Perks That Support You – a continuous learning stipend, paid parental leave with extended work-from-home flexibility for new mothers, company-wide celebrations, and an annual global summit that bring teams together.
• Snack & Beverage Fuel – a fully stocked kitchen with snacks, drinks, and grab-and-go options to keep energy high and focus sharp throughout the day.
• In-Office, Hybrid Schedule by Design – our team comes together in our Downtown Chicago office Tuesday through Thursday for high-impact collaboration, with Mondays and Fridays reserved for focused on remote work.
• Effortless commute options with valet parking on-site, quick access to the “L” at Chicago Station, a short walk to major Metra lines, direct CTA bus routes (37 and 66), and secure bike storage.
• A built-in dining scene just steps from your desk, including Starbucks, Hannah’s Bretzel, Sopraffina Marketcaffe, Rustle & Roux with an exclusive seo Clarity discount, Amazon Go, etc.
• A large, fully equipped fitness center with locker rooms and showers, making before-work, lunch-hour, or after-work workouts easy and convenient.
• Comfortable lounge spaces, ideal for recharging between meetings or after intense deal cycles.

• 10+ years of B2B SaaS sales experience, including significant time selling and closing complex enterprise deals while leading others.
• Bachelor’s degree in business, marketing, or a related field.
• A proven track record as a quota-carrying, producing sales leader with personal responsibility for closing high-value enterprise opportunities.
• Demonstrated success generating enterprise pipeline through outbound prospecting, strategic account targeting, and disciplined follow-up, not reliance on inbound flow or executive intervention.
• Extensive experience selling into large, complex organizations with multiple stakeholders, buying committees, and executive decision-makers.
• Strong understanding of enterprise SaaS buying motions and consultative, value-based selling in long-cycle environments.
• Experience leading, coaching, and developing enterprise Account Executives and supporting roles while remaining actively involved in live deals.
• Comfort operating with high autonomy and ownership, where leadership credibility is earned through execution and results.
• A collaborative leadership style paired with clear accountability for personal production and team outcomes.

• Hunt for, open, and close high-value enterprise opportunities, carrying a personal quota alongside team leadership responsibilities.
• Own the enterprise sales…