Account Executive, Cloud Solutions; Chicago

Account Executive – Enterprise (Chicago Based)

Join Sikich as an Account Executive – Enterprise (Chicago Based).

We are looking for a high‑performing sales professional to drive new client acquisition and nurture existing relationships in the Enterprise segment. The role focuses on understanding clients’ IT needs and proposing tailored managed services solutions.

• Leverage the full array of resources (solution consulting, professional services, marketing, industry experts, and management) to secure sales.
• Sourcing leads, qualifying opportunities, and closing deals – hunter mentality required.
• Maintain a strong execution focus; top of the leader board.
• Apply industry expertise throughout sales cycles.
• Demonstrate strong judgment, decision‑making, and a desire to succeed.
• Communicate complex information to executives/C‑level and convey the value of our cybersecurity services.
• Build relationships with referral partners, trade associations, and buying groups.
• Prospect and close managed IT services opportunities.
• Stay current with industry trends, business models, and compliance frameworks.
• Present with executive presence, communication, and presentation skills.
• Develop a strategic territory plan to sign new customers and meet revenue targets.
• Maintain leads, opportunities, and pipeline updates accurately in CRM.

• Hunter personality with proven success selling to mid‑market and enterprise companies.
• Track record of sales experience selling managed IT services (MSP, helpdesk, server and network monitoring), managed security services (EDR, SIEM), and IT project work (migrations, consultations, network assessments).
• Experience into a key industry vertical and familiarity with related solutions.
• Excellent communication, negotiation, and presentation skills.
• Results‑oriented with a passion to exceed quotas.
• Team player thriving in a fast‑paced environment.

• Servant Leader – focus on employee engagement and culture.
• Solutions focused – identify opportunities and implement solutions.
• Collaboration – build relationships across levels and units.
• Instills trust – act with integrity and follow through.
• Impact & Influence – gain support and mobilize without formal authority.

Sikich is a global professional services firm specializing in Accounting, Advisory, and Technical services.

• Flexible Time Off (FTO) Policy, paid holidays, and flexibility for last‑week‑of‑year breaks.
• Comprehensive wellness program with rewards.
• Flexible work arrangements.
• Health, dental, vision, life, and accident/disability insurance.
• HSA employer contribution.
• 9 paid holidays annually.
• Robust paid parental bonding leave.
• 401(k) with employer contributions.
• CPA bonus, tuition reimbursement, generous referral bonuses, pet insurance.
• FORCE – volunteer program with paid time.

Sikich is an Equal Opportunity Employer M/F/D/V. Sikich practices in an alternative practice structure in accordance with the AICPA Professional Code of Conduct and applicable law.