Account Executive - Managed IT & Cybersecurity - Chicagoland ($155K OTE)

Do you have a valid Driver’s License license?, Do you have experience in Outbound calling?, * 3+ years full-cycle B2B sales to SMB or mid-market in Chicagoland

• Track record of carrying and consistently hitting a quota
• Comfort with outbound - calls, email, LinkedIn, events, walking into Village Halls
• A listen-first, discovery-led approach - you’re interested in finding the right solution, not just generating a lead
• Ability to translate technical concepts into business outcomes for non-technical buyers, including elected officials and public administrators
• Valid driver’s license; willingness to travel ~40% within Chicagoland, Northern Indiana, and downstate Illinois

Preferred

• MSP, managed IT, MSSP, cybersecurity, cloud, telecom/UCaaS, copier/office tech, SaaS-to-SMB, payroll, or merchant services background
• Experience selling into municipalities, public safety, or fire protection districts
• Manufacturing, accounting/finance, or private equity vertical experience
• Familiarity with Sandler, MEDDIC, or Challenger

Not sure you check every box? If you’ve sold consultatively to SMB owners or public-sector administrators and want to own a territory at a 27-year-old MSP with real credibility in local government and an external coaching engine behind you, we want to talk. Don’t self-select out.

Pulled from the full job description

• Paid training
• 401(k)
• Health insurance
• Retirement plan
• 401(k) matching
• Paid time off
• Vision insurance, * Base: $90,000
• On-target commission at 100% quota: $65,000
• Total OTE: $155,000 (uncapped)
• Tiered commission on net-new MRR with accelerators above quota; residual commission on retained accounts past Year 1
• Paid training period, * Health, dental, and vision insurance
• 401(k) with company match
• 15 PTO days + 7 paid holidays

How you’ll work

Hybrid remote based out of our Frankfort, IL HQ - home-office with 2-3 days/week in the field across Chicagoland, plus regular in-person time at HQ for sales meetings, deal reviews, and team collaboration. Monday to Friday. Company-provided laptop and CRM access.

About RWK IT Services

Founded 1997 in Frankfort, IL. 2,000+ partners served across 27+ years. 2025 MSP Titans of the Industry finalist (Government/Public Sector). We’re a professional services consulting firm that empowers organizations to do what they do better - we bring the human element to IT, demystify technology, and deliver right-sized solutions for villages, townships, police and fire districts, manufacturers, accounting firms, PE-backed companies, and nonprofits running 10-300 endpoints. We have relationships with our partners, not just interactions. Three values - Passion, Purpose, Excellence - and one promise: No Excuses. Just Elite Protection.

Hiring process

• 30-min phone screen with Nick Golias, VP of Business Development (LinkedIn)
• 1-hour Zoom or in-person with CEO Jeff Reiter (LinkedIn)
• Conversation with your future sales coach at MSP Sales Partners
• Final conversation and offer

We respond to every qualified applicant within 3 business days. Decision within 14 days of final round.

Equal opportunity, accommodations, and fair chance

RWK IT Services is an Equal Opportunity Employer. We make employment decisions based on merit, qualifications, and business needs - without regard to race, color, religion, sex (including pregnancy, gender identity, gender expression, and sexual orientation), national origin, age, disability, genetic information, marital status, protected veteran status, or any other characteristic protected by law.

We provide reasonable accommodations to qualified applicants with disabilities - contact careers@rwksolvesit.com. We consider qualified applicants with criminal histories consistent with applicable federal, state, and local fair-chance laws.

Ready to go for the Super Bowl of IT sales? If you’ve sold consultatively to SMB owners or public-sector administrators and want to own a territory at a growing MSP with a CEO who already opens doors in your market and a dedicated sales coaching firm behind you, apply now. We respond within 3 business days.

Pay: $90,000.00 - $155,000.00 per year, * 401(k)

• 401(k) matching
• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Retirement plan
• Vision insurance

Are you a seasoned B2B closer ready to own a real territory at a 27-year-old Chicagoland MSP that already opens doors most reps spend years trying to pry open? RWK IT Services has served 2,000+ partners across Chicagoland and holds a sharp position in a vertical most MSPs can’t credibly serve: local government. You’ll sell managed IT and cybersecurity full-cycle, prospect-to-close, into municipalities, police and fire districts, manufacturers, professional services firms, and other organizations running 10-300 endpoints. You’ll work alongside CEO Jeff Reiter - a 2025 MSP Titans finalist (Government/Public Sector), national cybersecurity speaker, and Amazon best-selling author of The Cyber Playbook - and VP of Business Development Nick Golias, who co-leads new business today. We’re adding this seat alongside an existing AE who’s already producing in the model - you’re joining a proven motion, not building it from scratch.

What you’ll do

• Build pipeline through outbound, LinkedIn, municipal and public-safety associations, partner referrals, and the speaking platform Jeff already runs
• Run discovery and onsite risk assessments with Village Managers, City Administrators, Police and Fire Chiefs, business owners, CFOs, and Office Managers - listening first, qualifying for fit, and finding the right solution rather than just generating a lead
• Scope managed IT, cybersecurity, co-managed IT, and vCSO proposals - Jeff and Solutions Architect Mohammad are available for executive-level technical conversations and complex deals
• Close ~1 new logo per month at ~$5,500 average MRR; expand existing partners through QBRs and cross-sell into cybersecurity and vCSO

What support you’ll have

• Sales coaching & training: RWK has retained MSP Sales Partners - the leading sales coaching firm in the MSP industry - as your fractional sales coaching and training engine. You get playbooks, structured training, a sales mastermind, and a peer group of MSP sales operators. Your training period is paid. You will not be asked to figure this out alone.
• Technical: Jeff Reiter and Solutions Architect Mohammad available for executive-level deals, compliance-sensitive conversations, and complex scoping
• Credibility & lead-gen: Jeff is on the speaking circuit and sits on a township Planning Commission - you walk into rooms warmer than the market norm. The Cyber Playbook, the Municipal IT Risk Checklist, RWK Chicago Authority magazine, and “The Packet” blog are content assets you lead with
• Tech stack: Modern stack purpose-built for sales and marketing motion; specifics shared during the interview process
• Post-sale handoff: Service Delivery Managers and an Account Manager own ops after close. You stay on strategy and expansion - you don’t service the account

What success looks like

• 30 days: Ramped on services, ICP, municipal sales motion, stack, and the MSP Sales Partners playbook; outbound underway
• 60 days: Running discovery and risk assessments independently; first deals in late stage
• 90 days: Healthy pipeline coverage; proposals going out weekly; early wins
• Year one: At or above quota - 12 new logos averaging $5,500 MRR; expanding top accounts