RWK IT Services is expanding its outside sales team to drive the full sales cycle for managed IT and cybersecurity solutions across the Chicagoland area. This hybrid role is based in Frankfort, IL and emphasizes outbound prospecting, discovery, risk assessments, and formal proposals to win new logos, supported by a base salary and an on target earnings of 155,000. The position blends strategic outreach with hands-on deal development in a fast paced MSP environment.

Responsibilities

Build pipeline through outbound calls, email, LinkedIn, industry associations, partner referrals, and RWK's ongoing speaking and content programs
Conduct discovery and onsite risk assessments with business owners, executives, and administrative decision-makers
Translate technical concepts into business outcomes for non technical buyers
Scope and present proposals for Managed IT, Managed Cybersecurity, Co-Managed IT, and vCSO
Close approximately one new logo per month at an average monthly recurring revenue of about $5,500
Maintain disciplined CRM hygiene and provide proactive updates to leadership on wins, obstacles, and next actions

Requirements

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 activities including calls, email, LinkedIn, and industry events
Listen-first, discovery-led approach that qualify for fit and builds trust with buyers
Ability to communicate complex ideas simply and credibly to non-technical buyers
Valid driver’s license and willingness to travel about 40% within Chicagoland, Northern Indiana, and downstate Illinois

Technologies

Benefits

Health insurance
Dental insurance
Vision insurance
401(k) with company match
Paid time off
Life insurance
Retirement plan

The Role

As an outside sales professional, you will operate as a consultative seller who listens to determine fit, guides prospects toward the right solution, and avoids rushed closes. You will build pipeline, conduct discovery and onsite risk assessments, scope proposals for a range of services, and secure new logos within your designated vertical.

Targets & Expectations

Own your full sales cycle from prospecting through close
Maintain consistent outbound activity and follow-up cadence
Build professional, trust-based relationships with decision-makers and influencers
Provide weekly pipeline visibility with clear next steps for each opportunity

What Success Looks Like

30 days: ramp on services, ICP, sales motion, stack, and playbook; outbound started
60 days: discovery and risk assessments run independently; first deals in late stage
90 days: healthy pipeline and weekly proposals; early wins
Year one: at or above quota with 12 new logos averaging $5,500 MRR

Must-Have

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 activities — calls, email, LinkedIn, industry events
Listen-first, discovery-led approach that qualifies for fit and builds trust
Ability to communicate complex ideas simply and credibly to non-technical buyers
Valid driver’s license and willingness to travel ~40% within the region

Preferred

Background in MSP, managed IT, MSSP/cybersecurity, cloud, telecom/UCaaS, copier/office tech, SaaS-to-SMB, payroll, or merchant services
Experience in nonprofit, manufacturing, accounting/finance, professional services, or private equity verticals
Familiarity with Sandler, MEDDIC, Challenger, GAP, or other consultative sales methodologies

What Support You'll Have

Sales coaching and training from a leading MSP industry coaching firm, with paid training period
Technical support from Jeff Reiter and the Solutions Architect team for executive-level deals and complex scoping
Credibility and lead generation through speaking engagements and RWK content assets
Post-sale handoff to Service Delivery Managers and an Account Manager; you stay involved in strategy and expansion

Compensation

Base: $90,000
On-target commission at 100% quota: $65,000
Total OTE: $155,000 (uncapped)
Tiered commissions on net-new MRR with accelerators above quota; residuals on retained accounts after Year 1
Paid training period

How You'll Work

Based at the Frankfort, IL headquarters, you will operate with a hybrid schedule that includes 2–3 days in the field across your territory and regular in-person time at HQ for sales meetings, deal reviews, and collaboration with the team. The role follows a Monday to Friday workweek with a company-provided laptop and CRM access.

About RWK IT Services

Founded in 1997 in Frankfort, RWK IT Services is a professional services consulting firm that helps organizations do what they do better. The company emphasizes the human element in IT, demystifies technology, and delivers right-sized solutions for 10–300 endpoint environments across multiple verticals in the Chicagoland region. Core values are Be Indispensable and Deliver Reliable Outcomes, with a promise of No Excuses. Just Elite P.

Hiring Process

1. Short CriteriaCorp online video evaluation to assess thinking and communication style (20–40 minutes)
2. 30-minute phone screen with Nick Golias, co-lead on business development
3. 1-hour Zoom or in-person conversation with CEO Jeff Reiter
4. Conversation with the MSP Sales Partners sales coach
5. Final conversation and offer

Qualified applicants will receive a response within 3 business days, and decisions are typically made within 14 days after the final round.

Application Question

Please share your LinkedIn profile link

Work Location

In person

Outside Sales Rep — Managed IT & Cybersecurity ($155K OTE)

Job Description