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
