Frankfort, IL HQ · Office + field across Chicagoland, Northern Indiana, and downstate Illinois

Are you a seasoned B2B closer ready to own a real territory at a 27-year-old Chicagoland MSP with a marketing engine built to support you? RWK IT Services has served 2,000+ partners across Chicagoland and is a 2025 MSP Titans of the Industry finalist. You'll sell managed IT and cybersecurity full-cycle — prospect to close — into a focused vertical we've strategically chosen for this seat. We'll share which market in the interview, along with the marketing assets, social proof, and warm introductions already lined up to support you. We're adding this seat alongside an existing outside sales rep who's already producing — you're joining a proven motion, not building it from scratch.

You'll work alongside CEO Jeff Reiter — a 2025 MSP Titans finalist (Government/Public Sector category), 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.

The Role

Outside sales role for a consultative seller who listens first, qualifies for fit, and guides prospects toward the right solution — not just the fastest close. You'll build pipeline, run discovery and onsite risk assessments, scope proposals (Managed IT, Managed Cybersecurity, Co-Managed IT, and vCSO), and close new logos in your assigned vertical.

What you'll do

Build pipeline through outbound (calls, email, LinkedIn), industry associations, partner referrals, and the speaking and content platform RWK already runs
Run 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 (virtual Chief Security Officer)
Close ~1 new logo per month at ~$5,500 average MRR (our avg. MRR)
Maintain disciplined CRM hygiene and proactive communication with leadership — wins, obstacles, and next actions

Targets & expectations

Full-cycle ownership of your territory: prospecting → discovery → assessment → proposal → close
Consistent outbound activity and follow-up cadence — you're self-motivated and don't need to be chased
Professional, trust-building relationships with decision-makers and influencers
Weekly pipeline visibility and clear next steps for every active opportunity

What success looks like

30 days: Ramped on services, ICP, sales motion, stack, and the sales 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

What you bring

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 — calls, email, LinkedIn, industry events
A listen-first, discovery-led approach — you qualify for fit and lead with questions that build trust
Ability to communicate complex ideas simply and credibly to non-technical buyers
Valid driver's license; willingness to travel ~40% within Chicagoland, Northern Indiana, and downstate Illinois

Preferred

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

Not sure you check every box? If you've sold consultatively to SMB and mid-market buyers and want to own a territory at a 28-year-old MSP with a real marketing engine and an external coaching firm behind you, we want to talk. Don't self-select out.

What support you'll have

Sales coaching & training: RWK has retained 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 support: Jeff Reiter and our Solutions Architect team are 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 Plan Commission — you walk into rooms warmer than the market norm. The Cyber Playbook, the IT Risk Checklist, RWK Chicago Authority magazine, and "The Packet" blog are content assets you lead with. Additional marketing assets specific to your assigned vertical will be in place before you start
Post-sale handoff: Service Delivery Managers and an Account Manager own operations after close. You stay on strategy and expansion — you don't service the account

Compensation

Base
On-target commission
Tiered commission on net-new MRR with accelerators above quota; residual commission on retained accounts past Year 1
Paid training period

Benefits

Health, dental, and vision insurance
401(k) with company match
15 PTO days + 7 paid holidays

How you'll work

Based out of our Frankfort, IL HQ — home-office with 2–3 days/week in the field across your territory, 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 in 1997 in Frankfort, IL, RWK IT Services is 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 organizations running 10–300 endpoints across multiple verticals in the Chicagoland region. We have relationships with our partners, not just interactions. Our core values: Be Indispensable and Deliver Reliable Outcomes. Our promise: No Excuses. Just Elite Protection and Service.

Hiring process

1. Short CriteriaCorp online video evaluation — an objective baseline on how you think, communicate, and approach problem-solving before we connect live (20–40 minutes)

2. 30-minute phone screen with Nick Golias, co-lead on business development (LinkedIn)

3. 1-hour in-person conversation with CEO Jeff Reiter (LinkedIn)

4. Conversation with your future sales coach at MSP Sales Partners

5. Final conversation and offer

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

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.

Ready to apply?

If you've sold consultatively, you're comfortable creating a pipeline, and you want a territory with real credibility and a coaching engine behind you, we want to meet you. We're looking for someone with the drive you can't teach — consistent, self-motivated, and hungry to own a number. Apply today and include a brief note on why this role fits your career path.

RWK IT Services

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