Outbound Sales Executive (New Business)

Job Description

Job Description

Outbound Sales Executive (New Business)

Protek-IT | Chicago, IL

Do you like the part of sales that happens before there's anyone to call? Are you at your best opening doors rather than managing a book of business? Join Protek-IT as our first dedicated Outbound Sales Executive — a hunting role with uncapped commission and a comp plan built around new business signed. We're looking for someone upbeat and client-first, who leads with the customer’s problem, sincerely wants to help, and is honest enough to walk away when it's not a fit.

Position Summary

This is a full-time, quota-carrying role focused entirely on getting new business. You source the opportunity, qualify it, run it through our process, close it, then hand the client to onboarding and account management and move on to the next one.

This is not an account management role, so you won’t be asked to carry a support queue, chase renewals, or babysit a book. Your main role is filling your own pipeline.

The role ramps in two stages: no quota in your first 90 days while you learn our stack and market, then full quota from day 91 on. Quota is measured in managed services recurring revenue — the labor we perform, not licenses we resell. Your base salary is flat from day one — it does not step down as your commission builds — and you earn full commission on everything you close, including during the ramp.

What We're Looking For

Required:

• 2+ years carrying a quota and closing net-new B2B business

• Real experience with cold outbound as a primary source of pipeline, not just working inbound leads

• Comfortable running a multi-stage sales process alongside technical staff

• Able to hold a credible business conversation with an owner, controller, or office manager at a 10–100 employee company

• Disciplined CRM habits: accurate stages, next steps, and forecast

• Valid driver's license and reliable transportation (regular client visits across Chicagoland)

• Self-directed and comfortable being the only person in the seat

Nice to Have:

• Background in managed IT services, VoIP, cybersecurity, or B2B technology

• Experience selling into non-profits, labor unions, construction, property management, manufacturing, or legal

• Familiarity with per-seat pricing models

• Experience building an outbound motion somewhere it didn't previously exist

• An existing Chicagoland referral network — property managers, construction firms, bankers, attorneys, CPAs, etc.

• Experience with AI prompting tools (e.g., ChatGPT, Copilot) for research, list building, and outreach

Your Responsibilities

• Generate the majority of your own pipeline through cold outreach, networking, and referral partners

• Work marketing- and referral-sourced leads as they come in

• Run the full cycle of discovery, technical review with engineering, proposal, negotiation, close

• Qualify honestly against our ideal client profile and disqualify early rather than late

• Hand off signed clients cleanly to onboarding and account management

• Keep the CRM current — if it isn't in the system, it didn't happen

• Report back on what messaging works, which verticals bite, and where our positioning is weak

Key Duties

• Book and run first meetings with SMB decision-makers across Chicagoland

• Build outbound campaigns into our focus verticals: non-profits, labor unions, construction, property management, manufacturing, legal, and professional services

• Conduct fact-finding and discovery to size the opportunity: seat count, current stack, pain points, compliance obligations

• Log recurring pain points and objections from discovery calls, and flag the ones worth reflecting in our outreach campaigns and website copy

• Work alongside marketing to shape campaigns and sales materials for our focus verticals, informed by what you're hearing in live conversations

• Coordinate a technical review with our engineering team before any proposal goes out

• Build and present proposals for managed services agreements, VoIP, and related projects

• Pass every prospect through a fit review with a non-sales stakeholder before proposal stage

• Close agreements and coordinate the onboarding start date

• Maintain accurate pipeline, deal stages, and forecast in the CRM

• Attend local networking events and maintain referral partner relationships

Interview Process

1. 30-minute introductory call with the owner

2. In-person meeting at our office to meet the team

3. Working session: walk us through a deal you sourced and closed yourself, and your first 90 days in this territory

Company Overview

Protek-IT is a managed service provider (MSP) specializing in efficient, personalized IT support for small businesses and non-profits in the Chicagoland area. We support 100+ organizations across non-profits, labor unions, construction, property management, manufacturing, legal, and professional services. We're a tight team of 10 that goes above and beyond, communicates directly, and has each other's backs.

Our growth so far has come almost entirely from web leads, referrals, and reputation. This role exists to build a deliberate outbound motion on top of that.

Marketing Investment Behind This Role

Protek-IT invests roughly $7,500 per month in marketing — website and search, webinars, print and digital campaigns, and local networking and events — supported by an outside marketing consultant. You will have a real voice in where that spend goes, and what you hear in live conversations is expected to shape it.

To be clear about what this is: it is investment behind your market, not a promise of inbound lead flow. This is a hunting role, and the majority of your pipeline is expected to be self-generated. The marketing program exists so that when you reach a prospect, they have heard of us — not so that they call us first.

Compensation & Benefits

Base Salary:

Your base salary is $60,000 annually ($5,000 per month), flat from day one. It does not step down as your commission book builds.

What Counts Toward Quota:

Quota and commission are measured in Managed Services Recurring Revenue (MSRR) — the recurring management, support, and labor portion of a signed agreement. This is the work we perform.

• Counts: help desk and end-user support, managed user seats, server and hypervisor management, network and UniFi management, NAS management, 3CX server management and support, vulnerability management, Microsoft 365 monitoring and management

• Does not count: software licensing and cloud subscriptions of any kind — Microsoft 365 licenses, SentinelOne, backup and BCDR, phishing simulation, password management, eFax, cloud hosting

• Does not count: hardware, hardware leases, scheduled onsite visit blocks included in the agreement, and one-time onboarding or project fees

We sell two plans, Essentials and 360, with a ten-seat minimum. A managed seat carries roughly $150/month in MSRR, so a full quota of $3,000 is about 20 new seats — in practice, one or two new clients a month.

Commission & Bonus:

• Commission on company-sourced leads: 1× the first month's new MSRR

• Commission on self-sourced leads: 1.5× the first month's new MSRR — find your own deals and earn 50% more on them

• Days 1–90: full commission on everything you close, with no quota applied

• Payout timing: commissions pay 30 days after the client completes onboarding and has paid their first invoice

• Quarterly bonus: $1,000 for hitting your quarterly number, increasing by $1,000 for each consecutive quarter hit, up to $4,000

• Annual bonus: $20,000 for hitting all four quarters in a calendar year

• Commission is uncapped and never reduced for a month below quota — you are paid in full on everything you close

• On-target earnings: approximately $126,000 at full quota

Benefits:

• 100% paid Blue Cross Blue Shield healthcare (after 30 days)

• 401(k) with 4% company match (after first year)

• Unlimited PTO based on performance and coverage

• Professional development assistance

• Mileage reimbursement for client travel

Work Location

Monday–Friday, full-time

In-office, client sites, and networking events; flexible remote work as results allow.

Office: 5019 W Lawrence Ave, Chicago, IL

Experience

• B2B sales carrying a quota: 2 years (Required)

• Cold outbound prospecting: 2 years (Required)

• Managed IT services or B2B technology sales: 1 year (Preferred)

Education: High school diploma or equivalent (Preferred)

\nCompany Description

We're a close-knit team of ten who don't take ourselves too seriously, and we value open, direct communication.

Company Description

We're a close-knit team of ten who don't take ourselves too seriously, and we value open, direct communication.