IT Sales Executive

Abstrakt Marketing Group LLC•Chicago, IL

5d•Hybrid

About The Position

The Technical Sales Executive is responsible for new client acquisition and managing the front-of-house commercial relationship for JMA. This role is a relationship-driven, advisory sales function that connects JMA's proactive managed services and security solutions to prospective clients' business goals. The executive leads discovery, manages all client communication, and guides qualified opportunities through JMA's structured, multi-month sales cycle. The role acts as a commercial conduit, translating the architecture, scope, and pricing developed by the CTO/CISO into client-facing proposals and presentations. Solution architecture, technical scope, and pricing are determined internally, not by this role. The Technical Sales Executive reports primarily to the CEO/Owner, with a strong functional line to the CTO/CISO for technical aspects. The role is classified as a full-time, individual contributor position based in the Chicago area, with a hybrid or in-office work arrangement. Pricing authority rests with the CEO/Owner, and new clients require approval from both the CEO/Owner and CTO/CISO. The operating philosophy emphasizes acting as a trusted advisor, aligning IT services with client business outcomes like risk reduction, operational efficiency, and growth, rather than selling features. The role is the commercial conduit between the CEO/Owner and CTO/CISO, responsible for packaging and presenting technical information to clients. No client-facing commitments are made without internal sign-off from the CTO/CISO.

Requirements

Three or more years in B2B IT or MSP solution sales, with consistent quota achievement through consultative, relationship-based selling.
Technical fluency sufficient to represent JMA services credibly and independently: managed IT, cybersecurity, cloud (Microsoft 365 and Azure), networking, backup and disaster recovery, and IT asset lifecycle, enough to hold a substantive discussion and answer prospect questions without routine escalation.
Business-outcome orientation: the ability to connect IT services to a client strategic goal rather than sell features.
Strong bidirectional communication: simplifying technical concepts for executives and conveying business requirements accurately to technical teams.
Discipline to drive long, multi-month sales cycles through structured discovery, timely follow-up, and internal alignment.
A consultative, trust-first relationship style oriented to retention and referrals.
Proficiency with HubSpot for pipeline, funnel, forecasting, and deal tracking, and with a proposal or RFP platform such as Bidsketch or PandaDoc.

Nice To Haves

Experience selling to Chicago-area SMBs, enterprises, or AEC firms.
Familiarity with HubSpot, and with Bidsketch or PandaDoc for proposals.
Familiarity with JMA vendors and platform partners.
Interest in security-first IT and proactive managed services.
Bachelor’s degree in business, IT, or a related field.

Responsibilities

Prospect and engage qualified Chicago-area SMBs, enterprises, and Architecture, Engineering, and Construction firms.
Independently qualify prospects, assess fit against the JMA values-driven client standard, and conduct deep discovery that builds genuine trust.
Build and nurture long-term, high-fit client relationships through advisor-style listening and consistent follow-through, resulting in multi-year partnerships and referrals.
Own all client communication and presentation for prospective and onboarding clients.
Communicate technical value in plain language to executives and translate business requirements back to the CTO/CISO.
Lead discussions confidently without routine escalation.
Package the architecture, scope, and pricing provided by the CTO/CISO into proposals and RFP responses using the JMA proposal platform (currently Bidsketch, migrating to PandaDoc).
Own and advance the full sales cycle with discipline.
Manage the pipeline, funnel, and forecasting in HubSpot, and maintain momentum across extended cycles that commonly run six to twelve months or longer.
Route every prospective client and project through the CTO/CISO for architecture, scoping, and pricing, and through the CTO/CISO and CEO/Owner for new-client approval, before anything is presented as an option or commitment.
Coordinate a clean handoff from signed client to service delivery, so the relationship the role built transitions into operations without friction.
Establish JMA sales processes from the ground up, including CRM management, pipeline, funnel, and outreach cadence, and help build the sales function toward a small team as volume warrants.