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Position Summary
The Technical Sales Executive owns JMA new-client acquisition and the front-of-house commercial relationship. The role is a relationship-driven, advisory sales function. It connects JMA proactive managed services and security to a prospective client business goal, leads discovery and all client communication, and carries qualified opportunities through JMA structured, multi-month sales cycle.
The role is deliberately scoped as a commercial conduit. The Technical Sales Executive translates the architecture, scope, and pricing that the CTO/CISO builds into proposals and presentations for the client and owns the client-facing relationship from first contact through onboarding handoff. Solution architecture, technical scope, and pricing are set inside JMA, not by this role.
Reporting Structure
The Technical Sales Executive reports primarily to the CEO/Owner and maintains a strong functional line with the CTO/CISO.
Primary reporting, CEO/Owner
Employment, compensation, personal administration, and all activity and performance matters, including outreach volume, pipeline management, sales-cycle discipline, and general questions and assistance. The role goes to the CEO/Owner first.
Functional line, CTO/CISO
Architecture, scoping, and pricing for every prospective client and project, and any matter that only the CTO/CISO would know. This is a strong, regularly used functional relationship, not a general reporting relationship. The Technical Sales Executive can come to the CTO/CISO directly for anything the CEO/Owner would point to the CTO/CISO for anyway.
Conflict resolution
Where the CEO/Owner and the CTO/CISO give conflicting direction, the CEO/Owner decides.
Role Classification
Attribute
Definition
Position Type
Full-time, front-of-house commercial role. Chicago area, hybrid or in-office.
Status
Individual contributor.
Direct Reports
None at outset. See Open Items on sales-function build-out.
Primary Reporting
CEO/Owner.
Functional Line
CTO/CISO, for architecture, scoping, and pricing. Strong dotted line.
Pricing Authority
None. Pricing is built by the CTO/CISO and finalized by the CEO/Owner.
New-Client Approval
Requires CTO/CISO and CEO/Owner approval before any option or commitment reaches a client.
Operating Philosophy
Three principles govern how the role works:
1. Advisor, not vendor
JMA sells through genuine discovery and business alignment, not feature lists. The role positions JMA as a trusted advisor and connects proactive managed services and security to the client business outcomes: risk reduction, operational efficiency, and growth. Deals are earned across a multi-month cycle through listening and follow-through, not pushed.
2. The role is the commercial conduit
The Technical Sales Executive sits between the CEO/Owner and the CTO/CISO. It takes the structure, architecture, and cost the CTO/CISO builds and translates them into the proposal and presentation for the client and for the CEO/Owner. The CTO/CISO is out of proposal writing and co-presenting entirely. The role owns front of house and is brought into client communication by the CTO/CISO only when necessary.
3. Nothing reaches a client without internal sign-off
Every operational or technical requirement, option, or commitment, including those raised while pursuing a prospect, is approved by the CTO/CISO before it is presented. The role never sets, adjusts, or negotiates price.
Core Responsibilities
1. Prospecting and Qualification
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.
2. Relationship Development
Build and nurture long-term, high-fit client relationships through advisor-style listening and consistent follow-through, resulting in multi-year partnerships and referrals.
3. Client-Facing Communication and Presentation
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.
4. Proposal and RFP Packaging
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). The role assembles and presents. It does not author architecture or set price.
5. Pipeline and Sales-Cycle Management
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.
6. New-Client Approval Coordination
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.
7. Onboarding Handoff
Coordinate a clean handoff from signed client to service delivery, so the relationship the role built transitions into operations without friction.
8. Sales Function Development
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. See Open Items.
New-Client and New-Project Workflow
A new client or new project moves through a fixed sequence. The role owns the front and the back of this sequence; the middle is owned inside JMA.
1. Opportunity
The Technical Sales Executive sources and qualifies the opportunity and conducts discovery.
2. Architecture and pricing
The CTO/CISO scopes the solution architecture and builds the pricing. The role authors neither.
3. Final pricing approval
The CEO/Owner holds final pricing authority and may adjust the CTO/CISO pricing for any business reason. The role does not set or change price.
4. New-client approval
The CTO/CISO and CEO/Owner approve the client and the engagement.
5. Presentation
The Technical Sales Executive packages the approved solution and pricing into the proposal and presents to the client. The CTO/CISO is brought into client communication only if necessary.
6. Handoff
On signature, the role coordinates onboarding into service delivery.
NOTE: Pricing is built by the CTO/CISO and finalized by the CEO/Owner. The Technical Sales Executive presents price but never sets, adjusts, or negotiates it. No operational or technical requirement, option, or commitment reaches a client until the CTO/CISO has signed off.
Authority
What the Role May Do
• Prospect, qualify, and conduct discovery independently.
• Own all client-facing communication and presentation for prospective and onboarding clients.
• Manage the pipeline, funnel, and forecasting in HubSpot.
• Request architecture, scoping, and pricing from the CTO/CISO for any prospect or project.
• Package CTO/CISO-provided architecture and pricing into proposals and RFP responses.
• Go directly to the CTO/CISO for any matter only the CTO/CISO would know.
• Coordinate onboarding handoffs to service delivery.
• Recommend sales process, CRM, and pipeline improvements to the CEO/Owner.
What the Role May Not Do
• Set, adjust, or negotiate pricing.
• Author or alter solution architecture or technical scope.
• Present any operational or technical requirement, option, or commitment to a prospect before CTO/CISO sign-off.
• Commit JMA to scope, deliverables, or timelines without CTO/CISO and CEO/Owner approval.
• Accept a client that has not cleared CTO/CISO and CEO/Owner new-client approval.
• Represent the vCIO or vCISO functions to clients. Those functions are reserved.
• Route employment, activity, or performance matters around the CEO/Owner.
Required Qualifications
• 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.
Requirements
Preferred Qualifications
• 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.
Success Measures and Role Evaluation
The role is reviewed on a recurring cadence. Success indicators include:
• Qualified pipeline built and advanced against a defined cadence.
• New multi-year, high-fit clients closed, consistent with the JMA values-driven client standard.
• Sales-cycle discipline: accurate HubSpot hygiene, forecasting, and follow-through.
• Clean handoffs from signature into onboarding.
• Retention and referral generation over time.
• The CTO/CISO is fully out of proposal writing and co-presenting, with the role carrying front of house.