THE ROLEDGR Systems designs, builds, and delivers technology for organizations that depend on it working. We are an IT solutions provider and systems integrator headquartered in Tampa, and we are growing.
This is a quota-carrying role, and it is a relationship role. This is a hunter role focused on customers typically between $500M and $3B in annual revenue, with real IT complexity and teams that are lean for the size of the business.
You will own the full cycle: finding the opportunity, shaping the solution with our Solutions Consulting team, closing it, and making sure what was sold is what gets delivered. Your focus is the Florida mid-market, based out of Tampa / Central Florida, and your earning potential is uncapped.
You will report to our DGR sales team, and work closely with Inside Sales, Order Management, Solutions Consulting and Project Management teams to deliver on commitments.
WHY MID-MARKET IS ITS OWN DISCIPLINEIf you have sold into large enterprise, you are used to procurement teams and buying committees. If you have sold to small business, you are used to one decision-maker and a short conversation. Mid-market is neither, and we would rather say so now.
Our mid-market clients run multiple sites, hybrid workforces, compliance requirements, cyber insurance questionnaires, and infrastructure that is due for a refresh, often with an IT team that is lean for a business of that size and stretched across all of it. The IT leader you sell to usually answers to a CFO or COO who signs off on the investment and asks the hard questions. They do not have time for a vendor. They need a partner who knows their environment well enough to bring them the right next project before they ask.
The best mid-market relationships are built between deals. That is the skill we hire for: earning the role of trusted advisor to a lean IT team, and turning that trust into a multi-year roadmap rather than a series of one-off quotes.
WHAT YOU'LL OWNThis role covers both sides of the book: some clients we already serve and many we don't serve yet. The relationships you can bring to the table are of most importance to your success.
Client Growth- Maintain and grow your own base of mid-market clients, with account plans built around each client's priorities, refresh cycles, and renewal dates
- Become a trusted advisor to IT leaders and the executives they report to, so you hear about a need before it becomes a project
- Respond to client requirements accurately and within committed service levels
- Follow every order through to delivery, so the client's next call is about the next project rather than an issue with the last one
New Business- Prospect and open net new logos across Florida organizations in the $500M to $3B revenue range
- Execute campaigns that engage prospective clients and clearly articulate the value of DGR's solutions
- Respond to, qualify, and work incoming leads
- Research current and prospective clients to understand their business, their environment, and who makes the decision
Deal Ownership- Qualify opportunities honestly: budget, decision-maker, timeline, and the business problem behind the request
- Build proposals around business outcomes, and present them to both technical and executive audiences
- Negotiate pricing and terms that protect both the client relationship and DGR's margin
- Manage the full sales lifecycle, from quote and order management through close and client follow-up
Solution & Partner Programs- Maintain a strong working knowledge of our OEM solutions (Microsoft, HPE, Fortinet and others), deal registration programs, and pricing strategies
- Register opportunities early, and use incentives, and special pricing to win business
- Bring in our Solutions Consulting teams to shape security, infrastructure, and Microsoft solutions
- Track subscription and licensing renewals so none arrive as a surprise to the client or to us
You will also keep the CRM current, with opportunities and next steps someone else could act on without asking you. We treat that as part of the job, not as something to get to later.
HOW WE WORK- We sell outcomes, not line items. Mid-market clients buy because a business problem needs solving. Start with the problem; the bill of materials and statement of work follows.
- We sell what we can deliver. A quote is a commitment. Configuration, pricing, and availability should agree before it reaches the client, and you will work with our technical and inside sales teams to make sure they do.
- Margin is part of the deal. We win business we can deliver well and profitably. A discount is a decision, not a reflex.
- The pipeline tells the truth. Forecasts are built on what the client has said and done, not on what we hope. A deal that has stalled gets called stalled.
WHAT WE'RE LOOKING FORYou'llNeed- 5 or more years of experience in professional IT outside sales, carrying a quota
- Experience selling IT solutions to commercial organizations of comparable size, and a record of growing accounts over multiple years
- Knowledge of OEM direct and distribution sources of supply and the associated quote-to-order process
- A track record of opening new accounts, not solely focused on growing inherited ones
- The ability to hold a credible conversation with an IT director and with a CFO / CIO / CTO
- Working fluency with CRM tools
- The ability to travel to meet clients and partners in person
It Will Help If You Have- Sold cybersecurity and professional services solutions
- Worked with Microsoft licensing, including the Cloud Solution Provider (CSP) program
- Sold multi-year services or subscription agreements alongside hardware and software
- An existing network of IT and business leaders in the Tampa Bay area or across Florida
- Come from a VAR, MSP, or solutions provider
- Sold into industries with compliance requirements, such as healthcare or financial services
We'll Teach You- Our OEM and partner programs and how their mechanics work
- Our service portfolio, delivery teams, and how we scope solutions
- Our systems, tooling, and sales process
WHO THIS ISN'T FORWe would rather be direct than waste your time.
- If you want leads and pipeline handed to you, this is not that role. Most of your pipeline will be built by you.
- If you would rather close one big deal than earn a client's business year after year, mid-market will frustrate you. Our best accounts are built over many projects.
- If your instinct is to lead with a discount, we are not a match. We compete on judgment and delivery.
- If you are only comfortable talking to IT, this will stretch you. Many decisions here involve the CFO or COO.
COMPENSATION & BENEFITSBase salary range - Very Competitive
Variable compensation - Uncapped commission
Work arrangement - Hybrid - Field Based, Tampa Bay area
DGR Systems also offers a robust company benefits package designed to support employees and their families, including competitive health and welfare benefits, paid time off, retirement savings support, and other company-sponsored programs.
HOW TO APPLY FOR THIS ROLESend a resume and a short note about a client you grew from a single transaction into a long-term account: what the first deal was, and what you did between deals. We are more interested in how you earned the trust than in the size of the number.
Apply to: joinus@dgrsystems.com 
