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About: Gregory McDonald

Recent Posts by Gregory McDonald

Sales Development Representative (SDR) Full Time

We are Keystone Management Group LLC, owner and operator of the following trusted high-tech brands: Cloudstar, Teletonix, Dioloigx, Notary Transfer, Mortgagephish and Jacksonville Technology Services. We believe first and foremost in the principle of partnership.  We seek clients with an active, passionate, and vested interest in taking their organizations to the next level by partnering with us for our people, process, technology and infrastructure.  Our services are designed to increase an organization’s productivity, up-time, business continuity, reliability, cyber-security awareness, and profitability.

The Opportunity

We’re looking for a Sales Development Representative (SDR) with at least two years’ experience in a similar position to join our sales team. This role is suited to a smart, focused, detail-oriented candidate who is excited by the idea of playing a big part our company’s journey, in an all-hands-on deck environment. 

The role

As an SDR, you will start our sales process by researching prospective customers, qualifying new sales opportunities and crafting effective outreach strategies. You will have early conversations with potential customers to better understand their business and identify how our services could help them and their people. Your success as an SDR will ultimately be based on the number of qualified leads you pass on to our Sales Execs.

What you’ll be doing day to day

  • Prospect research. Use industry knowledge and tools to research and build lists of appropriate clients and key personnel.
  • Outbound prospecting. Engage in 80-100 sales related activities per day to generate interest and qualify leads. You’ll use a range of channels including LinkedIn, calls and emails.
  • Meeting set up. Schedule introductory meetings for our Sales Execs with qualified prospects.
  • Product learning. Learning and maintaining in-depth knowledge of our products and services and the value they bring to businesses.
  • Tracking and Analytics. Tracking and managing all your activities in HubSpot, analyzing what’s working well and what’s not and improving performance accordingly.
  • Developing new strategies. Developing and implementing new prospecting strategies.
  • Understand our ideal customer profile
  • Start to build lists of prospect companies and key personnel
  • Contact and nurture customers
  • Develop and master your pitch for different channels and different customers
  • Learn how to get customers to commit to meetings
  • Become familiar then expert in tracking your work in HubSpot – our CRM system

What you will need to have

  • Minimum of 2+ years’ experience in a consultative sales environment required.
  • Demonstrated record of phone sales success achieving/exceeding sales targets on a monthly/quarterly basis.
  • Excellent telephone communication and persuasion skills.
  • Ability to easily and quickly build trust and rapport with customers.
  • Demonstrate a high level of integrity and customer focus. Customer first!
  • Perseverance and resilience are key! Quickly overcome objections and move to the next.
  • Must be self-motivated and able to work with limited supervision while maintaining sales, attendance, and performance expectations.
  • Ability to sit for several hours at a time and adhere to an assigned schedule.
  • This role requires you to be physically present in the office.

Bonus Points

  • Research-oriented; enjoy learning about prospects and customers to help find innovative ways to drive sales.
  • Previous experience as an entrepreneur, small business owner or sales-focused role highly preferred.
  • Previous experience and success in a bonus or commission-based sales environment is a strong plus.

What’s in it for you?

  • $30,000.00 / year salary
  • 2 weeks paid vacation
  • Health, Vision and Dental Insurance
  • Life Insurance
  • 401k with employer contribution

Please FAX your resume to:  866-224-9075

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Mortgagephish, a Cloudstar company, to sponsor 2019 Cyber Security Report

Cyber security is the No. 1 threat facing the financial services industries today, according to regulators, and knowing what you need to protect your company and your clients from breaches and hackers can be the difference in business success or failure in the 21st century. The cybersecurity special report from The Legal Description will take readers through some of the biggest security threats and discuss actions being taken by federal and state regulators to prevent breaches.

Cloudstar is pleased to sponsor the 2018 cybersecurity special report and looks forward to continuing to provide cybersecurity products to the land title, settlement services, legal, mortgage, and real estate industries.

Please visit the October Research website HERE to download your FREE copy of the 2018 report.

The Legal Description Cyber Security Special Report
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MortgagePhish, a Cloudstar company, to exhibit at Mortgage Bankers Association Annual Expo 2019

We hope you’ll join us this year at MBA’s Annual Convention & Expo 2019
October 27-30 | Austin Convention Center

MortgagePhish, a Cloudstar company, will be exhibiting, and we look forward to seeing our friends and customers.

Every year, MBA’s Annual Convention & Expo is the place to come together to leverage our collective strength and achieve the bests results for your business and our industry. This year, the country’s largest gathering of real estate finance professionals is headed to our nation’s capital and it’s going to be MONUMENTAL

Home to both the MBA and decision-makers influencing the industry’s future, Washington, DC is an ideal location to join us for unparalleled networking, learning and access. Featuring the biggest names and the brightest minds in the industry and beyond — as well as thousands of your colleagues — there is no other event like it all year. 

The agenda is packed with general sessions, breakouts, meetings and networking events for a variety of experience levels in residential mortgage lending. From practical breakout sessions that dig deep on operations and strategy to inspiring general sessions that provide vision and insight on policy and market trends, there is something for everyone. See the schedule for more details.  

Make a compelling pitch – download our sample business case letter to show your manager exactly why you need join your peers and colleagues in Washington, DC for what will be a MONUMENTAL convention experience.


Mortgage Bankers Association
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Computer Technical Support Associate (Full Time)

We are Jacksonville, Technology Services, LLC – a subsidiary of Keystone Management Group, LLC DBA Cloudstar.  We seek clients with an active, passionate, and vested interest in taking their organizations to the next level by partnering with us for our people, process, technology and infrastructure.  Our services are designed to increase an organization’s productivity, up-time, business continuity, reliability, cyber-security awareness, and profitability. Our company provides end-to-end services including remote troubleshooting to onsite, hands on support and repair.

The opportunity

We are seeking a knowledgeable, passionate computer technical support associate.

The role

As an CTSA, you will work directly with internal systems and end customers to deliver managed technical support services for PC / Desktop workstations, Windows Servers and Network, Storage.  The position will require visiting customer’s locations to build new network environments, diagnose connectivity, administer workstations and servers, as well as diagnose and repair basic computer hardware.

What you’ll be doing day to day

In your job capacity of technical support representative, you will be working at our data center office, providing remote technical support via telephone and email to new and existing customers while traveling to customer locations as needed.

What you will need to have

  • Minimum of 2+ years’ experience in providing technical support & computer hardware repair.
  • Excellent telephone and email communications skills.
  • Strong knowledge in installing, managing, troubleshooting and maintaining Windows Operating systems including: Server 2008, Server 2012, Windows 7, 8, 10.
  • Experiencing creating and managing users and groups in Microsoft Active Directory.
  • Must be able to establish, configure and maintain a business network.
  • Demonstrated knowledge working with, managing and troubleshooting DHCP, DNS, TCP/IP
  • Possess an expert level of computer hardware knowledge including the ability to replace motherboards, RAM, CPU, Disk.
  • Strong knowledge in establishing, troubleshooting and managing Wireless Networks
  • Must be able to install, run, and properly terminate copper Ethernet lines.
  • Ability to lift objects weighing 75 pounds.
  • Troubleshoot and remediate security incidents, viruses, and malware.
  • This role requires you to be physically present in the office with reliable transportation.


Bonus Points

  • Ability to install Active Directory, manage domain migrations, establish trust relationships, and create and manage Group Policy Objects
  • Knowledge or experience in configuring site-to-site VPN (Cisco, SonicWall, Fortigate)
  • Exposure to VMware, Citrix, VEEAM
  • Experience with ticketing systems such as AutoTask or RepairShopper.


What’s in it for you

  • $30,000.00 / year salary
  • 2 weeks paid vacation
  • Room for advancement / promotion
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Join Cloudstar at RESPRO 26

Join Cloudstar, Mortgephish, and executives from the country’s leading real estate brokers, home builders, mortgage lenders, and title/settlement service companies for the premier conference on affiliated businesses and strategic alliances in the home buying and financing industry!

RESPRO26 will be March 25-27 at the New Orleans Ritz Carlton.  This conference will be full of the quality “Best Practices” Sessions, Regulatory Workshops, and Idea-Sharing Round-tables that RESPRO® conference attendees have come to expect.  In addition, the networking opportunities with your current and potential partners will be invaluable!


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Come Join Us at the WFG Executive Round Table

WFG National Title Insurance Company has continually raised the bar each year at their annual Executive Round Table Conference since its beginnings in 2011. Join title and settlement executives from across the country to discuss and resource issues that you face as we enter the new year.

Chris Cury and Roland DuBeau will be exhibiting on behalf of Cloudstar and Mortgagephish (a Cloudstar company). We look forward to seeing many of our customers and industry friends.

The Executive Round Table Conference is being held February 3 – 6 at the hotel Eldorado, Sante Fe, New Mexico.

WFG Title Insurance
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Billing Specialist (full time)

We are seeking a detail-oriented, thorough, and organized professional to join our growing team. In this position, you will play a key role in managing the finances of our business, including creating financial transactions and generating relevant reports. In this position you will report directly to the CFO and work in a tightly integrated team with an assistant book keeper / office manager. You will also collaborate and communicate with employees, vendors, and customers to ensure accuracy of financial transactions.



  • Reconcile internal systems to produce and or audit customer invoices
  • Ensure accurate customer payment information
  • Contact customers to collect outstanding invoices / debts
  • Enter vendor invoices and track payments
  • Record and process customer payments as needed
  • Coordinate bank deposits and report financial results on a regular basis to management
  • Tally and enter cash receipts and credit card transactions
  • Obtain tax documents from new venders
  • Process customer billing changes
  • Provide administrative support to the management team when required



  • Bachelor’s Degree in Accounting or related field or equivalent work experience
  • Strong knowledge in QuickBooks
  • Five years’ experience working in accounts payable and receivable, and general ledger
  • Strong knowledge of generally accepted accounting principles
  • Extensive experience with data entry, record keeping and computer operations
  • Proficiency in Microsoft Word, Excel and Outlook.
  • Experience in services related to payroll and submitting payroll taxes is beneficial but not mandatory
  • Basic understanding of business and income tax worksheets and computations is a plus



  • $35,000.00 / year salary
  • 2 weeks paid vacation
  • Health, Vision and Dental Insurance
  • Life Insurance
  • 401k with employer contribution


Please FAX your resume to:  866-224-9075

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Cloudstar Launches Mortgagephish To Protect Homebuyers



What will they do when they’ve got phishing email?


Jacksonville, Florida, January 22, 2019 – Cloudstar, a leading provider of technology solutions for the Land Title, Mortgage Banking, and Real Estate industries has just announced a new way to protect home-buyers against what could be their worst nightmare; wire fraud. According to CNBC, scammers are deceiving people out of enormous down payments within days or hours of sitting down at the closing table. Homebuyers are often tricked into wiring funds into fraudulent offshore accounts and these victims often report unrecoverable losses in the six-figures.

With FBI statistics pointing to 2017 losses at over 1 Billion dollars, and 95% of all successful cyber-attacks caused by human error, Cloudstar decided to address this problem head-on though a new product called Mortgagephish.
Real Estate Agents, Title Agents and Lenders purchase Mortgagephish and enroll in simulated targeted hacking. The Mortgagephish system sends custom tailored phishing emails to all parties in the real estate transaction, then monitors the results.

With the advanced reporting offered by Mortgagephish, lenders and agents can quickly identify employees that click on harmless simulated phishing emails and text messages, then quickly target those individuals for online cyber-security training, which the system also provides.

What makes Mortgagephish unique is the quality and content of the email phishing and mock cyber-attacks. Leveraging Cloudstar’s long standing industry knowledge, the emails, text messages, and corresponding online training are custom tailored specifically for the company purchasing the service.

“It’s as real as it gets.”, stated Roland DuBeau when asked how the simulated phishing emails stack up to emails from real cyber criminals. “The difference”, Roland added, “is that we’re the good guys, and we’re here to train those working on the front lines; those in charge of protecting the homebuyer’s hard-earned money.”

The results are clear. Mortgagephish produces trained and aware individuals who are the first line of defense against wire fraud, cyber attacks and ransomware.

For more information, please visit to download your free report or call 800-640-4950.



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Cloudstar to Present on Cyber Security at 2019 DiCom Software User Conference

DiCom Software, the industry leader in Loan Review, Financial Risk Management, Portfolio Analysis, and CQS Reporting for banks and lenders will be holding their annual conference in Orlando, Florida this February.  Cloudstar CEO Gregory McDonald and Roland DuBeau, SVP of Sales, will be presenting on the cyber security risks facing the industry for 2019 and beyond in a hands on session for financial professionals.

To learn more about DiCom Software please visit their website at

Dicom Software

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Fidelity National Title Group Maryland Agency + Cloudstar to Present Webinar

Do You Know What Your IT Person Really Does?

It’s Your Business, Do You Really have Control?

Probably that’s a question you just default to your IT person, after all… you’re a title professional.  Operations large and small need to tackle IT.  And, it’s important to have base line knowledge of what your IT person is doing for you… How is your network secured?  What do you do in the event of a security breach?  Is your IT person also advising the staff on best practices when it comes to security?

On this Resource Morning webinar, our main speakers – Greg McDonald and Chris Cury will educate us on things to look out for, questions to ask your IT, and the pitfalls of not staying in touch with your IT.

Join our Fidelity National Title Group Maryland Operations webinar on Friday November 16th 2018 at 9:30am Eastern. Register HERE

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