Website winslowtg Winslow Technology Group

The Professional Services Sales Executive (PSSE) is an expert in identifying and closing Professional Services business (Project Services and Managed Services).  In this role, the PSSE shall effectively articulate and justify the value of Winslow Technology Group’s (WTG) Professional and Managed Services offerings to increase customer value and success.  The PSSE functions as a collaborative role between customers and prospects, sales (WTG Account Executives and Solution Architects), and the WTG Professional Services organization.  In this role, the PSSE is responsible for closing Professional Services opportunities (sales) and helping with scoping, Statement of Work (SOW) development, and collaborating with the WTG VP of Services to enhance internal processes and external customer experience.  The candidate will have also have the opportunity to learn from other highly successful IT professionals, sharply honing their technical skills, and truly making an impact on the value, experience, and perception of WTG Professional Services.

Key Responsibilities:

  • As leads are generated by Business Development Representatives (BDRs), collaborate with the respective AE/SA team to architect Project Services and/or Managed Services that help customers achieve their objectives.
  • Collaborate with WTG’s end-user-compute (EUC) teams to identify unique opportunities that are EUC-centric, such as deployments, imaging, warehousing, etc.
  • Identify opportunities for new projects and services within existing engagements.
  • Collaborate with WTG’s Project Services and Managed Services (Professional Services) teams to align implementation – before, during and after the project (or on-going services, in the case of co-managed).
  • Assist with preparation and definition of Statements of Work (SOWs) including major work activities, estimation of effort and specification or scoping of services.
  • Take an active role in the “services close process” ensuring that the solutions, inclusive of services presented, fit the requirements (technical, functional, and budget) while making a compelling argument for client to move forward.
  • Support the services proposal process by creating supporting materials (sales collateral, RFP/RFI, ROI, CBA, etc.) and delivering in person or virtual presentations.

Required Skills:

  • Articulate and justify the value of Professional Services
  • Develop sales and proposal materials including ROI, CBA, etc. that are geared towards Professional Services
  • Ability to identify and qualify Professional Services opportunities
  • Ability to structure deals in creative and value-oriented ways
  • Excellent objection handling geared towards Professional Services
  • Demonstrated critical thinking skills
  • Strong sales acumen
  • Strong communication skills (written and verbal), ability to create and deliver written and oral content (including presentations)
  • Self-starting, ability to work independently with direction but minimal

Required Experience:

  • 5+ years of experience with technology sales, with at least 3 years in a strictly services-focused sales role
  • 10+ year of professional working experience desired
  • Experience with services automation tools (e.g. Autotask, Connectwise, etc.)
  • Bachelor’s Degree or equivalent experience
  • Experience with staffing and contractor management (staff augmentation)


Job Location

  • East Coast

Position Type

  • Full-Time/Regular

Travel Requirements

  • This position requires some local and regional travel, up to between 30-50%


Winslow Technology Group is an Equal Opportunity/Affirmative Action Employer.

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