Digital Workplace Specialist

WatchKeep•West Reading, PA

About The Position

Compensation range shown reflects total on-target earnings and includes base salary plus commissions, bonuses, and other performance incentives. Are you a consultative sales professional who loves solving real business problems with technology? Do cyber security, cloud solutions, and modern workplaces get you excited? If so, WatchKeep wants to talk to you. As a Digital Workplace Specialist, you’ll be on the front lines of growth—driving new business, expanding relationships, and helping organizations work smarter, safer, and more efficiently. You’ll collaborate closely with our service delivery and customer success teams while positioning WatchKeep as a trusted strategic IT partner.

Requirements

2–5 years of B2B sales experience, preferably in Managed IT, Cloud, or related technology services
Proven ability to prospect net-new customers and close deals
Comfortable selling to executives, owners, and decision-makers using a consultative approach
Self-starter mindset with strong time management and resilience
Entrepreneurial, goal-driven, and motivated by results
Bachelor’s degree (or equivalent professional experience)

Responsibilities

Proactively identify and engage prospects to uncover IT frustrations, risks, and growth roadblocks
Lead outbound prospecting through calls, email, LinkedIn, and in-person meetings
Build strong, trust-based relationships with internal sales partners to generate referrals and joint account strategies
Confidently ask thoughtful, sometimes tough questions that challenge the status quo and move deals forward
Conduct consultative discovery to uncover business pain, technical gaps, and urgency
Qualify opportunities effectively focusing your time on deals that matter
Partner with technical teams to scope, price, and present tailored solutions
Manage the full sales cycle from first meeting through signed agreement
Maintain a clean, accurate pipeline and report progress consistently
Position WatchKeep as a strategic advisor by tying IT solutions to business outcomes like productivity, uptime, security, and risk reduction
Advocate and sell our full suite of services, including: Managed IT Services Cybersecurity Backup & Disaster Recovery Cloud Transformation Unified Communications & Collaboration
Keep up with trends in cybersecurity, cloud, and managed IT
Use market insights to refine your sales approach and stay competitive
Act as a trusted advisor—helping clients make confident, informed decisions