Digital Workplace Solutions Sales Leader

Watchkeep; Reading, Northern (Berks County, KY); Hybrid; USD 150,000 - 175,000; Full time

Job summary

WatchKeep is seeking a Digital Workplace Specialist to drive growth and expand relationships, helping organizations work smarter, safer, and more efficiently. You’ll collaborate with service delivery and customer success teams while positioning WatchKeep as a trusted strategic IT partner.

As a frontline seller, you’ll identify prospects, conduct discovery, and guide the full sales cycle from initial meeting to signed agreement, selling managed IT, cybersecurity, cloud transformation, and unified

Qualifications

• 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
• Stay Sharp & Lead with Expertise
• 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

Skills

B2B sales

Prospecting

Closing deals

Consultative selling

Time management

Resilience

Entrepreneurial

Education

Bachelor's degree

Job description

WatchKeep is seeking a Digital Workplace Specialist to drive growth and expand relationships, helping organizations work smarter, safer, and more efficiently. You’ll collaborate with service delivery and customer success teams while positioning WatchKeep as a trusted strategic IT partner.

As a frontline seller, you’ll identify prospects, conduct discovery, and guide the full sales cycle from initial meeting to signed agreement, selling managed IT, cybersecurity, cloud transformation, and unified