Digital Workplace Specialist - Reading PA

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

Job Details

• Level: Experienced
• Position Type: Full Time
• Education Level: 4 Year Degree
• Salary Range: $150,000.00 - $175,000.00 Base+Commission/month
• Travel Percentage: Road Warrior
• Job Shift: Day
• Job Category: Sales
• 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.

Drive New Business & Build Relationships

• 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

Own the Sales Process

• 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

Sell Solutions That Matter

• 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

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)