Watchkeep

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)