Mid Market Account Executive

Summary

Join WorkRamp, a leading LMS company, as a Mid-Market Account Executive and lead full-cycle sales with fast-scaling companies. You will proactively generate pipeline, run discovery and demo cycles, sell consultatively, and drive strong internal collaboration. This role demands excellence in execution, including CRM hygiene and timely follow-ups. You will need a challenger-minded hunter mentality and a commitment to continuous learning and improvement. WorkRamp offers a remote-first culture and a comprehensive benefits package.

Requirements

• 5+ years of full-cycle SaaS sales experience closing deals in the $25K - $100K+ range, and selling to companies of up to 5k employees
• Proven ability to generate your own pipeline through outbound prospecting - not reliant on others to hit your number
• Experience balancing net-new acquisition with install base expansion - able to prioritize and execute both effectively
• Experience selling into multiple personas or product lines in hyper-competitive situations (4+ competitors per deal)
• Comfortable leading complex sales cycles with multiple stakeholders on both the buyer and internal side
• Strong track record of executing the fundamentals: CRM hygiene, pre-call prep, timely follow-up, and clear next steps
• Ability to challenge buyers constructively, ask hard questions, and guide deals with confidence
• Natural collaborator - works cross-functionally with SEs, CS, and leadership to win deals
• Demonstrated growth mindset - welcomes coaching, owns development, and brings solutions, not excuses
• Executive presence, structured communication, and the ability to drive urgency without being aggressive

Responsibilities

• Generate pipeline proactively through outbound and strategic prospecting into net new whitespace and install base
• Run crisp, well-prepped discovery and demo cycles, with clear agendas, next steps, and multithreaded alignment
• Sell consultatively - challenging assumptions, navigating friction, and guiding buyers with confidence
• Drive strong internal multithreading - aligning SEs, CS, leadership, and product to win key deals
• Execute “the little things” with excellence - daily Salesforce hygiene, timely follow-ups, strong next step discipline, and proactive pipeline management
• Stay disciplined in every stage of the deal cycle with relentless preparation
• Come in with an “always learning” mindset. You’ll own your development, seek feedback, continually improve, and help us uplevel as a team

Preferred Qualifications

Experience selling LMSs or adjacent solutions (e.g. sales enablement, talent management or customer success platforms) is a plus

Benefits

• Fully Remote - Work from anywhere in the US
• Generous Time Off - Paid vacation, sick leave, and 12 company-wide holidays
• Parental Leave - Paid leave to support you and your growing family
• Equity - Be a part of our success with meaningful ownership
• Comprehensive Healthcare - Full medical, dental, and vision coverage
• Financial Security - 100% employer-paid short-term & long-term disability, plus life insurance
• Work-From-Home Support - Stipend for your remote setup & a DeskPass account
• 401(k) Plan - Invest in your future with employer-sponsored retirement savings
• Wellbeing & Assistance - Access to One Medical, Wellhub+ (formerly Gympass), and Employee Assistance Programs