Mid Market Account Executive (Remote)

WorkRamp • San Francisco, CA

164d • $200,000 - $240,000

About The Position

At WorkRamp, we’re redefining learning for employees, customers, and partners alike. As an AE focused on the mid-market, you’ll lead full-cycle sales with companies scaling fast - across five distinct personas and one of the most competitive landscapes in SaaS. This is a role for someone who doesn’t wait. Someone who thrives on owning their book of business and shaping the way buyers buy. If you’re a challenger-minded hunter with the mindset, grit, and discipline to win, we want to hear from you.

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

Nice To Haves

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

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.

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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 51-100 employees