🙌 About WorkRamp
At WorkRamp, we believe that the best companies grow through learning. That’s why hundreds of market leaders such as Box, Lattice, and Brex choose the WorkRamp Learning Cloud to power employee and customer learning.
We are building the world’s best LMS through a highly effective, remote-first culture. Our culture revolves around our three core values:
#startupmode: We keep a startup mindset in everything we do. We move fast, we stay efficient, and treat every day like it’s day 1.
#customerfocus: We are customer-first and try to provide amazing experiences at every touch point.
#oneteam: We help each other succeed, collaborate often, and win together.
🚀 What’s the opportunity?
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.
🔧 What will I be doing?
- 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.
💡 What experience/skills/attributes do you need to have?
- 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
- Experience selling LMSs or adjacent solutions (e.g. sales enablement, talent management or customer success platforms) is a plus
✋ A Couple Notes Before You Apply
We operate in a culture of radical honesty - with ourselves and each other - because it’s the only way we improve.
Be real about your results.
You don’t need to inflate your quota attainment or dress up your metrics. We know the last few years have been tough across the board. We value truth and context over perfect numbers - and yes, we’ll be able to tell.
No lone wolves.
We judge success based on your ability to help us win, not in your ability to go it alone. If you do not seek a proactive, highly communicative environment, this position may not be right for you.
This isn’t a checkbox role - it’s a builder’s seat. If that excites you, let’s talk.
🏆 Perks
-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.
- At this time, WorkRamp does not sponsor work visas
