Mid Market Account Executive

Role Overview

DataGrail is the Agentic Data Privacy Platform, helping brands automate privacy and control risk. As a Mid-Market Account Executive, you’ll own the full sales cycle in a segment with strong win rates and fast, 30 to 40 day sales cycles. This role is remote within the United States and is part of a team that has consistently delivered strong results quarter over quarter.

What You Will Do

Build and manage a self-sourced pipeline at 3x coverage against quota through your own outbound efforts. Run a challenger-style sales process, leading with insight and creating urgency to keep deals moving through a compressed 30 to 40 day cycle. Identify and develop champions inside target accounts, negotiate pricing and contract terms quickly, and manage your full-cycle pipeline with disciplined forecasting and CRM hygiene.

Why It Might Be a Fit

You have a proven track record as a hunter, building pipeline largely from scratch through outbound effort. You are comfortable running a challenger sales style and have experience identifying and developing champions. You command a modern sales methodology like MEDDPICC and have a track record of consistent quota attainment in full-cycle B2B SaaS sales. The role offers equity, health insurance, remote-first environment, 401k, parental leave, wellness benefits, flexible time off, paid holidays, and a work from home stipend.

Requirements

• A proven track record as a hunter, having built pipeline largely from scratch through your own outbound effort.
• Comfort running a challenger sales style: you bring insight and create urgency rather than waiting for the buyer to move.
• Experience identifying and developing champions who move deals forward internally, even when you’re not in the room.
• Challenges prospects’ current thinking by connecting data privacy gaps to real business risk, pushing the conversation beyond features and into impact.
• Command of a modern sales methodology (MEDDPICC, Command of the Message, or similar) and the discipline to qualify rigorously and forecast accurately.
• Strong, agile negotiation skills, closing terms quickly without losing deal momentum.
• A track record of consistent quota attainment in full-cycle B2B SaaS sales, with experience navigating a high-velocity, mid-market sales motion.
• A coachable mindset and the ability to take feedback and adjust quickly, especially during ramp.

Benefits

• Equity
• Health insurance
• Dental insurance
• Vision insurance
• Remote-first working environment
• 401k savings plan
• Parental leave
• Wellness benefits
• Flexible time off
• Paid holidays
• Work from home stipend