About this role.
DataGrail is seeking a Mid-Market Account Executive to own a full B2B SaaS sales cycle for its agentic data privacy platform. The role emphasizes self-sourced outbound pipeline generation, challenger-style discovery, champion development, commercial negotiation, and rigorous forecasting. Sales cycles are high velocity at approximately 30 to 40 days, with expectations to build 3x pipeline coverage and contribute qualified pipeline within 90 days. The ideal candidate has consistent quota attainment in full-cycle mid-market SaaS sales and can sell business risk and privacy outcomes to senior privacy, legal, security, and IT stakeholders.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
4/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
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Sample interview questions
I segment target accounts by ICP fit, trigger events, and likely business pain, then combine personalized outbound, multithreaded outreach, and consistent follow-up. I qualify early against business impact, decision process, compelling event, and access to power so that pipeline coverage reflects real opportunities rather than activity volume.
In a prior SaaS sale, the buyer initially viewed the problem as a workflow inconvenience rather than a strategic risk. I used benchmark data and discovery questions to quantify the cost of inaction, tied the issue to executive priorities, and reframed our solution around business outcomes, which created urgency and advanced the deal.
I would first understand their privacy operating model, AI adoption plans, data footprint, regulatory exposure, and existing manual processes. I would then tailor the value narrative around reducing privacy risk, automating operational work, enabling responsible AI adoption, and giving teams a secure, scalable governance foundation.
I establish mutual next steps, stakeholder maps, qualification criteria, and a close plan immediately after discovery. I keep momentum through clear deadlines, multithreading, rapid follow-up, and early alignment on commercial and security requirements so that late-stage surprises do not delay the decision.
I forecast based on verified customer actions and exit criteria rather than optimism or stage age. I regularly inspect deal risks, validate decision process and champion strength, document next steps in CRM, and separate commit opportunities from upside opportunities based on objective evidence.
The Opportunity:
Data privacy has become one of the most strategic challenges facing modern enterprises, sitting at the intersection of AI governance, data operations, and customer trust. As companies adopt AI at scale, they need new ways to automate privacy and manage risk without slowing innovation. DataGrail has launched the first agentic privacy platform, and we’re entering a pivotal phase of growth as we scale toward the next stage of the business.
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. There’s a real market appetite for what we sell, giving you the opportunity to build your own pipeline, lead a challenger-style, insight-driven sales process, and quickly build momentum toward your first-year quota.
This team has consistently delivered strong results quarter over quarter, and you’re joining a motion with a proven track record. Sales cycles here are measured in weeks, not the year-plus timelines common in enterprise sales, so you’ll see the impact of your work sooner.
AI adoption is pushing privacy and governance higher on the priority list for the kinds of companies you’ll be selling to, and DataGrail’s product keeps pulling ahead of the competition. That combination gives you a strong foundation to build on from day one.
What You’ll Do:
- Build and manage a self-sourced pipeline at 3x coverage against quota, largely through your own outbound.
- Run a challenger-style sales process: lead with insight, create urgency, and keep deals moving through a compressed 30 to 40 day cycle.
- Identify and develop champions inside target accounts who advocate for you and carry deals forward internally.
- Negotiate pricing and contract terms quickly and confidently, protecting deal momentum without stalling progress.
- Manage your full-cycle pipeline with disciplined forecasting and CRM hygiene, from first outreach through close.
- Ramp quickly on DataGrail’s product, ICP, and sales process, contributing to pipeline within your first 90 days.
What You’ll Bring:
- 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. Specific numbers seem like something we should discuss in initial interviews.
- A coachable mindset and the ability to take feedback and adjust quickly, especially during ramp.
Bonus Points
- Experience selling privacy, data governance, security, compliance, or other regulated or technical software.
- Experience selling to privacy, legal, security, or IT stakeholders at the VP or Director level.
- Familiarity with a modern GTM tech stack (Salesforce, Gong, sales engagement tooling) and comfort using AI to work smarter.
What Success Looks Like
Within 90 Days You’ll:
- Complete onboarding and develop deep fluency in DataGrail’s platform, the privacy landscape, and our competitive differentiation.
- Begin generating qualified pipeline and running discovery calls with strong command of the message.
- Build pipeline at 3x coverage against a prorated quota with 1 to 2 deals already closed.
Within 180 Days You’ll:
- Own a healthy, well-qualified pipeline with multiple opportunities actively advancing through stage.
- Maintain 3x pipeline coverage against your full quota.
- Close your first new-business deals and demonstrate consistent, accurate forecasting.
Within 365 Days You’ll:
- Consistently meet or exceed your annual quota in new ARR through a repeatable, largely self-sourced pipeline motion.
- Own a defined book of mid-market accounts with a clear plan for continued penetration and growth.
- Develop multi-quarter account plans for your top mid-market accounts, identifying paths to expansion and long-term value beyond the initial deal.
The OTE compensation (salary + variable) range below is a guideline and the final compensation will be based on factors such as qualifications, skill level, and competencies. Our compensation ranges apply to all US-based job postings regardless of state.
All full-time regular employees are eligible for equity, health, dental & vision insurance plans, remote-first working environment, 401k savings plan, parental leave, wellness benefits, flexible time off, paid holidays, and a work from home stipend. Benefits are subject to change.
Compensation Range
$160,000—$190,000 USD
About Us:
DataGrail is the Agentic Data Privacy Platform. We help the world’s leading brands such as HubSpot, FanDuel, Dexcom, Major League Soccer, and Okta automate privacy and control risk with secure, human-governed AI that scales.
Powered by Vera, the complete privacy AI agent, and underpinned by an unrivaled 2,500+ integrations and no-compromise security architecture, DataGrail is built to solve complex privacy challenges that others can’t. DataGrail is rated 4.8/5 stars on G2 and is a two-time recognized privacy leader by IDC.
DataGrail provides equal opportunities for everyone that works for us and everyone that applies to join our team, without regard to sex or gender, gender identity, gender expression, age, race, religious creed, color, national origin, ancestry, pregnancy, physical or mental disability, medical condition, genetic information, marital status, sexual orientation, any service, past, present, or future, in the uniformed services of the United States (military or veteran status), or any other consideration protected by federal, state, or local law. Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.
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