Sales Director, Enterprise Sales

Jobicy; United States; Remote; USD 380,000 - 420,000; Full time

Benefits offered by this job

Travel stipend

Productivity stipend

AI tools stipend

Team lunch stipend

Home office stipend

Health insurance coverage

Equity in the company

Job summary

Roboflow is hiring a frontline enterprise leadership leader to guide a team of Enterprise Account Executives responsible for net-new logos and rapid expansion. You will drive seven-figure deals within the first year, with an open, transparent culture and a strong coaching discipline.

The role emphasizes ownership of pipeline, deal quality, and recruiting as a discipline, with a Land-and-Expand model and global AI/ML platform adoption across enterprise customers.

Qualifications

• Proven leadership of enterprise AEs and consistent quota attainment.
• Experience selling AI/ML or developer tools is a plus.
• Strong outbound pipeline development and discipline.
• Ability to run live deal reviews and surface truth over optimism.

Responsibilities

• Own full team quota attainment, coverage, pipeline quality, and forecast accuracy.
• Build and enforce a high-velocity, outbound culture with weekly meetings and opportunities.
• Lead weekly deal reviews to validate use case alignment and buyer access.
• Provide live coaching and uphold Command of the Message/Value selling standards.
• Drive talent density through proactive recruiting and hiring benchmarks.

Skills

Leadership

Enterprise sales

Outbound discipline

Deal review

Value selling

Hiring discipline

Job description

Who We Are

Our mission is to make the world programmable. Sight is one of the key ways we understand the world, and soon this will be true for the software we use, too.

We’re building the tools, community, and resources needed to make the world programmable with artificial intelligence. Roboflow simplifies building and using computer vision models. Today, over 1M+ developers, including those from half the Fortune 100, use Roboflow’s machine learning open source and hosted tools. That includes counting cells to accelerate cancer research, improving construction site safety, digitizing floor plans, preserving coral reef populations, guiding drone flight, and much more.

Roboflow is supported by great customers and investors, having raised over 63 million from Y Combinator, Google Ventures, Craft Ventures, Sam Altman, Lachy Groom, amongst other leading software investors.

Roboflowers love building great things with passionate teammates. We value ownership, accountability, and a bias toward action—whether it’s a big initiative or a small fix. Many of us have founder mindsets and thrive in Roboflow’s high-autonomy environment—some even started as side hustlers in school.

The Mandate

This is a frontline enterprise leadership role. You will lead a team of Enterprise Account Executives responsible for net-new logo acquisition and high-velocity expansion.

Our model is Land-and-Expand. Initial use cases convert into broader platform adoption, and it is common to build toward seven-figure deals within the first 12 months of a new enterprise relationship. Your team is expected to open the door and systematically expand the footprint.

What You Own

1. 1. The Number
   • Full team quota attainment. You manage coverage, pipeline quality, and conversion discipline with extreme ownership.
   • Forecast accuracy. We operate with transparency. If the number misses, you own the post-mortem and the correction.
2. 2. Pipeline Culture
   • The Standard: Minimum 2+ net new meetings and 1+ qualified net new opportunity per rep, per week.
   • Self-Sufficiency: Pipeline is generated by the reps, not outsourced to marketing or SDRs. Outbound discipline is enforced, inspected, and coached daily. We build pipeline; we don’t wait for it.
3. 3. Deal Quality & Inspection
   • Rigorous Qualification: Weekly structured deal reviews. We do not tolerate “framework theater”- you are expected to surface the truth of a deal, identify gaps in real-time, and drive a credible path forward.
   • Truth over Optimism: Deals are inspected for use case alignment, economic buyer access, and implementation feasibility.
4. 4. Coaching & Standards
   • Tell, Show, Observe, Feedback: You provide live deal coaching and call reviews. You don’t just tell reps what to do; you show them.
   • Methodology: We run Command of the Message–style value selling. You are expected to uphold and evolve this standard across the team.
5. 5. Recruiting as a Discipline
   • Talent Density: Proactive talent mapping and a continuous recruiting motion. You aren’t just backfilling; you are upgrading the team over time with a clear, high-bar hiring rubric.

Candidate Profile

Non-Negotiables

• Leadership Track Record: You have led enterprise AEs and consistently hit team quota.
• High-Performing IC Roots: You were a top-tier individual contributor before moving into leadership. You know what excellence looks like because that was you.
• Outbound Grit: You have built outbound pipeline discipline yourself and can explain how to replicate it.
• Deal Intuition: You can run a live, unscripted deal review and improve the deal’s probability of closing in real-time.
• Scale Experience: You have operated in the $10M–$200M ARR growth stage where structure is evolving and the pressure is constant.

Strong Preferences

• Experience selling AI/ML, developer tools, data infrastructure, or technical platforms.
• Experience with $100K+ ACV and multi-stakeholder enterprise cycles.
• Formal training in Command of the Message or an equivalent value-based methodology.
• Background of flourishing within rigorous enterprise sales organizations.

Why This Is a Meaningful Seat

Vision AI is becoming infrastructure for the physical world. Organizations are deploying vision systems in production now. They aren’t experimenting.

We are early enough that the leaders here will define how this category sells and scales. This is a durable business with real customers, real deployments, and a credible path to a meaningful exit.

The Interview Process

• Initial Conversation: Context, motivations, and standards.
• Deep Dive: Detailed walkthrough of your deals, hiring decisions, and operating rhythm.
• Challenge Interview: Present a 30/60/90-day plan and defend it under pressure.
• References: We triangulate beyond your provided list.

What You’ll Receive:

The target compensation for this role is $400k OTE- this uncapped.

In addition to our cash compensation, we offer generous perks and benefits. Below are some of the highlights:

• $4000/yr Travel Stipend to travel anywhere anytime to work alongside other Roboflowers
• $350/mo Productivity stipend to spend on things that make your work environment more productive, like high-speed internet at home or a co-working space
• $350/mo AI Tools stipend
• $150/mo team lunch stipend
• $500/one time home office stipend
• Cover up to 100% of your health insurance costs for you and your partner or family
• Equity in the company so we are all invested in the future of computer vision

Equal Employment Opportunity

At Roboflow, we believe great ideas come from everywhere—and everyone. We’re proud to be an Equal Opportunity Employer committed to building a diverse and inclusive team. We consider all qualified applicants regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, disability, age, veteran status, or any other legally protected characteristics.