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Craft Ventures Portfolio Job Board

Head of GTM Systems & Strategy

Roboflow

Roboflow

San Francisco, CA, USA · New York, USA · Remote
USD 225k-255k / year
Posted on Sep 30, 2025

Location

NY, SF or Remote

Employment Type

Full time

Department

Sales

About Roboflow

Roboflow is the end-to-end computer-vision platform trusted by 1M+ developers. We’re tripling ARR each year on our way from eight to nine figures and need an operator-builder who can weaponise data, automation, and enablement so the revenue engine scales as fast as the tech.

Why This Role Exists

You’ll start as a hands-on force-multiplier for Sales, Solutions, and CS- fixing what’s brittle, wiring what’s missing, wiring the tech, and proving impact fast. As the foundations harden, you’ll hire and lead a lean RevOps and Enablement team so you can scale yourself and the function. The ultimate goal is making the revenue team measurably more productive, predictable, and faster tomorrow-not next quarter.

Core Outcomes (first 6 months)

  1. Pipeline Generation- 2× increase in ‘qualified pipeline’ per AE without CAC blow-up.

  2. Cycle Compression- 25% reduction in median days-to-close through smarter routing and qualification/MEDDPICC rigor.

  3. Data & Automation- 80% of repetitive IC tasks automated; <2% data hygiene error rate.

  4. Enablement Velocity- New-hire ramp to productivity in ≤ 90 days; content library mapped to each sales stage for major selling motions/engagement models.

  5. Forecast Accuracy- Weekly forecast ±5% variance using live signals and scoring.

  6. Team Evolution- Draft hiring plan and success profiles for the next 1-2 RevOps/Enablement hires.

Key Responsibilities

  • Architect and Automate

    • Own the revenue tech stack end-to-end (Salesforce, Clay, custom work, etc.).

    • Design workflows that turn data signals into “next best actions”.

  • Strategy to Execution Loop

    • Codify GTM strategy (ICP refinement, packaging, pricing) and push it into systems and enablement assets.

  • Enablement and Process Excellence

    • Build modular playbooks and high-frequency team development content.

    • Implement and ship updates rapidly.

  • Analytics and Revenue Intelligence

    • Ship dashboards that reps use daily, leaders trust weekly, and the board loves quarterly.

  • Team Leadership

    • Recruit, coach, and retain a high-output team once baseline KPIs hit.

    • Foster a culture of experimentation, shipping fast, and craftsmanship.

  • Cross-Functional Glue

    • Partner with Product for usage-to-expansion loops and with Marketing for demand DNA tagging.

You’ll Thrive Here If

  • Hybrid profile: 7–10 yrs scaling large B2B SaaS from <$20M to $100M+ with proven RevOps + systems chops (SQL or Python scriptable).

  • Builder’s mentality: You prototype in Zapier on in-flight Wi-Fi and roll it company-wide the next day.

  • Opinionated: Bring frameworks and kill sacred cows when data says so.

  • Storyteller: Can explain a revenue architecture to the board in three slides or to an SDR in 30 seconds.

  • People leader: have hired and developed small but mighty ops and/or enablement teams.

  • Intangibles: Default-to-action, radical candour, craftsmanship, joy in the craft.

Nice-to-Haves

  • Certified in Command of the Message and Command of the Sale.

  • Implemented MEDDPICC and forecasting across multiple regions.

  • Implemented AI-driven lead scoring or autonomous SDR playbooks.

  • Exposure to computer-vision, edge AI, or manufacturing/logistics go-to-market.

Compensation & Expectations

  • Pay range: $225k-$255k OTE

  • Senior level

  • 8+ years of experience in sales strategy and operations

  • Working out of our NYC hub 3+ days a week is highly preferred. The role is US-centric.