Director GTM (Operator/Advisor-in-Residence)

About the role

Cultivation Capital is a small, hands-on seed/early-stage fund, and this is a Director-level, operator/in-residence GTM role inside the portfolio.

The Work

• Own the outbound ABM motion end-to-end, from target account selection to outreach strategy and pipeline creation.
• Build and run the demand generation engine: AI-assisted messaging, sequencing, and cadence that consistently produce qualified pipeline.
• Partner closely with sales to turn demand into outcomes—so pipeline created becomes pipeline that moves (sales is the conversion engine; ABM is the demand engine).
• Use partnerships as a supporting lever to expand reach and accelerate demand where it matters most.
• Establish the operating rhythm for the GTM system (what gets measured, what gets iterated, and how quickly learnings turn into changes).
• Bring structure to execution: define the playbook, set clear targets, and ensure the team can run the motion repeatedly—not just “campaign once.”

What You’ll Need

• You’ve built outbound ABM programs that created pipeline (not just activity) in a B2B environment.
• You can translate “demand generation” into concrete execution: targeting, messaging, sequencing, and iteration—grounded in what’s actually working.
• You’ve worked tightly with sales (or owned the handoff) to ensure pipeline created is pipeline that converts.
• You can show direct, owned business impact in an early-stage context—material contribution to moving revenue meaningfully (e.g., from ~zero toward up to ~$30M), without needing strict ABM-attributed attribution.
• You’re comfortable operating in a fast-paced, hands-on environment where clarity and speed matter.
• You can implement and operationalize AI for ABM go-to-market, with specific examples such as:
• using AI to generate and refine account-specific messaging and value propositions,
• improving lead/account research and personalization at scale,
• optimizing outreach sequences based on performance signals,
• tightening targeting and segmentation using data you can actually access.

Even Better If

• You’ve used partnerships or channel relationships to drive demand alongside outbound.
• You’ve worked in seed/early-stage or similarly dynamic environments where GTM is still being shaped.
• You’ve led AI-enabled GTM projects end-to-end (from requirements and data access through rollout, measurement, and iteration), and can share specific examples of what changed in the pipeline process.

Who Thrives Here

• You like narrowing ambiguity quickly and getting to a clear plan you can execute.
• You operate with autonomy with high standards—you’ll move fast, but you won’t ship sloppy.
• You’re energized by working directly with founders/teams and making the GTM motion real, not theoretical.
• You communicate in a crisp, decision-ready way—clear updates, clear asks, and fast alignment.
• You enjoy being accountable for outcomes: pipeline creation, conversion handoff, and continuous improvement of the ABM engine—backed by direct impact on early-stage revenue growth.

The Team

This is a portfolio-company seat with an operator mindset.

Comp and Benefits

Base compensation is $100,000 to $150,000, based on experience, with equity offered separately. Benefits are competitive and include health coverage and time off.

Non-Traditional Backgrounds

If you’ve done GTM execution from the trenches—whether at a startup, a growth-stage company, or in a role that required building outbound systems from scratch—you’ll fit right in. If you’ve also implemented AI in practical ways for ABM (not just experimentation), you’ll be especially well matched.

What you'll bring

How you work

About Cultivation Capital

Cultivation Capital invests in young companies whose ideas have potential to transform the way we live and work.