GTM Strategy Associate

Competencies

We are looking for an ambitious, sharp, and highly proactive Associate to join our Office of the CEO. This is a high-trust, high-exposure role ideal for someone who thrives at the intersection of strategy, operations, and execution.

What stands out to us:

• Sharp and structured: you think clearly under pressure, communicate top-down, and can distill complex problems into sharp, executive-ready insights without losing the nuance
• Builder mentality: you don't wait for instructions. You take a defined problem, figure out the path forward, align the right people, and deliver — fast
• Proven in high-performance environments: 2–3 years in management consulting, tech, VC/PE, or a cross-functional startup role. You've worked with senior leaders before and earned their trust
• High EQ and discretion: you read the room, handle sensitive information with care, and know when to push and when to listen
• Ambitious and curious: you want to be at the heart of building something big and you're not here to watch from the sidelines

Trajectory

Trailer Hat started with two people and no external funding. Today we're 250 people strong, powering thousands of teams globally across 30+ nationalities and 27 countries. We've built this by hiring people who take ownership, move fast, and care deeply about what they're building. The Office of the CEO is an extension of our leadership team — and this role puts you at the center of it. Here's what that looks like:

• Drive strategic priorities and cross-functional projects spanning operations, go-to-market, marketing, and people
• Own project management for high-impact, time-sensitive efforts — aligning stakeholders, managing timelines, and making sure nothing falls through the cracks
• Prepare materials, research, and internal communications that enable better and faster decision-making
• Help structure and operationalize executive workflows, business reviews, and leadership meetings
• Identify gaps, propose solutions, and implement improvements

Definition of Success

You are consistently moving the company's most important priorities forward with speed, structure, and clarity

You are seen as a trusted partner by the leadership team — someone who can be handed a hard problem and trusted to solve it

You are building deep cross-functional knowledge of Planhat's business, product, and go-to-market motion

You are proactively identifying gaps and operationalizing solutions before they become blockers

Pay

The salary range for this position is $100,000 - $140,000 per year. Please note that actual salaries will vary based on factors including but not limited to location, experience, and performance. Please also note the range listed is just one component of the company’s total rewards package for exempt employees. Other rewards may include performance bonuses, long term incentives, a generous PTO policy, and other benefits.