Huddle | Head of GTM Strategy (Contract)

About Huddle Huddle is a go-to-market enablement company for early-stage startups. We combine human expertise with AI-powered systems to deliver fast, rigorous GTM clarity — helping founders validate their market, define their positioning and focus their strategy. We are a startup ourselves, made up of a small team of entrepreneurial experts, working to refine our offering and leverage/create additional AI-powered tools that learn from our experts, automating the manual analysis and synthesis that slows down great strategy work. Our model: short, high-intensity strategy sprints that reveal where a company should play, who they should target and what they need to deliver. We are building the future of GTM advisory: sharp analysis, standardized frameworks, and intelligent automation. About The Role We're looking for a Head of Go-to-Market Strategy to run our sprints, plus help inform the AI tools that can replicate and scale their approach with their oversight. This is a role for someone who can cut through noise quickly, synthesize qualitative and quantitative data, and turn ambiguity into a clear, defensible narrative. You will:

• Lead diagnostic research and analysis
• Build the strategic backbone of each sprint deck
• Make the tough calls on ICP, whitespace, positioning, and validation priorities
• Drive the discipline and clarity that early-stage founders need

You'll need the agility to toggle between strategic leadership and hands-on work — and the discipline to make fast, informed decisions with incomplete data.

Responsibilities

GTM Sprints & Strategic Analysis

• Lead discovery with founders, extracting hypotheses, contradictions, and blind spots
• Translate business goals, signals, and gaps into a structured GTM problem statement
• Build whitespace maps, ICP segmentation, value props, and positioning direction
• Develop early pricing logic and PMF criteria
• Synthesize cultural, category, customer, and company insights into a coherent narrative

Strategic Deliverables

• Own the creation of high-quality strategy decks for an executive and/or investor audience
• Produce clear frameworks, validation roadmaps, and metrics to prove or disprove hypotheses
• Articulate "what to do," "what not to do," and "what must be done first."

Decision Support & Founder Coaching

• Pressure-test founder assumptions and correct fuzzy thinking with clarity and rigor
• Guide early-stage teams toward disciplined, evidence-based decisions
• Present recommendations to founders and (occasionally) investors with confidence and precision

Collaboration with AI/Automation

• Identify repetitive analytical tasks that can be automated
• Provide strategic logic and frameworks to guide AI tool development
• Test early versions for validity and alignment with GTM best practices
• Test, refine, and document tool functionality to ensure accuracy and repeatability

Requirements

• 8-12 years of experience in growth strategy, marketing strategy, or management consulting, with direct experience supporting early-stage startups
• Must have: Demonstrated success in building or refining GTM or marketing strategy for early-stage startups
• Ability to structure a complex problem fast and synthesize insights into clear direction
• Strong analytical instincts; comfortable with imperfect data
• Exceptional strategy deck-writing and storytelling skills (non-negotiable)
• Entrepreneurial mindset: resourceful, fast-moving, and comfortable telling founders hard truths
• Preferred: Prior experience at a top consulting firm (e.g., McKinsey, Bain, BCG, or similar) with exposure to structured problem-solving and rigorous analytical methods
• Experience with or interest in AI, automation, and the future of consulting is a plus

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