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 Apply tot his job