Huddle | Head of GTM Strategy (Contract)
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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
- 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
Seniority Level
Director
Employment Type
Contract
Job Function
Other
Location
Boston, MA
Salary
$250,000.00–$300,000.00
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