Huddle | Head of GTM Strategy

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

$–$

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