Senior Product Strategist

About the Role Whale Song is a digital product studio backed by Golden Section, serving mid-market, enterprise, and government clients with custom software development, AI-enabled solutions, and product strategy services. We build right the first time, which means strategy before execution, clarity before build, and measurable outcomes before feature output. We're looking for a Senior Product Strategist who brings genuine senior-level product thinking and the presence to deploy it in a client-facing consulting environment. This is not a pure internal PM role. Depending on the engagement, you'll move fluidly between setting product strategy and owning hands-on product management execution — leading discovery, scoping, requirements strategy, delivery oversight, and stakeholder alignment across multiple client engagements simultaneously. The right person has led products, not just managed them. You understand the difference between writing user stories and driving outcomes. You can walk into a room with a VP of Engineering or a CMO and credibly lead a strategy conversation. And you know how to bring structure and clarity to ambiguous, complex product problems, and then stay in the work long enough to see it through. What You'll Do Your work will span the full arc of our client engagements from initial discovery through active delivery: Discovery & Strategy Lead client discovery sessions to define business problems, goals, constraints, and success criteria before a line of code is scoped. Translate complex, ambiguous client needs into clear product strategy, prioritization frameworks, and phased roadmaps. Develop and present strategic recommendations to executive stakeholders with confidence and credibility. Scoping & Requirements Produce development-ready requirement documents, user stories, acceptance criteria, and functional specifications grounded in business outcomes. Assess technical feasibility and integration requirements in collaboration with engineering leads. Own scoping calls end-to-end: structure the conversation, identify risks, and produce the deliverable. Product Management Execution Step into hands-on Product Management ownership when engagements require it; managing backlogs, facilitating sprints, and driving delivery accountability. Serve as the product authority during active delivery; guiding sprint execution, scope management, and release coordination. Identify and escalate scope creep, delivery risks, and client expectation gaps before they become problems. Client Relationship Act as a trusted advisor to client stakeholders, building credibility through consistent delivery and strategic thinking. Maintain proactive communication across multiple concurrent client engagements. Represent Whale Song professionally in all client interactions — written, verbal, and in person. Internal Contribution Support pre-sales solutioning and proposal development for new engagements. Contribute to methodology refinement as Whale Song's product practice continues to mature. Mentor and support junior team members on requirements quality and product thinking. What We're Looking For Experience & Background 7+ years in product management, product strategy, or business analysis — with meaningful time spent in a client-facing, consulting, or agency delivery environment. Demonstrated track record leading product work across B2B SaaS, custom software, or enterprise application development. Comfortable moving between strategic advisory work and hands-on PM execution depending on what the engagement requires. Experience working with cross-functional remote teams including engineering, UX, and business stakeholders. Prior exposure to multiple industries preferred — healthcare technology, fintech, real estate tech, or enterprise software are all relevant backgrounds. Core Skills Product Strategy and Roadmapping Requirements and User Story Writing Client-Facing Delivery Agile/Hybrid-Agile Methodologies Business Analysis Software Scoping & Estimation UX Collaboration Stakeholder Management SaaS & Custom Application Delivery AI-Enabled Product Operations Backlog Management Product QA & Release Coordination What Sets You Apart You lead with strategy before jumping to solutions — you ask why before you ask how. You can hold your own in a room full of executives or engineers, and you know which conversation you're in. You're comfortable with ambiguity and skilled at bringing structure to it. You write with precision. Your requirements documents don't leave room for misinterpretation. You manage your own workload without being managed — you flag issues early, communicate proactively, and follow through. You take quality personally. Rework is not an acceptable outcome. Our Methodology & Culture Whale Song operates on a set of principles that are non-negotiable, and we hire people who already believe in them: Build Right the First Time: Every engagement starts with clarity, not code. Clarity before build: Strategy before execution, always. Financial and delivery discipline: Delivery must be feasible, margin must be healthy, and client expectations must be set honestly. Client partnership, not vendor relationship: We are an extension of our clients' teams, and we show up like it. AI-enabled operations: We actively adopt AI-enabled tools and workflows to improve delivery quality and team efficiency. We're a remote team. That means high trust, high autonomy, and high accountability. You'll have the freedom to do your best work — and the expectation that you will. Role Details Location: Remote (must be based in the United States) Type: Contract (10 to 40 hours per week, depending on active engagements) Availability: Must be available during standard U.S. business hours for client calls and team collaboration Travel: Occasional client visits or team offsites may be required How to Apply Apply via our online application portal. You'll be asked to upload your resume and a brief cover sheet (please include both). In your cover sheet, tell us why this role is the right fit for you. Specifically, describe a product engagement where you drove measurable business outcomes, not just a list of features you shipped. We want to understand how you think, not just what you've done. We review every application and respond to candidates who are a genuine match. No recruiters or agencies, please.