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Head of Product
Head of ProductBlack Spectacles • Chicago, IL, US
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Head of Product

Head of Product

Black Spectacles • Chicago, IL, US
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About Black Spectacles

Are you a strategic, customer-centric Head of Product who can balance big-picture vision with detailed execution — connecting every decision to measurable business impact?

At Black Spectacles, we’re proud to be the leader in our space — with the strongest brand, a thriving business, and an incredible opportunity for continued growth. As an entrepreneurial company, we’re ambitious in our plans to support the architecture community, fostering an environment where excellence, innovation, and collaboration thrive.

We believe that success in product comes from curiosity, collaboration, and a relentless focus on creating value for customers — and at Black Spectacles you’ll find all three.

We’re seeking a Head of Product to work closely with our CEO to shape and execute the roadmap for our SaaS-based online learning platform and eLearning products. You'll bring analytical rigor and a thoughtful, straightforward communication style. You listen deeply, anticipate risks, and organize complex problems into clear, actionable steps. You’ll play a key role in turning strategy into action — partnering across teams to deliver products that create measurable impact for customers and drive business growth.

At Black Spectacles, you’ll benefit from :

  • A team that lives and celebrates our values daily.
  • Regular opportunities to see and feel the impact of your work.
  • A fully remote work environment, complemented by semi-annual company trips to build connections.

Black Spectacles has been recognized by Great Place to Work and Built In as a great place to work, by the American Institute of Architects for the national impact we’re having on the profession of architecture, and by Inc. Magazine as one of the fastest growing companies in the country.

Our Ideal Teammate

We’re looking for someone who :

  • Is motivated by contributing to a mission-driven company that supports the architecture and design community.
  • Is analytical and detail-oriented, producing precise, high-quality work while respecting plans, timelines, and standards.
  • Brings creative problem solving while staying grounded in customer insight, financial responsibility, and solid execution.
  • Balances customer needs, business priorities, and product execution with sound judgment.
  • Takes ownership and accountability for outcomes.
  • Encourages calculated risks and shares ideas in a supportive environment.
  • Takes a world-class approach to their work and values collaboration.
  • Lives our values of excellence, innovation, and taking care of our people.
  • Role Overview

    As a Head of Product, you’ll own major areas of our SaaS-based online learning platform and eLearning products. You’ll translate strategic direction into actionable product plans, oversee backlogs, and guide cross-functional execution to deliver high-quality releases. You’ll work closely with Engineering, Learning / Content, Marketing, Sales, and Customer Success to ensure decisions are grounded in customer insight and business outcomes such as ROI — with clear trade-offs, success metrics, and risk rationale. You'll help maintain clarity and momentum by organizing priorities, setting steady rhythms, and supporting teams to deliver high-quality products.

    We offer a competitive base salary of $140,000 to $190,000, commensurate with experience and qualifications.

    Responsibilities

    Product Strategy & Roadmap

  • Define and sequence priorities with clear business cases (ROI, cost, and time-to-value) and establish a regular review cadence.
  • Own customer insight — build a consistent discovery rhythm through customer calls, surveys, and experiments, and communicate insights clearly and practically across teams.
  • Develop, prioritize, and maintain the product roadmap in collaboration with stakeholders.
  • Requirements & Documentation

  • Define clear, testable requirements, user stories, and acceptance criteria in JIRA and related tools that reflect customer insight and business outcomes.
  • Collaborate with design and engineering to scope features and ensure alignment with customer needs.
  • Execution & Delivery

  • Strengthen structure through launch plans, checklists, and decision logs to support collaboration and predictable delivery.
  • Track leading indicators and post-launch results, communicating lessons learned and next steps.
  • Partner with Engineering to ensure timely, high-quality product releases.
  • Apply the right delivery approach for each initiative, drawing on experience with both Agile and Waterfall methodologies.
  • Collaborate with Marketing and Sales to coordinate product launches, communications, and go-to-market strategies.
  • Cross-Team Collaboration

  • Build alignment and trust across Engineering, Learning, Marketing, Sales, and Leadership through clear, data-informed communication.
  • Ensure alignment on priorities, timelines, and success metrics.
  • Serve as a strong advocate for the customer while balancing business needs.
  • Mentor and coach an early career teammate on discovery, backlog management, and outcome-driven planning.
  • Business & Financial Accountability

  • Favor small, testable experiments before large investments.
  • Make disciplined trade-offs between opportunity, effort, and business impact, presenting clear ROI or payback expectations.
  • Proactively surface constraints and mitigation plans.
  • Requirements

  • Bachelor’s degree in Business, Computer Science, or a related field, or equivalent experience.
  • 12+ years of professional experience, including 8+ years in product management roles.
  • Proven success owning and scaling SaaS-based products, ideally in online learning or related industries.
  • Experience working effectively in both Agile and Waterfall environments.
  • Strong track record of delivering measurable customer and business impact through product strategy and execution.
  • Deep financial literacy (ROI, unit economics, payback) with a disciplined, results-oriented approach to decision-making.
  • Experience leading customer discovery and translating insights into actionable product direction.
  • Skilled with analytics tools (e.g., Mixpanel, Amplitude, GA) to guide decisions and measure outcomes.
  • Effective collaborator who builds trust across Sales, Marketing, Engineering, Content, and Leadership.
  • Excellent communication and influencing skills to align stakeholders and drive execution.
  • Experience mentoring or coaching product team members is a plus.
  • Ability to travel quarterly for in-person meetings and company events.
  • Benefits

  • Work From Home : Enjoy the flexibility of working remotely year-round.
  • Comprehensive Benefits : Starting day one, access to BCBS Health, Dental, Vision, Disability, and Life Insurance coverage.
  • Savings & Retirement Plans : FSAs, HSAs, and a 401(k) plan with company match up to 4%.
  • Generous Paid Time Off : Accrue up to 3 weeks of vacation annually, along with 8 holidays, 2 floating holidays, and up to 1 week of sick leave.
  • Referral Program : Earn rewards by referring top talent to our team.
  • Team Building : Enjoy semi-annual team gatherings and events that foster collaboration and camaraderie.
  • If you’re ready to take the next step in your career and make a meaningful impact at Black Spectacles, we'd love to hear from you. Please submit your resume and tell us why you’re interested in this role.

    Black Spectacles is an equal-opportunity employer.

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