Senior Content Designer II, Handshake AI at Handshake

📍 Job Overview

Job Title: Senior Content Designer II, Handshake AI Company: Handshake Location: San Francisco, California, United States Job Type: FULL_TIME Category: Content Operations / Product Operations Date Posted: 2025-08-25 Experience Level: Mid-Senior (5-10 years) Remote Status: Hybrid (Remote OK within the United States)

🚀 Role Summary

Drive the strategy and execution of large, impactful initiatives through data-informed content design and product thinking.
Develop and maintain robust content systems, patterns, and style guides to ensure clarity, conciseness, and accessibility across diverse product surfaces and audiences.
Collaborate extensively with product design, research, product management, engineering, operations, analytics, brand, and marketing teams to deliver best-in-class user experiences.
Elevate the overall product organization's capabilities through contributions to culture, operations, and design execution, including product narratives, voice and tone, and systems thinking.
Contribute to the development of well-informed strategic visions and pragmatic execution plans, fostering an environment of continuous experimentation, iteration, and learning.

📝 Enhancement Note: While the title is "Senior Content Designer," the emphasis on "AI," "operations," and cross-functional collaboration with "operations" teams suggests a strong need for someone who can not only design content but also manage and optimize content processes and systems. This role likely requires a blend of creative content expertise and operational rigor, akin to a Product Operations or Content Operations specialist. The "Senior II" level indicates a significant level of autonomy and strategic input.

📈 Primary Responsibilities

Organize, craft, and iterate on large-scale, strategic product initiatives by leveraging data, user research, and deep product thinking to inform content decisions and user experience flows.
Develop and refine comprehensive content systems, including reusable patterns, style guides, and voice and tone frameworks, ensuring consistency, clarity, and usability across diverse user segments and product features.
Actively participate in and contribute to cross-functional design activities such as design workshops, user research synthesis, usability testing, and content critique sessions to gather insights and drive iterative improvements.
Foster strong, collaborative partnerships with product design, research, product management, engineering, operations, analytics, design systems, brand, and marketing teams to ensure seamless product development and launch, and to iterate on strategic, user-centric products.
Contribute to raising the bar for the entire product organization by enhancing team culture, operational processes, and the execution of design work, including articulating product narratives, establishing voice and tone, presenting product reasoning, and demonstrating systems thinking.
Support the product organization in experimenting, iterating, and learning by developing well-informed strategic visions and breaking them down into pragmatic, phased implementation plans to guide forward progress.
Mentor and guide junior designers and cross-functional partners on content strategy, design best practices, and operational excellence.

📝 Enhancement Note: The description emphasizes "organize, craft, and iterate on large, strategic initiatives" and "develop and iterate content systems, patterns, and style guidelines." This points towards responsibilities that go beyond traditional content creation, including process definition, system design, and strategic roadmap contribution, which are core to operations roles. The need to "raise the bar on culture, operations, and execution of design work" further solidifies the operational aspect of this role.

🎓 Skills & Qualifications

Education:

Bachelor's degree in Design, English, Communications, Human-Computer Interaction, or a related field, or equivalent practical experience.

Experience:

5-10 years of experience in content design, UX writing, or a similar role, with a proven track record of shipping successful, user-centered products.
Demonstrated experience in organizing and executing large-scale, strategic initiatives that require cross-functional collaboration and data-driven decision-making.
Experience developing and maintaining content systems, style guides, and design patterns, with a focus on scalability and consistency.

Required Skills:

Content Strategy & Design: Proven ability to translate complex information, business goals, and user needs into clear, concise, and effective content for digital products across various platforms and user segments.
Data & Research Integration: Strong capability to synthesize and integrate data, user research findings, business objectives, and technical constraints into actionable content design decisions and strategic product direction.
Cross-Functional Collaboration: Exceptional ability to partner effectively with Product Design, Product Management, Engineering, Research, Analytics, Brand, and Marketing teams, fostering strong working relationships and driving alignment.
Systems Thinking & Pattern Development: Expertise in designing and implementing scalable content systems, patterns, and style guides that promote consistency, efficiency, and a cohesive user experience.
Product Thinking & Iteration: Demonstrated ability to contribute to product strategy, understand user journeys, and iterate rapidly based on feedback, data, and evolving business requirements.

Preferred Skills:

Usability Testing & Feedback Synthesis: Experience in conducting and synthesizing usability testing to inform content improvements and product iterations.
Voice and Tone Expertise: Deep understanding of developing and applying brand voice and tone guidelines to create a consistent and engaging user experience.
Prototyping & Facilitation: Skills in prototyping content variations and facilitating design workshops and stakeholder conversations effectively.
Educational Technology or AI Domain Experience: Familiarity with the educational technology landscape, learning platforms, or AI technologies is a significant plus.
Mentorship & Team Development: Experience in mentoring junior team members and contributing to a positive and productive team culture.

📝 Enhancement Note: The "Desired Capabilities" section directly translates into required skills, emphasizing the ability to "systematically, clearly articulate what it took to make that happen, from high-level strategy down to word-level decision-making" and the skill to "roll data, research, business goals, technical constraints, and customer needs together into strongly-crafted content." This highlights the need for a strategic and process-oriented approach.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

Strategic Initiative Case Studies: Showcase at least two comprehensive case studies detailing large, strategic initiatives you led or significantly contributed to, from conception through launch and iteration. These should highlight your process, decision-making rationale, and the impact achieved.
Content System Design: Include examples of content systems, style guides, pattern libraries, or voice and tone guidelines you have developed or significantly improved. Demonstrate how these systems ensure consistency and scalability.
Data & Research in Action: Present examples where data analysis, user research, or A/B testing directly informed your content decisions and led to measurable improvements in user experience or business outcomes.
Cross-Functional Collaboration Showcase: Artifacts or descriptions that illustrate your collaborative process with engineering, product management, and other stakeholders, demonstrating how you effectively partnered to bring products to life.
Process Optimization Examples: If applicable, include examples of how you streamlined content workflows, improved content production efficiency, or implemented operational improvements within a design or product team.

Process Documentation:

Demonstrate an understanding of how to document and communicate content processes, design decisions, and system architecture to enable knowledge sharing and onboarding for new team members or cross-functional partners.
Ability to articulate the lifecycle of content, from strategy and creation to governance and maintenance, within a product development context.

📝 Enhancement Note: For a role emphasizing "operations" and "systems," a portfolio that showcases not just finished content but the processes and systems behind it is crucial. This includes demonstrating how you've organized work, collaborated operationally, and managed content at scale. The ability to articulate "what it took to make that happen, from high-level strategy down to word-level decision-making" is key.

💵 Compensation & Benefits

Salary Range:

The salary for this position in San Francisco, California, for a Senior Content Designer II with 5-10 years of experience, typically falls within the range of $140,000 to $190,000 annually. This estimate is based on industry benchmarks for similar roles in high-cost-of-living tech hubs, considering the company's funding and growth stage, and the seniority of the position.

Benefits:

Ownership: Equity grants in a fast-growing company, providing a stake in Handshake's success.
Financial Wellness: Comprehensive 401(k) matching program, competitive compensation packages, and access to financial coaching services.
Family Support: Generous paid parental leave, fertility benefits, and parental coaching to support employees and their families.
Wellbeing: Robust medical, dental, and vision insurance plans, mental health support resources, and a $500 annual wellness stipend.
Growth & Development: A $2,000 annual learning stipend for professional development, including courses, conferences, and certifications, along with ongoing internal development opportunities.
Work Flexibility: Stipends for home office setup, internet, and commuting. For employees based in or near San Francisco, access to office amenities, including free lunch and gym facilities.
Time Off: Flexible Paid Time Off (PTO) policy, 15 company holidays plus 2 additional flex days, and a company-wide winter "ShakeBreak" where all operations cease for a week.
Connection & Recognition: Opportunities for team outings and referral bonuses to foster a strong company culture and reward employee contributions.

Working Hours:

Standard full-time work week is typically 40 hours. While flexibility is offered, particularly for remote employees, core collaboration hours will likely be established to facilitate cross-functional teamwork, especially during the workday within the US time zones.

📝 Enhancement Note: The provided benefits list is extensive and aligns with competitive tech industry offerings. The "Ownership" equity, "Financial Wellness," and "Growth" stipends are particularly attractive for senior roles. The "Remote & Office" stipends highlight flexibility. The "ShakeBreak" is a unique perk indicating a strong focus on employee well-being and work-life balance.

🎯 Team & Company Context

🏢 Company Culture

Industry: Educational Technology (EdTech) / Career Networking Company Size: While specific numbers aren't provided, Handshake is described as a category leader with 18 million knowledge workers, 1,500 educational institutions, and 1 million employers on its platform. This implies a substantial, well-established, and rapidly scaling organization. The employee count is likely in the hundreds, indicative of a mature startup environment. Founded: 2014. This suggests a company with a solid foundation, a proven product-market fit, and a history of navigating growth and evolution, now strategically expanding into the AI economy.

Team Structure:

The role reports into a product or design leadership structure, likely a Head of Product Design or VP of Product.
The content designer will be embedded within product teams, working closely with Product Managers, Product Designers, Researchers, and Engineers.
There's a strong emphasis on cross-functional collaboration with departments like Operations, Analytics, Brand, and Marketing, indicating a matrixed or highly integrated operational model.

Methodology:

Data-Driven Decision Making: The role explicitly calls for using "data, research, and product thinking" to inform work, suggesting a strong reliance on analytics and user insights for strategy and content decisions.
Iterative Design Process: Emphasis on "craft, and iterate," "develop and iterate content systems," and "experiment, iterate, and learn" highlights a commitment to agile development and continuous improvement.
Process & System Optimization: The need to "develop and iterate content systems, patterns, and style guidelines" and "raise the bar on culture, operations, and execution of design work" points to a focus on establishing and refining operational processes for design and content.

Company Website: https://joinhandshake.com/

📝 Enhancement Note: Handshake's mission to build the career network for the AI economy, backed by a strong existing job network, positions it as a significant player. The mention of leadership from companies like Scale AI, Open AI, and xAI suggests a high-caliber team with deep expertise in AI, which will likely influence product strategy and the types of content challenges the designer will face. The company's growth trajectory and significant funding indicate a dynamic and resource-rich environment.

📈 Career & Growth Analysis

Operations Career Level: Senior II. This designation indicates a significant level of expertise, autonomy, and strategic influence. The individual is expected to lead complex projects, mentor others, and contribute to the operational framework of the design team and broader product organization. They are not just executing but shaping how work gets done. Reporting Structure: The Senior Content Designer II will likely report to a Director or VP of Design/Product. They will work closely with Product Managers, Product Designers, and Engineers as peers within product squads. Collaboration will extend to operations, analytics, and marketing teams, requiring strong communication and influence skills across departments. Operations Impact: This role has a direct impact on the usability, clarity, and effectiveness of Handshake's AI-focused products. By creating intuitive and accessible content and optimizing content processes, the designer influences user adoption, engagement, and overall satisfaction for students, employers, and internal operators. Their work can directly contribute to operational efficiency and the successful scaling of the platform.

Growth Opportunities:

Leadership in Content Operations: Potential to evolve into a leadership role focused on content operations, design systems, or product content strategy, shaping the direction and operational standards for content across Handshake.
AI Specialization: Deepen expertise in content design for AI-driven products and platforms, becoming a subject matter expert in this rapidly growing field.
Cross-Functional Expertise: Expand knowledge and influence across product management, engineering, and operations, potentially transitioning into product management or operations roles with a content focus.
Mentorship and Team Building: Formalize mentorship responsibilities, contribute to hiring and onboarding, and help build out the content design function within Handshake.
Strategic Influence: Play a key role in defining the product narrative and user experience for Handshake's AI initiatives, influencing the company's strategic direction.

📝 Enhancement Note: The "Senior II" title and the emphasis on elevating the "overall product organization's ability to experiment, iterate, and learn" suggest a path toward leadership, process ownership, and strategic contribution, moving beyond individual contributor work into shaping the team's operational excellence and strategic direction.

🌐 Work Environment

Office Type: Handshake maintains a physical office in San Francisco. The description mentions stipends for commuting and free lunch/gym in the SF office, indicating a hybrid work model where employees can leverage office resources. Office Location(s): San Francisco, California. This location is a major tech hub, offering excellent networking opportunities and access to talent. Workspace Context:

The environment is described as collaborative, with a need to "collaborate closely with your partners, both cross-functionally and within design." This suggests an open and communicative workspace that encourages teamwork.
Access to "stipends for home office setup, internet, commuting, and free lunch/gym in our SF office" indicates a supportive setup for both remote and in-office employees, promoting productivity and well-being.
The culture prioritizes "learning and teaching" and "curiosity," fostering an environment where knowledge sharing and continuous improvement are valued. Work Schedule: While the standard is 40 hours, the emphasis on "flexible PTO" and the company-wide "ShakeBreak" suggests a culture that values work-life balance and provides flexibility. However, for a hybrid role, core hours will likely be expected for effective collaboration with distributed teams.

📝 Enhancement Note: The hybrid model with stipends for both remote and office work suggests a modern, flexible approach to work environments, catering to diverse employee needs while maintaining team cohesion and operational effectiveness.

📄 Application & Portfolio Review Process

Interview Process:

Initial Screening: A recruiter or hiring manager will review your application, resume, and portfolio. Be sure your portfolio clearly showcases your relevant experience and strategic thinking.
Hiring Manager/Team Interview: Expect a discussion focused on your experience, approach to content design, and how you've handled strategic initiatives. Be prepared to articulate your "why" behind decisions.
Skills Assessment/Design Exercise: This may involve a take-home assignment or an in-person/virtual design exercise where you'll be asked to solve a specific content design problem, potentially involving data interpretation or system thinking.
Cross-Functional Interviews: You will likely meet with Product Managers, Product Designers, Engineers, and potentially representatives from Operations or Marketing to assess collaboration skills and strategic alignment.
Final Interview: A discussion with senior leadership to assess cultural fit, strategic vision, and overall impact potential.

Portfolio Review Tips:

Storytelling is Key: Structure your case studies to tell a compelling story: the problem, your process and rationale (emphasizing data and strategy), the solution, and the measurable impact.
Highlight Operations & Systems: For this role, explicitly showcase examples of how you've developed or improved content systems, managed processes, and collaborated operationally. Quantify impact whenever possible (e.g., "reduced content production time by X%," "improved user task completion by Y%").
Showcase Strategic Thinking: Demonstrate how you connect content decisions to broader business goals and user needs. Articulate your thought process, not just the final output.
Clarity and Conciseness: Your portfolio itself should reflect your content design skills – it should be well-organized, easy to navigate, and clearly communicate your value proposition.
Tailor to Handshake AI: If possible, research Handshake's current product and brand voice. Consider how your work aligns with their mission and the specific challenges of designing for an AI-focused platform.

Challenge Preparation:

Focus on Process: If given a design challenge, think about the process you'd follow to solve it, not just the final content. How would you gather information? Who would you consult? How would you iterate?
Data Interpretation: Be ready to interpret data, even if hypothetical, and explain how it would inform your content decisions.
Strategic Rationale: Prepare to explain the strategic reasoning behind your content choices, linking them to user goals and business objectives.
Voice and Tone: Practice articulating how you would adapt voice and tone for different audiences or product contexts.

📝 Enhancement Note: The emphasis on "organize, craft, and iterate on large, strategic initiatives" and "develop and iterate content systems, patterns, and style guidelines" means your portfolio should highlight your ability to manage complex projects, build scalable solutions, and think systematically, not just create individual pieces of content.

🛠 Tools & Technology Stack

Primary Tools:

Content Management Systems (CMS): Experience with various CMS platforms for managing and publishing content.
Design & Prototyping Tools: Proficiency in tools like Figma, Sketch, Adobe Creative Suite (Illustrator, InDesign), or similar for creating wireframes, mockups, and prototypes.
Collaboration Platforms: Experience with tools like Slack, Asana, Jira, Trello for team communication, project management, and workflow tracking.
Documentation Tools: Familiarity with tools like Notion, Confluence, Google Workspace for creating and sharing documentation, style guides, and process flows.

Analytics & Reporting:

Web Analytics: Proficiency with tools like Google Analytics, Amplitude, Mixpanel to track user behavior, content performance, and identify areas for improvement.
Data Visualization Tools: Experience with tools like Tableau, Looker, or Power BI to create dashboards and reports that communicate insights effectively.

CRM & Automation:

CRM Systems: Familiarity with CRM platforms such as Salesforce, HubSpot, or others, understanding how content integrates with customer data and workflows.
Automation Tools: Knowledge of marketing automation or workflow automation tools that might support content deployment or operational processes.

📝 Enhancement Note: Given the role's emphasis on "operations" and "systems," expect to use tools that facilitate workflow management, process documentation, and data analysis. Proficiency in Figma/Sketch for design, Google Analytics/Amplitude for data, and Notion/Confluence for documentation is highly probable.

👥 Team Culture & Values

Operations Values:

Clarity and Simplicity: A core value is bringing clarity and simplicity to both process and product through thoughtful content and efficient operations.
Data-Driven Impact: Decisions are informed by data and research, with a focus on measuring and demonstrating the impact of content and operational improvements.
Continuous Learning and Teaching: The team culture encourages curiosity, learning new technologies and industries, and sharing knowledge with colleagues.
Collaboration and Humility: A humble and kind approach to teamwork, valuing diverse perspectives and fostering a supportive environment for cross-functional collaboration.
Efficiency and Iteration: A drive to improve processes, iterate quickly, and deliver high-quality, usable products efficiently.

Collaboration Style:

Cross-Functional Integration: Seamless collaboration with product, engineering, research, operations, and marketing teams is fundamental to success. This involves active participation in shared rituals and a proactive approach to communication.
Feedback-Driven: An open culture for providing and receiving constructive feedback on design work, processes, and strategic thinking.
Knowledge Sharing: Encouragement of sharing insights, best practices, and learnings across teams to foster collective growth and operational excellence.

📝 Enhancement Note: The values highlight a blend of creative excellence (clarity, simplicity) and operational discipline (data-driven, efficiency, process improvement), all underpinned by a strong collaborative and learning-oriented culture.

⚡ Challenges & Growth Opportunities

Challenges:

Balancing Strategic Vision with Tactical Execution: The role requires holding a high-level strategic vision for content and operations while meticulously executing on detailed, word-level decisions.
Navigating Complexity in AI: Designing content for AI products, which are inherently complex and evolving, requires continuous learning and the ability to translate sophisticated concepts into accessible language for diverse user groups.
Cross-Functional Alignment: Ensuring consistent content strategy and operational standards across numerous departments and product surfaces can be challenging, requiring strong influence and communication skills.
Scaling Content Systems: As Handshake grows and its AI offerings expand, maintaining and scaling content systems, patterns, and guidelines effectively will be a significant operational challenge.

Learning & Development Opportunities:

Deep Dive into AI Products: Gain hands-on experience and expertise in designing content for cutting-edge AI applications, a highly in-demand skill.
Content Operations Specialization: Develop a strong portfolio in content operations, process management, and design systems, positioning for leadership roles in these areas.
Industry Exposure: Work within the EdTech and AI sectors, gaining insights into market trends, user behaviors, and technological advancements.
Mentorship and Skill Development: Benefit from working with experienced leaders and peers, with access to learning stipends to further develop technical, strategic, and leadership skills.

📝 Enhancement Note: The challenges presented are typical for senior roles in fast-growing tech companies, particularly those venturing into new domains like AI. The growth opportunities are directly tied to developing specialized skills in AI content and maturing in operational and leadership capacities.

💡 Interview Preparation

Strategy Questions:

"Describe a complex strategic initiative you led from conception to launch. What was your process, how did you use data and research, and what was the outcome?" (Focus on your structured approach, decision-making, and impact measurement.)
"How would you approach developing a new content system or style guide for a product like Handshake AI? What factors would you consider, and how would you ensure adoption?" (Highlight your understanding of scalability, process, and cross-functional buy-in.)
"Walk us through a time you had to simplify a highly technical or complex concept for a broad audience. What was your strategy, and how did you test its effectiveness?" (Demonstrate your ability to translate complexity and iterate based on feedback.)
"How do you collaborate with product managers, designers, and engineers to ensure content is integrated effectively into the product development lifecycle?" (Showcase your partnership skills and understanding of product workflows.)

Company & Culture Questions:

"What interests you about Handshake's mission, particularly in the context of the AI economy?" (Research Handshake's mission, values, and recent AI news.)
"How do you contribute to a positive and productive team culture, especially in a hybrid or remote-first environment?" (Emphasize your collaborative, teaching, and learning-oriented approach.)
"Describe a time you had to influence stakeholders to adopt your content strategy or design recommendations. What was your approach?" (Prepare examples of persuasive communication and strategic alignment.)

Portfolio Presentation Strategy:

Structure for Impact: Organize your portfolio around the key responsibilities: strategic initiatives, content systems, data integration, and cross-functional collaboration.
Quantify Success: For each case study, clearly state the problem, your specific contributions, the process you followed (especially operational aspects), and quantifiable results (e.g., engagement metrics, efficiency gains, user satisfaction scores).
Articulate Your "Why": Be prepared to explain the rationale behind every significant content and process decision you made.
Showcase Systemic Thinking: Highlight instances where you built scalable patterns, improved workflows, or contributed to operational efficiency through your content design work.
Practice Your Narrative: Rehearse presenting your portfolio pieces concisely, focusing on the story and impact, ensuring you can speak to both the high-level strategy and the granular details.

📝 Enhancement Note: The interview preparation should strongly focus on demonstrating strategic thinking, process ownership, and the ability to quantify impact. Given the "operations" and "systems" aspects, be ready to discuss how you manage complexity, drive efficiency, and collaborate operationally.

📌 Application Steps

To apply for this Senior Content Designer II position:

Submit your application through the provided link on Ashby.
Portfolio Customization: Tailor your resume and portfolio to highlight experience in strategic initiatives, content systems, data integration, and cross-functional collaboration. Specifically, include examples that demonstrate your ability to organize, craft, and iterate on complex projects and optimize content processes.
Resume Optimization: Ensure your resume clearly articulates your years of experience, key achievements, and proficiency with relevant design, analytics, and collaboration tools. Use keywords from the job description naturally.
Interview Preparation: Thoroughly review Handshake's mission, products, and values. Prepare detailed examples for behavioral questions, focusing on your strategic thinking, problem-solving skills, and collaborative approach. Practice presenting your portfolio with a focus on process and impact.
Company Research: Gain a deep understanding of Handshake's position in the EdTech and AI markets, its user base, and its competitive landscape to inform your interview responses and demonstrate genuine interest.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.

Senior Content Designer II, Handshake AI