As a Technical Writer at Attentive, you are the critical bridge between complex product capabilities and the end-user experience. Attentive operates at the forefront of conversational commerce and SMS marketing, building powerful, data-driven platforms used by thousands of innovative brands. In this role, your primary mission is to translate sophisticated technical concepts into clear, actionable, and engaging documentation that empowers users to maximize the platform's value.

Your impact extends far beyond simple user manuals. You will shape how developers, integration partners, and internal teams understand and interact with the Attentive ecosystem. Whether you are documenting APIs, creating onboarding guides, or standardizing internal engineering wikis, your work directly reduces friction, accelerates product adoption, and minimizes support tickets. At a fast-growing tech company, high-quality documentation is treated as a core product feature.

Expect a dynamic, startup-oriented environment where you will collaborate closely with product managers, engineers, and customer success teams. The scale of the problem space requires you to be proactive, inquisitive, and highly adaptable. You will not just be documenting what has already been built; you will be an active participant in the product development lifecycle, advocating for clarity and user-centric design from day one.

While the exact questions will vary based on your interviewers and the specific team, the following examples represent the core themes tested during the Attentive interview loop. Use these to identify patterns and practice structuring your responses.

Writing and Content Strategy

These questions assess your editorial judgment, your understanding of information architecture, and how you tailor content to specific audiences.

• Walk me through your process for taking a complex technical topic and breaking it down for a non-technical audience.
• How do you ensure consistency in tone, style, and formatting across a large documentation portal?

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Preparing for the Technical Writer interview at Attentive requires a balance of demonstrating your hard writing skills and showcasing your ability to thrive in a collaborative, fast-paced startup culture. Your interviewers will look for evidence that you can untangle complexity while remaining adaptable and open to feedback.

Focus your preparation on the following key evaluation criteria:

Writing and Editing Excellence – This is the foundation of the role. Interviewers evaluate your ability to produce clear, concise, and structurally sound documentation under time constraints. You can demonstrate strength here by executing flawlessly on the writing assignment and articulating the strategic reasoning behind your editorial choices.

Technical Comprehension – You do not need to be a software engineer, but you must understand how software works. Interviewers will assess your comfort level with APIs, integrations, and SaaS architecture. Show your strength by discussing how you research unfamiliar technical concepts and extract necessary details from subject matter experts.

Collaboration and Stakeholder Management – A Technical Writer rarely works in a silo. Attentive highly values teamwork and transparency. Interviewers want to see how you handle feedback, manage conflicting priorities, and build relationships with busy engineers and product managers to get the information you need.

Culture Fit and Adaptability – Attentive is known for its supportive yet rigorous startup culture. Interviewers look for candidates who are genuinely curious, transparent, and resilient. You can demonstrate this by being open about your past challenges, showing enthusiasm for the company's mission, and engaging your interviewers with thoughtful questions.

The interview loop for a Technical Writer at Attentive is widely regarded by candidates as one of the best, most transparent processes in the industry. The company practices the values it preaches, offering an intensive but highly rewarding experience. You will find that there are no tricks or "gotchas"; instead, the focus is on mutual discovery to ensure a strong fit for both you and the team.

Your journey typically begins with a recruiter phone screen, which is highly communicative. The recruiter acts as your partner, providing preparation materials and continuous feedback throughout the loop. This is followed by a Zoom call with a senior team member to assess baseline alignment. If successful, you will move on to a timed writing and editing assignment, which is a critical gatekeeper for the role.

The final stages consist of multiple Zoom panel interviews and executive interviews. While the process involves up to six or seven touchpoints, Attentive is known for moving incredibly fast—sometimes completing the entire loop, from initial screen to final offer, within a single week. The interviewers are consistently described as friendly, engaged, and genuinely interested in what you have to say.

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This visual timeline outlines the progression from your initial recruiter screen through the technical assessments and final executive panels. Use this to pace your preparation, ensuring you are ready for the timed writing test early in the process while saving stamina for the behavioral and cross-functional deep dives in the final rounds. The speed of the process means you should have your portfolio and technical examples ready to discuss from day one.

To succeed in the Attentive interview, you must prove your capabilities across several distinct areas. The process is thorough, and each round is calibrated to test a specific facet of your technical writing and professional toolkit.

Writing and Editorial Strategy

Because clarity is paramount, your actual writing ability is rigorously tested, primarily through a timed writing and editing assignment. Attentive wants to see not just that you can write, but that you can structure information logically, adhere to style guidelines, and edit for conciseness and tone. Strong performance means delivering polished, user-centric content even when the clock is ticking.

Be ready to go over:

• Information Architecture – How you organize complex guides so users can find answers quickly.
• Tone and Voice – Adapting your writing to match the company's brand—professional, clear, and approachable.
• Editing and Peer Review – How you give and receive constructive feedback on documentation drafts.
• Advanced concepts (less common) – Content reuse strategies, localization considerations, and managing documentation debt.

Example questions or scenarios:

• "Take this highly technical engineering brief and rewrite it for a non-technical marketing user within 45 minutes."
• "Walk us through your process for editing a document written by a subject matter expert whose first language is not English."
• "How do you decide what information belongs in a quick-start guide versus a comprehensive reference manual?"

Technical Aptitude and Translation

You will be documenting sophisticated SaaS products and integrations. Interviewers will probe your ability to grasp technical concepts quickly and translate them into accessible language. Strong candidates demonstrate a systematic approach to learning new technologies and a comfort level with the tools modern development teams use.

Be ready to go over:

• API Documentation – Explaining endpoints, parameters, and authentication methods clearly.
• Developer Tools – Your familiarity with tools like Postman, GitHub, Markdown, and static site generators.
• SME Interviews – Your strategy for extracting accurate information from busy engineers without wasting their time.
• Advanced concepts (less common) – Reading code snippets (e.g., JSON, Python, JavaScript) to document expected inputs and outputs.

Example questions or scenarios:

• "Tell us about a time you had to document a technical feature you initially did not understand. What was your approach?"
• "How do you verify the technical accuracy of your documentation before publishing?"
• "Explain how a REST API works to someone who has no background in software engineering."

Cross-Functional Collaboration and Problem Solving

A Technical Writer at Attentive must navigate a fast-paced environment where product requirements frequently change. This area evaluates your project management skills, your ability to influence without authority, and your resilience. A strong performance involves sharing concrete examples of how you have successfully aligned different stakeholders toward a common goal.

Be ready to go over:

• Prioritization – How you manage multiple documentation requests from different product teams simultaneously.
• Handling Ambiguity – Operating effectively when product features are still being actively developed.
• Advocating for the User – Times you pushed back on a product design because it was too difficult to explain or use.
• Advanced concepts (less common) – Establishing new documentation processes from scratch within an engineering organization.

Example questions or scenarios:

• "Describe a situation where an engineer disagreed with your documentation approach. How did you resolve the conflict?"
• "How do you keep your documentation up to date in an agile environment with continuous deployment?"
• "Tell me about a time you missed a deadline or published an error. What happened, and how did you fix it?"

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As a Technical Writer at Attentive, your day-to-day work revolves around making the complex simple. Your primary responsibility is to create, maintain, and continuously improve a wide range of documentation. This includes external-facing user guides, API references for integration partners, release notes, and internal knowledge base articles that support the customer success and implementation teams.

You will embed yourself within product and engineering squads, participating in agile ceremonies like stand-ups and sprint planning. This ensures you are aware of upcoming features long before they ship. You will proactively interview subject matter experts, test the features yourself in a staging environment, and draft content that aligns with the Attentive style guide.

Beyond writing, you will act as a documentation strategist. You will analyze user feedback and support ticket trends to identify gaps in the existing documentation. You will collaborate with product designers to improve in-app copy and tooltips, ensuring that the user experience is intuitive from the moment a customer logs in. Ultimately, you are the champion of the user's understanding, driving initiatives that make the platform self-serve and accessible.

To be highly competitive for the Technical Writer position at Attentive, you must bring a blend of editorial sharpness, technical curiosity, and strong interpersonal skills. The company looks for professionals who can operate independently but thrive in a team setting.

• Must-have skills – Exceptional written and verbal communication. A proven track record of creating user-focused documentation for software products. The ability to manage multiple projects simultaneously in a fast-paced environment. Strong analytical skills to structure complex information logically.
• Technical requirements – Proficiency with modern documentation tools and markup languages (e.g., Markdown, HTML/CSS). Experience with version control systems (like Git) and working within an agile software development lifecycle.
• Experience level – Typically requires 3 to 5+ years of experience as a technical writer, ideally within the B2B SaaS, e-commerce, or developer tools space.
• Soft skills – High empathy for the end-user. Exceptional stakeholder management and the ability to interview engineers effectively. A transparent, feedback-oriented mindset.
• Nice-to-have skills – Experience documenting RESTful APIs using OpenAPI/Swagger. Familiarity with SMS marketing compliance or telecommunications concepts. Basic proficiency in a programming language (like Python or JavaScript) to better understand developer workflows.