Obvious

Compensation

Full Description

Executive Assistant to VP of Product & Engineering Why this role exists Obvious operates in a high-autonomy, high-judgment environment where people work hard and smart for a mission that matters. We need an elite Executive Assistant who can also function as a program manager and lightweight chief of staff—someone who keeps the train running, anticipates needs, and turns priorities into execution without constant prompting or direction. This isn't a traditional "calendar + inbox" EA role, though you'll handle those fundamentals exceptionally well. This is a force-multiplier position: part executive support, part executive operations, part culture-and-connection builder. About the working culture at Obvious Autonomy is the default. We expect people to take ownership, make calls, and operate with excellent judgment. Low hierarchy, high standards. Great ideas and execution win, regardless of title. We work a lot—on purpose. We're building fast, which means intensity at times, but also a commitment to working smart, prioritizing well, and protecting what makes sustained performance possible. Mission energy matters. We want someone genuinely animated by impact, who loves their work and enjoys serving a team going after something big. Who you'll support (Jon) Jon Bell is the VP of Product & Engineering at Obvious, leading product, design, engineering, and marketing. He is an entrepreneurial operator and product leader with a bias toward action, clarity, and leverage. He moves quickly, thinks strategically, and cares deeply about outcomes, culture, and human potential. He also creates thought leadership content and needs a strong operational backbone to keep that engine consistent. You'll succeed here if you're highly proactive and comfortable with ambiguity, a strong writer and listener, calm and organized, and relational while being direct and execution-focused. What you'll do 1. Executive support that creates leverage Own Jon's calendar with a strategy-first mindset: Protect deep work, cluster meetings intelligently, and ensure time matches priorities Manage inbox and communications triage: Flag urgent items, draft responses, and create systems so nothing important slips through Prepare Jon for key meetings: Build agendas, briefing docs, pre-reads, attendee context, and decision prompts Capture and drive outcomes: Take notes, document decisions, and run tight follow-up loops 2. Executive operations + program management Maintain visibility on commitments and milestones: Build simple dashboards, reminders, and escalation paths Proactively check in on projects: Gather status, surface risks, and drive next steps on work Jon doesn't have bandwidth to track Run structured operating rhythms: Weekly priority reviews, meeting hygiene, delegation lists, and decision logs 3. Team moments, culture, and connection Help plan and execute team experiences: Holiday parties, off-sites, hackathons, team travel coordination, and dinners with prospects and industry peers Support employee wellness and enablement: Ensure leaders and teams get what they need from Jon, remove friction, and keep the human layer healthy 4. Content workflow backbone Build and manage Jon's content operations: Scheduling, tracking topics and ideas, outlining support, coordinating drafts and editorial passes, managing posting cadence and deadlines Keep the content pipeline moving consistently: Coordinate collaborators (internal and external) including producers, designers, editors, guests, and partners 5. Relationship and reputation management Help Jon show up exceptionally: Thoughtful outreach, meeting prep, and timely follow-ups Manage sensitive information: Handle confidential matters with discretion and maturity What success looks like (first 90 days) Jon's calendar and communications feel lighter, tighter, and more aligned with top priorities A simple, reliable system exists for tracking commitments and milestones, surfacing risks early, and ensuring follow-through At least one major event or convening runs smoothly end-to-end The content workflow has a real backbone with a clear pipeline, deadlines, and sustainable cadence People across the company experience you as calm, competent, and massively helpful—someone who makes things happen Who you are High-judgment, high-autonomy operator. You don't need step-by-step instructions to produce excellent work High CPU. You learn fast, grasp context quickly, and connect dots Elite communicator. Excellent writing, crisp summaries, strong listening, and the ability to represent an executive well Organized to the bone. You manage multiple streams—events, schedules, projects—without dropping details Relational and emotionally intelligent. You build trust easily and navigate personalities and priorities smoothly Execution-minded. You love turning ideas into shipped outcomes and closed loops Qualifications Required 2+ years in an EA, executive operations, program management, or chief-of-staff-adjacent role (startup or high-performance environment strongly preferred) Demonstrated excellence in managing complex calendars, travel, and priorities for a senior leader Strong writing ability: you can draft clear emails, briefs, agendas, and internal updates Demonstrated project management ability: systems thinking, timelines, dependencies, follow-up High discretion and comfort handling sensitive information Nice to have Experience supporting product/engineering or operating in a product-driven startup Event and community building experience (off-sites, dinners, VIP logistics) Content operations experience (editorial workflows, publishing cadence, creator ops) Familiarity with tools like Notion, Asana, Jira, Linear, Google Workspace, Slack, and scheduling/travel tools Keen and creative use of AI tools to create leverage for your time What you'll get at Obvious Competitive compensation—optimized for you and your future. Meaningful equity—you’ll own a real piece of something that could be huge. Founding team influence—your voice will shape direction. Creative freedom—evolve and steer both current and future product identity. Platform to shine—use Obvious’s reach to amplify your personal brand and design voice. Room to grow—as we scale, opportunities are limitless. In-person hackathons—we’re semi‑distributed and regularly meet in person to lock in and build together. Excellent benefits—fully covered health, vision, and dental, 401k match, parental leave, home office stipend, and more. Work comfortably—choose between a $10,000 home office makeover stipend or paid co-working spaces. (Available for US-based full-time employees only)