• Maintain and proactively manage calendars for multiple companies; adjust schedules in real time to accommodate shifting priorities without waiting for instructions. • Track CEO-led initiatives, push deadlines when necessary, flag bottlenecks, and ensure projects progress smoothly. • Serve as the primary point of contact for internal teams and external clients seeking the CEO; draft, screen, and initiate correspondence with clear escalation when needed. • Plan and confirm meetings, conferences, and travel; prepare agendas, collate materials, and take actionable minutes. • Compile reports, presentations, and briefs tailored to the CEO’s needs; identify gaps or inconsistencies before submission. • Identify inefficiencies in office workflows, suggest actionable solutions, and implement approved changes across multiple companies. • Conduct needs analysis, SWOT analysis, root cause analysis, and action planning for initiatives, presenting actionable recommendations. • Handle urgent or unexpected tasks without supervision; escalate only when resolution is impossible.

• CEO Calendar & Schedule Management: Proactively update the CEO’s calendar, confirm appointments, and resolve conflicts before escalation. Ensure daily schedule supports executive priorities. • Meeting Coordination & Briefing: Prepare agendas, meeting materials, and post-meeting summaries. Ensure executives enter meetings ready to act, not review raw data. • Professional Correspondence & Reporting: Draft, review, and manage emails, internal communications, and operational reports. Flag sensitive or high-impact items for CEO attention. • Department & Stakeholder Liaison: Act as the virtual point-of-contact between CEO and department heads. Follow up on delegated tasks to ensure deadlines are met without repeated reminders. • Operational Oversight & Documentation: Maintain digital files (Dropbox, Google Docs), track KPIs, monitor progress on initiatives, and ensure all critical information is accurate and accessible. • Project & Special Initiative Support: Assist with onboarding, document organization, and special projects, identifying gaps and proactively suggesting improvements. • Client & Process Administration: Support client management processes, track automation workflows in GoHighLevel, and manage related administrative tasks.

• Execute administrative duties to support founders. • Manage operations and systems. • Align teams and boost productivity. • Coordinate hiring and interviews. • Handle executive communications and logistics.

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better. This is not a traditional EA role. You'll be a force multiplier to the COO of a category-defining healthcare company — and the architect of how executive support works across the entire organization. In a year, you won't just be running the COO's calendar. You'll have built the function that makes Headway's leadership team operate at its best. The Role We're hiring an Executive Assistant / Head of EA Program to partner directly with Rob Sadow, our Chief Operating Officer, in a high-impact, high-visibility role. You'll own Rob's calendar, commitments, and operating rhythm — ensuring his time and energy are consistently focused on the highest-leverage priorities across a portfolio that spans CX, Operations, Legal, Compliance, Accounting, Finance, and the Executive Team. But this role goes beyond supporting one executive. Headway is scaling rapidly, and we need someone to define what world-class executive support looks like here — setting the standard, building the team, and ensuring every senior leader at Headway gets exceptional EA support. What You'll Own COO Time, Energy & Focus (70%) - Own the COO's calendar end-to-end — not just scheduling, but making hard prioritization decisions about what gets Rob's time and what doesn't - Design schedules for deep work, energy, and presence — not just efficiency - Prep Rob for every meeting with full context on attendees, purpose, relevant documents, and key decisions needed — he should never walk into a meeting cold - Own travel logistics end-to-end, including events and personal travel - Manage key relationships on Rob's behalf — knowing who to prioritize, who to push, and when to escalate - Track action items and commitments across Rob's portfolio so nothing falls through the cracks - Support personal and family logistics where relevant — including protecting boundaries that matter (like being offline for family time in the evenings) EA Program & Team (30%) - Define what exceptional EA performance looks like at Headway — set the operating model, tools, rituals, and standards for the function - Hire, manage, and coach EAs supporting the CEO and other executives - Own performance management, career development, and onboarding for the EA team - Build an EA-specific leveling framework and ensure compensation, expectations, and growth paths are clear and competitive You'd be a great fit if... - You are based in the NY area and are excited to be in the office 3-4 days / week - You have 8+ years of experience supporting C-suite executives at high-growth technology companies — and you genuinely love being an EA. This isn't a stepping stone; it's the career you've chosen and you want to be exceptional at it - You have experience managing other EAs — hiring, coaching, giving direct feedback, and building a team culture of excellence - You manage your executive, not the other way around — you're comfortable being vocal, direct, and decisive with a senior leader, and you make independent judgment calls and see three steps ahead - Your written and verbal communication is flawless — grammar, punctuation, tone, and clarity are non-negotiable. You represent your executive in every interaction - You build strong relationships cross-functionally — other leaders and EAs trust you, enjoy working with you, and see you as someone who makes things easier, not harder - You thrive in fast-paced, high-standards environments — Headway operates at an Olympic performance standard, and you're energized by that, not intimidated - You are excited by our mission to rewire mental healthcare for access and affordability Compensation and Benefits: The expected base pay range for this position is $200,000 - $250,000, based on a variety of factors including qualifications and experience. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level. We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential. - Benefits offered include: - Equity compensation - Medical, Dental, and Vision coverage - HSA / FSA - 401K - Work-from-Home Stipend - Therapy Reimbursement - 16-week parental leave for eligible employees - Carrot Fertility annual reimbursement and membership - 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st - Flexible PTO - Employee Assistance Program (EAP) - Training and professional development We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview. Headway participates in E-Verify. To learn more, click here. A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.