Executive Assistant to the Founder

Unify America•Chicago, IL

44d•Onsite

About The Position

We are seeking a highly organized and proactive Executive Assistant (who loves to laugh) to support Founder Harry Nathan Gottlieb. This is a critical role for a professional who will thrive in a fun, busy, mission-driven environment and is looking for a long-term position where they can make a palpable difference in an ambitious non-profit and the life of its Founder. About Unify America We’re on a mission to replace political fighting with collaborative problem-solving. Yeah, we know it sounds audacious. It is. But we’re doing it—by creating civic experiences that reduce polarization, teaching essential civic skills, and inviting Americans to use their differences to better solve common problems together. Where we work: Higher Education (Civic Gym): Over 30,000 college students have engaged in meaningful cross-partisan conversations. Think of it as training for democracy—reps, sweat, and all. Cities (Democracy Leagues): We partner with communities to run Civic Assemblies, where residents—across the ideological spectrum—solve shared problems together. Our first pilot is in Akron, with Dayton and Chicago close behind. Thought Leadership: Our founder and CEO, Harry Nathan Gottlieb, is stirring the civic conversation with fresh ideas on social media and an upcoming book that points toward a hopeful new era of democracy. About the Role You will be the organizational backbone for the logistics of Harry’s life and work, allowing Harry to focus his energy on strategic priorities and high-level relationship management. The ideal candidate will enjoy not only supporting Harry, but also having exposure to, and the opportunity to work with, Unify America staff, Board Members, strategic partners and Investors (we use the term “investors” because we assume our donors are, in fact, expecting a return in the form of measurable progress toward our mission). When we hire the Sr. Director of Strategic Relations, this role will likely expand to support that individual as well, as they will be working closely with Harry to drive Investor engagement. If you love getting to know interesting people and winning their lifelong gratitude by taking care of the details so they can focus on the big picture, this role could be a great fit for you!

Requirements

Experience: Significant experience (3+ years) as an Executive Assistant supporting a C-suite executive, founder, or principal in a high-intensity environment.
Mindset: A strong relationship-building mindset—you like meeting folks, getting to know their preferences, and anticipating their needs before they arise - and a proactive approach to your role.
Organizational Prowess: Exceptionally organized with strong attention to detail, particularly in calendar and data management. You must love scheduling and logistics.
Tech Savvy: Proficient in Google Calendar, HubSpot (or similar CRM), Fireflies (or similar transcription service), and comfortable learning and using new tools (like ChatGPT for drafting/editing communications). Bonus points if you bring amazing new tools we’re not familiar with that will help streamline things.
Discretion & Professionalism: Capable of handling confidential information with discretion and maturity.
Communication: Excellent written and verbal communication skills, with an ability to mirror Harry’s friendly, professional tone.

Responsibilities

Calendar, Travel, and Information Management:
Scheduling: Expertly manage a complex and shifting calendar, prioritizing meetings, resolving conflicts, and ensuring Harry remains on schedule (he travels extensively for Unify America and other democracy-building initiatives).
Proactive Coordination: Coordinate meetings by proactively suggesting dates, managing "holds," and sending detailed calendar invites.
Logistics & Travel Planning: Coordinate all aspects of travel (domestic and potentially international), including booking flights (United preferred, aisle seat, you get the idea), hotels, and local transportation. Meticulously track flight details, confirmation codes, and travel time buffers in the calendar.
Location Expertise: Book preferred meeting locations near Harry’s home in Evanston and the Chicago office (3701 N. Ravenswood), as well as locations across the country when Harry is traveling, prioritizing appropriate event/audience fit and quiet environments where deep listening and engagement can occur.
Meeting Preparation & Follow-Up: Ensure all meeting logistics are confirmed the day prior (location, time, address, etc.).
All the tech: Manage travel, software, and service logins and passwords.
Relationship & Communication Management:
Partner in Relationship Management. Harry does not have a great mental rolodex in his head. He needs someone who does – who loves people, who remembers names, biographies, stories, where they work, what they do, who they’re connected to, etc. Yes, you’ll log this kind of data in the CRM, but Harry needs someone who naturally tracks all of this in their brain - and can be his partner in making connections. The goal is for you to get to know Harry’s growing network - through personal contact (as much as possible) - but at least through Harry’s reporting back.
On-site work: To help with that mind-melding, when Harry is in Chicago and working from the office (3-4 days a week when he is in town), you should also plan on being there as often as possible.
Travel. To help with that mind-melding even more, and take as much off Harry’s plate as possible, you’ll travel with him for certain events and meet the folks he’s meeting. This could be as often as two or three times a month. (Best if this is something that you find exciting rather than taxing).
Communication Hub: Routinely review Harry’s email and LinkedIn correspondence, crafting professional draft emails on Harry’s behalf, and ensuring all communication is prompt, clear, and sounds like Harry. Act as a reliable daily reminder for pending items.
Note-taking and follow-through: Sit in on select meetings with Board Members, Investors and other partners to take notes and track action items.
Information Management: Maintain meticulous notes, detailed profiles, and follow-up tasks within our CRM (Hubspot) to stay on top of the multitude of important relationships Harry is juggling as we seek to grow Unify America. Ensure meeting summaries and transcripts (from recorded meetings) are logged accurately in the CRM, and all contact and other data are updated and correct.
General Support & Initiative:
Personal Assistance: Handle select personal tasks, including coordinating personal appointments and sourcing external service providers (e.g., cleaners, caterers).
Expenses: Keep track of which charges/receipts are for Unify America, a democracy-building initiative he’s leading, or personal purposes (or occasionally also related to Harry’s two for-profit companies, Jackbox Games and Jellyvision), and submit expense reimbursements accordingly.
Ad Hoc Requests: So many and varied that we can’t begin to list them all, but if you’ve been an EA long, you know you’ll also handle lots of random additional tasks as they arise - fielding requests from different sources seeking Harry’s bio, or working with the social media team to post or email things under Harry’s name, or needing to set up catering, or a notary, or an express delivery service, etc. etc.
Process Improvement: Beyond basic administration, we’re looking for a process minded person who will make improvements, streamline operations, and take initiative to enhance overall efficiency.