Unreasonable Group

Executive Assistant to the CEO

At Unreasonable Group, we believe entrepreneurs building rapidly scalable businesses are our best bet for solving the world’s most significant social and environmental challenges. Every day, our team strives to give these entrepreneurs tackling BFPs an “unfair advantage.” We do this by connecting entrepreneurs with the networks of mentors, investors, businesses, policy makers, and specialists they need to scale.

We are now searching for an experienced Executive Assistant to the CEO (“EA”); one who prides themself with impeccable attention to detail, is voraciously passionate about execution, and loves streamlining communication and processes to maximize effectiveness.

Directly reporting to and working hand-in-hand with Daniel Epstein, our founder and CEO, the EA will be one of the most strategic roles in our organization. The ideal candidate will demonstrate strategic thinking and an ability to develop new (and run existing) project management and organizational systems; shows empathy and poise; has no problem speaking “truth to power;” is obsessively detail oriented and enjoys both the research of and the implementation of new and routine tasks; has multiple years of experience as an Executive and/or Personal Assistant to other CEOs and/or high-net-worth individuals; and is a team player in every way. Although this role is primarily that of an Executive Assistant, to ensure his time is leveraged and in the absence of having a personal assistant, it should be noted that some tasks will revolve around the CEO’s personal life.


  • Schedule meetings and manage complex calendars for the CEO.

  • Provide strategic guidance to ensure that the CEO has the time, resources, and materials needed to accomplish his goals.

  • Communicate regularly with the CEO, when he is in the office and working remotely (about 50% of his time, he is traveling for work), to ensure he is apprised of changes to his calendar or to the work of his teams.

  • Travel with CEO when requested and appropriate (likely ~10% of time and occasionally for the duration of a two-week Unreasonable program).

  • Keep the CEO organized with meeting materials and immediate priorities (who needs what by when); this includes inbox management and communication/response strategies.

  • Monitor and help manage the CEO’s email inbox; responding, organizing, and escalating priority messages when appropriate.

  • Run errands on behalf of the CEO to ensure his bandwidth is as leveraged as possible for key priorities of the organization. (Ex: dog walks, overseeing property management, ensuring the CEO has healthy food and drinks, going to the post office to send timely packages...etc).

  • Research, identify, and organize extensive lists of prospective investors, partners, entrepreneurs, etc., and reach out to them directly on behalf of the CEO to schedule meetings and extend relevant invitations.

  • Help to organize, plan, and manage small events and gatherings when requested by the CEO (ex: private dinner with investors in Unreasonable’s fund).

  • Manage a heavy travel schedule and arrange all of the CEO’s travel in accordance with his preferences and priorities.

  • When requested, sit in on meetings with the CEO and take detailed notes, as well as communicate and manage follow up from all parties involved.

  • Help manage relationships with Unreasonable’s Board of Directors and Advisory Boards on behalf of the CEO (ensuring quarterly calls and annual meetings are planned many months in advance, taking notes and sending out minutes within 72 hours of all board meetings, keeping board members up to date with invitations to on Unreasonable programs they can be a part of...etc).

  • Develop and maintain an accurate contact database, ensuring personal notes and customized gifts are sent out to key contacts and relationships of the CEO (ex: birthdays, holidays, thank you packages for mentors after they participate in an Unreasonable program...etc).

  • Prepare and submit monthly expense reports in accordance with our accounting practices on behalf of CEO.

  • Help with the upkeep of the CEO’s apartment when he is traveling — including hiring cleaning crews and managing short and long term rental relationships.

  • Help with the upkeep, cleanliness, and organization of Unreasonable’s global headquarters offices in Boulder, CO.

  • Ensure the CEO takes care of his health — helping to book and manage doctor and wellness appointments, manage his health insurance policies, and any followup needed with doctors’ offices.

  • Manage and care for your own health and energy to prevent burnout and avoid feeling overly stressed. This is a fast paced job with significant responsibility and hours will vary depending on which timezone the CEO is working from. You need to be comfortable in this environment and although it may sound antithetical to the role, we want to ensure you able to prioritize your personal sense of well being above all else.

  • Work with CEO to secure speaking and press engagements globally and take briefing calls on behalf of the CEO as well as manage all invoicing, travel, and logistics associated with keynote and media opportunities.

  • Curate and source semi-annual outdoor experiences for the CEO including travel, itineraries, certifications/credentials when relevant, as well as coordinating with others joining the CEO on these “Adventures.”

  • Help with pet care for the CEO’s adorable dog, Kaya; feeding, walking, administering medication, scheduling vet appointments...etc.


  • You are excited to work out of our headquarters in beautiful Boulder, Colorado! This position is based out of our Boulder HQ and qualified candidates must either already live in the Boulder/Denver area or be willing and able (i.e. visa status) to relocate here in order to take the position. Relocation assistance for eligible candidates will be provided but visa sponsorship will not.

  • You have multiple years of experience as a personal and/or executive assistant with high-profile individual(s).

  • You think and operate strategically. You are responsible for prioritization and planning. We are looking for someone who is three steps ahead of the CEO, constantly anticipating problems and fixing them before they occur—then fixing them again when everything changes.

  • You are always on time with everything you do.

  • You represent Unreasonable with graciousness and poise, minimize the ripple effect on your team should problems arise.

  • You’re curious and passionate about entrepreneurship and strive to work with a team that is oriented around a mission of solving pressing global challenges – the rhythms and dynamics that make Unreasonable work.

  • You demonstrate courage and optimism. You use excellent communication skills to gain the context necessary to perform tasks, and you adopt a can-do attitude. You are unfazed and adaptable in the face of change.

  • You recognize what’s most important to tackle, in what order, and are prepared to make informed, independent decisions.

  • You take pride in accuracy and professionalism. You show great attention to detail, thoroughness, and follow-through; you believe that when work is done well, the magic is in the details.

  • You don’t hesitate to speak truth to power. If the CEO is falling behind on key priorities or not being as effective as possible when strategy demands it, you will not hesitate to tell him that he needs to self-correct. You are candid, honest, and kind in your feedback, but you do not hold back.

  • You are a trusted confidant. In this role you will have access to more sensitive and important information about our company than likely any individual at Unreasonable.

  • You do not give in to workplace gossip — it’s not in your nature.

  • You are a flawless multi-tasker, able to seamlessly shift between people, tasks, modes of communication, and technology platforms.

  • You believe deeply in the importance of transparent and honest communication in what you write, how you interact with your team, and by always following up and following through on your word.

  • You are not the type of person who says, “That’s not my job."

  • You are willing to work flexible hours, including some evenings and weekends, and you understand that this comes with working with an entrepreneurial CEO who is often working from international time zones. You will approach this job with an on-call 24/7 mentality.

  • You don’t hesitate to ask for help when it is needed and before it is too late.

  • You have experience building and managing contact management systems.

  • You consider yourself an:

    • Expert in Google Docs, Sheets, Slides, and Gmail

    • Expert or a very quick learner on CRM platforms (we use Copper)

    • Highly proficient in Mac OS and Microsoft Office

  • You love dogs. Our CEO is obsessed with his dog “Kaya,” and watching her will certainly be a part of this role.

  • As you read about ​Unreasonable’s core values​, you get more and more excited with each value you come across.


    • January 12th: Application goes live.

    • February 18th: Your application is due. 

    • February 24th and 25th: If you are invited to the next round of the process, we will schedule a 20 minute phone call with you.

    • February 26th - March 3rd: We will give select applicants a small “trial project” representative of the type of work associated with this position. Though we will give you 6 days to finish your "trial project," it should only take a couple of hours to complete.

    • March 16th Week: Assuming both of us want to continue exploring the potential of working together, we'll invite you to meet with our team for a half day interview. Simultaneously we’ll be conducting background checks and reference checks on the two to three most compelling applicants for this position.

    • March 24th: Assuming you made it through the reference checks, you will be notified whether or not the position is yours.

    • April 13th: Ideally, those accepted will be able to join the company full time no later than April 13th, but preferably before. That said, knowing this timeline is tight, we will work with the selected candidate to ensure a smooth transition from their old job to new, on a timeline that works best for all.

“The object of life’s journey is not to arrive at the grave safely in a well preserved body, but rather to skid in sideways, totally worn out, shouting, ‘Holy Sh*t, What a Ride!'”—Mavis Leyrer


At Unreasonable, our goal is to become a global brand with a diverse team that is representative of the community we serve. We are an Equal Opportunity Employer and do not discriminate on the basis of race, ethnicity, religion, creed, sex, gender, gender identity, pregnancy, national origin, ancestry, age, disability, veteran status, marital status, genetic information, sexual orientation, political affiliation or any other non-job-related factors. We value diversity and are committed to building a team and an inclusive culture that represents a global perspective of experiences, skills, backgrounds, and expertise. The more inclusive we are, the better we can deliver our mission of driving resources to and breaking down barriers for entrepreneurs solving BFPs.

Role posted - 2020-01-13T16:30:01Z 9:30am, 13th Jan 2020 MST