Chief of Staff

New York, NY
Oct 27, 2021
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Simplero’s founder and CEO is looking for a Chief of Staff to help us scale Simplero and launch some newer brands. The vision is a Richard Branson-style house of brands, united by a common culture, brand, and value prop, under the founder’s personal brand.

You will manage projects, solve problems, make good decisions, facilitate communication, and promote accountability to realize this vision.

This is a phenomenal opportunity for you to learn the ins and outs of a growing SaaS business, launch brands in multiple expanding markets, and prepare you for a CEO or leadership role if that is your desired career path. It will no doubt provide you with lots of autonomy, fun, challenge, as well as personal and professional growth.

Simplero is our most established business. This SaaS company helps coaches and educators transform lives at scale by simplifying their businesses and lives.

Our overall mission is to raise the level of maturity on the planet by providing software, services, and community for visionaries in the personal growth industry.

Although Simplero is currently fully remote, this position is New York based, so you and Calvin can work closely together in person.

What you’ll do:

  • Help the CEO set and communicate the vision and direction of the company
  • Drive and coordinate company-wide and department planning processes, including the development of annual and long-term goals and objectives
  • Develop and manage department budgets in partnership with the CFO.
  • Initiate and manage strategic projects, coordinate projects with departments and communicate project updates to CEO
  • Facilitate communication, make sure projects aren’t bottlenecked, keep departments aligned and watch for risks
  • Establish a Human Resources structure and process to support recruiting, hiring, salary administration, and performance management.
  • Assist CEO in management of staff, including direct and indirect oversight
  • Manage department communication, including organizational announcements, executive updates, department meetings, and status and performance reports
  • Manage preparation for and follow up on meetings and presentations
  • Identify areas of continuous improvement related to process, execution, delivery, efficiency, satisfaction and business results
  • Partner with the executive administrative assistant to ensure efficient administrative support for the CEO, manage and protect executive time and boost executive productivity, including daily briefings and deliverable tracking
  • Serve as proxy or designate for executive, representing executive in meetings and communications, and act as liaison between executive and others when necessary

Here are the skills you have:

  • Clear communication
  • Analytical and strategic thinking
  • Strong execution
  • Experience building high performing teams
  • A sense of humor

**Here’s what’s in it for you: **

  • Compensation $120-$150k + bonus
  • 4 weeks of paid vacation + 10 holidays per year
  • Learn direct from the CEO
  • Lots of autonomy, effectively being “CEO” of multiple business units

Why you might be excited about us:

  • You want to create massive impact (see
  • You’re obsessed with growing and optimizing your life and work
  • You love to see visions become reality
  • You want to accelerate your career and have the opportunity to work with an inspiring, fun, and loving team
  • You’re ready to do the best work of your life

Why you might NOT be excited about us:

  • You hate accountability and responsibility
  • You hate learning and growing
  • You hate being challenged and trying new things
  • You don't take coaching well

Our culture

  • We love having big dreams and finding innovative ways to make them real
  • We hire smart, driven people and then get out of their way
  • We expect you to hold yourself accountable
  • We’re very real and candid with each other
  • We’re obsessed with getting better every single day, and invest heavily in personal and professional growth

Where we go from here:

  • If you’re excited to learn more, submit your application below.
  • If we think you might be a good fit, we’ll ask you a few questions in writing.
  • Then you’ll have a call with some folks on the team who help assess fit
  • If we’re still on, you’ll meet with Calvin to start getting to know each other
  • Next, you’ll  meet with other members of our leadership team
  • Then we’ll figure out a short term project we can do to learn how well we enjoy working together
  • Then we’ll nail down the details, sign a contract, and start really crushing it together!

We’re pumped to hear from you!

Apply Now
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