Chief of Staff at Mainstay

| Boston, MA
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Mainstay is seeking an exceptional operator who will thrive in a fast-paced and frequently changing environment and be motivated to empower Executives to bring structure and order to rapid change; inclusive of their own development as people and leaders. This position will primarily partner with our co-founder/CEO in executing on the day-to-day strategic operations and direction of the business including operationalizing our vision of being a deliberately developmental organization (DDO). Reporting to our CEO this individual will be able to have influence and access to several aspects of how to strategically scale a business.

We are looking for an individual who has hands-on experience working in startup cultures, has translated business strategy into operational execution and who has a passion for joining us to build a one of a kind culture that puts the growth of people first. 

About Us

At Mainstay, we believe one conversation can spark a brighter future. Our Engagement Platform makes it easy for colleges and businesses to start and measure conversations that drive action at scale. From our rigorous research methods to our Behavioral Intelligence framework — everything we do is designed to help people take the next step toward achieving their goals.

At Mainstay, you will be working in a cutting edge space on new and exciting problems, driving large scale social impact, help solve unique scalability challenges and be part of an exciting stage of a high-growth company.

What You’ll Do

Proactively identify and act on opportunities to increase the CEO’s efficacy and efficiency including but not limited to the following:

  • Lead Executive Project Management: Ensure all cross-team initiatives are functionally sound. This includes ensuring there is documentation, clear roles and responsibilities, consistent monitoring and reporting of project status, and providing advisorship on productive cross collaboration and communication at all levels
  • Translate Strategic Thought to Action and Documentation: Translate project status updates, data, and preliminary ideas into fully thought through presentations for various levels including the Executive Team, External Partners, BOD and the Company as a whole. 
  • Hold us Accountable: Take ownership and scale our Company Goal process which includes partnering with leaders across the company to document, refine, align and track our Annual and Quarterly Goals to showcase work against them. 
  • Operationalizing our DDO Goals: Partnering closely with SVP People Ops, CFO and CEO you will develop clear strategic direction and a roadmap to answer “How we become a deliberately developmental organization (aka DDO)”, you will also own the diligence of external partners for us to work with as we build a DDO.
  • Support Executive Dialogue: Help facilitate ET meetings and offsites including follow ups and follow through on commitments made during offsites and meetings and supporting the CEO and Exec team in internal and external communications via various forms including email, slack, blog, and Mainstay’s own product.

Please keep in mind that these are just a few examples of what you’ll work on. This role will evolve and change as we do and you will apply being ready, willing and able to flex to those changes.

Who You Are

  • 7+ years of work experience in operational and strategic roles
  • Experience working directly and speaking candidly with C-suite and VP-level executives 
  • Exceptional communicator (written, verbal, visual) 
  • Business case modeling experience - you can spin up a quick model to analyze different opportunities and enjoy doing so
  • Strong project management skills with a desire to bring structure to undefined processes 
  • Natural leader who excels at building relationships with many different types of people 
  • Strong context switching skills, easily transitioning between the big picture and tactical execution for multiple projects 
  • Self starter - you can figure things out without a playbook 
  • Thrives on helping others reach their full potential 
  • High level of integrity 
  • Excellent judgement

***Because this role will need strong writing skills, please submit a cover letter along with your CV, to tell us more about yourself.***


Mainstay is committed to creating a company where all employees regardless of background can show up and feel they belong. This is an ongoing journey, and we welcome questions one here we’re at during your interview process. We are proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or fitness level.


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Technology we use

  • Engineering
    • PythonLanguages
    • ReactLibraries
    • DjangoFrameworks
    • Node.jsFrameworks
    • MongoDBDatabases
    • PostgreSQLDatabases

What are Mainstay Perks + Benefits

Mainstay Benefits Overview

We have a great, comprehensive healthcare package, Flexible Time Off, paid parental leave, and more!

Culture
Volunteer in local community
Partners with Nonprofits
Friends outside of work
Eat lunch together
Intracompany committees
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Diversity
Unconscious bias training
Diversity Employee Resource Groups
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Wellness Programs
Retirement & Stock Options Benefits
401(K)
401(K) Matching
AdmitHub's 401(k) retirement plan contributes 3% of an employee's annual base salary, regardless of whether they make an contribution or not, with no vesting period for the contribution.
Company Equity
Child Care & Parental Leave Benefits
Generous Parental Leave
We provide up to 10 weeks of parental leave for the primary caretaker and 6 weeks of leave for the secondary caretaker.
Flexible Work Schedule
Remote Work Program
Our remote work program includes the opportunity for employees to be full-time remote for specific positions, and all employees are encouraged to work remotely on occasion as needed.
Family Medical Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Stocked Kitchen
Some Meals Provided
Professional Development Benefits
Diversity Program
Lunch and learns
Cross functional training encouraged
Promote from within
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