Back to jobs

Chief of Staff

Burlingame, CA

Guideline is looking for a Chief of Staff, reporting directly to the CEO & Founder. This is an in-person role based in our Burlingame, CA office, with regular travel. 

Chief of Staff is a rare role that can make an impact in all corners of the business. Think of this role as the CEO's right hand and the Executive Team multiplier, where you move the business forward through sound business decisions. 

The ideal candidate is proactive, independent, resourceful, and with excellent judgment. They don’t need the CEO to tell them what to do on a regular basis – instead, they bring opportunities up and take things on. A “doer” with a “no task is too small” approach to getting things done.

What you will work on

  • CEO & Executive team multiplier
    • Facilitate weekly Executive Team standups
    • Own end-to-end planning, execution, and facilitation of Executive Team offsites
    • Advise the CEO and senior management team on a wide range of items
    • Own execution of CEO special projects
    • Facilitate effective decision-making throughout the organization, proactively setting the context, documenting, and cascading decisions 
  • Cross-functional forums
    • Own end-to-end planning, execution, and facilitation of monthly Company All-Hands, Quarterly Business Reviews (QBRs), ad-hoc Town Halls, etc. 
    • Coordinate and support the Executive Team in preparation and follow-up for Board Meetings
  • Cross-functional planning
    • Work with the Executive Team to articulate vision, priorities, and KPIs for the year and beyond, helping identify dependencies and make tradeoffs
    • Drive annual and quarterly strategic planning across the company
  • High priority initiatives
    • Program manage high-impact cross-functional initiatives 
    • Conduct ad-hoc deep-dives as needed

What we are looking for

  • 5+ years experience in management consulting or a similar role; BA/BS required
  • Able to build trust across the organization and influence stakeholders
  • Intellectually curious, willing to dive deep and learn new things, strong analytical skills
  • Resourceful, proven ability to manage multiple priorities in parallel and make sure things don’t slip thru the cracks
  • Ambitious - you want to be a Founder, CEO, or COO one day and are looking for the quickest way to get experience
  • Fast-paced - you move fast and make things happen
  • Excellent judgment - you know how to spend your limited time and have a high level of integrity with sensitive information
  • Decisive - you know how to get to the root of an issue and drive towards a decision

More About Guideline

Our values serve as a compass that guides our decisions and are considered non-negotiable, especially when it comes to hiring. Together with our employees, partners, and customers, we live these values every day.  

Everyone has hopes and dreams for the future, but it seems like only some of us are able to financially invest in them. That’s something we’ve made it our mission to solve - to help everyone arrive at a safe, secure retirement. Whatever type of work you choose, whatever the size of your business.  

We’ve done this by building the easiest, most affordable, most comprehensive platform for investing in your financial future.  It replaces doubt and fear with transparency, knowledge and understanding. It makes it possible, even enjoyable, to participate in a retirement plan as an employer, employee or partner.  

Because when you know how to safely, smartly invest today, you’ll be able to do more of what you love when the future arrives. And that is something everyone should be able to look forward to.

Compensation

At Guideline, we believe compensation should be fair and equitable. We take a data-driven approach to set our compensation bands; the successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, and work location. We are always evaluating our pay zones to be as competitive as possible, so keep in mind these may be subject to change in the future.

Please speak with a recruiter for additional information regarding our tier locations and compensation philosophy
  • Metro+:
    • The base salary range for this position is $181,000-$220,000 annually.
In addition to base salary, this position is eligible for equity in the form of Incentive Stock Options (ISOs).

At Guideline, base salary is just one component of the overall Total Rewards package offered to employees.  All employees are offered comprehensive benefits and perks to help support you and your family.
  • Health
    • Opt-out credit for waiving coverage
    • Medical, dental, and vision insurance — We offer multiple plan options with varying company premium contributions
    • Health Savings Account and Flexible Spending Account
    • Company paid disability and life insurance
    • Optional Voluntary life insurance
    • Mental health benefit navigation with Rula for employees and dependents
  • Parental Leave
    • Paid parental leave for birthing and non-birthing parents
  • Generous Time Off
  • 401(k) Plan
    • We use our own platform and contribute 100% of employee contributions up to 5%
  • Other Benefits
    • 1-month paid Sabbatical after 5 years of employment
    • Annual learning and development stipend — We reimburse approved professional development expenses, up to $750 per employee per year
Guideline provides equal employment opportunities to all employees and applicants for employment without regard to race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.  Additionally, Guideline participates in the E-Verify program in certain locations, as required by law.

Guideline is an equal opportunity employer. Applicants in need of special assistance or accommodation during the interview process can reach out to peopleops@guideline.com.

Guideline is committed to protecting the privacy and security of the personal information of our applicants. Please refer to Guideline's Privacy Policy for information about our privacy and security practices.
 
#LI-Onsite

Expected Salary Range

$181,000 - $220,000 USD

Apply for this job

*

indicates a required field

Resume/CV*

Accepted file types: pdf, doc, docx, txt, rtf

Cover Letter

Accepted file types: pdf, doc, docx, txt, rtf

Select...
Select...
Select...
Select...

If your target number includes bonuses/commissions, please specify the breakdown.

Select...
How did you hear about this opportunity? (select all that apply) *
Please check the reasons you're interested in working at Guideline:

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Guideline, Inc.’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Select...
Select...
Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Select...

Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury
Select...

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.