Chief of Staff, Guideline
$181-220k
+ Stock Options (ISO's)
Retirement plans for small business
Job no longer available
Retirement plans for small business
201-500 employees
Job no longer available
$181-220k
+ Stock Options (ISO's)
201-500 employees
Company mission
To help everyone arrive at a safe, secure retirement, whether they're a small business owner, an employee, or self-employed.
Role
Who you are
- 3+ 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
What the job involves
- 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
- 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
Our take
When businesses offer a 401(K) plan, a message is sent to employees and potential employees that their future is valued by their employer. However, small businesses are often left behind, being charged extortionate fees or ignored by 401(K) providers altogether, leaving many American families with no retirement savings and the potential of retiring into poverty.
Guideline spotted this oversight as an opportunity to jump in and offer small businesses an affordable 401(K). It generates income by charging each business a flat monthly fee per participant.
The company now manages retirement plans for hundreds of thousands of people in over 40,000 companies and has accumulated over $8 billion in assets under management. Benefits providers Intuit, Gusto, and Square all use Guideline as their 401(K) partners.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-6% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Jun 2021
$200m
SERIES E
Jul 2020
$80m
SERIES D
Total funding: $339m
Company benefits
- Comprehensive medical, dental and vision plans—100% for employees, 70% for dependents
- Generous 401(k) match
- Paid time off + unlimited vacation days
- Paid parental leave
- Mental health coaching and therapy
- Learning and development stipend
- Cash referral bonus
- Commuter benefits
Company HQ
Downtown, Burlingame, CA
Leadership
Kevin Busque
(CEO)Majored in Computer Information Science at Fitchburg State University. Started out as an Advisory Unix Systems Administrator at IBM and then founded LinkedUp.net, an Open Source consulting company, in 1996. Acted as Chief Information Security Officer at the Institute for Health Metrics and was Director of IT at Humedica. Co-founded TaskRabbit in 2008, acting as its VP of Technology until 2015.
Mike Nelson
(CTO)Majored in Mechanical Engineering at the University of Southern Maine. Was Mobile Developer and CTO at TechStars-backed Accelgolf from 2007 to 2010. Joined SkillSlate as Rails Engineer and CTO, before being hired by TaskRabbit as Staff Engineer in 2012.
Jeremy Caballero
(Co-Founder & CPO)Started out as a Junior Programmer at Mail Boxes Etc. Worked as a Photographer and Videographer from 2007 to 2011, and then as a Freelance Digital Designer. Was Lead Designer at lifestyle adventure brand Targa Trophy before joining TargetSafety's UX team. Was made Lead Product Designer at TaskRabbit in 2012.
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