Chief of Staff, Guideline

Technical Engineer

$215-298.5k

+ Equity in the form of Incentive Stock Options

Senior and Expert level

San Francisco Bay Area

Retirement plans for small business

Job no longer available

Retirement plans for small business

201-500 employees

FintechB2BHRPersonal financeFinancial ServicesSaaS

Job no longer available

$215-298.5k

+ Equity in the form of Incentive Stock Options

Senior and Expert level

San Francisco Bay Area

201-500 employees

FintechB2BHRPersonal financeFinancial ServicesSaaS

Company mission

To help everyone arrive at a safe, secure retirement, whether they're a small business owner, an employee, or self-employed.

Job

Company

Role

Who you are

8+ years of experience in engineering leadership or operations, with at least 3+ years in a Chief of Staff, Operations Lead, or similar strategic role
Proven track record of leading complex engineering initiatives in high-growth, fast-paced environments
Experience with cross-functional project management, with the ability to prioritize tasks and manage multiple initiatives simultaneously
Deep understanding of engineering workflows, development methodologies (Agile, Scrum, etc.), and best practices for scaling engineering teams

What the job involves

We are seeking a highly skilled and strategic Chief of Staff, Technical Engineer to join our team
Working directly with the CEO as an individual contributor, you will drive key projects related to engineering productivity, on-track delivery, and risk mitigation
Support engineering and executive leadership in strategic decision-making, resource allocation, and performance management
As an individual contributor, lead and execute special projects for the CEO
Test and experiment with solutions to long existing problems in our offering
Take products from 0 to 1 quickly as proof of concepts
Act as a thought partner on business growth and experimentation mindset

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

Top investors

-6% employee growth in 12 months

Glassdoor (3.8)

Trustpilot (2.4)

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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