Guideline
Guideline provides low-cost, automated 401(k) plans for small businesses and their employees. The company was acquired by Gusto in 2023 after raising $339M in venture funding. Guideline sells retirement savings plans to small businesses, automating administration to make them affordable and easy to offer. Its acquisition by Gusto suggests it will integrate with Gusto's payroll platform. Guideline's customer success and support team is its largest function, with 18 employees. The company has a median tenure of 3 years, suggesting stable retention. Guideline hires heavily from financial services firms like Better and Wells Fargo, with Gusto being the top destination for departing employees. Its alumni have founded 14 companies, including Atomic Invest and Greenboard.
The growth story
Guideline grew from 402 to 127 employees between 2023 and 2026, raising $339M along the way, most recently a Series E in June 2021.
About
Guideline provides automated 401(k) plans for small businesses, aiming to make retirement savings accessible through low costs and simplified administration. Its acquisition by Gusto positions it to integrate payroll and retirement benefits into a single platform.
The company raised $339M before its 2023 acquisition, including a Series E round in 2021. With 127 employees, it has built a customer-focused team, particularly in support roles, and maintains stable employee retention with a median tenure of 3 years.
Founders and leadership
Guideline's largest function is customer success and support, with 18 employees. The company has a median tenure of 3 years, indicating relatively stable retention.
The Guideline org chart
Jeremy Caballero (Co-founder, Chief Product Officer) leads 31 mapped leaders with 8 direct reports. Click +N to expand a team; names link to the person’s public profile.
Departments, and which ones grew
Headcount by function: Operations 26 (-58% YoY), Engineering 17 (-76% YoY), Sales 17 (-77% YoY), Customer Success and Support 11 (-65% YoY), Information Technology 10 (-67% YoY), Marketing 6 (-60% YoY).
Talent flow
Guideline hires primarily from financial services firms like Better and Wells Fargo. Its alumni often move to Gusto, with 63 departures to the acquiring company, followed by smaller numbers to Rippling and Datadog.
Most common previous employers of Guideline staff: Better (3), Wells Fargo (3), WeWork (2), Human Interest (2), Oracle (2), Wayfair (2). Former Guideline employees most often moved to Gusto (63), Rippling (3), Datadog (3), Charles Schwab (3), Boulevard Recruiting (2), Collective (2).
Alumni worth knowing
The Guideline mafia
Guideline alumni have founded 14 companies, including Atomic Invest, Greenboard, and Worthy, showcasing a strong entrepreneurial streak among former employees.
14Michael Hahn, CFA, was Senior Director, Customer & Investment Operations until 2021Dave Feldman, was Senior Product Manager until 2023Ben Rounds, was Product Manager until 2020Rosanna Leroe-Muñoz, was VP Sales until 2019Kevin Yu, LMFT, was Account Executive until 2017
Amanda Holt, was Marketing Team until 2017
Melissa Chambers, was Senior Director, Growth Strategy RevOps & Product Analytics until 2025
Christine Rimer, was Chief Customer Operations Officer until 2024
Joseph Stember, was Business Operations Manager until 2021
Dimitri Trembois, was Sales until 2024
Marco Diaz, was Founding Senior Data Engineer until 2019
James von der Lieth, was Senior Product Manager until 2024Web traffic
Traffic mix: 58% direct, 19% search, 1% social, 0% paid.
What this company is made of
Most common skills at Guideline: Public Speaking (90), Research Skills (85), Data Analysis (80), Project Management (52), Leadership (35), Customer Service (33), Microsoft Office (31), Management (29).
Where the team actually sits
Guideline people are concentrated in Texas, United States (15), California, United States (12), Maine, United States (9), Colorado, United States (8).
Search footprint
Guideline attracts about 25,060 organic search visits a month, traffic worth roughly $609K a month if bought through ads. It gained 6,330 ranking keywords and lost 6,527 in the last period.
What employees say
- Compensation
- 3.40 / 5
- Career opportunities
- 3.20 / 5
- Senior management
- 3.20 / 5
- Work-life balance
- 3.90 / 5
Frequently asked
Guideline has 127 employees as of September 2026.
Guideline has raised $339M in total, most recently a Series E round in June 2021.
Guideline was founded in 2015 by Jeremy Caballero.
Jeremy Caballero (Co-founder, Chief Product Officer) sits at the top of Guideline's reporting structure, with 8 direct reports.
The most common previous employers of current Guideline staff are Better (3 people), Wells Fargo (3 people), WeWork (2 people).
Former Guideline employees most often move to Gusto (63), Rippling (3), Datadog (3).
At least 14 companies have a founder who previously worked at Guideline, including Gusto, Atomic Invest, Greenboard.
Guideline attracts about 25,060 organic search visits a month, worth roughly $609K a month in equivalent ad spend.
The most common skills among Guideline staff are Public Speaking, Research Skills, Data Analysis, Project Management, Leadership.
Guideline staff are concentrated in Texas, United States (15), California, United States (12), Maine, United States (9).
Guideline has about 26 people in Operations, down 58% over the past year, as of September 2026.
Guideline has about 17 people in Engineering, down 76% over the past year, as of September 2026.
Computed from 89 current and 292 former Guideline profiles, as of September 2026. Source: Crustdata.
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