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🛬 Onboarding


At Flexpa, we believe that a successful onboarding is the foundation for the rest of our time working together. Our goal is to ensure that within 90 days, anyone who joins will be fully integrated into our team, culture, and work, to the point where they would be truly missed if they left.

The foundation for a successful onboarding is a written plan - an onboarding guide - that is given to the new Flexpal on their first day. This guide should be a living document that is updated and improved over time. It should be a comprehensive resource that covers everything the new Flexpal needs to know to be successful in their role.

How to write an onboarding guide


  1. Be direct and honest from the start: We value direct communication and feedback. New Flexpals should feel comfortable both receiving and providing candid feedback.
  2. Encourage productive disagreement: We want everyone to disagree productively, offering solutions and alternatives rather than just objections.
  3. Make work visible: New Flexpals should communicate their work and progress clearly, ensuring everyone understands the purpose and value of their tasks. No one should wonder if things are working out or not. It should be obvious. This principle is especially important for us as a remote first team
  4. Understand our product and customers: It's crucial for all Flexpals to deeply understand our product, use cases, and the problems our customers face.

Essential Sections

  1. Welcome and mission: A welcome message from the hiring manager that sets the tone for the new Flexpal's onboarding experience and outlines the first mission of anyone new: onboarding successfully.
  2. Week 1 Agenda: A detailed day-by-day schedule for the new Flexpal's first week, including meetings, introductions, and tasks to complete. All week-one agenda's must include:

    • A day 1 welcome, identity and access control setup
    • Team introduction
    • Introductions to Product, Design, and GTM
    • 1:1s with everyone on the team - these sessions should focus on getting to know each other and understanding what each person does on the team
    • 1:1 with the hiring manager where the recurring 1:1 format is introduced
    • An end of week 1:1 with Andrew
  3. 30/60/90 Day Plan: Outlines expectations and milestones for the new Flexpal's first 90 days, broken down into three phases:

    • Phase I [Day 0-30]: Become knowledgeable. Adapt to the team and culture. Understand how we work and why. Soak in context.
    • Phase II [Day 30-60]: Become productive. Take on more direct responsibilities of the role. Ship, ship, ship.
    • Phase III [Day 60-90]: Become indispensable. Contribute to Flexpa's growth and success. If they left, we would miss them.
  4. Why We Hired You: Shares the team's decision-making process and feedback from the hiring process to boost the new Flexpal's confidence and understanding of how they fit into the team. This is our opportunity to practice being direct. You should provide not just the specific reasons, but the literal, direct feedback collected from the team during the interview process.

  5. Reference Checks: Includes detailed notes from reference checks conducted by the hiring manager, providing additional context on the new Flexpal's strengths, working style, and areas for growth. Lots of companies never do this.

Example Onboarding guide

This example is example of a guide we've developer for a software developer / software engineer. You should always ensure this is role specific.

Welcome and mission

Your very first mission is to onboard successfully. The ultimate test of a successful onboarding means that in 90 days from now, people would truly miss you if you left.

There are some common onboarding failure points that you should know about. Knowing these in advance will help you avoid them.

  • Being uncomfortable with receiving or providing direct feedback. We are a small team on a small boat. We will be direct with you, and we need you to be direct with us. (See 🍒 Cherry Pickers)
  • Being unable to disagree productively. Failure here either means avoidance of disagreement entirely or of disagreeing without offering any solutions. (See 👿 Counter Productive Contrarians)
  • Not making your work visible and being unable to communicate about why something needs to be done. Use your standups to be visible! Do them first thing in the morning and make sure you understand why you’re doing something first so that you can tell everyone else. (See 🚧 Barrier Builders)
  • Not getting to know Flexpa’s product, use case, and our customer’s problems. It’s all too easy to solve problems that don’t really matter or to simply avoid really getting to know the problems we are trying to solve. This is especially true for developers (there’s always another CSS fix around the corner). (See 🧛 Runway Vampires)

There are, likewise, some common onboarding indicators of success. You should aim for these.

  • Ship early and ship often. If an issue is just too hard, don’t worry about it – communicate, ask for help. We will help you ship, but you’ve got to create the momentum (See 🏃 Momentum Makers)
  • Fix problems you see along the way. If there’s something broken in the README or onboarding docs, fix it. Show that you take pride in your work. (See 🛒 Put the Shopping Cart Back)
  • Absorb, listen to, and interact with customers as much as possible. Listen to every GTM call you can, read every Slack support message as much as possible, and soak it in. Write summaries of calls you listen to, share them, and ask questions. Improve our collective understanding. Really try to understand the problems we are trying to solve. (See ❤️ Empathy Experts)

Your onboarding buddy is X. You’ll get a chance to meet each other on Wednesday. She will act as your first line of support over the first two weeks.

What does success look like at the end? In 90 days you are fully up to speed on Flexpa product, GTM, culture, tools, and team. You are responsible for making momentum and shipping meaningful contributions that move the needle on the KPIs the company sets during its quarterly retreats.

Week 1 Agenda


  • 9:00AM: Welcome, identity setup, and access control
    • Check that you’ve onboarded each of the items
    • Say hello and introduce yourself in #hallway on Slack
  • 10:00AM: Dev environment setup
    • Ensure you have the Flexpa monorepo cloned and running
  • 11:00AM: First issue and PR
    • We’ve made a few starter issues for you - they are tagged by impact / effort to help you figure out what might best to start with
    • The goal here is to accomplish the task of having shipped something on day one
    • Tomorrow morning, we’ll do a deeper dive into the monorepo
  • 1:00PM: Flexpa team intro
    • Team intro attended by everyone!
  • 1:30PM: Intro to Product Dev
    • Please review Product Development in the OS prior to this meeting
    • The “how” of product dev @ Flexpa: mechanics of software development cycle. We’ll review:
      • Issue writing, review examples, house style, issue lifecycle
      • How we use GitHub projects
      • Milestones
      • Status checks
      • The issue backlog we’ve created for you


  • 9:00AM: Guided Dev Walkthrough
    • Post a #standup
    • A schema-out walkthrough of code with Joshua Kelly
    • We will start from the lowest level and work our way up the stack
  • 1:00PM: GTM at Flexpa
    • A walk through of key GTM resources and process
    • Understand Hubspot and the GTM stages we have at Flexpa
  • 2:00PM: GTM EOW
    • This is a weekly ritual run by Claudio that is always an open invite - it’s important for you to hear about customers and their problems as much as possible
    • For the first 90 days, you need to attend to get up to speed on as much of our customer funnel (wins and losses) as possible
  • 2:30PM: Product Past, Present, and Future
    • The “What” and “Why” of product dev at Flexpa with Brendan Keeler
    • Review previous product quarterlies together
    • Discuss work in flight, including milestones
    • Discuss roadmap ahead


  • 9:00AM: Role 1:1 w/ XYZ
    • XYZ is a software developer who has driven development for the major external front end applications at Flexpa (Docs, Link, Portal, Connections). XYZ is now focussed on our next major feature release.
    • You can discuss XYZ’s experiences with development, and XYZ's' current work in flight – the goal here is to get you up to speed on a major initiative.
  • 12:00PM: Speaker Series (“Learning Time”)
    • Occasionally, we bring in external speakers who we think we can learn something from.
    • This week it’s ABC the CEO of ASDF
  • 1:00PM: Customer Engineering w/ XYZ
    • XYZ is a software engineer who has a focus customer / sales engineering
    • You can discuss XYZ’s experiences with customer-driven development, sales processes, and current work
  • 3:00PM: 1:1 with XYZ
    • XYZ is your direct manager and you will have your first 1:1
    • How does Flexpa do 1:1s?
    • Introduction of 30 / 60 / 90 plan


  • 11:30AM: Customer Support w/ XYZ
    • Meet with XYZ to understand our current support processes and also XYZ’s experience as a software engineer
  • 1:30PM: Flexpa Townhall
    • This is our only all-team meeting for the week. We use Townhall to do a few important things:
      • Celebrate accomplishments via kudos and Alligator Wrestler of the Week
      • Make commitments for the next week
      • Hold each other accountable for last week
    • We also have a few other standing rituals:
      • Review metrics
      • Show the best and most important things via demo


  • 10:00AM: Design and User Testing at Flexpa
    • Covering our testing program, how we validate and improve our network
    • Review of all design processes and tools at Flexpa.
  • 3:00PM: EOW 1:1 w AA
    • Week 1 wrap up with Andrew Arruda
    • Schedule recurring time
    • How did your first week go? What went well? What needs improvement?
  • 5:00PM: Summary Loom
    • Create an Loom walking through your first week and what you accomplished in the first week for the team
    • Were there any improvements you can think of?

30 / 60 / 90

Really, anyone who joins a new group successfully goes through an evolution that looks like: becoming knowledgeable, becoming productive, and becoming indispensable - meaning that you would be missed if you left! Everything you do beyond the first week should target going through this evolution in your first 3 months. Your 30/60/90 is a living document and your guide on this path.

  • Phase I: Be knowledgeable

    • Attending all rituals at least once (Townhall, GTM EOW, Learning Time, first manager 1:1)
    • Complete the development setup and update the README if you find anything broken or incorrect
    • Onboarding onto all relevant Flexpa applications and tools
    • Ship and solve at least one issue a week
    • Read about the different types of insurance in America
    • Shadow GTM calls in each of the Qualifying and Engaging / Developing stages
  • Phase II: Be productive (deliver things that really matter)

    • Create a 30 day summary Loom focusing on your commitments, successes, challenges, and changes, as well as what’s ahead.
    • Ship and solve at least one issue a week
    • Lead a Townhall
  • Phase III: Be indispensable

    • Lead a milestone meeting
    • Lead a customer-facing call

Why we hired you

Rarely do companies make available their hiring decisions to the people they hire.

We’re different – here’s what we really thought about you. These comments are unfiltered. They will contain valuable information about the impressions you’ve created. Some impressions you might be really encouraged by, others might be opportunities to grow.

Our feedback

Here, we list out the actual, real internal feedback we gathered during our hiring process.

Reference check notes

Here, we share our actual notes from the reference check calls we completed.