Onboarding Jobs

This guide walks you through configuring an onboarding job in Trig, with detailed explanations of why each configuration choice matters and how to think through decisions for your specific business.

Worked Example: Throughout this guide, we’ll follow TeamFlow, a collaborative project management tool. TeamFlow has discovered that the first 30 days determine everything—customers who reach their “aha moment” become long-term retained customers, while those who never quite get started churn at renewal.

Why onboarding matters

The onboarding truth

Here’s what the data consistently shows across B2B SaaS:

Onboarding Outcome	Long-term Retention
Reached “aha moment” in first week	85-95%
Reached “aha moment” in first month	70-80%
Never reached “aha moment”	15-30%

The pattern is stark: customers who experience value quickly almost always stay. Customers who don’t almost always leave.

The silent failure problem

The challenge with onboarding failure is that it’s invisible:

Customers don’t complain—they just stop logging in
They don’t ask for help—they assume the product isn’t for them
They don’t cancel immediately—they drift until renewal and then churn

By the time you notice a customer didn’t onboard successfully, it’s usually too late.

The intervention window

Stage	Intervention Window	Customer Mindset
Onboarding	Days	”I’m trying to figure this out”
Adoption	Weeks	”I’m forming habits”
Renewal	Months	”I’ve made up my mind”

A customer stuck on Day 3 is still open to help. A customer who’s been stuck for 3 months has already checked out mentally.

Step 1: Define your onboarding stage

What you’re configuring

The onboarding stage parameters define when customers enter onboarding, how long they have to complete it, and what success looks like.

How to think about onboarding boundaries

Entry considerations:

When does the customer first have access to your product?
Do they need prerequisites before real onboarding begins?
Is there a “Day 0” setup phase that should be tracked separately?

Duration considerations:

How long does it typically take successful customers to onboard?
How long are you willing to actively nurture before considering them stalled?
When do diminishing returns kick in?

Exit considerations:

What specific milestone(s) indicate successful onboarding?
When should you stop trying and either escalate or accept failure?

Example configuration

TeamFlow's Decision
Configuration

TeamFlow analysed their customer data and found clear patterns:

Successful customers typically completed onboarding in 7-14 days
Customers who took >30 days had 3x higher churn
After Day 30, additional onboarding effort showed minimal retention impact

TeamFlow defined success as: “Customer has at least one active project with 2+ team members collaborating”

Stage Duration: Day 1 to Day 30 (from first login)

Entry Criteria:
- First login completed
- Account status = Active
- Not a demo or test account

Exit Criteria (Success):
- Objective #4 achieved (team actively collaborating)
- → Move to Adoption stage

Exit Criteria (Failure):
- Day 30 reached without completing Objective #4
- → Move to At-Risk Onboarding job

Step 2: Define your onboarding objectives

Objective design principles

The best onboarding objectives are:

Principle	What It Means	Example
Sequential	Each objective builds on the previous	Create project → Add task → Invite teammate
Measurable	Binary yes/no, detectable in data	”Created a project” not “understands the product”
Value-connected	Each moves customer closer to value	Not just setup steps—actual value realisation
Time-bounded	Clear target date for completion	”By Day 3” not “eventually”

Finding your “aha moment”

One objective should be your critical “aha moment”—the single milestone most predictive of long-term retention. To identify your “aha moment”:

Look at retained customers: What did they all do early on?
Look at churned customers: What did they fail to do?
Find the behaviour with the biggest retention gap between doers and non-doers

Example: TeamFlow’s onboarding objectives

#	Objective	How We Measure It	Target	Why This Matters
1	First Login	`first_login_timestamp` exists	Day 1	Entry point—no login, no onboarding
2	Create First Project	`projects.count >= 1`	Day 3	Container for all value
3	Add First Tasks	`tasks.count >= 5` in project	Day 7	Real work, not just exploring
4	Invite Team Member ⭐	`active_team_members >= 2`	Day 14	AHA MOMENT - 4x retention impact
5	Team Activity	`distinct_users_with_activity >= 2`	Day 21	Confirms real collaboration

Critical “Aha Moment”: TeamFlow’s data showed that customers who invited a teammate by Day 14 had 89% retention, while customers who never invited a teammate had only 31% retention—a 58 percentage point gap.

Step 3: Configure onboarding interventions

Intervention design principles

Specificity: One intervention per objective (don’t bundle)
Timing: Intervene soon after the target date passes
Helpfulness: Focus on unblocking them, not guilting them
Urgency calibration: Earlier objectives warrant faster intervention
Escalation path: Plan for what happens if intervention doesn’t work

Example intervention design

Intervention 2: No Project (Day 3 target missed)

Problem: Customer logged in but didn’t create a projectUrgency: Medium-high (they’re exploring but not committing)Timing: Day 4 if no project createdGoal: Help them create their first project

Intervention 3: No Tasks (Day 7 target missed)

Problem: Customer created a project but it’s emptyUrgency: Medium (they started but got stuck)Timing: Day 8 if fewer than 5 tasksGoal: Help them add real work to their project

Intervention 4: No Teammate (Day 14 target missed) ⭐ PRIORITY

Problem: Customer is working alone—hasn’t invited anyoneUrgency: Highest (this is the aha moment!)Timing: Day 10 (early intervention—don’t wait until Day 15)Goal: Make inviting a teammate feel easy and valuable

Intervention 5: No Team Activity (Day 21 target missed)

Problem: Teammate was invited but isn’t engagingUrgency: Medium (teammate may need their own nudge)Timing: Day 22 if teammate hasn’t taken actionGoal: Get the invited teammate to participate

Step 4: Write your intervention messages

Message philosophy

Onboarding messages should feel like a helpful friend, not a marketing automation.

Feels Like Automation	Feels Like Help
”You haven’t completed your setup!"	"Need help getting your first project started?"
"Don’t forget to invite your team!"	"Here’s a quick way to bring your teammates in"
"Complete these steps to get started"	"Most teams find it useful to start with…”

Message structure

Effective onboarding messages follow a simple structure:

Acknowledge where they are (not accusatory)
Explain the benefit of the next step (not the feature)
Make the action extremely easy (direct link, clear CTA)
Offer help if they’re stuck (open the door)

Example messages

No Login
No Project
No Teammate ⭐

Subject: Your [Product] account is ready

Hi {first_name},

Your [Product] account is set up and ready to go. You can log in
here and create your first project in about 2 minutes:

[Log In to {Product} →]

If you hit any snags getting in, just reply to this email and
I'll help you sort it out.

Sarah
Customer Success

Subject: Quick tip for getting started

Hi {first_name},

I saw you logged into [Product]—great! The fastest way to see
how it can help is to create a project for something you're
actually working on right now.

It doesn't have to be perfect. Most people start with a simple
project and build from there. You can create one here:

[Create Your First Project →]

If you're not sure what kind of project to start with, I'm
happy to share some examples from teams like yours.

Sarah
Customer Success

Subject: [Product] works better with your team

Hi {first_name},

I noticed you're using [Product] solo right now. That's a great
start, but here's what I've seen: teams that use [Product]
together spend way less time in status meetings and "where's
that file?" conversations.

The easiest way to try it: invite one teammate to collaborate
on {project_name}. Takes about 30 seconds:

[Invite a Teammate →]

They'll get an email with everything they need to jump in.
You can always add more people later.

If you'd prefer to keep this project private, that's totally
fine too—just let me know and I'll adjust your setup.

Sarah
Customer Success

Step 5: Configure sender identity

Options

Sender Type	Best For
Real onboarding specialist	Maximum authenticity, but scalability issues
Automated/Team sender	Clearly automated, lower engagement
Dedicated persona	Consistent, human-feeling, scalable

Recommendation: Use a dedicated persona (like “Sarah Chen”) for most customers, with real CSM names for enterprise accounts ($25K+) to establish relationships early.

Step 6: Set message timing

Timing principles

Objective	Recommended Timing	Reasoning
First login (Day 1)	24 hours after signup	Give them a chance to log in organically
Early objectives (Day 3-7)	Morning of target day +1	Catch them when they’re fresh
Critical objectives (Aha moment)	Earlier than target	Don’t wait—intervene proactively
Later objectives (Day 14+)	Next business day	Less urgency, avoid weekends

Step 7: Configure follow-up logic

Follow-up design

Not every customer will respond to the first message. You need a plan for:

Persistence: Some customers need multiple touches
Escalation: When to involve humans
Exit: When to stop trying (to avoid annoying customers)

Example: “No teammate” follow-up sequence

Days After First Message	Action
Day 0	First message sent
Day 3	Follow-up message (different angle, offer help)
Day 7	Internal notification (human may need to intervene)
Day 14	Exit job → Move to “at-risk onboarding” segment

Follow-up message example

Subject: Quick thought on [Product]

Hi {first_name},

I wanted to share something I've noticed: the teams that get the
most from [Product] usually start by inviting just one other
person—not the whole team, just someone they work closely with.

Would it help if I showed you how to set that up? I can do it
in a 5-minute call: [Book a Quick Call →]

Or if you'd prefer to just try it yourself: [Invite Someone →]

Sarah

Step 8: Configure internal notifications

Tiered notification system

Level	Trigger	Channel	Action Expected
1: Logging	All interventions sent	Dashboard log	Daily digest review
2: Reply Handling	Customer replies	Slack DM to CS	Respond within 4 hours
3: High-Value	$15K+ customer triggers intervention	CSM DM	Personal attention
4: Escalation	”Aha moment” intervention failed twice	Slack channel + CSM	Consider outreach
5: Abandonment	No login 14+ days	Leadership alert	Executive review

Sample high-value alert

⚠️ High-Value Onboarding Alert

Customer: Acme Corp ($28,000/year)
Onboarding Day: 10
Stuck At: No teammate invited (Objective #4)

Progress:
✅ First login (Day 1)
✅ Created project (Day 2)
✅ Added tasks (Day 5)
❌ Invited teammate ← BLOCKED

Intervention sent today. This is the "aha moment" objective.
Consider personal outreach.

📊 View Customer → [link]

Step 9: Define success metrics

Metrics to track

Metric Type	What It Measures	Example
Objective Completion	Did the intervention work?	% who complete objective after intervention
Time to Completion	How quickly do they complete?	Days from intervention to completion
Response Rate	Are customers engaging?	% who reply or click
Retention Correlation	Does completion predict retention?	Retention rate by objective status

Setting benchmarks

For your first month, focus on establishing baselines:

What % complete each objective without intervention?
What % complete after intervention?
How does timing affect completion?

Then iterate: adjust messaging, timing, and targeting based on data.

Summary checklist

Onboarding stage defined with entry/exit criteria

4 to 7 objectives identified with clear completion criteria

”Aha moment” objective identified

Intervention triggers configured for each objective

Plain text messages written for each intervention

Follow-up sequences designed

Internal escalation paths configured

Success metrics defined

Next steps

Configure Adoption Jobs

Build sticky habits after customers complete onboarding

Building Jobs Guide

Detailed guide on job configuration

​Why onboarding matters

​The onboarding truth

​The silent failure problem

​The intervention window

​Step 1: Define your onboarding stage

​What you’re configuring

​How to think about onboarding boundaries

​Example configuration

​Step 2: Define your onboarding objectives

​Objective design principles

​Finding your “aha moment”

​Example: TeamFlow’s onboarding objectives

​Step 3: Configure onboarding interventions

​Intervention design principles

​Example intervention design

​Step 4: Write your intervention messages

​Message philosophy

​Message structure

​Example messages

​Step 5: Configure sender identity

​Options

​Step 6: Set message timing

​Timing principles

​Step 7: Configure follow-up logic

​Follow-up design

​Example: “No teammate” follow-up sequence

​Follow-up message example

​Step 8: Configure internal notifications

​Tiered notification system

​Sample high-value alert

​Step 9: Define success metrics

​Metrics to track

​Setting benchmarks

​Summary checklist

​Next steps

Configure Adoption Jobs

Building Jobs Guide

Why onboarding matters

The onboarding truth

The silent failure problem

The intervention window

Step 1: Define your onboarding stage

What you’re configuring

How to think about onboarding boundaries

Example configuration

Step 2: Define your onboarding objectives

Objective design principles

Finding your “aha moment”

Example: TeamFlow’s onboarding objectives

Step 3: Configure onboarding interventions

Intervention design principles

Example intervention design

Step 4: Write your intervention messages

Message philosophy

Message structure

Example messages

Step 5: Configure sender identity

Options

Step 6: Set message timing

Timing principles

Step 7: Configure follow-up logic

Follow-up design

Example: “No teammate” follow-up sequence

Follow-up message example

Step 8: Configure internal notifications

Tiered notification system

Sample high-value alert

Step 9: Define success metrics

Metrics to track

Setting benchmarks

Summary checklist

Next steps