The Last Company They'll Ever Work With
High-touch first 30 days = they refer their best friends and never look back.
TL;DR
Core Insight: Momentum is highest when someone joins. Give them clarity on where to find the resources they need. Don't be the host who invites people to the event and then disappears.
Focus on These 3 Things:
- The 100x Frame: Every hire will improve 100x during their time. Set them up for that transformation.
- Ship in Week 1: Even something small. Momentum beats perfection.
- Fresh Lens: New hires have a pass on not knowing anything. Ask as many questions as possible. If something doesn't make sense to them, it won't make sense for the next 10 hires.
The Core Philosophy
- Keep your promises. What you said in interviews must be real
- The 100x frame. Every hire will improve 100x during their time here
- Full transparency. Clarity on value add, honesty about change
- Fresh lens. New hires see what the team is blind to. Encourage questions.
The 100x Frame
"What would I want as a candidate? Because if I can map out what I would love, other people would too - we're all human beings."
The Mindset
Every person we hire will improve by 100x during their time at the company.
The entire goal of onboarding and the first 7-30-60 days - including what success looks like after 18 months - is to get them to become their best version that they dream of becoming.
This Requires
| Element | What It Means |
|---|---|
| Full Transparency | Of what they want |
| Clarity | On how they will add value |
| Honesty | About how things can shift in the AI era |
We're not just filling a seat. We're investing in someone's transformation.
First Step
Understand how the company currently does onboarding. Then layer in what's missing.
Make Them Feel Part of the Team
They already said yes. Now go out of your way to make them feel welcome.
The 60-Minute Welcome
Within 60 minutes of accepting the offer, at least 5 team members send personalized messages.
Not generic "welcome aboard." Actual personalized notes showing excitement.
Why: Sets the tone: "You just joined a team that's genuinely pumped to have you."
New Hire Scope of Work
See the full template below in "Define Success Before They Start."
| When | Action |
|---|---|
| Before they start | Created and ready |
| During offer stage | Shared with candidate |
| Day 1 | Reviewed together |
The Trial Period (14-28 Days)
While Wispr Flow wants to hire full-time, some candidates are open to trial periods where they test the company and the company tests them. Not possible for every candidate, but should be an option.
Real work, not fake projects. Both sides evaluate fit. If it doesn't work, part ways early (better for both sides).
Define Success Before They Start
Note: This is CRITICAL for every role. When someone joins, their scope of work should be clear so they know exactly what to work on.
Why This Matters
| Benefit | Result |
|---|---|
| Clarity from Day 1 | New hire knows exactly what's expected |
| Objective evaluation | Success criteria are defined upfront |
| Faster ramp | No ambiguity about priorities |
| Better retention | People stay when they know they're winning |
Template Structure
Section 1: Team Structure Overview
Where this role fits:
• Department: [X]
• Reports to: [Hiring Manager]
• Works closely with: [Cross-functional teams]
Section 2: Core Responsibilities (First 30 Days)
1. [Onboarding task - familiarize with business/codebase/systems]
2. [First deliverable - ship something small but meaningful]
3. [Audit/assessment task - find areas of improvement]
4. [Optional stretch goal]
Section 3: Success at Month 3 & Month 6
Month 3:
• [Key outcome 1]
• [Key outcome 2]
• [Key outcome 3]
Month 6:
• [Bigger outcome 1]
• [Bigger outcome 2]
• [System/process they own]
Section 4: The Main Lever (Trial Period Focus)
What's the ONE thing that matters most? If they nail this, everything else follows.
Main Lever: [Describe the critical challenge or opportunity]
Why this matters: [Context on why this is the priority]
What success looks like: [Specific, measurable outcome]
Example: Engineering Role
Core Responsibilities (First 30 Days):
- Familiarize with codebase architecture, deployment pipeline, and team workflows
- Ship one small feature or bug fix to production
- Audit current latency issues and propose improvements
Month 3: Owns one core feature end-to-end. Reduced latency on key user flow by X%. Contributed to on-call rotation.
Month 6: Owns entire subsystem (e.g., voice processing pipeline). Shipped 2-3 major features independently. Mentoring new engineers joining the team.
Main Lever:
Our voice-to-text latency has regressed over the past month. Need someone to come in and immediately diagnose and fix it. P95 latency back under 200ms within first 2 weeks.
How to Use This Template
| When | Action |
|---|---|
| Before hire | Draft this during intake with Hiring Manager |
| During offer | Share with candidate so they know what to expect |
| Day 1 | Review together and align on priorities |
| Week 2 | Check-in on progress against 30-day goals |
| Day 30 | Formal review against this scope |
| Month 3 & 6 | Performance review anchored to these outcomes |
First 7 Days
The Daily Breakdown
| Day | Focus |
|---|---|
| Day 1 | Review scope of work, meet the team, get systems access |
| Day 2-3 | Shadow team members, understand workflows |
| Day 4-5 | First small contribution (even if minor) |
| Day 6-7 | Check-in with manager, adjust expectations if needed |
Key Insight
They should ship something (anything) in the first week.
Even a small win creates momentum.
Talent Acquisition's Role in First 7 Days
Talk to the new hire every single day. Help them, introduce them to people. Run the 25-5 Playbook for them immediately.
The 25-5 Playbook
Your job is to find people on the team, chat with them, and download what they know.
The Process
- Find someone on the team and schedule a quick 30 minute call
- For the first 25 minutes: Ask them to tell you everything they think you should know that they wish they knew when they started
- Put everything they say into your 30-60-90 tracker
- Stop them if you do not understand something
- Once 25 mins is up, for the next 3 minutes: Ask them the biggest challenges the team has right now
- Once those 3 mins are up, ask them who else you should talk to
- Rinse and repeat until you run out of names
For Entry-Level People
You will likely run out of names fast. Your goal is to branch out to different teams and figure out what they're doing too. Make yourself known. Show these teams the respect they deserve. Try to understand what they are working on.
Why This Works
| Benefit | Result |
|---|---|
| Build relationships quickly | Network established in first week |
| Show curiosity about challenges | Demonstrates initiative |
| Help future new hires | Your tracker doc becomes an asset |
The Fresh Lens Advantage
The first 30 days are PRIME POV time. New hires see everything with fresh eyes - things the team has become blind to.
What This Means
New hires notice friction in processes, confusing workflows, cultural quirks, product opportunities, and things that "just work that way" but shouldn't.
This is free consulting. They'll spot things everyone else stopped noticing months ago.
Talent Acquisition Should
Check in daily to capture what they're seeing. Pass insights to the team (product, ops, culture observations). Or create a #new-hire-fresh-eyes Slack channel where new hires can share.
Day 7-10: The Hiring Process Feedback Interview
Run a fun, informal interview with the new hire while the experience is still fresh:
| Question |
|---|
| What worked in the hiring process? |
| What didn't work? |
| What would you like to see different? |
| Any moments where you almost didn't continue? |
| What made you say yes? |
This is how you continuously improve the recruiting process.
The Perfect Time for Referrals
They just said yes, they're excited.
Ask them: "Who are 1-2 of your best friends who would be great at the company?"
Great people know great people.
Why People Stay
The 5 Retention Drivers
| Reason | How to Deliver |
|---|---|
| Growth | Clear path to next level, learning opportunities |
| Impact | See their work matter, connection to mission |
| Autonomy | Trust, ownership, freedom to solve problems |
| Team | Work with people they respect and enjoy |
| Compensation | Fair pay, equity that matters |
Month 3 & Month 6 Milestones
Success criteria defined in scope of work. Performance reviews anchored to these outcomes. Not surprises. Expectations were set from Day 1.
Retention Starts at Recruiting
The promises you make in interviews must be real. Don't oversell. Deliver on what you said. Culture fit goes both ways. If someone's not thriving, address it early.
Close the Loop with Every Candidate
The Problem: Companies open job roles, get a ton of applications, fill the job... and then never tell the people who applied.
The ROI of Closing the Loop
| Investment | Return |
|---|---|
| <30 mins of time | Brand equity that compounds |
| One email template | Bench candidates who stay in touch |
| Offering intros | Goodwill for founder & company |
People will remember how they felt when they worked with you.
Why Every Applicant Matters
Every applicant is a potential future hire (timing wasn't right), referral source (they know other great people), customer (they already like your company), or advocate (they tell others about their experience).
When you ghost them, you lose all of that. When you close the loop thoughtfully, you gain it.
The System
Step 1: Notify Everyone Who Applied
Send a message to every applicant you didn't move forward with. Not just the finalists. Everyone.
Step 2: Connect Them to the Founder
Instead of just saying "sorry, role is closed," ask them to follow the founder on LinkedIn/Twitter. Offer to look through the founder's connections. See if there's anyone you can introduce them to.
Step 3: Make Introductions
If you find a connection that could help them, make the intro. You're connecting people to each other, regardless of whether they got the job at your company or not.
The Email Template
Hey [Name],
Hope you had a great [holiday break / week / etc].
We recently adjusted this role (downgrading level & current need).
Would it be ok for us to catch up in [month] when we restart this search?
Talk soon,
[Your Name]
PS
We're connected to companies across a variety of industries.
Take a look to see if you're connected to any of [Founder]'s
connections on LinkedIn.
If there's a specific company/person that you'd love to speak to,
I'll try to help make the introduction.
Why This Works
| Element | Effect |
|---|---|
| Short and human | Not corporate-speak |
| Leaves door open | "Catch up when we restart" |
| PS offers real value | Intro to founder's network |
| Turns rejection into opportunity | Candidate gains something |
The CEO Status Flywheel
- Rejected candidates follow the founder
- Founder's network grows
- Larger network = more intros to make
- More intros = more goodwill = more referrals back to you
- CEO's status rises (helps recruiting, fundraising, everything)
Recruiting is connecting people. The network compounds.
Wispr Flow Application: ML Engineer Onboarding
How to set up ML engineers for success at Wispr, where the constraints are the challenge.
Day 1: Constraint Immersion
| Time | Focus |
|---|---|
| Morning | Product demo of Wispr Flow (use it yourself). Watch user feedback videos showing latency complaints. Review the 6 Technical Challenges doc. |
| Afternoon | Meet the ML team, understand current architecture. Get dev environment set up. Run inference benchmarks on your machine. |
End of Day: They should understand WHY we're building on-device.
Week 1: The Pipeline Tour
| Day | Focus |
|---|---|
| Day 2 | Audio capture pipeline, understand where latency comes from |
| Day 3 | Whisper model setup, quantization work we've done |
| Day 4 | LLM cleanup layer, how we handle accuracy post-processing |
| Day 5 | Ship something small - a latency measurement, a benchmark, anything |
Key Metric: They should be able to explain our pipeline end-to-end by Friday.
The "Zero Edit Rate" Immersion
First 30 days: Use Wispr Flow for all their own writing. Log every time they have to edit. Bring observations to 1:1s.
Why: Nothing teaches the accuracy problem like using the product.
ML-Specific 25-5 Conversations
Who they should talk to:
| Person | What to Learn |
|---|---|
| Sahaj (CTO) | Technical vision, architecture decisions |
| Other ML engineers | Current pain points, what's been tried |
| iOS engineers | On-device constraints, Metal optimizations |
| Product | User feedback, what accuracy issues hurt most |
| Support/Community | Edge cases, accents, domains that struggle |
Success Criteria: First 30 Days
| Milestone | Evidence |
|---|---|
| Understands the pipeline | Can diagram and explain it |
| Shipped something | Even a small improvement or measurement |
| Using the product daily | Personal experience with accuracy issues |
| Integrated with team | 25-5 conversations completed |
| Has opinions | Can articulate what they'd tackle first |
Red Flags in First 30 Days
| Behavior | Concern |
|---|---|
| "Let's just use a bigger model" | Doesn't respect on-device constraint |
| Not using the product | Won't understand user pain |
| Only wants to research, not ship | Wrong stage for pure research |
| Can't explain the pipeline | Learning velocity concern |
| No opinions after 30 days | May lack agency |
The 90-Day Check-In
By 90 days, they should have shipped a meaningful improvement (latency OR accuracy), owned a piece of the pipeline (clear area of responsibility), built relationships across teams (not siloed), and demonstrated the "Zero Edit Rate" mindset (user-obsessed, not metric-obsessed).
The question to ask: "Do we want to keep building with this person?"
| Answer | Action |
|---|---|
| Yes | Discuss growth path, increase ownership |
| Uncertain | Address concerns directly, set clear expectations |