
Leading a remote team of 14 engineers across three squads at Heard taught me that remote work amplifies both the best and worst aspects of engineering culture. Without intentional design, isolation and burnout become default states.

#### The Remote Work Paradox

Remote work offers flexibility and eliminates commutes, but it also blurs boundaries between work and life. For engineers who already struggle with work-life balance, remote work can make it worse.

#### Building Connection

We implemented several practices to maintain team cohesion:

**Daily Standups with Personal Check-ins**
Not just "what did you do?" but "how are you doing?" This simple shift made space for people to share when they were struggling.

**Virtual Coffee Chats**
Random pairings for 15-minute chats. No agenda, just connection. These became some of the most valuable interactions.

**Asynchronous Communication**
Not everything needs to be a meeting. We used Slack threads, Loom videos, and documentation to reduce meeting fatigue.

#### The Active Lifestyle Component

I noticed that engineers who maintained active lifestyles-running, cycling, hiking-handled remote work better. There's something about physical movement that helps with mental clarity and stress management.

#### Metrics That Matter

We tracked:
- Meeting hours per week (target: &lt;20)
- Response time expectations (not everything is urgent)
- Vacation usage (encouraged, not discouraged)
- Team satisfaction scores

> "Remote work isn't about replicating the office-it's about creating something better."

#### Technical Infrastructure for Remote Wellbeing

**Asynchronous Communication Tools:**
- Slack for real-time chat (with clear response time expectations)
- Loom for async video updates
- Notion for documentation and knowledge sharing
- GitHub Discussions for technical conversations

**Code Review Best Practices:**
- Async code reviews (no blocking on reviews)
- Clear review guidelines and SLAs
- Automated testing to reduce review burden
- Pair programming sessions for complex problems

**Monitoring and Observability:**
- Comprehensive logging and monitoring
- Alert fatigue reduction (only actionable alerts)
- On-call rotation with clear handoff procedures
- Incident post-mortems focused on learning, not blame

#### Engineering Practices for Remote Teams

**Documentation Standards:**
```markdown
# Every PR must include:
- Clear description of changes
- Testing approach
- Rollback plan
- Monitoring considerations
- Documentation updates
```

**Knowledge Sharing:**
- Weekly tech talks (recorded for async viewing)
- Architecture decision records (ADRs)
- Runbooks for common operations
- Pair programming sessions

**Code Quality:**
- Automated testing (unit, integration, e2e)
- Code review guidelines
- Linting and formatting automation
- Security scanning in CI/CD

#### Metrics for Remote Team Health

**Technical Metrics:**
- Deployment frequency
- Lead time for changes
- Mean time to recovery
- Change failure rate

**Team Health Metrics:**
- Meeting hours per week (target: &lt;20)
- Response time expectations (documented)
- Vacation usage (encouraged)
- Team satisfaction scores

**Communication Metrics:**
- Async vs sync communication ratio
- Documentation coverage
- Knowledge sharing frequency
- Cross-team collaboration

#### Lessons Learned

The teams that thrived had:
- Clear boundaries around work hours
- Regular physical activity
- Strong social connections outside work
- Managers who modeled healthy behavior
- Comprehensive documentation
- Automated testing and deployment
- Clear communication protocols
- Focus on async-first workflows



Wellbeing in remote engineering teams


After managing teams at Mercury, Elevate Security, and now Heard, I've learned that running an engineering organization is less about technology and more about people, systems, and strategy.

#### The Three Pillars

**1. People**
Hiring, developing, and retaining talent. This means creating growth opportunities, providing clear feedback, and building a culture where people want to stay.

**2. Systems**
Processes that scale. From code review to incident response, systems should make good outcomes easy and bad outcomes hard.

**3. Strategy**
Knowing what to build and why. This requires deep understanding of business goals and customer needs.

#### Common Mistakes

- Optimizing for velocity over outcomes
- Building systems before understanding problems
- Neglecting developer experience
- Focusing on technology over business value

#### What Works

- Clear communication of priorities
- Empowering teams to make decisions
- Investing in developer productivity
- Measuring what matters (outcomes, not outputs)

> "Good engineering management is about creating conditions where great work can happen."

#### The Hard Truth

You can't optimize everything. Trade-offs are constant. The key is making explicit decisions about what you're optimizing for and communicating those decisions clearly.



Running an engineering organization


After years of experience in engineering leadership and fintech, I've learned that remote team communication requires careful attention to both technical excellence and human factors.

#### The Challenge

Remote team communication is something I've encountered throughout my career at companies like Mercury, Heard, Ness, and now Pangea. The key is understanding both the technical and human aspects.

#### Key Insights

1. **Technical Excellence**: Whether it's Python, TypeScript, or infrastructure, solid technical foundations matter.

2. **People First**: Engineering is ultimately about people-building systems that serve users and teams that thrive.

3. **Balance**: Finding the right balance between technical depth and practical application.

#### Lessons Learned

- Start with understanding the problem deeply
- Build iteratively and get feedback early
- Invest in both technical skills and soft skills
- Take care of your mental and physical health

> "The best engineering solutions come from understanding both the code and the people who use it."

#### Next Steps

Consider how remote team communication applies to your own work. What can you learn? What can you improve? How can you help others?



Remote team communication


At Heard, I recruited 8 engineers (mid to staff level), scaling team capacity by 60% while maintaining a mission-driven culture. Scaling teams requires balancing growth with culture fit.

#### The Challenge

Scaling teams requires:
- Finding great talent
- Maintaining culture
- Onboarding effectively
- Retaining talent
- Managing growth

#### Our Hiring Process

**1. Sourcing**
- Employee referrals (best source)
- Direct outreach
- Job boards
- Recruiters (selective)

**2. Screening**
- Resume review
- Phone screen (30 min)
- Technical assessment
- Culture fit interview

**3. On-Site**
- Technical deep dive
- System design
- Culture fit
- Team fit

**4. Decision**
- Debrief meeting
- Reference checks
- Offer negotiation

#### What We Looked For

**Technical Skills**
- Strong fundamentals
- Problem-solving ability
- Growth mindset
- Relevant experience

**Culture Fit**
- Mission alignment
- Collaboration skills
- Ownership mindset
- Growth orientation

#### Interview Process

```typescript
interface InterviewProcess {
  phoneScreen: {
    duration: 30; // minutes
    focus: 'communication', 'basic technical';
  };
  technicalAssessment: {
    duration: 60; // minutes
    format: 'take-home' | 'live-coding';
    focus: 'problem-solving', 'code quality';
  };
  onSite: {
    technicalDeepDive: 60;
    systemDesign: 45;
    cultureFit: 30;
    teamFit: 30;
  };
}
```

#### Onboarding

**Week 1:**
- Setup and orientation
- Meet the team
- First small task
- Pair programming

**Month 1:**
- Larger features
- Code reviews
- Team meetings
- Regular check-ins

**Month 3:**
- Full ownership
- Mentoring others
- Process improvements

#### Maintaining Culture

- Clear values and principles
- Regular culture discussions
- Lead by example
- Address issues quickly
- Celebrate wins together

#### Results

- 8 engineers hired
- 60% capacity increase
- Strong culture maintained
- High retention rate
- Mission-driven focus preserved

> "Hire for culture fit, train for skills."

#### Lessons Learned

1. Referrals are the best source
2. Culture fit matters as much as skills
3. Onboarding is critical
4. Retention starts with hiring
5. Growth requires intentional culture work

#### Common Mistakes

- Hiring too fast (quality over quantity)
- Ignoring culture fit (skills aren't enough)
- Poor onboarding (sets people up to fail)
- Not investing in retention (expensive to replace)
- Growing without structure (chaos)



Recruiting and scaling engineering teams


Leading engineering teams at Heard, a company supporting mental health professionals, gave me a unique perspective on the intersection of technology and wellbeing. The irony wasn't lost on me: we were building tools for therapists while navigating our own mental health challenges in a high-pressure startup environment.

#### The Stigma Problem

There's still a stigma around discussing mental health in tech leadership. We expect leaders to be unflappable, but the reality is that engineering executives face immense pressure-deadlines, budget constraints, team dynamics, and the constant need to make decisions with incomplete information.

#### Creating Space for Vulnerability

At Heard, we implemented practices that normalized mental health discussions:
- Weekly check-ins that went beyond project status
- Encouraging time off without guilt
- Modeling healthy boundaries ourselves

#### The Business Case

Teams with better mental health support have higher retention, better decision-making, and more sustainable productivity. It's not just the right thing to do-it's good business.

> "You can't pour from an empty cup. Leaders need to model self-care."

#### Practical Steps

1. Normalize therapy and mental health support
2. Create psychological safety for difficult conversations
3. Measure team wellbeing alongside velocity metrics
4. Lead by example in taking breaks and vacations



Mental health in tech leadership


At Cloudentity, I managed an overseas team delivering solutions in Scala and React. Managing distributed teams across time zones requires different skills than managing co-located teams.

#### The Challenges

Distributed teams face:
- Time zone differences
- Cultural differences
- Communication barriers
- Lack of face-to-face interaction
- Coordination overhead

#### What Works

**1. Overlap Hours**
Establish core hours when everyone is available. We had 4 hours of overlap between US and overseas teams.

**2. Async-First Communication**
Default to async (Slack, email, docs) with sync meetings only when necessary.

**3. Clear Documentation**
Write everything down. Don't rely on verbal communication.

**4. Regular Check-ins**
Weekly 1:1s, daily standups, and regular team meetings.

**5. Cultural Awareness**
Understand and respect cultural differences in communication and work styles.

#### Communication Practices

**Daily Standups**
- Async updates in Slack
- Video standup once per week
- Focus on blockers and progress

**Documentation**
- Architecture decisions in ADRs
- API contracts in OpenAPI specs
- Runbooks for operations
- Meeting notes shared immediately

**Code Reviews**
- Clear guidelines and expectations
- Timely reviews (within 24 hours)
- Constructive feedback
- Pair programming when possible

#### Tools

- **Slack**: Daily communication
- **Zoom**: Video meetings
- **GitHub**: Code collaboration
- **Notion**: Documentation
- **Jira**: Project tracking

#### Building Trust

- Be available during overlap hours
- Respond to messages promptly
- Follow through on commitments
- Recognize good work publicly
- Address issues directly

#### Handling Conflicts

- Address issues early
- Use video calls for difficult conversations
- Focus on facts, not assumptions
- Seek to understand different perspectives
- Find win-win solutions

#### Results

- Successful project delivery
- Strong team cohesion
- Good work-life balance for all
- High code quality
- Positive team culture

> "Distance doesn't have to mean disconnection."

#### Lessons Learned

1. Communication is everything
2. Documentation is critical
3. Trust takes time to build
4. Cultural awareness matters
5. Overlap hours are essential



Managing an overseas engineering team


At Heard, I established engineering KPIs tied to company OKRs, increasing feature delivery velocity by 12% and retention by 15%. The key was aligning engineering metrics with business outcomes.

#### The Problem

Traditional engineering metrics (lines of code, commits, velocity) don't connect to business value. We needed metrics that:
- Align with company goals
- Measure outcomes, not outputs
- Drive the right behaviors
- Are actionable

#### Our Approach

**1. Start with Company OKRs**
Understand what the company is trying to achieve.

**2. Map Engineering Work to OKRs**
Connect engineering initiatives to business outcomes.

**3. Define Measurable KPIs**
Create metrics that track progress toward OKRs.

**4. Review Regularly**
Weekly reviews, monthly deep dives, quarterly planning.

#### Example: User Retention OKR

**Company OKR:**
- Increase user retention by 20%

**Engineering Contribution:**
- Reduce time to value (onboarding)
- Improve product reliability
- Fix critical bugs faster

**Engineering KPIs:**
- Time to first value: < 5 minutes
- Uptime: > 99.9%
- Critical bug resolution: < 4 hours

#### KPI Dashboard

```typescript
interface EngineeringKPIs {
  // Feature Delivery
  featureDeliveryVelocity: number; // features per week
  timeToMarket: number; // days from idea to production
  
  // Quality
  bugRate: number; // bugs per feature
  uptime: number; // percentage
  customerSatisfaction: number; // NPS score
  
  // Team Health
  retention: number; // percentage
  engagement: number; // survey score
  burnoutRisk: number; // calculated metric
}

function calculateKPIs(metrics: Metrics): EngineeringKPIs {
  return {
    featureDeliveryVelocity: calculateVelocity(metrics),
    timeToMarket: calculateTTM(metrics),
    bugRate: calculateBugRate(metrics),
    uptime: calculateUptime(metrics),
    customerSatisfaction: metrics.nps,
    retention: calculateRetention(metrics),
    engagement: metrics.engagementScore,
    burnoutRisk: calculateBurnoutRisk(metrics),
  };
}
```

#### Tracking and Reporting

**Weekly Reviews**
- Review KPIs vs targets
- Identify blockers
- Adjust priorities

**Monthly Deep Dives**
- Analyze trends
- Root cause analysis
- Action planning

**Quarterly Planning**
- Set new KPIs
- Align with company OKRs
- Plan initiatives

#### Results

- 12% increase in feature delivery velocity
- 15% increase in retention
- Better alignment with business goals
- More focused engineering work
- Improved team motivation

> "What gets measured gets managed."

#### Lessons Learned

1. Align metrics with business outcomes
2. Measure outcomes, not outputs
3. Review regularly
4. Adjust based on results
5. Keep it simple

#### Common Pitfalls

- Too many metrics (focus on 5-7)
- Vanity metrics (measure what matters)
- Setting and forgetting (review regularly)
- Ignoring context (understand why metrics change)
- Gaming the system (prevent manipulation)



Establishing engineering KPIs tied to company OKRs


Burnout is an epidemic in engineering. After seeing too many talented engineers leave the industry due to burnout, I've made it a priority to build teams and cultures that prevent it rather than just treat it.

#### What is Burnout?

Burnout isn't just being tired. It's a state of emotional, physical, and mental exhaustion caused by prolonged stress. Symptoms include:
- Exhaustion
- Cynicism and detachment
- Reduced performance
- Loss of motivation

#### Root Causes

**1. Unrealistic Expectations**
Deadlines that can't be met, scope creep, constant "urgent" requests.

**2. Lack of Control**
No say in what you work on or how you work.

**3. Insufficient Rewards**
Not feeling valued or compensated fairly.

**4. Breakdown of Community**
Isolation, conflict, lack of support.

**5. Absence of Fairness**
Favoritism, unfair policies, inconsistent treatment.

#### Prevention Strategies

**For Individuals:**
- Set boundaries (work hours, availability)
- Take regular breaks and vacations
- Maintain hobbies and relationships outside work
- Exercise regularly
- Seek help when needed

**For Leaders:**
- Model healthy behavior
- Set realistic expectations
- Provide autonomy and control
- Recognize and reward good work
- Create psychological safety
- Encourage time off
- Monitor team health

**For Organizations:**
- Reasonable work hours
- Generous time off policies
- Mental health support
- Clear career paths
- Fair compensation
- Healthy culture

#### Early Warning Signs

Watch for:
- Increased sick days
- Decreased productivity
- Negative attitude changes
- Withdrawal from team activities
- Quality issues in work

#### Intervention

If you notice burnout:
1. Have a private conversation
2. Listen without judgment
3. Offer support and resources
4. Adjust workload if possible
5. Check in regularly

#### The Business Case

Preventing burnout:
- Reduces turnover (expensive!)
- Improves productivity
- Increases innovation
- Better code quality
- Higher team morale

> "An ounce of prevention is worth a pound of cure."

Investing in burnout prevention isn't just the right thing to do-it's good business.

