Table of Contents
PagerDuty CEO Jennifer Tejada reveals how responsibility-centered leadership, talent development, and personal resilience create sustainable competitive advantages in tech companies. Jennifer Tejada shares insights on building resilient organizations through people development, maintaining high standards consistently, and leading with responsibility rather than ego.
Key Takeaways
- Responsibility-centered leadership prioritizes obligation and service over personal rewards, creating more sustainable organizational cultures than ego-driven approaches
- Tech companies risk long-term leadership quality by failing to invest in systematic management development programs like traditional companies
- Talent retention during market bubbles becomes harder as employees chase short-term IPO gains rather than building careers with great companies
- Personal resilience and grit can be developed through deliberate practice of failure recovery, but many employees don't stay long enough to experience meaningful setbacks
- Professional CEOs bring outside perspective and complementary experience that can accelerate company growth beyond founder capabilities alone
- Work-life integration requires protecting non-negotiable personal practices while accepting that perfect balance remains impossible for executive roles
- Building multi-product platforms from single-product companies represents one of the hardest business transitions but creates sustainable competitive advantages
- High performance standards must remain consistent rather than fluctuating with moods or circumstances to build predictable, manageable leadership culture
Timeline Overview
- 00:00–12:45 — Market Corrections and Retention: How overheated markets created irrational job-hopping behavior and made talent retention harder during growth periods
- 12:45–28:30 — Leadership Development Crisis: The tech industry's failure to systematically develop leaders compared to traditional companies like P&G, GE, and IBM
- 28:30–45:15 — Responsibility vs Reward Leadership: Contrasting leadership motivated by service and obligation versus leadership driven by ego, power, and personal advancement
- 45:15–62:00 — Personal Foundation and Resilience: Tejada's Midwest upbringing, early responsibility, and how losing her father at 23 shaped her leadership approach
- 62:00–78:45 — Career Breaks and Identity: Taking sabbaticals between roles, sailing adventures in Australia, and maintaining perspective beyond work achievements
- 78:45–95:30 — PagerDuty Transformation: Leading the evolution from $30M single-product company to multi-product platform approaching $370M revenue
- 95:30–112:15 — Professional vs Founder CEOs: Advantages of outside perspective, complementary experience, and different approaches to company leadership
- 112:15–129:00 — Building Consistent High Standards: Maintaining predictable leadership through "you're never done" mentality and continuous improvement focus
- 129:00–145:45 — Crisis Leadership and Loss: Leading through the sudden death of beloved employee PJ, vulnerability in leadership, and supporting organizational grief
- 145:45–END — Teaching Grit and Resilience: Why these essential leadership qualities aren't taught systematically and how to develop them in organizations
The Leadership Development Crisis in Tech
Tech companies have systematically failed to invest in leadership development programs that historically created great business leaders, creating long-term risks for industry innovation and management quality.
- Traditional companies like GE, Procter & Gamble, and IBM institutionalized management skills, leadership development, and financial acumen through structured programs that created legendary business leaders
- Modern tech companies rely on executives learning through job-hopping every 18-24 months, which provides exposure but lacks systematic skill development
- Current leaders often lack fundamental management capabilities like conducting performance reviews, behavioral interviews, and basic people development skills
- The democratization of leadership development has stagnated, requiring MBA programs or executive education rather than internal company investment
- PagerDuty invests heavily in foundational management and leadership development as long-term competitive advantage rather than accepting industry norms
- Employees increasingly view career growth as requiring company changes rather than building deep expertise and leadership capacity within organizations
Tejada draws directly from her Procter & Gamble foundation, still utilizing principles learned in her first five years post-college decades later. The company's systematic approach to developing talent created a pipeline of business leaders across industries.
The short-term thinking prevalent during market bubbles exacerbates this problem. Employees focus on accumulating IPO experiences rather than building sustainable career skills, creating a generation of leaders with broad exposure but shallow developmental depth.
This industry-wide failure to develop leadership systematically means companies compete for externally developed talent rather than building internal capabilities, creating inflationary pressure on executive compensation while undermining organizational continuity and culture development.
Responsibility-Centered vs Reward-Centered Leadership
The fundamental distinction between viewing leadership as privilege and obligation versus seeking leadership for personal advancement determines both individual effectiveness and organizational culture sustainability.
- Responsibility-centered leadership treats positions as privilege requiring deep obligation to business success, people development, and stakeholder value creation
- Reward-centered leadership pursues roles for titles, power, visibility, and ego gratification rather than service to others and organizational mission
- Long growth cycles and positive markets created generations of leaders who haven't experienced significant setbacks or obstacles that build character
- Without experiencing failure and recovery, leaders don't develop resilience, grit, and the ability to learn from mistakes that characterize great leadership
- Current employees often don't stay at companies long enough to experience meaningful failure, limiting their development of essential leadership qualities
- Financial stability and strong economies can prevent the character-building experiences that develop perseverance and authentic leadership strength
The contrast reflects broader cultural shifts from viewing work as service to viewing work as personal advancement vehicle. Responsibility-centered leaders focus on developing others, creating value, and fulfilling obligations to stakeholders rather than accumulating personal benefits.
Tejada's Midwest upbringing emphasized contribution over achievement, asking "what have you done for others today" rather than celebrating personal accomplishments. This foundation shapes her approach to leadership as fundamentally about serving others rather than self-advancement.
Building Personal Resilience Through Adversity
Personal resilience and grit develop through experiencing and recovering from setbacks, but modern work environments often prevent the failure experiences necessary for character development.
- Tejada's family emphasized work ethic, self-sufficiency, and contribution from early childhood through paper routes, household responsibilities, and community service
- Losing her father suddenly at age 23 while working at P&G taught crucial lessons about crisis leadership, accepting help, and the importance of supportive workplace culture
- The experience of organizing family affairs, supporting siblings, and managing grief while maintaining professional responsibilities built crisis management capabilities
- Learning to accept help from others challenged her independent nature but revealed how support systems enable better leadership during difficult periods
- Taking deliberate career breaks between roles allows for reflection, skill development outside work, and maintaining perspective on achievement versus fulfillment
- Physical challenges like sailing and competitive sports provide different types of resilience training that complement professional development
The modern tendency to shield young people from failure through participation trophies and constant support prevents the character development that comes from learning to lose gracefully, recover from setbacks, and build inner strength through adversity.
Tejada's approach with her own daughter includes allowing failure, requiring self-sufficiency, and teaching recovery skills rather than preventing all negative experiences that might build resilience.
Work-Life Integration for Executive Leaders
Sustainable executive performance requires deliberate integration strategies rather than pursuing impossible work-life balance, with particular challenges for working mothers in demanding roles.
- Work-life balance remains mythical for executive roles, but work-life integration can create sustainable approaches to managing multiple stakeholder demands
- Protecting morning routines and workouts becomes non-negotiable for maintaining physical and mental health necessary for high performance
- The "plate spinning" metaphor recognizes that some responsibilities (family) represent "fine china" that cannot drop while others (work tasks) can be managed more flexibly
- Male executive peers often had structural advantages through stay-at-home partners handling family logistics, making self-care practices easier to maintain
- Working mothers bear disproportionate unpaid household labor even with supportive partners, requiring more deliberate boundaries and self-care practices
- The transition from "run until failure" maintenance to proactive health management typically occurs in late career as consequences become more apparent
Tejada's evolution from ignoring physical limits to protecting health practices reflects learning that sustainable performance requires maintenance rather than crisis management of personal wellness.
The concept of working "for" family rather than despite family obligations reframes home responsibilities as primary stakeholder relationships requiring the same focus and energy as professional obligations.
Professional CEO vs Founder Leadership Models
Professional CEOs bring complementary advantages to founder-led companies through outside perspective, operational experience, and different approaches to talent development and scaling challenges.
- Professional CEOs provide outside perspective that founders may lack due to emotional proximity to their creation, similar to how coaches see athlete potential more clearly than parents
- Extensive leadership transition experience across multiple companies creates pattern recognition for common scaling challenges and solution approaches
- Operational depth across multiple business functions prepares professional CEOs for the integration challenges that define successful CEO performance
- Honoring founder contributions while bringing complementary skills creates partnerships that leverage both entrepreneurial vision and scaling expertise
- The "refunder" concept describes professional CEOs who adopt companies as deeply as founders while bringing different capabilities to growth phases
- Structural differences like board accountability and shareholder responsibility create different risk profiles compared to founder-controlled companies
The debate over founder-led versus professional-led companies misses the point that different leadership styles serve different company stages and challenges. Both approaches can create exceptional outcomes when matched appropriately to business needs.
Tejada's experience across multiple industries, functions, and company stages provides pattern recognition that first-time founders typically lack, while founders bring innovation and risk tolerance that professional managers might not possess.
Building Multi-Product Platform Companies
The evolution from single-product to multi-product companies represents one of the most challenging business transformations but creates sustainable competitive advantages when executed successfully.
- PagerDuty's platform characteristics existed from founding through proprietary data collection, integrated workflows, and architectural decisions that enabled expansion
- Brand evolution challenges emerge when company names strongly associate with original product categories, requiring careful navigation to avoid losing core customer relationships
- Developer community trust and brand loyalty can outweigh naming considerations when products deliver consistent value across broader use cases
- The transition from SMB to enterprise markets requires simultaneous product expansion and customer segment evolution, creating multiple complex challenges
- Platform success depends on identifying which integrated capabilities can be monetized separately while maintaining core product integrity
- Market education and brand repositioning take significantly longer than product development when expanding beyond original category definitions
PagerDuty's journey from notification tool to operations platform illustrates how technical architecture decisions made early can create expansion opportunities that weren't initially obvious to markets or customers.
The challenge of moving customer perception beyond original product associations requires sustained marketing investment and consistent product demonstration rather than simple rebranding approaches.
Maintaining Consistent High Standards
Effective leadership requires maintaining predictably high standards rather than fluctuating expectations, creating organizational cultures that can perform reliably under various conditions.
- "Predictable is manageable" philosophy helps teams understand expectations and perform consistently rather than adapting to changing leadership moods
- The "you're never done" mentality drives continuous improvement without accepting complacency when achieving milestones or exceeding targets
- Celebrating achievements followed immediately by raising standards creates cultures of continuous evolution rather than satisfaction with current performance
- High standards applied equally to self and team members create credibility and shared commitment rather than perceived hypocrisy
- Professional examples like Tiger Woods transforming golf or Yo-Yo Ma elevating cello performance illustrate how individual excellence can raise entire field standards
- Consistency in leadership approach enables team members to optimize their performance around known expectations rather than constantly adapting to leadership variability
This approach contrasts with leadership styles that vary standards based on circumstances, moods, or external pressures, which create unpredictable environments that inhibit team performance optimization.
The key insight is that sustainable high performance cultures require consistent rather than intense leadership, enabling teams to build processes and capabilities around stable expectations.
Crisis Leadership and Organizational Grief
Leading through sudden organizational loss requires balancing personal grief with responsibility for helping others process difficult experiences while maintaining business continuity.
- The sudden death of beloved employee PJ required immediate organizational communication while processing personal and collective grief
- Sharing vulnerability and authentic emotion with teams creates permission for others to process difficult experiences rather than maintaining artificial professional distance
- Writing about loss publicly provides cathartic processing while honoring departed colleagues and helping broader communities understand impact
- Supporting family members of lost employees extends leadership responsibility beyond immediate organizational boundaries to broader human obligations
- Learning to accept help during crisis contrasts with typical executive self-reliance but enables better support for others experiencing similar difficulties
- Maintaining business operations while processing grief requires different leadership approaches than typical crisis management scenarios
Tejada's evolution toward greater vulnerability during PJ's loss contrasted with her more controlled response to her father's death decades earlier, reflecting leadership development toward authentic connection rather than stoic management.
The experience reinforces that responsibility-centered leadership extends beyond business metrics to include genuine care for people as complete human beings rather than just professional resources.
Common Questions
Q: What distinguishes responsibility-centered from reward-centered leadership?
A: Responsibility-centered leaders view positions as privilege requiring obligation to develop people and create value; reward-centered leaders seek roles for personal advancement.
Q: Why is talent retention harder during market bubbles?
A: Employees chase short-term IPO opportunities rather than building long-term careers, attracted to guaranteed pops over sustainable development.
Q: Can professional CEOs match founder passion for companies?
A: Yes, "refounders" can adopt companies as deeply as founders while bringing complementary operational experience and outside perspective.
Q: How do you maintain work-life integration as an executive?
A: Protect non-negotiable personal practices, treat family as primary stakeholders, and accept integration rather than pursuing impossible balance.
Q: What makes multi-product platform transitions so difficult?
A: Brand evolution, market education, and customer perception changes take longer than product development while maintaining core relationships.
Conclusion
Jennifer Tejada's leadership philosophy demonstrates that sustainable business success emerges from responsibility-centered approaches that prioritize people development, consistent high standards, and authentic service to stakeholders over personal advancement. Her journey from P&G through multiple CEO roles illustrates how systematic leadership development, personal resilience built through adversity, and integration of professional excellence with human vulnerability create more effective organizational cultures.
The tech industry's current talent development crisis represents both challenge and opportunity for companies willing to invest in systematic leadership capabilities rather than relying on external hiring to fill capability gaps. Most importantly, her approach shows that maintaining high performance while remaining authentically human requires deliberate integration of personal values with professional responsibilities rather than compartmentalizing different aspects of life.
Practical Implications
- Leadership Development: Implement systematic management training programs rather than assuming leaders will develop skills through job rotation alone
- Talent Strategy: Focus on long-term career development within organizations rather than accepting constant turnover as inevitable industry norm
- Performance Management: Maintain consistent high standards regardless of circumstances while providing predictable expectations that teams can optimize around
- Crisis Leadership: Develop vulnerability and authentic connection skills alongside traditional crisis management capabilities for better organizational support
- Work-Life Integration: Establish non-negotiable personal practices and treat family obligations as primary stakeholder relationships requiring dedicated energy
- Platform Strategy: Identify existing product capabilities that can expand into new markets rather than building entirely separate product lines
- Professional Development: Take deliberate career breaks for reflection and skill development outside traditional business contexts to maintain perspective
