Table of Contents
Gem CRO Lesley Young reveals her proven playbook for scaling sales organizations, building founder relationships, and why she joined a recruiting platform during the worst hiring market in decades.
Lesley Young's career journey from early-stage companies to leading enterprise sales at Box demonstrates how data-driven leadership, systematic feedback, and founder collaboration create sustainable growth engines.
Key Takeaways
- Systematic feedback processes starting from company formation prevent performance issues from derailing growth and build stronger team cultures
- Working effectively with founders requires matching their level of detail obsession and demonstrating genuine care about the business mission
- Data preparation serves as a security blanket that enables confident decision-making and builds credibility with analytical leaders
- Early-career sales roles benefit significantly from in-person collaboration due to peer learning opportunities and relationship building
- Purpose statements help experienced leaders understand their motivations and make better career decisions during transitions
- Tough feedback conversations require specific examples and genuine concern for the recipient's growth rather than just performance correction
- Remote sales management places disproportionate burden on frontline managers who must compensate for lost peer learning and cultural connection
- Career resilience comes from viewing obstacles as growth opportunities rather than reasons to avoid challenging situations
Timeline Overview
- 00:00–12:30 — Stage Fright and Preparation Rituals: The Psychology of Public Speaking — Discussion of presentation anxiety, preparation methods, and meeting expectations versus reality with business leaders
- 12:30–25:15 — Early Career Foundations: From UCLA Financial Struggles to Sales Leadership — College financial independence, family achievement orientation, and early management experiences at Informatica and MySQL
- 25:15–42:20 — The Box Era: Eight Years of Scaling Commercial Sales — Building enterprise sales teams, working with Aaron Levie, and learning founder collaboration dynamics
- 42:20–58:45 — Purpose-Driven Career Transitions: Facebook to Segment Journey — Writing personal purpose statements, failed stints at Facebook and another company, joining Segment for the right reasons
- 58:45–75:30 — Founder Collaboration Mastery: Working with Aaron Levie and Peter Reinhardt — How to prepare for founder meetings, understanding their detail obsession, and building trust through shared commitment
- 75:30–90:15 — Management Philosophy: Feedback Systems and People Development — MySQL team revolt experience, delivering tough feedback, and building systematic performance review processes
- 90:15–END — Gem Strategy: Recruiting Platform in a Downturn Market — Why joining a talent management company during hiring freezes makes strategic sense and remote work challenges
Stage Presence and the Art of Preparation
The conversation opens with Young's candid discussion about presentation anxiety and her meticulous preparation process for public speaking engagements. Her approach reveals the psychological foundations that drive her leadership effectiveness.
- Stage fright stems from being naturally observational rather than expressive, preferring to listen and analyze before speaking
- Preparation involves extensive note-taking and narrative development to ensure appreciation for team members comes through authentically
- The rotating stage disaster at an Informatica Vegas event required spending an entire night walking in squares to master the presentation
- Comparing herself to previous speakers creates self-doubt, but the focus remains on serving the people who work for her
- Meeting business legends like Steve Young creates imposter syndrome despite significant personal achievements in sales leadership
- Purpose-driven preparation ensures that recognition and appreciation for team accomplishments becomes the central message
Young's preparation rituals demonstrate how successful leaders compensate for natural tendencies that might limit effectiveness. Her investment in preparation stems from genuine desire to serve her team rather than personal glory.
The psychological honesty about imposter syndrome resonates throughout her career narrative. Despite leading major sales organizations, she maintains perspective about her role as an observer and supporter rather than the primary attraction.
Her preparation methodology focuses on storytelling that highlights team achievements rather than personal accomplishments. This approach reflects deeper leadership philosophy about lifting others rather than self-promotion.
Formative Financial Independence and Achievement Culture
Young's character formation occurred through necessity when her parents' divorce during college forced her to become financially self-sufficient. This experience shaped her resourcefulness and achievement orientation.
- Parents' divorce created immediate financial uncertainty requiring multiple jobs to continue UCLA education
- Her father, a Depression-era child, instilled scarcity mindset and belief that everything must be earned through hard work
- Achievement-oriented dinner conversations focused on her father's journey from struggle to successful attorney with his own firm
- She wasn't expected to be the high achiever among three siblings, with her father later admitting surprise at her career success
- The financial crisis taught resourcefulness, including leaving a towed car in impound until she could afford retrieval
- Early management roles at companies like Informatica and MySQL provided foundational leadership experience during technology industry growth
The scarcity mindset inherited from her father created both drive and anxiety that persists throughout her career. This psychological foundation explains her later emphasis on data preparation and systematic approaches to management.
Financial independence during college required developing problem-solving skills under pressure. These early experiences with resource constraints translated into business acumen for scaling organizations efficiently.
The family achievement culture created competitive drive while also establishing patterns of seeking validation through professional accomplishment. This dynamic continues to influence her decision-making and motivation.
The Box Journey: Eight Years of Enterprise Sales Excellence
Young's tenure at Box represented her longest and most formative leadership experience, working closely with founder Aaron Levie to scale commercial and enterprise sales operations. This period established her reputation as an elite sales leader.
- Box provided stability and growth opportunity spanning eight years, comparable to her earlier Informatica experience
- Aaron Levie's authentic passion for the product made him an exceptional sales partner who genuinely believed in customer success
- The company's "open for business" mentality under Levie's leadership contrasted with founders who aren't naturally sales-oriented
- Working through competitive threats from Google and Microsoft required strategic pivots and platform development
- User conferences became Aaron's obsession because they provided direct access to customer use cases and expansion opportunities
- Her collaboration with Levie involved breaking down his visionary ideas into operational components that could be systematically executed
The Box experience taught her how founders and operators can complement each other effectively. Levie's visionary thinking combined with her systematic execution created sustainable growth.
She learned to translate founder enthusiasm into repeatable business processes. This skill became crucial for later roles where she had to operationalize ambitious founder visions.
The eight-year tenure provided stability that allowed deep relationship building and long-term strategic thinking. This contrasted with later shorter stints that didn't provide sufficient time for full impact.
Box's platform evolution during her tenure demonstrated how companies can successfully navigate major competitive threats through strategic positioning and customer focus.
Purpose-Driven Career Navigation and Transition Challenges
Following her successful Box run, Young experienced two brief and unsuccessful career moves before joining Segment. This period required deep self-reflection about motivations and career direction.
- Writing a personal purpose statement helped clarify motivations beyond external achievements and parental expectations
- The Facebook workplace experiment failed because large corporate culture didn't align with her startup preferences
- Running away from Facebook disappointment led to another brief stint that also didn't work out
- These failures occurred when she had financial cushion to take risks but made decisions based on emotion rather than data analysis
- Her purpose statement emphasized fulfillment from watching people develop careers, scaling repeatable processes, and helping mindset transformations
- The teaching aspect of leadership provided deeper satisfaction than pure achievement or title accumulation
The purpose statement exercise revealed that her core motivation involved developing others rather than personal advancement. This insight influenced her approach to subsequent leadership roles.
Career failures taught important lessons about fit and decision-making process. The pattern of leaving successful situations for new challenges required better frameworks for evaluation.
The financial security from previous success enabled taking calculated risks, but emotional decision-making led to poor choices. This experience reinforced the importance of data-driven approaches to major decisions.
Mastering Founder Collaboration: Levie and Reinhardt Case Studies
Young's success working with founders Aaron Levie at Box and Peter Reinhardt at Segment provides a masterclass in founder-operator collaboration. Her approach demonstrates how operational leaders can effectively support visionary founders.
- Founders throw out seemingly impossible ideas intentionally to force operators to break them down into manageable components
- Preparation for founder meetings requires deep knowledge because founders ask precisely calibrated questions despite lacking operational experience
- Aaron Levie's detail obsession extended to hiring decisions based on capacity ahead of current needs, requiring operational justification
- Peter Reinhardt's environmental attention included precise plant placement for oxygen balance and noise machine positioning for optimal acoustics
- Founders can't quit when businesses struggle, creating different risk tolerance and commitment levels than employees
- Earning founder respect requires demonstrating equal care about the business mission and willingness to match their level of detail focus
The founder mindset involves viewing the business as legacy and identity rather than just professional opportunity. Understanding this psychological difference enables better collaboration.
Founders often know what questions to ask without knowing why, based on intuitive understanding of their business. Operators must be prepared for unexpectedly precise inquiries.
The savant-like quality of successful founders enables them to identify operational gaps despite lacking direct experience. This creates high preparation standards for supporting team members.
Building trust with founders requires demonstrating genuine commitment to their mission rather than just professional competence. The "in it with them" mentality becomes crucial for effective partnership.
Systematic Feedback Culture and Performance Management
Young's approach to feedback and performance management reflects lessons learned from early career mistakes and successful team building experiences. Her systematic approach prevents small issues from becoming major problems.
- The MySQL team revolt taught her that management style must adapt to company culture and individual team needs
- Early spreadsheet-based feedback systems required every employee to give constructive feedback to every colleague
- Performance reviews occur every six months for all employees including founders, with peer feedback, manager input, and upward reviews
- Difficult feedback conversations require specific behavioral examples and genuine concern for individual growth rather than just performance correction
- She actively seeks tough feedback because avoiding it creates paranoia about missing important development areas
- The story of helping an employee transition to renewal business after discovering family medical challenges demonstrates feedback as problem-solving tool
The systematic feedback approach creates culture where honest communication becomes normal rather than exceptional. This prevents issues from festering and damaging relationships.
Early career feedback disasters taught valuable lessons about adapting leadership style to organizational culture and individual needs. Flexibility within systematic frameworks enables better outcomes.
Regular performance review cycles provide structure for development conversations and prevent surprises during evaluation periods. The systematic approach ensures no one falls through cracks.
Seeking feedback actively demonstrates vulnerability and commitment to improvement. This modeling encourages similar behavior throughout the organization.
Gem Strategy: Recruiting Platform During Market Downturn
Young's decision to join Gem as CRO during the 2022 market downturn demonstrates strategic thinking about timing and long-term positioning. Her rationale reveals sophisticated understanding of market cycles and platform opportunities.
- Joining a recruiting platform during hiring freezes seemed counterintuitive but positioned for recovery upside
- Talent management remains critical even during downturns because companies must prepare for eventual growth
- The candidate relationship management concept addresses real pain points she experienced during rapid hiring phases
- Steve Sellen's founder persistence and business detail sharing during recruitment process demonstrated authentic commitment
- Remote work challenges in early-career sales roles require additional management support and in-person collaboration benefits
- The platform opportunity resembles early Box positioning where long-term category creation outweighs short-term market challenges
The timing decision reflects confidence in market cycle patterns and belief that hiring will eventually accelerate. Positioning during downturns enables capturing upside when markets recover.
Her personal experience with recruiting challenges at Twilio/Segment provided direct validation of the problem Gem addresses. First-hand pain point experience created conviction about solution value.
The founder evaluation process demonstrated how recruiting best practices apply to executive hiring. Persistence, detail orientation, and authentic business sharing convinced her to join.
Remote work challenges in sales development roles create opportunities for platforms that improve virtual collaboration and training. The shift to distributed teams increases demand for better management tools.
Common Questions
Q: What makes feedback conversations more effective than traditional performance reviews?
A: Specific behavioral examples combined with genuine concern for growth rather than just performance correction creates development rather than evaluation.
Q: How do successful operators work effectively with visionary founders?
A: Match their level of detail obsession, demonstrate genuine care about the mission, and break impossible-sounding ideas into operational components.
Q: Why join a recruiting platform during the worst hiring market in decades?
A: Talent management remains critical during downturns for preparation, and positioning during low points captures maximum upside when markets recover.
Q: What's the difference between early-career remote work and experienced remote work?
A: Early-career roles benefit significantly from peer learning and cultural connection that's difficult to replicate virtually.
Q: How do you develop grit and resilience in sales teams?
A: Create systematic feedback processes, normalize constructive criticism, and help people view obstacles as growth opportunities rather than roadblocks.
Young's career demonstrates how systematic approaches to people development, founder collaboration, and market timing create sustainable leadership success. Her experience spanning multiple market cycles provides valuable insights for building resilient sales organizations.
