Holly Leonard
Early Stage Startup & CEO Whisperer I Swiss Army Knife of Culture, Operations & Strategy for scaling organizations
About
With over 15 years of leadership experience across technology, startups, non-profits, and small businesses, I specialize in strategic partnership and operational excellence. My expertise lies in:
- Collaborating with CEOs to translate visionary goals into measurable results
- Optimizing organizational ecosystems: people, communications, objectives, and systems
- Implementing the PPO framework (People, Process, Outcome) to boost efficiency
- Fostering a culture of seamless communication, collaboration, and community
- Executing long-term growth strategies and driving company expansion
My proven track record demonstrates success in:
- Turning ambitious concepts into practical achievements
- Tackling internal challenges and enhancing operational efficiency
- Cultivating high-engagement, high-performance teams
- Adapting quickly to diverse industries and business models
My expertise and passion lie in organizations of 10-100 people looking to 10x their people, process and outcomes. As your CoS or Operations + People leader, I'll bring a holistic approach to your startup, ensuring that your vision is not just articulated, but fully realized through strategic execution and team empowerment. Ready to transform your startup's potential into tangible success? Let's connect and discuss how I can help drive your company's growth and prosperity.
Portfolio
Chief of Staff + Head of Operations
HR Tech I Grant Funded I Early Stage Company Scaled the People function from 2 to 16 members in 8 months, while implementing comprehensive strategies that reduced annual subscription costs by over $10k. Established and achieved company-level OKRs for three consecutive quarters, ensuring strategic alignment and measurable outcomes. Enhanced core infrastructure across data, engineering, HR, and operations, fostering a culture of continuous improvement that significantly boosted organizational efficiency and effectiveness.
Operations Manager
Co-founded and scaled a 200+ member DEI Women's Forum, implementing cohort-based manager training and development plans that empowered leadership across a 32-person team of engineers and scientists. Orchestrated recruitment, onboarding, and cultural programs that facilitated 6x growth, including a company-wide TA strategy that supported expansion from 250 to 550 employees in 18 months. Streamlined operations across multiple programs, reducing CEO involvement in business operations by 75% while managing a $7M+ annual budget, leading strategic planning, and implementing process improvements that enhanced efficiency across 8 work verticals and a 30+ person team.
Reach out to meet with qualified candidates, both listed and unlisted. Our goal is to get you top notch, pre-vetted talent perfect for your role within 24 hours.
