Natalie Ledbetter

New York, NY, USA

3X Startup People Operations Leader | Fractional CPO/CHRO | Former VC Operating Partner | Building and Repairing People & Talent Infrastructure

I’m a business-first startup People Operations leader, fractional exec and former VC Operating Partner working (mostly) with Series A/B founders (though I've seen scale and have worked with orgs through series D) at crucial inflection points.


I do two things:

1) Build the People & Talent operating infrastructure (from scratch) that allows teams to scale with clarity, including:

- Stage-aligned talent acquisition strategy

- Clear org design and ownership

- Leadership effectiveness, performance ma…

Natalie Ledbetter

Testimonials

  • Working w/ Natalie was transformative. From day 1, she operated as a true partner to me and the executive team, quickly diagnosing gaps and helping us remove roadblocks and scale smarter. She helped reset some of our teams and hire top talent, driving a high-performing team & culture! We credit Natalie for continuously resetting our thinking about talent and ensuring they are "stage-appropriate"! If you're leading through growth/change, you'd be lucky to have Natalie as your People Ops leader!

    YA

    Younes Amar

    VP Product, Wallaroo.AI
  • "I had the privilege of working alongside Natalie at Stash, where as VP of People, she expertly built & led the HR, Recruiting & Employee Experience divisions from scratch. Her leadership was instrumental in scaling from 27 to 350 in 2.5 yrs, while prioritizing a culture of DEIB. She not only strategized but executed on benefits, performance management and L&D initiatives that significantly enhanced our org effectiveness & EE satisfaction. Her impact was profound, leaving a lasting legacy. . ."

    ER

    Ed Robinson

    Founder/CEO, Stash

Work

  • Why HR Can't be an Afterthought in Startups

    Why HR Can't be an Afterthought in Startups

    In the third installment of our HR Expert Series, we sit down with Natalie Ledbetter, fractional Chief People Officer, startup advisor, and consultant, to explore the role of HR in early-stage companies. Natalie shares why bringing HR in too late can create “people debt,” how hiring strategically early on can change the trajectory of a Series A or B startup, and why DEI is far more than a complian…

    open.spotify.com
  • The Ops Drop S2E3: Hiring & Growing Your StartUp's Team with CPO, Natalie Ledbetter

    In this episode of The Ops Drop, we chat with Natalie Ledbetter. Natalie cut her teeth in the startup world as a Chief People Officer - she has also worked in VC, and has now brought her show on the road as a Fractional/Advisory CPO with Ledbetter Advisory.


    When you're building a company - your first few hires matter the most - and figuring out the right fit can be daunting. Natalie has worked wit…

    youtube.com
  • The Critical Role of People Leaders in Startups

    Natalie’s journey illustrates the multifaceted nature of HR roles in startups, which often require wearing multiple hats and spearheading initiatives from scratch. This conversation sets the stage for discussing the unique challenges and opportunities that people leaders in startups face

    skillcycle.com
  • Fast Company: "5 things every leader must know about building their HR team" -  8.20.23

    Fast Company: "5 things every leader must know about building their HR team" - 8.20.23

    I contributed to this Fast Company article by Lars Schmidt, Founder of Amplify and Amplify Academy.

    drive.google.com
  • Winning at Talent Acquisition & Operations in the VC community

    Will Bourne, Director of Consulting at Rekall Consulting, talks to Natalie Ledbetter! Natalie Ledbetter is a People Ops Leader and a former Operating Partner at Boldstart Ventures. She has built and scaled 3 early-stage through hyper growth tech startups (B2C and B2B), owning people operations end-to-end (HR, Talent Acquisition, Employee Experience/Culture, L&D). The thread that is woven through every role she has taken in her career is the desire to solve hard, unique, new "people problems."

    open.spotify.com
  • Rocket Ship Founder Podcast

    Rocket Ship Founder Steve August Podcast May 2023:

    This week's Rocket Ship Founder podcast features my first ever interview episode! I speak with Natalie Ledbetter, People Ops Exec, Startup Advisor, TedX Speaker and Former Operating Partner & Head of People at boldstart ventures in NYC.


    We discuss:

    • Natalie's fascinating international personal journey to and through the startup world

    • The most common pitfalls for Seed Stage Startup Founders

    • What you'd be surprised to know about how VC's operate

    • Why People Ops is critical and how to nail it



    podcasters.spotify.com
  • Productwise | Podcast on Spotify

    As a talent professional and in my conversations with the founders and CEOs, stage appropriate hiring comes up 100% of the time. That is why I am so glad that we are covering this very topic as the first episode of the new 10 minute series. We had been running longer here, as the subject in question is so vast that myself and Natalie can hold a 2 day conference on this.


    Natalie had been working as …

    open.spotify.com
  • What The Culture | A Founder Podcast

    In this fantastic episode of the Organizational Health podcast, we have Natalie Ledbetter – a People Operations Exec, Startup Advisor, TedX Speaker, and Former Operating Partner & Head of People at Boldstart Ventures.


    During her illustrious career, Natalie's insights on scaling organizational health in an early-stage company have influenced countless startups' success.


    She is a veritable guru in…

    podcasts.apple.com

Experience

  • Virtual Sapiens

    Virtual Sapiens

    Board of Advisors

    Jan 2025 - Jan 2026

    AI Roleplay Coaching That Makes Training Stick Virtual Sapiens is an AI Roleplay Communication Coach for mastering pitches, difficult conversations, and meetings, built by expert communication coaches & trusted by global teams. 90% of training is forgotten within days. Our AI Roleplays and patented, science-backed feedback reinforce real-world skills across body language, tone, and verbal content. Our Practice Portal provides immersive learning journeys that turn ‘soft’ skills into strategic superpowers.

  • Bubble.io

    Bubble.io

    Fractional CPO

    Jan 2025 - May 2025

    - Partnered with founders and executive leadership to assess organizational design, leadership capability, and team alignment, implementing talent and structural changes that restored execution velocity and supported scale. - Ran talent audits across Engineering and Product to identify (and fix) leadership and workflow bottlenecks impacting execution speed, delivery, and team effectiveness. - Implemented operational and policy changes to internal mobility practices, and team design to improve time to productivity. - Unraveled complex employee relations matters, led two investigations and partnered with Founders to rebuild employee trust amidst cultural toxicity, exiting performance and behavior risks that were slowing delivery and increasing attrition. - Managed and developed a six-person People Operations & Talent Acquisition function while strengthening management capability through training, coaching, and performance practices that increased accountability and team effectiveness.

  • Wallaroo.AI

    Wallaroo.AI

    Fractional People Operations Leader

    May 2023 - Jun 2024

    Wallaroo.AI empowers enterprise AI teams to operationalize machine learning (ML) to drive positive outcomes with a unified software platform that enables deployment, observability, optimization and scalability of ML in the cloud, in decentralized networks, and at the edge.

    • Partnered with the Founder/CEO to drive large-scale talent changes, creating a leaner, more focused organization with the right people in the right roles.
    • Trained the entire company on, built and ran an engagement survey to identify organizational issues, shift culture and build new company-wide programs for retention.
    • Built end-to-end interview processes for every open role, closing candidates in Sales and Solutions Engineering.
    • Worked as a thought partner to Founder/CEO
  • Boldstart Ventures

    Boldstart Ventures

    Operating Partner, Head of People and Platform

    Nov 2019 - Dec 2022

    Day one partner + true believer for enterprise infrastructure/SaaS founders

    • Harnessed pattern recognition from scaling three early-stage startups to hyper-growth, building "People Ops as Service."
    • Architected bespoke People Ops programs covering the entire employee lifecycle, from attraction to separation.
    • Worked with founders to develop their "employer brand," codify values, and design employee value propositions to hire top talent globally.
    • Created scalable, structured, and equitable recruitment processes; trained portfolio co. teams on interviewing, negotiating offers, and using data to measure recruitment effectiveness.
    • Introduced executive talent, saving companies over $2.7M.
    • Built total rewards systems, including compensation bands, leveling, equity grants, and strategic benefits (relocation, mental health, education stipends, compassionate leaves).
    • Ensured the development of DEIB programs to engage and retain employees.
    • Developed toolkits for internal and external communications on COVID, RIFs, terminations, employee deaths, sexual harassment, and other ER scenarios.
    • Counseled founders on codifying cultures and threading values through feedback, hiring, performance reviews.
    • Drove strategic organizational design exercises to enhance team velocity and effectiveness.
    • Acted as a sounding board for 30+ founders, providing People Ops support and actionable feedback.
    • Drove strategic organizational design exercises to enhance team velocity and effectiveness.
    • Acted as a sounding board for 30+ founders, providing People Ops support and actionable feedback.
    • Built and ran thought leadership events, offering founders access to C-suite executives and stage-specific content (e.g., freemium models, pricing strategy, scaling mindset, DevRel). Presented to LPs on enhancing portfolio companies
    • Presented yearly at the Annual General Meeting, which included 90+ LP's, founders and potential investors
  • Text Iq (acquired by Relativity)

    Text Iq (acquired by Relativity)

    Advisor to the Head of People and People Operations Team

    Aug 2019 - Jul 2021

    AI for Sensitive Information

    • Mentored the People Operations team to uplevel the existing talent, provide thought partnership with the Head of People and drive strategic programs
  • Stash Invest

    Stash Invest

    Vice President of People Operations

    Jan 2017 - Jul 2019

    Banking. Investing. Education. One seamless experience.

    • Built the HR, Talent Acquisition, Employee Experience, L&D and Facilities functions from the ground up, represented the people function on the Executive team and in board meetings
    • Owned and forecasted (with CFO) people ops budget annually, ensuring transparency into people and spending
    • Lead a team of seven HR, Recruiting and Facilities professionals, owning strategy and execution for all People Ops initiatives at Stash
    • Scaled the company from 27 people by over 750% to nearly 300 in 2.5 years while staying highly focused on diversity, inclusion, equity and belonging (ask about this!)
    • Benchmarked and built benefits offerings and policies for all Stash employees--medical, dental, equity in the company, 401k, FSA, Commuter, flexible time off, parental leave, education stipends, catered lunches etc.
    • Leveled the org and developed comp banding and career ladders for every role in the org
    • Built performance management including bi-annual performance reviews and a separate bi-annual compensation review process, running company-wide trainings prior to each launch
    • Developed end-to-end interviewing processes for every role, across every team at the company and all interview training (responsibility of all recruiters on my team) including a required kick off meeting and candidate profile intake with hiring managers
    • Built and scaled a 2 day onboarding process for all new employees with all department heads presenting and familiarizing new teammates with the history, vision, strategy and all key members of the executive team
    • Built all processes/policies and executed trainings (when needed) for OKR's, All Hands, promotions, comp adjustments, employee referrals and bonuses, sexual harassment, visa sponsorship, team building events, 30 and 60 day check-ins with new hires etc
    • Owned L&D, including introducing required manager bootcamp (LifeLabs) for all people managers
    • Moved two offices and project managed a move and 8-month build out of a custom space for Stash
    • Presented people strategy to BoD
  • Curalate (Acquired by Bazaarvoice)

    Curalate (Acquired by Bazaarvoice)

    Director of Talent Acquisition

    Dec 2014 - Nov 2016

    Curalate is a marketing and analytics suite for visual social media platforms.

    • Built Curalate’s recruiting organization and all programs and processes around hiring from the ground up, as the company entered hyper growth
    • Scaled the company by over 240% in 1.8 years across New York, Philadelphia and Seattle offices
    • Lead all strategy around employer branding, marketing and positioning in the marketplace, including thought leadership pieces, speaking engagements and events
    • Maintained an 83% positive candidate experience rating based on survey results sent to all candidates interviewing at the company (Greenhouse benchmark is 73% positive rating); integrated a “white glove” policy for bringing candidates through the intervie
    • Developed all interviewing processes for every role, across every team (45+ unique positions); provided all goals, competencies and lines of questioning for every interviewer
    • Drove process around running effective kick off meetings with hiring managers to hone in on desired qualities and competencies and developing candidate personas
    • Implemented highly data-driven method of hiring, utilizing Greenhouse reporting, slicing and analyzing pipelines, identifying and rectifying process bottlenecks
    • Established KPI’s for the People Ops Team of 5 holding weekly 1:1’s and bi-weekly team meetings, providing continuous coaching, running role-plays, negotiation scenarios
    • Unveiled surveying of new hires (by their managers) at 90 days ensuring employees are set up for success, identifying management/training issues and continuously improving our hiring processes; current metric: What is the probability that you would hire t
    • Made all key senior hires and managed a company-wide push to up-level our existing team; senior hires included CFO, VP of Client Success, VP of Product Management, Director of Demand Generation, Director of Sales Development, Director of Enterprise Sales,
  • Shapeways

    Shapeways

    Director Talent Acquisition

    May 2013 - Nov 2014

    Enabling product creation at scale is the core of Shapeways’ innovative technology platform.

    • (Company IPO 2021) • Led all recruitment strategy and execution efforts for all roles at Shapeways NYC--as only member of HR/Recruiting team--from end to end. Growing the team from approximately 80 to 200, with two disparate populations: knowledge/corporate workers, and manufactering employees. • Owned all employer branding strategy including managing budgets, execution of plans and outside vendor relationships • Acted as main HR point of contact (until I brought on an HR Manager) on ER issues, terminations, foreign visas, discrimination claims, on-boarding of new employees and HR policies and procedures • Helped devise all company retention strategies and employee engagement initiatives including the roll out of the company's first engagement survey via Culture Amp • Cultivated relationships with our VC funds, fund portfolio organizations, city and county organizations, universities, professors, consultancies etc. to help build our talent funnel • Orchestrated deal to scale manufacturing services and packing for Google: Made With Code partnership

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