Taylor Bradley

CEO

Orlando, Florida, United States17 yrs 8 mos experience
Most Likely To SwitchAI Enabled

Key Highlights

  • Led 10x global growth at Turing.
  • Integrated AI to automate 80% of PeopleOps workflows.
  • Recognized for award-winning People teams.
Stackforce AI infers this person is a strategic HR leader with expertise in AI integration and talent management in SaaS environments.

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Skills

Core Skills

Human ResourcesTalent Strategy

Other Skills

LeadershipAI IntegrationPeople ManagementWorkflow AutomationM&A IntegrationPeople AnalyticsData VisualizationTalent AcquisitionEmployee DevelopmentIPO ReadinessHR InfrastructureC-suite AdvisorySocial Media StrategyRecruitmentEmployee Engagement

About

Transformative HR Executive | AI-Empowered Talent Strategy | CNBC Workforce Council My background as a firefighter-paramedic taught me that clarity and decisive action are critical in chaos. I apply this discipline to architect the AI-Native Workforce—bridging Human Capital and Generative AI to drive efficiency. I’ve built a career on getting hard things done, turning People strategy into a revenue engine without sacrificing the human experience. At Turing, I lead the People function through 10x global growth and a GenAI integration, featured by CNBC and Google, that automates 80% of PeopleOps ticket workflows. I contribute as the SME for HR RL Gyms and slash ramp-time from weeks to hours for Talent Development while driving record eNPS. As a trusted thought partner to the CEO and executive team, I leverage prior IPO-readiness leadership at DocuSign, Squarespace, and Datto to drive award-winning results (TransformHR, Fast Company) and a disciplined approach to scaling HR's business impact and developing a culture that attracts and retains the world's leading AI talent. Contributing to industry thought leadership as a CNBC Workforce Council member, TroopHR podcast and development of research mechanism for CHROs of AI-enabled organizations.

Experience

17 yrs 8 mos
Total Experience
2 yrs 9 mos
Average Tenure
3 yrs 11 mos
Current Experience

Turing.com

Vice President Talent Strategy & Success

Jun 2022Present · 3 yrs 11 mos · Palo Alto, California, United States · Remote

  • Transformative HR Executive | AI-Empowered Talent Strategy | CNBC Workforce Council
  • As VP of Talent Strategy & Success, Taylor built an award-winning People team—recognized by Fast Company’s Best Workplaces for Innovators (2025) and Transform HR’s Top 5 Talent Development Teams (2025)—while scaling headcount 10x, launching global onboarding, and advancing IPO readiness, backed by CNBC and Google featured AI in HR use cases.
  • Please note: Due to volume, Taylor is unable to respond to candidate or sales inquiries via LinkedIn.
  • Founder-Led | Late-Stage Series D > E
LeadershipHuman ResourcesAI IntegrationTalent StrategyPeople Management

Squarespace

Principal Human Resources Business Partner

Aug 2020May 2022 · 1 yr 9 mos · New York, New York, United States

  • Senior HRBP & HR Program Manager | Squarespace | M&A Integration & HR Effectiveness
  • Handpicked by the CHRO, Taylor led critical initiatives that propelled the People Team's impact at Squarespace. As a versatile principal HRBP, he spearheaded M&A integration efforts, ensuring a seamless transition. Taylor specialized in the development of actionable and detailed People Analytics specific to their R&D functions, leading to what the Head of Data Science said, "It's not every day you get to work with an HR partner who can talk distributions and has A+ Data Viz skills," providing data-driven workforce analytics to R&D leaders, enabling informed decision-making.
  • Known for his impact, Taylor contributed to improving people governance initiatives that empowered IPO readiness and the successful listing (NYSE: SQSP). He adeptly managed multiple client groups, covering gaps while the HRBP team navigated restructuring, demonstrating his ability to drive results and align people practices with business objectives in a fast-paced, founder-led, late-stage environment.
  • Founder Led | Late-Stage Series D to IPO (NYSE:SQSP)
Human ResourcesM&A IntegrationPeople AnalyticsData Visualization

Datto, inc.

Human Resources Director

Dec 2018Aug 2020 · 1 yr 8 mos · New York, New York, United States

  • People Leadership Team | Head of Product Development HRBPs & Talent Acquisition Team
  • As a key player on the People Leadership Team at Datto, Taylor led the Product Development HRBPs and Talent Acquisition Team for the Global Product Development Team. Known for his expertise in building HR infrastructure from the ground up, Taylor successfully rolled out multiple strategic programs that bridged the gap on M&A integration, implemented a record-breaking talent acquisition strategy, and established the company's first career architecture.
  • Taylor's transformative impact extended beyond optimizing HR processes. He made significant contributions to the establishment of employee development initiatives, employee resource groups, and the IPO readiness program, effectively aligning people practices with business objectives during a critical stage of the company's growth.
  • Navigating the cultural complexities of a founder-to-career-CEO transition, Taylor demonstrated his ability to drive results in a fast-paced, late-stage, pre-IPO environment, even amidst a restructuring.
  • Founder Led to Career CEO Transition | Late-Stage Series D to IPO Readiness (NYSE:MSP)
Human ResourcesTalent AcquisitionEmployee DevelopmentM&A Integration

Docusign

Global Human Resources Business Partner

Nov 2017Nov 2018 · 1 yr · Seattle, Washington, United States

  • Chief of Staff CHRO | Lead HRBP Product Development | Late-Stage to IPO (Nasdaq: DOCU)
  • Taylor was Chief of Staff to the CHRO and a key support figure for the CTO and Engineering Leadership. His multifaceted role included C-suite advisory, volunteered to spearhead HR leadership recruitment, and leading people analytics projects. Taylor's career has been significantly influenced by his former grad school professor and CHRO, Michael Erisman, who continues to serve as a pivotal mentor.
Human ResourcesPeople AnalyticsC-suite Advisory

Remote medical international

Head of People

Jul 2015Nov 2017 · 2 yrs 4 mos · Seattle, Washington, United States

  • Leadership Team Member & Head of HR (Talent Acquisition and HRBPs) | Startup 0 to 1 HR Infrastructure Building
  • As a key member of the Leadership Team and a direct report to the CEO, Taylor led the HR function at Remote Medical International, a fast-paced startup. Known for his expertise in building HR infrastructure from the ground up, Taylor shaped the company's talent strategy and established a robust online social media presence geared towards candidate engagement.
  • Taylor's innovative and adaptable strategies significantly influenced talent acquisition and business development, driving the company's growth. He launched the cost-effective #RMILive outreach program, which became a top YouTube search for Remote Paramedics, attracting top talent to the organization.
  • Additionally, Taylor initiated the 'Domestic Project Team' (DPT), diversifying the company's revenue streams and expanding its market reach.
  • Leveraging his strong business acumen and understanding of the company's objectives, Taylor implemented scalable HR processes and systems, including the administration of the eQUIP platform. His ability to align people practices with organizational goals played a crucial role in Remote Medical International's success during his tenure.
Human ResourcesTalent AcquisitionSocial Media Strategy

Princess cruises

Talent Acquisition Partner | Medical Officer

Jan 2013Jan 2015 · 2 yrs · Worldwide

  • Regal Princess Inaugural Medical Team | HR & Recruitment for Global Medical Team
  • In a unique role, Taylor served on the select Regal Inaugural Medical Team in Treiete Italay while directly supporting the Chief Medical Officer (CMO) and the Global Medical Team. He played a crucial role in identifying and achieving headcount goals, designing targeted outreach strategies, and leading retention boosting initiatives.
  • Leveraging his medical expertise and understanding of the healthcare industry, Taylor developed innovative recruitment strategies to attract top medical talent to the organization. He collaborated closely with the CMO to align recruitment efforts with the company's overall objectives and growth plans.
  • Known for his ability to drive employee engagement, Taylor implemented a series of morale-boosting initiatives that significantly enhanced the Global Medical Team's overall success and job satisfaction. His people-centric approach and commitment to fostering a positive work environment contributed to the retention of key medical personnel.
  • Through his strategic HR and recruitment support, Taylor played a vital role in building and strengthening Princess Cruise Line's Global Medical Team.
RecruitmentEmployee EngagementRetention StrategiesHuman Resources

Paramedic

Firefighter - Medic

Jan 2008Jan 2015 · 7 yrs · Worldwide

  • Taylor's journey as a global medic has shaped his unique perspective on leadership. Though he has hung up his stethoscope, the invaluable lessons gained from serving communities worldwide continue to inform and enrich his people-centric approach in the field of human resources.

Education

University of Cincinnati

Master of Business Administration (MBA)

Seattle Pacific University

Master of Arts - MA — Human Resources Management

University of Cincinnati

EMS Technology (Paramedic)

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