Pleshette S.

Senior HR leader and strategic partner to enterprise technology and corporate leadership, driving people strategy across AI, data, digital platforms, cybersecurity, and enterprise architecture. Partner to senior leadership across a 400+ organization, supporting 40+ senior leaders, leading workforce strategy, organizational design, and operating model transformation aligned to business and technology priorities. Lead enterprise initiatives spanning AI transformation, platform engineering, and product-centric operating model adoption, including workforce planning, executive hiring, talent strategy, and large-scale organizational change. Focused on building high-performing, technology-driven teams and enabling faster, more data-driven decision-making to accelerate business outcomes.

Founded and led a strategic HR consultancy supporting innovative, high-growth organizations in building best-in-class people functions that align with business, culture, and leadership goals. Key Focus Areas: -Leadership Development: Designed and delivered scalable programs for high-potential and emerging leaders, frontline managers, and first-time people leaders. -Executive Coaching: Advised senior leaders on personal brand, leadership transitions, and first-90-day success strategies to accelerate impact. -Diversity, Equity & Inclusion (DEI): Built inclusive hiring pipelines, developed inclusive leadership programs, launched ERGs, and fostered diversity of thought within evolving organizations. -Provided fractional CHRO support and strategic guidance on org design, culture, and people strategy for startups and scaling companies.

As HR Director for the NY/NJ region, I partnered with senior business leaders across Claims, Business Insurance, and Legal to shape and execute workforce strategies aligned to performance, transformation, and growth. I led a team of HR generalists supporting regional operations, talent planning, and organizational development across a multi-location field model. Key Achievements: -Developed a regional workforce plan that enabled 5% revenue growth while reducing headcount by 20% and consolidating operations—improving profitability per business unit. -Launched a high-potential leadership program that increased internal mobility by 20% and expanded the leadership pipeline by 30%, reducing external recruiting costs by $100K. -Retained 75% of the region’s top 100 employees by deploying analytics-based succession and retention strategies. -Led a regional change champion network through multiple business transformations, resulting in 35% retention of top sales leaders and improved change readiness. -Elevated HR support through leadership of a 3-person HR team, embedding strategic consulting and organizational design practices.

Led the full HR function for 500 employees across Technology, Engineering, Product, Marketing, Sales, Client Services, and Operations in a highly matrixed, post-acquisition environment. Served as a strategic advisor to senior leaders in both the U.S. and Canada, with a focus on organizational transformation, workforce planning, and cultural integration. Key Achievements: -Oversaw post-merger HR integration during the Cox acquisition of Dealertrack; retained 40% of the executive team and ensured business continuity through clear communication and leadership alignment. Supported Agile transformation by partnering with engineering leadership to transition teams and embed agile principles within product delivery culture. -Developed and implemented a workforce planning strategy to address business and technical talent needs across multiple functions. -Increased engagement by 25% through cross-border culture-building, internal communication strategy, and leadership alignment. -Designed a leadership development framework leveraging high-potential internal talent, saving $200K in training costs and building a stronger succession pipeline. -Redesigned Lender sales compensation, aligning incentives to business outcomes and delivering $200K in savings. -Transformed a transactional HR support team in Toronto into a consultative business partner function, resulting in promotions and elevated impact.

Served as trusted advisor and people/organizational SME for key Technology Leaders on HR strategies and initiatives that fostered growth, innovation, and organizational effectiveness across several businesses; Influenced Technology Leaders in the effective deployment and utilization of human resources strategy to drive continuous improvement across each business; Monitored policies, data, and people practices to successfully identify trends; Direct supervision of three human resources generalists. Key Achievements: •Change Management: Designed and updated Producer and Client Services compensation plans. The new plans resulted in 10% retention on regions top producers plans as well as a $5 Million (15%) growth in new business. •Performance/Talent Management: Implemented a functional performance/talent management tool to assess current talent. • Leadership Development: Created a middle management leadership program designed specifically for high potential and performers strengthen our management bench. The program resulted in an increase in the management pool by 20%.