Digital Transformation Salesforce Platform

David Kestenberg

Salesforce Technology Leader Digital Transformation Executive

Pittsburgh, PA linkedin.com/in/davidkestenberg *****@**********.** 412-***-****

Professional Summary

Transformational technology executive with over 15 years in Salesforce platform ownership, engineering, and large-scale digital transformation. Proven leader in CRM optimization, Agile SDLC, and scalable, secure platform management, aligning technology strategies with organizational goals for enhanced efficiency and user experience. Experienced in developing Salesforce and engineering roadmaps, ensuring seamless integration, data integrity, and regulatory compliance. A collaborative leader and Dreamforce speaker, committed to driving impactful results through continuous improvement and innovation in forward-thinking organizations.

Core Competencies

Salesforce Platform Strategy: Salesforce Lightning, Service Cloud, Health Cloud, Sales Cloud, MuleSoft, Slack, Tableau, Copado, and more.

CRM Optimization & Customer Experience

Team Leadership & Cross-Functional Collaboration

Data Integration & System Migration

Digital Transformation & Process Improvement

Compliance & Security (InfoSec) Audits

Agile SDLC & Best Practices Implementation

Professional Experience – Salesforce focused

Chief Information Officer - REE Medical Feb 2023 - May 2024

Led all Salesforce and IT initiatives, focusing on implementing systems that streamline veterans' healthcare assessments and Disability Benefit Questionnaires (DBQs).

Directed the technology integration post-acquisition, ensuring seamless Salesforce and IT infrastructure compatibility with acquired entities.

Enhanced Salesforce platform customization to meet compliance standards and improve team efficiencies across multiple departments.

Director of IT, Enterprise Salesforce Solutions - Highmark Health Nov 2021 - Feb 2023

Spearheaded the Enterprise Salesforce Solutions & CLM group, managing a team across various locations to provide efficient support for Salesforce implementations.

Orchestrated system migrations, integrations, and customizations, improving platform performance and user adoption.

Optimized Health Cloud and Service Cloud solutions to enhance patient engagement and streamline customer support workflows.

Conducted regular InfoSec audits and implemented strategies to meet security standards, directly addressing and resolving audit findings.

Salesforce Product Owner - Highmark Health Nov 2019 - Nov 2021

Led Salesforce teams responsible for end-to-end development cycles, focusing on enhancing system capabilities and user experience.

Implemented Salesforce Lightning upgrades, driving a 30% increase in system usability and performance.

Created robust onboarding and training programs, empowering users and administrators at all levels to effectively leverage Salesforce.

Championed best practices for data migration, aligning legacy systems with upgraded Salesforce infrastructure and ensuring data integrity.

Director of Business Operations & Deal Flow Generational Transfer Entrepreneurs May 2017 - Dec 2017

Managed Salesforce CRM for deal flow tracking and analysis, optimizing M&A activities and reporting accuracy.

Enhanced CRM functionality to support data-driven insights, increasing efficiency in deal sourcing and evaluation.

CEO & Lead Salesforce Consultant - Kestenberg Consulting 2012 - Nov 2021

Delivered tailored Salesforce and IT solutions to clients across finance, healthcare, and Ed-Tech industries, emphasizing CRM optimization and digital transformation.

Advised private equity firms on Salesforce platform integration during M&A activities, ensuring smooth transitions and system alignment for acquired companies.

Designed and implemented comprehensive Salesforce data migration plans, integrating legacy systems and enhancing reporting capabilities.

David Kestenberg

Email: *****@**********.** Phone: 412-***-**** LinkedIn: www.linkedin.com/in/davidkestenberg

SUMMARY

Strategic IT Executive with over 18 years of experience driving digital transformation and operational improvements across diverse industries, including healthcare, fintech, and private equity. Proven expertise in M&A due diligence, post-acquisition IT integration, and aligning technology strategies with business objectives to drive revenue growth and enhance scalability. Adept at leading cross-functional teams, optimizing enterprise technology, and delivering measurable business value.

CORE COMPETENCIES

Enterprise Technology Optimization

M&A Due Diligence & Technology Integration

Cloud Solutions & Digital Infrastructure

Data Analytics & Business Intelligence

Vendor & Stakeholder Management

Budgeting & Cost Optimization

Cybersecurity & Risk Management

Agile & Waterfall Project Management

ERP & CRM Expertise

Digital Transformation Leadership

PROFESSIONAL EXPERIENCE

Chief Information Officer — REE Medical Nov 2022 – May 2024

Spearheaded a comprehensive digital transformation, modernizing REE Medical’s IT infrastructure to support scalable growth, enhance operational efficiency, and ensure regulatory compliance (HIPAA, VA).

Led post-acquisition IT integration following a private equity acquisition, aligning systems with strategic goals, resulting in a 20% reduction in operational costs within 12 months.

Developed and implemented a robust cybersecurity framework to safeguard sensitive veteran health data, achieving full regulatory compliance and passing external audits year over year with outstanding success.

Strategically implemented Salesforce CRM Service Cloud for Operations and Sales, integrated MuleSoft as the core integration layer, deployed Slack for seamless internal communication, and optimized release management with Copado, all within a comprehensive agile framework.

Negotiated vendor contracts and implemented cost-saving measures, reducing IT expenses by 15% while maintaining service quality and performance.

Director of IT, Enterprise Salesforce Solutions & CLM — Highmark Health Nov 2019 – Feb 2023

Directed a large-scale transformation of Highmark Health’s Salesforce ecosystem, managing a 250-member team across multiple geographies, driving system improvements and post-acquisition integration.

Oversaw 31 Salesforce environments, including Health Cloud, Sales Cloud, and Service Cloud, while managing enterprise-wide Tableau analytics and large-scale MuleSoft and Copado deployments, supporting 11.4 million members and 55,000 employees across the organization.

Managed the full Salesforce product development lifecycle, focusing on seamless integration during M&A transitions, reducing technical debt, and driving system optimization.

CEO & Founder — Kestenberg Consulting 2012 – 2024 (Part-Time)

Provided IT consulting services to private equity firms and portfolio companies, specializing in post-merger technology integration, digital transformation, and IT strategy.

Led technology due diligence for PE investors, identifying risks and opportunities in acquisitions, improving post-close technology landscapes for enhanced operational efficiency.

Director of Business Operations — Generational Transfer Entrepreneurs May 2017 – Apr 2018

Led deal flow management for search funds, providing IT and operational insights to inform acquisition strategies.

Managed post-acquisition IT integrations, aligning infrastructure with business objectives, enhancing technology synergies, and driving value creation for portfolio companies.

Interim CEO — ISA Learning Oct 2016 – May 2017

Directed product development, go-to-market strategy, and fundraising efforts for an Ed-Tech startup, scaling technology infrastructure to support a 40% increase in users.

Led the overhaul of technology systems, enabling operational efficiency while expanding digital learning solutions for educational institutions.

Founder & CEO — FocusFeed Jan 2015 – Oct 2016

Founded and launched a B2B SaaS company offering personalized content solutions for businesses, driving client engagement and retention.

Managed all aspects of product design, business development, and technology implementation, achieving successful revenue growth post-launch.

Associate — Rosemore Capital Jan 2012 – Dec 2014

Conducted deal flow analysis, evaluating potential acquisitions from a technology and operational perspective.

Supported M&A transactions by assessing IT infrastructure and cybersecurity postures, contributing to successful integration and technology strategy for portfolio companies.

Foreign Exchange Trader — Mizrahi-Tefahot Bank Sep 2010 – Oct 2011

Traded foreign currencies at the bank’s headquarters in Israel, optimizing currency portfolios and minimizing financial risk in a high-pressure environment.

ADDITIONAL EXPERIENCE

Reconnaissance Commander (Major) — Israel Defense Forces (Active Duty: 1996-2001, Reserve: 2001-2012)

Led a specialized reconnaissance unit during active duty, responsible for mission-critical operations and team leadership in high-stress environments. Continues to serve as a reserve officer with the rank of Major.

EDUCATION

Reichman University (IDC Herzliya) — BA, Government, Strategy, and Diplomacy 2007 – 2010

Leadership Development: Selected for and participated in Leadership Pittsburgh Class LPXXXIV, enhancing strategic leadership skills and expanding regional impact through cross-sector collaboration. (2017)

ADDITIONAL INFORMATION

Speaker at Dreamforce (5 times) - Dreamforce is Salesforce's annual global conference, where industry leaders, innovators, and experts gather to discuss the latest trends in technology, business, and customer success.

Board member at two non-profit organizations and advisory board member for three early-stage tech companies, providing strategic guidance and leadership across diverse sectors.

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