Born from Real Business Pain,
Inspired by Human Care
Our Story
Our founder, Jeffrey Marks, grew up in an emotionally challenging environment where expressing feelings felt unsafe. But his grandfather had a gift—he always seemed to know when Jeffrey was struggling. In those moments, his grandfather would offer him a lollipop, creating an instant safe space where Jeffrey felt permission to open up and share what was really going on.
That simple gesture taught Jeffrey that care isn't complex—it's about noticing, creating safety, and being genuinely present.
The Business Problem
Years later, as Jeffrey built and scaled Titan Brands Restaurant Group across multiple locations, he lived the employee wellness problem every day. Traditional platforms were useless for his frontline teams—servers couldn't download apps during shifts, kitchen staff had no company email, and by the time quarterly surveys revealed problems, his best people had already walked out the door.
Jeffrey watched managers struggle to connect with overwhelmed teams. He saw employees suffering in silence because there was no easy way to say "I'm not okay today." He calculated the crushing cost of frontline turnover—not just the $15,000 per replacement, but the impact on service, team morale, and customer experience.
The Solution
So Jeffrey built what he desperately needed: a way for any employee to quickly share how they're doing, and for any manager to respond with care before small problems became resignation letters. The first Lollipop check-in went to a stressed server who'd been struggling with childcare issues for weeks but hadn't told anyone. Her manager reached out, helped coordinate schedule adjustments, and prevented what would have been another costly turnover.
Our Mission
At Lollipop, we believe that great workplaces aren't built by perks — they're built by people feeling genuinely seen, heard, and supported. Born from real challenges with traditional wellness tools and driven by a founder's personal journey, Lollipop was created to transform how teams connect and care for one another.
Our platform brings simple, human-centered check-ins to the heart of your culture — no apps to download, no training manuals to read, just real moments of connection that help reduce turnover, boost engagement, and empower more empathetic leadership. It's well-being that works for every worker, every day.
Executive Team
Jeffrey Marks
Jeffrey Marks is an entrepreneur and founder with over three decades of experience building, operating, and scaling businesses across technology, SaaS, ecommerce, and hospitality. A former big-firm corporate attorney, Jeffrey brings a unique operator's perspective shaped by founding and growing multiple ventures through periods of rapid growth, capital formation, and successful exits. Jeffrey has founded and helped scale companies including Titan Nightlife Group, a Las Vegas–based restaurant development business, ConversionPoint Technologies, an ecommerce technology platform, and Culture Software Solutions, a SaaS company focused on employee sentiment and engagement. His entrepreneurial work spans early-stage formation through maturity, including product development, go-to-market strategy, financing, and acquisition readiness. Drawing on deep experience in mergers, acquisitions, and corporate strategy, Jeffrey has guided both his own companies and those of other founders through hundreds of transactions, financings, and strategic milestones. He is an active participant in the Harvard Business School Executive MBA Program and a long-standing member of the Young Presidents' Organization (YPO), where he has held leadership roles. Jeffrey is known for bridging vision and execution, helping companies grow with discipline while preserving founder intent.
Ray Thompson
Ray Thompson is a SaaS operator and executive leader with more than three decades of experience helping B2B software companies scale through periods of rapid growth, operational transformation, and strategic expansion. A seasoned COO and public company executive, Ray specializes in building the systems, processes, and leadership structures that enable technology companies to grow efficiently and create lasting enterprise value. Throughout his career, Ray has worked across venture-backed startups, high-growth SaaS businesses, and public companies, leading teams through go-to-market expansion, operational scaling, acquisitions, and complex organizational change. As President and COO of Akerna (NASDAQ: KERN), he helped guide the company through its public market journey, led multiple acquisitions, and oversaw the integration of teams, products, and operations across a rapidly evolving software platform. Today, Ray partners with founders, CEOs, and executive teams as a fractional and interim COO, helping B2B SaaS companies establish operational rigor, improve execution, and align growth strategies with measurable business outcomes. Known for his hands-on leadership style and ability to turn complexity into clarity, Ray helps organizations build scalable operating models that support sustainable growth and long-term success.
Richard Wolpow
Richard Wolpow is a seasoned entrepreneur, operator, and investor with more than 25 years of experience building, advising, and scaling small to mid-sized private and public companies, primarily in healthcare and technology. He brings deep operational expertise shaped by founding and leading businesses through growth, acquisition, and complex industry transitions. Most recently, Richard was the founder, Chief Operating Officer, and Vice Chairman of Dispensing Solutions Inc. (DSI), a pharmaceutical manufacturer operating a state-of-the-art repackaging facility in California, which was acquired by PSS World Medical (NASDAQ: PSSI). He is also the founder and Chairman of POC Network Technologies, dba TransactRx, a medical technology company that developed a proprietary Cross Benefit Clearinghouse Platform to streamline healthcare transactions. In addition, Richard serves as an Operating Partner at BelHealth Investment Partners, a healthcare-focused private equity firm based in Newport Beach, California. Earlier in his career, Richard was the primary investor and principal shareholder of Trinity Health Ventures, which became Odyssey Healthcare Inc. (NASDAQ: ODSY) through a Goldman Sachs–led roll-up and was later acquired by Gentiva Health Services (NASDAQ: GTIV) in a transaction exceeding $1 billion. He was also a principal in Freedom Health, Inc., an early innovator in intelligent health debit card technology, and began his healthcare career in 1995 leading TheHealthChannel.com.
David McCullough
David McCullough is a seasoned technology executive and Chief Technology Officer with deep expertise in SaaS, enterprise software, and blockchain-enabled platforms. He has led product and engineering organizations at scale, including overseeing teams of 50+ and guiding technology strategy for a NASDAQ-listed company operating complex, highly regulated systems. David brings a rare blend of hands-on engineering depth and executive leadership, with a track record that includes driving major digital transformations, leading technical due diligence and post-merger integrations across multiple acquisitions, and significantly improving code velocity, infrastructure efficiency, and system reliability. He is a pending patent holder in blockchain-based anti-counterfeit technology and is known for translating emerging technologies into practical, customer-focused solutions. Throughout his career, David has built and mentored high-performing teams, partnered closely with executive leadership, and delivered scalable platforms that support rapid growth, regulatory compliance, and mission-critical operations.
Christopher Della Sala
Chris Della Sala is a senior sales and distribution executive with more than 20 years of experience leading large, multi-market revenue organizations across the employee benefits and worksite insurance ecosystems. He has built and scaled enterprise go-to-market strategies, owned P&Ls and revenue targets exceeding $100 million annually, and consistently driven growth through broker, carrier, and partner distribution models. Chris currently leads Broker Sales for the Western United States at Aflac, where he is responsible for regional growth, broker strategy, and key partner relationships across a complex, multi-market territory. Under his leadership, the organization has delivered nearly 100% year-over-year revenue growth for three consecutive years while maintaining strong execution against quarterly and annual operating plans. His performance has been recognized at the highest levels of the organization, including national distinction, President's Club qualification, and the Amos Award—Aflac's most prestigious individual honor. Previously, Chris served as Head of Broker and Partner Sales for Washington National and Optivize, the worksite division of CNO Financial, where he led national sales and distribution strategy across multiple brands and expanded the company's presence in the voluntary and worksite benefits markets. Earlier roles include Regional Vice President of Sales at TBX and senior leadership positions at Colonial Life, where he led large-group broker sales and regional market expansion initiatives. As a Board Member and Principal Consultant to Lollipop, Chris serves as a strategic advisor focused on advancing national sales and distribution strategy, expanding enterprise partnerships, and strengthening the company's go-to-market execution. He brings deep industry knowledge and long-standing relationships with senior and C-suite leaders across carriers, brokerages, and benefits platforms, helping position Lollipop for scalable, disciplined growth.
Guided by Industry Leaders
David H. Rosmarin, PhD
Psychology Professor, Harvard Medical School Chief Clinical Officer, LINKS Network
Dr. David Rosmarin is an Associate Professor at Harvard Medical School and Director of McLean Hospital's Spirituality & Mental Health Program, where he studies how anxiety, values, and meaning can be integrated into evidence-based care. He also serves as Chief Clinical Officer of the LINKS Network, guiding strategy across a growing system of mental health organizations. Founder of Center for Anxiety and author of Thriving with Anxiety, he helps individuals and leaders harness anxiety as a catalyst for resilience and purpose.
Dr. Steven Phillips
Organizational Development
Dr. Steve Phillips is a senior executive, organization development expert, and executive coach with deep experience leading human capital strategy for a $1B, 10,000-employee company. He has advised leaders at Microsoft, PepsiCo, Boeing, and others, helping organizations implement lasting change. A bestselling author and award-winning HR thought leader, he serves on multiple boards, is a Certified YPO Forum Facilitator, and has taught at Purdue, Pepperdine, SDSU, and USC.
Karenjo Goodwin
Founder & CEO, Exact Staff
Karenjo Goodwin is the founder of one of the largest woman-owned staffing firms in the U.S., bringing deep HR and workforce expertise to Lollipop's people-first strategy. She serves as Chairman of the American Staffing Association and is a Regional Board Member of YPO. A longtime member of ANSERTEAM, she has led Exact Staff, Inc. since 1996, building a nationally recognized staffing platform grounded in operational excellence and industry leadership.
Amber Clouse
Human Resources Leader
Amber Clouse is an executive Human Resources leader known for building scalable people strategies that enable growth, strengthen culture, and drive business performance. She has led HR functions across high-growth and transformation environments, partnering closely with executive teams to align talent, organizational design, and operational infrastructure with strategic objectives. Amber's expertise spans organizational scaling, cultural transformation, leadership advisory, talent strategy, and HR operating model design. She is particularly recognized for her ability to balance strategic vision with hands-on execution, building practical solutions that improve both business outcomes and employee experience. Her career includes leadership roles within complex, evolving organizations where she has guided workforce integration, built HR capabilities from the ground up, and supported periods of rapid expansion and change.
Tony Fogel
President, TriSearch
Tony Fogel is a senior HR and talent acquisition executive with more than three decades of global leadership experience across consumer products, financial services, and technology. He has served as Managing Director at Lehman Brothers, CHRO of two public companies (NYSE: LVLT, CBR), and a leader within multiple private equity–backed organizations, including oversight of a $300M IT staffing business. As President of TriSearch, he partners with CEOs, boards, and investors to modernize talent strategy and drive organizational performance. An advisor to HR technology ventures and private equity firms, he has contributed thought leadership on diversity, engagement, and candidate experience, and is recognized for advancing innovation in talent acquisition and workforce strategy.
Anthony Manganello
EVP, Practice Leader USI Insurance Services
Anthony Manganello is an employee benefits and total rewards executive with more than 25 years of experience advising organizations on human capital strategy, benefit design, and cost optimization. He currently serves as Employee Benefits Practice Leader at USI in Irvine, where he partners with corporate clients to improve benefit programs and drive stronger workforce outcomes. He began his career representing insurance carriers, gaining deep expertise in underwriting and insurance operations. He later served as a consultant with Willis Towers Watson and Arthur J. Gallagher, advising mid-to-large organizations across industries including financial services, technology, healthcare, and education. His work focuses on helping companies align benefit strategies with business performance while managing long-term costs.
Jessica Billingsley
Founder/Managing Partner, Amata Capital
Jessica Billingsley is an accomplished technology executive, founder, and board leader with experience launching and scaling public and private companies, including through IPO. She has served on public, private, and nonprofit boards in chair, audit, compensation, and governance roles. Her expertise spans strategic growth, capital markets, M&A, AI, cybersecurity, and risk management. Securities licensed (7, 79, 63, 24), she is also a speaker, author, and global operator fluent in English, Spanish, and French.
Michael Caito
Strategic Coach
Michael Caito is CEO of Management Action Programs (MAP), a consulting firm helping CEOs align and execute on growth metrics for over 60 years. A former 15-year MAP client, he previously co-founded Restaurants on the Run, scaling it from a $6,000 startup to a $40M, 10-market company sold to Grubhub at 12x EBITDA. A past Global Chairman of EO and active YPO leader, Mike mentors founders, teaches entrepreneurship at USC, and is known for driving results through disciplined, data-driven leadership.
Ready to Build a More Caring Workplace?
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