Executive coaching and candid advice.

Building a company is hard. As former operators and entrepreneurs, we help.

What we do

Executive coaching for growth stage founders, CEOs, executives, boards and investors.

CEO Coaching

Support your journey from visionary to leader. We offer advice and act as a sounding board to help you make informed strategic decisions and grow as an executive.

CTO Coaching

Grow your product and engineering leadership. Get candid feedback in solving challenges, optimizing your product engineering teams and improving your technology processes.

Executive Team Development

Build and develop your executive team, improving team dynamics, accountability and alignment.

Board Management

Navigate the complexities of managing your board, establishing sound governance and operating cadences. Leverage and build your board team.

Additional Services

Product & Technology Diligence

Investors should look “under the hood” of a potential investment. Hoola Hoop has a team of product/engineering experts who examine technology investments. We conduct in-depth product risk assessments and technology capabilities, analyze codebases, and examine an organization’s security posture, overall R&D spend, and team competencies and development opportunities.

Board Member & Observer

Hoola Hoop partners have extensive experience in serving on boards as both observers who are there to help the CEO build a strong board team, and as board members actively working on behalf of the organization.

Board Development

We help identify gaps and opportunities for the board team to operate effectively, as well as key inhibitors and accelerants for it to successfully scale and meet the company’s future needs.

Nonprofit Coaching

Hoola Hoop has years of experience serving nonprofit organizations, executives and boards with coaching, advisory and technical expertise.

PE & VC Partner Coaching

We help investors as they navigate increasing responsibilities in their work with founders, CEOs, boards, limited partners and within their own partnerships. Hoola Hoop provides venture capital and private equity partners with coaching and guidance based on our understanding and experience with these organizational dilemmas.

People Management

Organizational DevelopmentWe help hone your culture and develop your leaders and teams, developing your company’s mission and belief system to guide how people work.

HR OperationsHoola Hoop has an experienced team of human resource professionals who can advance an organization’s capacity to manage people.

Performance ManagementHoola Hoop revamps performance management for large and small organizations. We implement agile performance feedback systems with clear accountability and aligned roles and responsibilities to achieve the client’s objectives.

Operating System — We help clients develop a company operating system that defines how often teams meet, communicate and measure results.

People AssessmentHoola Hoop provides deep assessments of people, teams and organizations. Whether interpersonal or group compatibility, team formation, role-fit, performance in role, etc., an organization needs the right people in the right roles interacting in productive ways. 


Hoola Hoop conducts interview-based 360 reviews that distill the critical areas of development for executives, managers, boards and teams to help understand how they are performing.

Who We Help

Founders and CEOs

CEOs have an enormous challenge making sure there is a compelling vision, funding, a sound strategy and great execution. We advise CEOs on a wide array of topics, ranging from strategy, board management and executive team building, to personal coaching to ensure self-awareness and professional growth.

C-suite Executives

We support both the individual executive and the executive team in their professional development, alignment and cross-functional collaboration.

The Board

For companies to thrive and scale, their board team must be effective. We identify the key inhibitors and accelerants for the board to successfully scale, while working with the CEO to improve a board’s agenda, priorities, corporate governance and processes.


We work with investors to assess teams and technology, and provide our operating knowledge to help them with their portfolio companies.

Supporting 100+ companies worldwide
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The Partners

We are former operators with decades of experience as CEOs, C-level execs, board members, and limited partners.

Eyal Goldwerger

Eyal is a seasoned operator and experienced CEO, board member, advisor, and investor. He has led technology ventures through fast growth to market leadership and M&A in a wide variety of industries, and has a rich expertise in venture-backed companies. He holds an MBA from INSEAD. Eyal is a passionate Kung Fu practitioner, an avid heliskier, and dabbles in jazz piano. He is also an amateur barista who pulls a near perfect espresso on his La Marzocco machine.

Marc Maltz

Marc brings over 40 years of experience as an organizational clinician. He has helped for profit and nonprofit executives, boards and senior managers develop and transform their organizations. Marc teaches organizational psychology and sits on a number of boards. He has held executive positions at AT&T, Westinghouse Electric Company, NYNEX Corporation (Verizon) and Music Mining Co. Marc is a former musician known for his selective yet abundant coffee consumption, collection of whiskey and vinyl records.

Leigh Newsome

Leigh is a CTO and advisor with 25 years of experience scaling product and engineering teams. He has worked for a wide range of giants and startups including Avid, Digidesign, WPP, Kantar/Millward Brown, etc. He successfully led TargetSpot (investors: Union Square Ventures, Bain Capital Ventures, and CBS) through its acquisition to Radionomy Group (Vivendi). A fixed wing pilot that writes songs on his guitar but not at the same time!

Staff Coaches

In addition to our partners, Hoola Hoop has a team of experts in leadership, human resources and technology development.

Cheryl Swirnow

Cheryl Swirnow brings over 22 years of HR experience working with prestigious brands such as Four Seasons Hotels and Resorts, Quintessentially, Nike, and Rent The Runway.  She is a commentator on HR trends and her work has been featured in New York Magazine, Marie Claire, Bloomberg Television and Elle.

Niall Smart

Niall is an entrepreneur, CTO and advisor who has a broad range of experience in early stage technology innovation. He has worked and consulted in embedded systems, digital media, and vertical SaaS. Niall was co-founder and CTO of Hightower/VTS, an early PropTech pioneer who created a new market category for leasing management software. More recently, his focus is on helping early stage ventures scale up teams and technology. At weekends you’ll find him exploring new cycling routes in upstate New York or setting an alarm for early morning races in Central Park.

Crystal Proenza

Crystal Proenza is a strategic consultant and leadership development expert who works to empower leaders, drive performance and guide career paths, especially in times of change. She is an experienced operator who spent 10 years as a member of leadership teams across several organizations. Crystal has advised leaders at all levels of corporate and startup environments, guiding clients to success during a recession and through mergers and acquisitions, all with a focus on leadership, operational efficiency and communication.

Jackie Shiff

Jackie Shiff is a lawyer, executive coach, and facilitator. She helps leaders and management teams operate more effectively, often increasing awareness, focus and accountability. Jackie’s clients span startups, venture capital and private equity, academia and philanthropy. She received coach training at Columbia University and is certified in the Deeper Signals personality assessment. Previously, she was part of leadership teams at the Aspen Institute and the University of Chicago. She also served as a judicial clerk to the Honorable Mary L. Mikva.

Cliff Hazelton

Cliff Hazelton is the former Chief Technology Officer of Stash, a financial services platform revolutionizing how millions of Americans save. Cliff’s product and engineering expertise spans two decades across many industries, including Boeing Intelligence & Analytics, Capture Media, the U.S. Army Research Laboratory and Stash.

Working with a coach

Hoola Hoop believes that the success of an executive’s coaching depends on the relationship between the executive and the coach and on the executive’s desire to change.

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Motivation, Meaning and Resilience

Purpose, motivation, and resilience are essential for an organization to sustain success. These client case studies focus on what happens when an organization faces significant challenges due to trauma, M&A, market conditions, etc. All show a lack of clear purpose and confused organizational responses to change. We emphasize the importance of leadership in fostering a […]

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Succession Planning

This analysis details succession planning and management practices across 14 companies from various industries. It examines the choices companies face when creating or improving their succession planning and management systems. The study identified several themes, including the role of human resources, the criteria for identifying high potential candidates, the relationship between performance and potential, and […]

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Performance Management

Today’s performance management systems need a more effective approach that aligns with modern workforce requirements, emphasizing the importance of specific, in-the-moment feedback. One of today’s most valuable workplace assets is actionable, in-the-moment feedback, which is too often buried, lost or just not delivered in today’s ineffective performance management systems. Traditional performance management systems are out-of-sync […]

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Complexity of Leadership

In complex organizations, leaders face multidimensional psychological challenges. Using the case of Arthur Andersen, a company that failed due to leadership’s inability to respond to the powerful dynamics of authorization, we discuss the importance of adaptive leadership, psychodynamic organization theory and Interpersonal psychoanalysis to understand the complexities leaders face. Successful leadership requires transparency, emotional competence, […]

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Framework For Roles

Role is a complex key component of all organizations. We offer a framework for defining the way one works-in-role: their specific assigned duties, part in the overall mission, unconscious function, and the way they understand and work within an organization’s systems of tasks and sentience.

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Finding You in Me

The 9/11 attacks on the World Trade Center devastated this investment bank. We discuss our work in helping Sandler O’Neill & Partners’ remaining managing director, employees and families, recover from the trauma of losing 39% of their friends and colleagues. We present the challenges and successes of bringing together survivors, families, volunteers and new employees […]

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Thinking, Leadership and Action

Through a case study of a senior executive at a foreign bank, we look at the complex dynamics between leadership, teamwork and organizational culture, and how to help leaders navigate the challenges of a rapidly changing business landscape. We address the importance of understanding the psychological factors that drive individual and organizational behavior and decision-making; […]

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Psychological Containment

“Psychological containment” is an important but overlooked leadership capability. Leaders must be able to identify and manage workplace stresses and anxieties, what we call “troubling, frightening bits” or TFBs, that originate from employees, work, organizational dysfunction, and external events. If unaddressed, TFBs can severely impact organizational functioning and output. Psychological containment is the ability to […]

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Let’s Talk

Thank you for your interest in Hoola Hoop’s approach to executive coaching.

We’re excited to help you unlock your and your organization’s full potential. Please share a few details about yourself and your coaching needs. Let’s start this transformative journey together.

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