Rayna Lesser Hannaway, CFA
Coach & Advisor, Fractional Chief Investment Officer @ Pure Path Ventures
About
Most people and organizations focus on visible outcomes: performance, capital raised, promotion, a polished strategy. I look underneath them.After nearly three decades as a buy-side analyst, portfolio manager, and team leader, including nearly 12 years at Fidelity Investments, I kept seeing the same thing: the gap between good and great was almost never about intelligence or information. It was about judgment, self-awareness, leadership, and the humans behind the decisions.That’s the work I do now through Pure Path Ventures, at the intersection of investor discipline and human insight.I do my best work with investors, founders, and executives in lean, high-accountability environments. People who are already exceptional at what they do and are navigating the harder work of leading, building, and making consequential decisions as the stakes grow. I work across the whole of it: strategy, leadership, the organization you’re building, and the judgment and decision quality behind it.Because I’m independent, people tell me things they haven’t said out loud before. That’s often where the real work begins. I bring an investor’s lens to those conversations: looking beneath the visible problem, testing assumptions, and finding what is creating or eroding value. We might stress-test an investment or business strategy, work through a leadership or team decision, or uncover something in your own thinking or behavior that is getting in the way. We solve what’s in front of you while building the judgment and capacity for what comes next.I also work with rising professionals who need real counsel and can’t always get it inside the building. Remote work has made apprenticeship harder. I know what excellent investment work looks like from the inside, and I help people build the reps, judgment, communication, and confidence that compound over a long career.Engagements range from ongoing coaching and advisory relationships to fractional CIO, investment committee, and board roles.
United States
Greater Boston
Management Consulting
Board of Directors, Financial Advisory, Coaching, Equity Research, Financial Analysis, Portfolio Management, Investment Management, Asset Management, Financial Modeling, Valuation
Experience

Coach & Advisor, Fractional Chief Investment Officer
Beverly, MA
I work with investors, founders, and executives on the real decisions and challenges in front of them. That might mean pressure-testing an investment or business decision, navigating a difficult team dynamic, becoming a better leader, or recognizing when your own habits and assumptions are getting in the way. I bring nearly three decades as an investor and team leader to the work, alongside the coaching skills to help you see what you may not see on your own. I also work directly with investment firms and family offices, providing fractional investment research and portfolio management, as well as fractional CIO support.

Independent Director
BioStem Technologies (BSEM)
Board Member at BioStem Technologies, a leading innovator in the development, manufacture, and commercialization of allografts for regenerative therapies. BioStem harnesses the natural properties of perinatal tissue through its proprietary BioRetain processing method. Serves on the Audit Committee and the Governance and Nominating Committee.

Founder
RHK Mountain Ventures
Warren, VT
I co-founded RHK Mountain Ventures with my husband to identify mispriced properties in the Mad River Valley and transform them into high-performing short-term rentals. We brought modern, guest-first housing to a market with aging inventory and launched short-term rentals before the platforms were mainstream. We’re not actively acquiring now. The focus is disciplined portfolio management—operational excellence and selective sales. I contribute investment judgment, capital allocation, and exit strategy. My husband leads the daily operations.

Head of Team, Portfolio Manager & Analyst
Greater Boston Area
I built and led a global investment team managing three high conviction, innovation focused small and mid cap growth strategies. I developed and institutionalized a proprietary research framework centered on durable growth, reinvestment potential, moat strength, capital efficiency, and leadership quality. My role was deeply hands on in investment analysis and decision making, guiding company research and helping the team strengthen judgment, analytical discipline, and emotional composure. A big part of my leadership was instilling the behavioral foundations of successful long term investing including clear thinking under pressure, maintaining research quality, and holding conviction through market volatility. I also represented Polen Capital publicly on CNBC, Bloomberg, Barron’s, podcasts, and at industry events, sharing insights on markets, strategy, and investing. Beyond investing, I contributed to thought leadership and marketing efforts by collaborating on client communications and strategic messaging for institutional and high net worth audiences. Mentoring was a priority throughout my career. I developed talent across the firm and founded Polen’s WISE (Women Inspiring Success and Engagement) Employee Resource Group to champion inclusive leadership and professional growth.

Portfolio Manager
At Fidelity, I managed concentrated portfolios in the technology, telecom, consumer, and industrials sectors. We were often among the largest institutional shareholders, which gave me direct access to leadership teams and a seat at the table in their strategic conversations. I became a resource to management, offering perspective while gaining insights that sharpened my investment edge. I focused on identifying high quality businesses with strong growth potential and the leadership to unlock it. Through rigorous fundamental research, complemented by quantitative analysis, I built conviction, managed risk, and delivered results. Many of the companies I backed were later acquired or taken private at attractive valuations, validating the strength of the long term thesis and the discipline behind the work.
Rayna Lesser Hannaway, CFA's Contact Information
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