Investing in Advising Building

new companies

in FinTech

Fenway Summer is a venture capital firm focused at the intersection of finance, technology, and regulation.

A history of doing things differently

Deep Financial Services Expertise

Our investment partners, advisors, and extended network enable us to leverage deep and diversified expertise across all sub-sectors in U.S. financial services. Collectively, we have seen every part of the business cycle and served in practically every kind of role in financial institutions: marketing, operations, finance, credit, strategy, compliance, and legal.

A Habit of Entrepreneurship

We’ve sponsored or co-sponsored startup ventures in mortgage, student lending, credit cards, banking, wealth management, and compliance. Outside of core financial services, we’ve launched media properties, charitable organizations, and even a government agency. We bring entrepreneurial energy to every executive team with whom we are privileged to work.

Support that starts where most VCs stop

The advantage our portfolio companies have is not just capital, it’s execution. We support regulatory strategy and compliance infrastructure from the earliest days of company building, and our connectivity across the finance industry enables founders to move faster and de-risk earlier.

Our Investments

Print
ADF
Aniline
Armstrong
Banyan
Better Mortgage
card
Circle
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College+Ave+Logo
Crossbeam Logo
Deserve
DigitalPay_Logo
DriveWealth
EarnUp-HighRes-Logo-CMYK-1
elemeno+health
ethos
2560px-Flexport_logo
Print
5ee9e23a640ea
EMS
Unknown
logo
Green+Check
Imperitive
Insurvia white background
ledger+x
Lendable+Logo
Lumida
matic-network-logo-vector
Maxex
megalith
Merlon+Logo
Nav
new issue IQ
Notarize
Numerated
Overture
payjoy-logo
Open Banker
Parlay
PeerIQ-Logo
pinwheel
Polleyx
prosper
quotanda
reserve
resolve_logo_dark
RevolutionCredit
rtx
shift
spring
StreetShares
summer
Supply+Financ
TangoTrade
Transend
Trunomi.PNG
tuition.io
vault
veem
WunderLogo_FS

A team purpose-built for fintech investing

Raj Date and Casey Williams represent a combination that doesn’t exist elsewhere in venture. Raj spent years at the highest levels of financial regulation, including as Deputy Director of the CFPB, before building and backing some of the most consequential fintech companies of the last decade. Casey is a financial services operator turned venture builder. From her work inside major institutions, launching and leading businesses from the ground up, and building her own policy and regulatory fluency she is well equipped to support founders doing the same. Together they bring regulatory expertise, operating credibility, and investing judgement to the next generation of fintech leaders.
RAJ DATE
CASEY WILLIAMS
ALEX ACREE
CHRISTOPHER TREPEL
ETHAN SINGLETON
MARK LEFANOWICZ
JAVIER SAADE
MATT PERLMAN

Our Affiliates

FS Vector is a strategic consulting firm for financial services clients in a rapidly evolving industry and complex regulatory environment. 

RightWise Wealth is a modern firm helping high-earners organize an optimize their whole financial lives.

Open Banker curates the perspectives of top policy professionals in the evolving landscape of financial services in the United States.

Past Affiliates

crossbeam_logo.original
fscard
college-ave-logo--color
grasshopper
fs-advisory
fs-mortgage

Backing the future of financial services - built on expertise, not just capital.

If you are building a company in lending, payments, capital markets, data analytics, financial infrastructure, crypto or asset management, let’s connect.

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RAJ DATE

Managing Partner & Chair of the Investment Committees

Raj Date is the Managing Partner of Fenway Summer, a Washington, DC-based venture investment firm focused on the financial services sector. He is also the co-founder of FS Vector, an advisory firm that counsels financial services companies on regulatory strategy, compliance and public policy.

Raj has served on the boards of directors of a number of public and private companies across financial services — spanning sectors including banking, payments, insurance, and consumer finance.

For Raj, Fenway Summer is the latest chapter in a long and varied career in and around U.S. financial institutions — as a senior policymaker, as a bank executive, and on Wall Street.

Raj was the first-ever Deputy Director of the U.S. Consumer Financial Protection Bureau (CFPB). As the Bureau’s second-ranking official, he helped steward the CFPB’s strategy, its operations, and its policy agenda. He also served on the senior staff committee of the Financial Stability Oversight Council, and as a statutory deputy to the FDIC Board.

Before being appointed Deputy Director, Raj acted as the interim leader of the new agency, serving as the Special Advisor to the Secretary of the Treasury. He led the CFPB for most of the first six months after its launch.

Before his time in public policy, Raj was a Managing Director in the Financial Institutions Group at Deutsche Bank Securities, where he led the firm’s investment banking coverage for the largest U.S.-based banks and thrifts. His client work focused on calibrating credit deterioration, evaluating capital-raising alternatives, and generating liquidity. Before that, Raj was Senior Vice President for Corporate Strategy and Development at Capital One Financial, where he led M&A development efforts across the U.S. banking and specialty finance markets. He began his business career in the financial institutions practice of the consulting firm McKinsey & Company. He has also served as an attorney in both private practice and government service.

He is a graduate of the College of Engineering at the University of California at Berkeley (highest honors) and the Harvard Law School (magna cum laude).

e: raj.date@fenwaysummer.com

CASEY WILLIAMS

Partner & COO

Casey Williams is a Partner & COO at Fenway Summer.

She focuses on companies building infrastructure for the financial system, with a particular conviction for founders raising their first institutional round in complex, policy-adjacent markets where most generalist investors struggle to underwrite the risk.

Casey has walked a non-linear path to venture capital. She began her career as a fourth-grade math teacher through Teach for America, an experience that shaped how she thinks about problem-solving, resilience, and working in under-resourced environments. She then moved into financial inclusion work at Kiva Microfinance and, later, product and R&D at Wells Fargo. That trajectory, from classroom to microfinance to banking to venture, is not incidental: it means Casey evaluates founders and businesses through a wider lens than most investors operating at her stage, with genuine fluency across the regulatory, operational, and human dimensions of building in financial services.

Casey has a demonstrated pattern of conviction on non-consensus founders, looking for ideas that sit outside the comfortable consensus of what fintech “should” look like, and a track record of being early. She was the lead investor in the pre-seed rounds for Transend, Parlay, and Wavvest, and the seed rounds for Occupi and Prism Layer. She has held board observer seats at a number of Fenway Summer portfolio companies.

Her venture capital career began on the operating side of the business, when she first joined the Fenway Summer team in 2020 as an Operations Associate. She was quickly promoted to COO and has spent years managing every aspect of the business side of the firm, from fund administration to tax and audit processes.

Casey holds a Master’s in Public Administration from the University of Oklahoma and a B.A. in English Literature from Elon University. She lives in Washington, D.C. with her husband, two kids, and a growing collection of rescue animals that have claimed them as their own.

ALEX ACREE

Venture Partner

Alex Acree has spent his career at the intersection of technology, finance, and law as an attorney, advisor, and investor in financial services and other regulated industries.  

Alex currently is Chief Legal Officer at Unit. Prior to joining Unit, Alex was a partner at Mitchell Sandler, a boutique financial services-focused law firm. In that role, Alex advised clients on a wide range of matters, including legislative and regulatory issues, transactions, and corporate governance. Alex has deep experience counseling banks on regulatory matters, innovative technology companies through their lifecycles, as well as investment firms in connection with the formation and management of private funds.  

Alex previously served as Managing Director and General Counsel at Fenway Summer, where he served on the investment committee and invested in and advised fintech and regtech companies. Earlier in his career, Alex worked as a bank regulatory and investment funds attorney at a global law firm. 

Alex serves as a director on the board of FinRegLab, a nonprofit innovation center that tests new technologies and data to inform public policy and drive the financial sector toward a responsible and inclusive financial marketplace. Alex holds a J.D. from Yale Law School, an M.B.A. from Yale School of Management, and a B.A. from Boston College.  

e: alex.acree@fenwaysummer.com 

CHRISTOPHER TREPEL

Venture Partner

Chris is an Operating Partner at Fenway Summer Ventures; in this role, he contributes technical expertise in the areas of analytics, credit, data science, and consumer behavior.  In addition, Chris serves as a senior data science leader for several financial service and fintech firms in the US and UK.

Chris was previously Group Chief Science Officer at UK-based Lowell, leading both the data science function and Lowell Labs Amsterdam, an analytics center of excellence focused on advanced statistics and machine learning methods. At Lowell, he partnered with the Urban Institute to create the UK Financial Vulnerability Index.

Before that he was Chief Scientific Officer at Encore Capital Group, where he built and directed the analytics and corporate affairs functions, launched a pioneering research platform focused on consumer financial decision making, and wrote the industry’s first Consumer Bill of Rights. Earlier still, Chris served in analytic and strategic roles at Wells Fargo Bank and McKinsey & Company.

Chris holds a Ph.D. in Experimental Psychology, is a Fellow of the British Psychological Society, has completed postdoctoral fellowships in Neurophysiology and Behavioral Economics, and is lead or co-author of more than 70 academic and professional publications across five research areas. His work has appeared in the Wall Street Journal, Washington Post, Chicago Tribune, NPR, USA Today, and CNN Money.

e: christopher.trepel@fenwaysummer.com 

ETHAN SINGLETON

Venture Partner

Ethan is a Partner in FS Vector’s Advisory Practice who helps clients navigate the complexities of launching and scaling innovative financial products. At FS Vector, he leads and coordinates bank–fintech partnership programs, working closely with state and federally chartered banks, fintechs, digital asset companies, technology providers, and other ecosystem partners. He brings deep expertise in supporting innovators from concept to launch, providing end-to-end leadership across regulatory and compliance strategy, product design, and operational readiness.

Prior to joining FS Vector, Ethan was a Manager in the Advisory practice at BDO USA, where he led anti-money laundering program assessments and consultations on unique compliance issues related to fintech partnerships. Earlier in his career, he was a member of the Financial Crimes Regulatory Compliance group at HSBC Bank USA.
Ethan received a B.A. in Political Science and an M.B.A. from the University of Delaware, and a J. D. from the Delaware Law School of Widener University.

MARK LEFANOWICZ

Venture Partner

Mark joins Fenway Summer Ventures from Springleaf Financial, where he served as Senior Vice President responsible for Internet lending, call center operations, and new business initiatives. Mark is also the Executive Chairman of Ethos Lending. Previously, Mark served as CFO of Provident Funding Associates, and was responsible for the company’s treasury, finance, accounting, and administrative functions. 

From 2004 to 2008, Mark served as CEO/President of E-LOAN, a publicly traded Internet mortgage, home equity, and auto lender.  As CEO, he led the company’s sale to Banco Popular, resulting in an 89% per share price appreciation from the time Mark joined E-LOAN to its sale. 

Earlier in his career, Mark served in numerous executive positions at Bay View Capital and as a partner at Coopers & Lybrand, which later merged with Price Waterhouse to form PWC.  He has served on the Board of Directors for several consumer financial institutions, including Credit Karma. Mark has also been an active angel investor in consumer finance and fintech companies.  

He is a Certified Public Accountant and holds a Bachelor of Science in accounting from the University of Wyoming.  Mark resides in Lafayette, CA with his wife Kathy and his three daughters. 

e: mark.lefanowicz@fenwaysummer.com 

JAVIER SAADE

Venture Partner

Javier is Venture Partner at Fenway Summer Ventures and has decades of experience as a venture capitalist and private equity investor, entrepreneur, operating executive and policymaker. He serves on the Board of Directors of Softbank’s SVF Investment Corp. (NASDAQ: SVFA) and as Chairman of the Board of GP Funding, Inc., a private equity owned financial services company. 

Until recently, Javier served on the Board of Directors of Porch Group (NASDAQ: PRCH), Board of Trustees of Pan American Development Foundation, Board of Trustees of The Nature Conservancy, Board of Directors of Foundation for Puerto Rico, Global Advisory Board of Docusign, Inc. (NASDAQ: DOCU), Corporate Responsibility Board of Univision Communications, Inc., and Board of Advisors of Harvard’s Rock Center for Entrepreneurship. He also served full-time on the Biden Transition Team focused on Treasury and the economy. 

Before Fenway, he served as Associate Administrator of the U.S. Small Business Administration (SBA) during the Obama Administration.  Javier led the agency’s innovation and investment programs which since inception have invested over $120 billion in 320,000 high-growth small businesses.   He worked with the White House on a broad swath of economic, innovation and financial policy making.  He also held a seat at the U.S. Securities & Exchange Commission’s (SEC’s) Advisory Committee on Small & Emerging Companies.   

Prior to public service, Javier spent 20 years in a variety of operating, entrepreneurial, investment and advisory roles at firms that include McKinsey & Company, Booz Allen & Hamilton, Bridgewater Associates, GEM Group, Pacific Community Ventures, and Abbott Laboratories.  He has co-founded several businesses, including Air America Media.  

Javier also held short-term roles including Executive in Residence (XIR) at Columbia University’s Columbia Technology Ventures, Senior Fellow at Georgetown University’s Beeck Center for Social Innovation and Mentor at Stanford University’s Latino Entrepreneurship Leaders Initiative.  He writes and speaks frequently on topics that include corporate diversity, leadership, tech-driven innovation, financial inclusion, mission-driven business, social and impact capital, entrepreneurial ecosystems, and digital-era policymaking.    

He holds an MBA from Harvard Business School, an MS in Operations & Technology from Illinois Institute of Technology, and a BS in Industrial Management from Purdue University.  

e: javier.saade@fenwaysummer.com 

MATT PERLMAN

Venture Partner

Matt has 15 years of experience as an investor and advisor to financial services companies. Matt is currently a Partner at IA Capital Group, an NYC-based early and growth stage investment firm focusing on insurtech and fintech, and was part of the founding team at Fenway Summer Ventures.  

Prior to his venture capital career, Matt held various roles in private equity and investment banking focusing on the financial sector. He graduated magna cum laude from Princeton University’s School of Public and International Affairs and holds an M.B.A. from Columbia Business School. 

e: matthew.perlman@fenwaysummer.com