Financial Services Marketing · Growth Advisory · New York
Rob Simone is a New York–based growth strategist and three-time agency founder who has spent twenty-five years marketing financial brands like Morgan Stanley, JPMorgan, Bank of America, and BNY Mellon. He's co-founder and President of Summer Friday and advises founders and leadership teams on growth, capital raising, and M&A. He's sold an agency, bought one, and built three.
About
Rob has spent twenty-five years at the place where creative work becomes a business: assembling talent, winning clients, and building companies worth working for.
He came up through New York's storied shops: Grey, BBDO, Sapient, and JWT. In 2006 he co-founded Hiccup Media with creative partner Michael Cruz and spent the next decade scaling it, ultimately selling the boutique to the partners with whom he would acquire another agency and found DRUM. He led the 170-person firm as President until its majority owners shut it down in the first weeks of COVID.
Within a month, he was building again. Summer Friday, founded with Sarah Roberts, Michael Cruz, and Alicia Wiedemann at the height of the pandemic, is now a sustained, profitable creative partner to enterprise brands that demand rigor and early-stage brands that demand speed.
Most of that time has been spent in financial services: banking, wealth and asset management, brokerage and trading platforms, lending, insurance, and now fintech and digital assets. It's a category where the marketing is harder and the ceiling is higher. Rob's view is that compliance has never been what holds financial brands back. Not knowing the category is. The firms that win know the product, the audience, and the regulatory lines cold, and treat those lines as the edge of the brief, not the excuse for a dull one.
At Summer Friday, Rob owns vision, talent, and business development. His conviction is simple: great creative companies are built deliberately, at a size where the work and the culture can both stay excellent.
He lives on Long Island, New York.
Summer Friday is a boutique strategy, creative, and content firm with deep roots in financial services. Founded in 2020 by Rob with partners Sarah Roberts, Michael Cruz, and Alicia Wiedemann, it has partnered with Morgan Stanley, E*TRADE, JPMorgan, Chase, Bank of America, BNY Mellon, VanEck, TradeStation, and iFlip, along with category leaders in healthcare and energy. It stays deliberately boutique: creating the ideal conditions for great work.
The firm's financial services practice covers banking, wealth and asset management, trading platforms, lending, insurance, and digital assets. Its newest practice takes a solutions-architect approach to AI-enabled content, helping enterprise teams diagnose the problem before buying the tool.
The Summer Friday partners, New York City.
Independent Advisory Work
Independent engagements with fintech founders, financial services marketing leaders, and the agencies and founder-led companies that serve them. Usually the trigger is a raise, an acquisition, a rebrand, or growth that has stalled in a category where trust is the product.
Positioning, go-to-market, and customer acquisition for fintechs and financial brands, from launch to scale.
Getting a regulated company to say what it is in a sentence, in language compliance will approve and customers will believe.
Pipeline discipline for agencies and firms selling into financial services, where the buyers are cautious and the cycles are long.
Guiding founders through raises, acquisitions, and exits, from narrative to negotiation. Advice from someone who has signed both sides of the deal.
Now: Fractional Chief Growth Officer at iFlip, an AI-powered investing platform, leading growth strategy and customer acquisition for a retail-investor product in a crowded, regulated category.
Boutique strategy, creative, and content firm serving Morgan Stanley, E*TRADE, JPMorgan, BNY Mellon, VanEck, TradeStation, Cigna, and Sony.
Sold Hiccup, then partnered with its buyers to acquire and rebrand another agency as DRUM. Led the 170-person firm, with clients including BNY Mellon and Bank of America, until its majority owners wound it down at the onset of COVID.
Co-founded the boutique content shop with Michael Cruz and grew it for nine years, with clients including TD Ameritrade and BNY Mellon, before selling to the partners who would become DRUM's owners.
Account leadership and digital strategy at New York's storied shops, much of it on financial services accounts: the foundation for three companies of his own.
Writing
On the idle Tuesday in April 2020 when DRUM's owners shut the agency down with a phone call, and what starting over from zero taught Rob about growth, culture, and control. The origin story of Summer Friday.
Read the essay →"When the universe rips off the band-aid for you, there's a whole lot less to fear."
Press & Appearances
Questions
A fractional CGO owns growth strategy and customer acquisition for a company that needs senior leadership before it can justify a full-time executive. For a fintech, that means positioning, go-to-market, acquisition channels, and the marketing-to-product handoffs that decide whether a launch converts. Rob currently serves in this role at iFlip, an AI-powered investing platform.
The product is abstract, the audience is skeptical, and every claim passes through compliance. Most agencies treat that last part as the reason the work is dull. Rob's view is the opposite: compliance is a fixed constraint, and the teams that know the product, the audience, and the regulatory lines cold are the ones free to be bold inside them. Category fluency is the creative advantage.
Fintech founders, marketing leaders at banks, wealth and asset managers, trading platforms and insurers, and the owners of agencies and founder-led companies that serve them. Engagements usually begin at an inflection point: a raise, an acquisition, an exit, a rebrand, or a growth plateau.
Summer Friday is a full strategy, creative, and content firm; it builds and ships the work. Rob's advisory is independent and personal: strategy, positioning, business development, and deal guidance for founders and leadership teams, often before there is anything to produce. Some advisory clients go on to work with Summer Friday. Many don't, and that's by design.
Contact
For Summer Friday partnerships, advisory engagements, speaking, or podcast invitations, reach out directly or connect on LinkedIn.