About

About

I'm an entrepreneur and fractional executive, and although my interests are broad, my experiences and thus my wheelhouse is in bridging main street and institutional capital in tech-enabled services — through two successfully executed buy-and-build strategies, taking platforms from relative infancy through institutional funding and beyond. To be clear, less as an intermediary or investment banker and more so a strategist focused on value creation. The biggest obstacle to that value creation is business transformation, and generally, that's where I live.

At the time of my writing this, the primary purpose of this website is casual marketing for my fractional executive/ advisory work, as such you'll find a cut of my experience below much akin to a resume as well as some information about how I work.

Much of my work falls within the following three critical categories:

  1. Disentanglement of legacy organizations, processes, and technology stacks.
  2. Designing systematized operating models driven by first-principles thinking that are capable of leveraging technology, absorbing change, and providing critical visibility to leadership.
  3. Architecting corporate development strategies and playbooks that allow organizations to successfully source add-on opportunities, diligence them, and truly integrate them such that value creation is assured.

At the forefront of my working philosophy is the study and use of influence and alignment. Use blunt tools and you're prone to hurt yourself. There's a random quote I love from Ray Dalio: "whether or not we could have our cake and eat it too was merely a test of our creativity and character." Oftentimes, for founders, principals, and investors alike, the proverbial 'cake' is growth and prosperity without sacrificing the culture and sustainability of the business.


Experience

Your Policy (2020–2026) — Co-Founder, Board Member, then Chief Strategy Officer of a PE-backed insurance distribution platform spanning commercial P&C, personal lines, employee benefits, and payroll/HRO services. Recapitalized by an institutional sponsor mid-tenure; named to the Inc. 5000 (#425, 2025). As internal transaction lead, served as primary representative through the sell-side process that resulted in the majority recap, including building the investment narrative and articulating the value creation thesis to institutional investors. Post-close, architected the operating foundation that allowed the platform to scale enterprise complexity at pace:

  • Acquired and integrated 27 owner-operated insurance agencies through a single repeatable framework — greenfield operating model construction rather than incremental absorption.
  • Designed the platform's Agency Success Model: a stratified labor architecture combining onshore, offshore, and systems-enabled workflows that delivered meaningful margin expansion and per-employee revenue lift.
  • Directed enterprise technology stack rationalization (AMS, ERP, HRIS, CRM) and established the data governance foundation required for institutional-grade reporting and decision-making.
  • Owned enterprise planning, board communications, and organizational design — translating sponsor objectives into coordinated execution across the leadership team.

Fervent Capital Advisors (2020–2023) — Founder and Principal of a capital markets advisory practice focused on operating businesses in alternative real estate. Executed a meaningful volume of transactions across self-storage, outdoor hospitality, and adjacent asset classes. Represented ownership in the sale of a sizable self-storage portfolio to a publicly traded REIT — coordinating diligence across multiple ownership entities and navigating the structural complexities of a cash-consideration public REIT acquisition.

StorSuite (formerly Pinnacle Storage Properties) (2018–2020, 2024) — Early hire and Acquisitions Lead at a vertically integrated self-storage investment platform during its primary growth phase; built and ran the acquisitions function from cradle to grave — sourcing, underwriting, debt capital raising, and investor relations. Returned in 2024 as Board Member to advise the vertical integration of an affiliated marketing services company, tenant insurance program, and proprietary PropTech platform.


Credentials

Certified Birkman Professional — behavioral and occupational assessment, applied to organizational design, leadership development, and team structure.

BBA, Entrepreneurship — University of Houston, Wolff Center for Entrepreneurship. Led commercialization of Exostretch, a patented stretchable thin-film battery (NASA iTech, Caltech First Look West, Baylor New Venture).


Where I tend to add the most value

Different engagements call for different cuts, but the work usually concentrates here:

  • Pre-close investment readiness. Preparing owner-led businesses for institutional ownership — building the investment narrative, surfacing the value creation levers a sponsor will want to underwrite, and getting the operating foundation honest enough to survive diligence. Most often done as the internal company-side lead through the transaction itself.
  • Disentangling legacy organizations. Most operating foundations were built for an earlier version of the business. The work is pulling apart the legacy of processes, roles, technology, and talent — and rebuilding in the right sequence. Tasks before roles, roles before technology, technology before talent, talent before path. Skipping steps compounds drag.
  • Designing operating models from first principles. Architecting how the business actually runs end-to-end — process, systems, structure, and the visibility leadership needs to operate institutionally. Destination-state design rather than incremental fixing.
  • End-to-end M&A execution. Designing the corporate development strategy, then running the playbook — sourcing, underwriting, diligencing, and integrating acquisitions so the value creation thesis survives contact with reality. Integration is project-managed work, but it's also a relationship — most acquisitions quietly lose their thesis because the operating discipline and the human integration weren't both being run.
  • Scoring talent against where the business is going. Evaluating people for destination roles rather than legacy ones, with learning velocity as a separate axis. The institutional knowledge sitting in acquired companies is almost always more valuable than it looks in the deal model — and displacement, even on financial terms, tends to produce worse outcomes than the model would suggest.
  • Putting AI and systems leverage in the right sequence. AI is the train; the operating model is the tracks. Figuring out what gets automated, what stays human, and what gets outsourced before adding headcount — not after. Most operating models get built backwards.

How I engage

I work in a few different modes, depending on the situation:

  • Fractional executive — embedded operating leadership (typically Chief Strategy Officer, COO, or chief-of-staff equivalent) on a part-time basis. Best for owner-led businesses preparing for institutional capital, or platforms in the post-close stretch where the work is real but a full-time hire is premature.
  • Advisory — retainer-based, lower-touch. Strategic sounding board, deal review, organizational design, hiring help. Good for sponsors managing multiple PortCos who need a consistent operator perspective without the FTE commitment.
  • Board — independent director or board observer on PE-backed platforms.
  • Project-based — scoped engagements for specific transitions: post-close integration, operating model redesign, M&A diligence support, value creation plan stand-up.

I try to be honest about which mode fits the situation. Sometimes that means saying "you don't need me yet" or "you need someone else."


Take a look at my essays for some (hopefully) helpful resources on business transformation and strategy. Feel free to reach out if you're interested in engaging me for a project, calling bulls**t on my ramblings, or just making the world smaller.

connect@rosssmolen.com